In this episode, I'm joined by Mandy Mooney — author, corporate communicator, and performer — for a wide-ranging conversation about mentorship, career growth, and how to show up authentically in both work and life.

We talk about her path from performing arts to corporate communications, and how those early experiences shaped the way she approaches relationships, leadership, and personal authenticity. That foundation carries through to her current role as VP of Internal Communications, where she focuses on building connections and fostering resilience across teams.

We explore the three pillars of career success Mandy highlights in her book Corporating: Three Ways to Win at Work — relationships, reputation, and resilience — and how they guide her approach to scaling mentorship and helping others grow. Mandy shares practical strategies for balancing professional responsibilities with personal passions, and why embracing technology thoughtfully can enhance, not replace, human connection.

The conversation also touches on parenting, building independence in children, and the lessons she's learned about optimism, preparation, and persistence — both in the workplace and at home.

If you're interested in scaling mentorship, developing your career with intention, or navigating work with authenticity, this episode is for you. And if you want to hear more on these topics, catch Mandy speaking at Snafu Conference 2026 on March 5th.

00:00 Start 02:26 Teaching Self-Belief and Independence

• Robin notes Mandy has young kids and a diverse career (performing arts → VP of a name-brand company → writing books).

• Robin asks: "What are the skills that you want your children to develop, to stay resilient in the world and the world of work that they're gonna grow up in?" Emphasis on meta-skills.

• Mandy's response: Core skills

• She loves the question, didn't expect it, finds it a "thrilling ride."

• Observes Robin tends to "put things out there before they exist" (e.g., talking about having children before actually having them).

• Skill 1: Envisioning possibilities

• "Envision the end, believe that it will happen and it is much more likely to happen."

• Teaching children to see limitless possibilities if they believe in them.

• Skill 2: Independence Examples: brushing their own hair, putting on clothes, asking strangers questions.

• One daughter in Girl Scouts: learning sales skills by approaching strangers to sell cookies.

• Independence builds confidence and problem-solving abilities for small and big life challenges.

• Skill 3: Self-belief / Self-worth

• Tied to independence.

• Helps children navigate life and career successfully.

• Robin asks about teaching self-belief

• Context: Mandy's kids are 6 and 9 years old (two girls).

• Mandy's approach to teaching self-belief

• Combination of:

• Words Mandy uses when speaking to them.

• Words encouraged for the children to use about themselves.

• Example of shifting praise from appearance to effort/creativity:

• Instead of "You look so pretty today" → "Wow, I love the creativity that you put into your outfit."

• Reason: "The voice that I use, the words that I choose, they're gonna receive that and internalize it."

• Corrective, supportive language when children doubt themselves:

• Example: Child says, "I'm so stupid, I can't figure out this math problem."

• Mandy responds: "Oh wow. That's something that we can figure out together. And the good news is I know that you are so smart and that you can figure this out, so let's work together to figure it out."

• Asking reflective questions to understand their inner thoughts:

• Example: "What's it like to be you? What's it like to be inside your head?"

• Child's response: "Well, you worry a lot," which Mandy found telling and insightful.

• Emphasizes coming from a place of curiosity to check in on a child's self-worth and self-identity journey.

04:30 Professional Journey and Role of VP of Internal Comms

• Robin sets up the question about professional development

• Notes Mandy has mentored lots of people.

• Wants to understand:

• Mandy's role as VP of Internal Communications (what that means).

• How she supports others professionally.

• How her own professional growth has been supported.

• Context: Robin just finished a workshop for professionals on selling themselves, asking for promotions, and stepping forward in their careers.

• Emphasizes that she doesn't consider herself an expert but learns from conversations with experienced people like Mandy.

• Mandy explains her role and path

• Career path has been "a winding road."

• Did not study internal communications; discovered it later.

• Finds her job fun, though sometimes stressful:

• "I often think I might have the most fun job in the world. I mean, it, it can be stressful and it can't, you know, there are days where you wanna bang your head against the wall, but by and large, I love my job. It is so fun."

• Internal communications responsibility:

• Translate company strategy into something employees understand and are excited about.

• Example: Translate business plan for 2026 to 2,800 employees.

• Team's work includes:

• Internal emails.

• PowerPoints for global town halls.

• Speaking points for leaders.

• Infusing fun into company culture via intranet stories (culture, customers, innovation).

• Quick turnaround on timely stories (example: employee running seven marathons on seven continents; story created within 24 hours).

• Storytelling and theater skills are key:

• Coaching leaders for presentations: hand gestures, voice projection, camera presence.

• Mandy notes shared theater background with Robin: "You and I are both thespian, so we come from theater backgrounds."

• Robin summarizes role

• Sounds like a mix of HR and sales: supporting employee development while "selling" them on the company.

• Mandy elaborates on impact and mentorship

• Loves making a difference in employees' lives by giving information and support. Works closely with HR (Human Resources) to:

• Provide learning and development opportunities. Give feedback.

• Help managers improve.

• Wrote a book to guide navigating internal careers and relationships.

• Mentorship importance:

• Mentors help accelerate careers in any organization.

• Mandy's career journey

• Started studying apparel merchandising at Indiana University (with Kelley School of Business minor).

• Shifted from pre-med → theater → journalism → apparel merchandising.

• Took full advantage of career fairs and recruiter networking at Kelley School of Business.

• "The way that I've gotten jobs is not through applying online, it's through knowing somebody, through having a relationship."

• First role at Gap Inc.: rotational Retail Management Training Program (RMP).

• Some roles enjoyable, some less so; realized she loved the company even if some jobs weren't ideal.

• Mentor influence:

• Met Bobby Stillton, president of Gap Foundation, who inspired her with work empowering women and girls.

• Took a 15-minute conversation with Bobby and got an entry-level communications role.

• Career growth happened through mentorship, internal networking, and alignment with company she loved.

• Advice for her daughters (Robin's question)

• Flash-forward perspective: post-college or early career.

• How to start a career in corporate / large organizations:

• Increase "luck surface area" (exposure to opportunities).

• Network in a savvy way.

• Ask at the right times.

• Build influence to get ahead.

• Mentorship and internal relationships are key, not just applying for jobs online.

12:15 Career Advice and Building Relationships

Initial advice:

• "Well first I would say always call your mom. Ask for advice. I'm right here, honey, anytime."

• Three keys to success:

• Relationships

• Expand your network.

• "You say yes to everything, especially early in your career."

• Examples: sit in on meetings, observe special projects, help behind the scenes.

• Benefits:

• Increases credibility. Shows people you can do anything.

• Reputation

• Build a reputation as confident, qualified, and capable.

• Online presence:

• Example: LinkedIn profile—professional, up-to-date, connected to network.

• Be a sponsor/advocate for your company (school, office, etc.). Monthly posts suggested: team photos, events, showing responsibility and trust.

• Offline reputation:

• Deliver results better than expected.

• "Deliver on the things that you said you were gonna do and do a better job than people expected of you."

• Resilience

• Not taught from books—learned through experience.

• Build resilience through preparation, not "fake it till you make it."

• Preparation includes: practicing presentations, thinking through narratives, blocking time before/after to collect thoughts and connect with people.

• "Preparation is my headline … that's part of what creates resilience."

• Mandy turns the question to Robin:

• "I wanna ask you too, I mean, Robin, you, you live and breathe this every day too. What do you think are the keys to success?"

• Robin agrees with preparation as key.

• Value of service work:

• Suggests working in service (food, hospitality) teaches humility. "I've never met somebody I think even ever in my life who is super entitled and profoundly ungrateful, who has worked a service job for any length of time."

• Robin's personal experience with service work:

• First business: selling pumpkins at Robin's Pumpkin Patch (age 5).

• Key formative experience: running Robin's Cafe (2016, opened with no restaurant experience, on three weeks' notice).

• Ran the cafe for 3 years, sold it on Craigslist.

• Served multiple stakeholders: nonprofit, staff (~15 employees), investors ($40,000 raised from family/friends).

• Trial by fire: unprepared first days—no full menu, no recipes, huge rush events.

• Concept of MI Plus: "Everything in its place" as preparation principle.

• Connecting service experience to corporate storytelling:

• Current business: Zandr Media (videos, corporate storytelling).

• Preparation is critical:

• Know who's where, what will be captured, and what the final asset looks like.

• Limited fixes in post-production, even with AI tools.

• Reinforces importance of preparation through repeated experience.

• Advice for future children / young people:

• Robin would encourage service jobs for kids for months or a year.

• Teaches:

• Sleep management, personal presentation, confidence, energy.

• "Deciding that I'm going to show up professionally … well … energetically."

• Emphasizes relentless optimism: positivity is a superpower.

• Experience shows contrast between being prepared and unprepared—learning from both is crucial.

16:36 The Importance of Service Jobs and Resilience

• Service jobs as formative experience:

• Worked as a waitress early in her career (teenager).

• Describes it as "the hardest job of my life".

• Challenges included:

• Remembering orders (memory).

• Constant multitasking.

• Dealing with different personalities and attitudes.

• Maintaining positivity and optimism through long shifts (e.g., nine-hour shifts).

• Fully agrees with Robin: service jobs teach humility and preparation.

• Optimism as a superpower:

• "I totally agree too that optimism is a superpower. I think optimism is my superpower."

• Writes about this concept in her book.

• Believes everyone has at least one superpower, and successful careers involve identifying and leaning into that superpower.

• Robin asks about the book

• Why did Mandy write the book?

• Inspiration behind the book?

• Also wants a deep dive into the writing process for her own interest.

• Mandy's inspiration and purpose of the book

• Title: "Corporating: Three Ways to Win At Work"

• Primary goal: Scale mentorship.

• Realized as she reached VP level, people wanted career advice.

• Increased visibility through:

• Position as VP.

• Connection with alma mater (Indiana University).

• Active presence on LinkedIn.

• Result: Many young professionals seeking mentorship.

• Challenge: Not sustainable to mentor individually.

• Solution: Writing a book allows her to scale mentorship without minimizing impact.

• Secondary goals / personal motivations:

• Acts as a form of "corporate therapy":

• Reflects on first 10 years of her career.

• Acknowledges both successes and stumbles.

• Helps process trials and tribulations.

• Provides perspective and gratitude for lessons learned.

• Fun aspect: as a writer, enjoyed formatting and condensing experiences into a digestible form for readers.

• Legacy and contribution:

• "I had something that I could contribute meaningfully to the world … as part of my own legacy … I do wanna leave this world feeling like I contributed something positive. So this is one of my marks."

21:37 Writing a Book and Creative Pursuits

• Robin asks Mandy about the writing process:

• "What's writing been like for you? Just the, the process of distilling your thinking into something permanent."

• Mandy: Writing process and finding the "25th hour"

• Loves writing:

• "I love writing, so the writing has been first and foremost fun."

• Where she wrote the book:

• Mostly from the passenger seat of her car.

• She's a working mom and didn't have traditional writing time.

• Advice from mentor Gary Magenta:

• "Mandy, you're gonna have to find the 25th hour."

• She found that "25th hour" in her car.

• Practical examples:

• During birthday party drop-offs:

• "Oh good. It's a drop off party. Bye. Bye, honey. See you in two hours. I'll be in the driveway. In my car. If you need anything, please don't need anything."

• Would write for 1.5–2 hours.

• During Girl Scouts, swim, any activity.

• On airplanes:

• Finished the book on an eight-hour flight back from Germany.

• It was her 40th birthday (June 28).

• "Okay, I did it."

• Realization moment: "You chip away at it enough that you realize, oh, I have a book."

• Robin: On parents and prioritization

• Parents told him:

• "When you have kids, you just find a way."

• Children create:

• Stricter prioritization.

• A necessary forcing function.

• Mandy's self-reflection:

• "I believe that I am an inherently lazy person, to be totally honest with you."

• But she's driven by deadlines and deliverables.

• Kids eliminate "lazy days":

• No more slow Saturdays watching Netflix.

• "They get up. You get up, you have to feed these people like there's a human relying on you."

• Motherhood forces motivation:

• "My inherent laziness has been completely wiped away the past nine years."

• Writing happened in small windows of time.

• Importance of creative outlet:

• Having something for yourself fuels the rest of life.

• Examples: writing, crocheting, quilting, music.

• Creativity energizes other areas of life.

• Robin mentions The 4-Hour Workweek by Tim Ferriss.

• Advice from that book:

• Have something outside your day job that fuels you.

• For Robin:

• Physical practice (gym, handstands, gymnastics, ballet, capoeira, surfing).

• It's a place to:

• Celebrate.

• Feel progress.

• Win, even if work is struggling.

• Example:

• If tickets aren't selling.

• If newsletter flops.

• If client relationships are hard.

• Physical training becomes the "anchor win."

• Mandy's writing took over two years.

• Why?

• She got distracted writing a musical version of the book.

• There is now:

• "Corporating: The Book"

• "Corporating: The Musical"

• Three songs produced online.

• Collaboration with composer Eric Chaney.

• Inspiration from book: Time, Talent, Energy (recommended by former boss Sarah Miran).

• Concept: we have limited time, talent, and energy.

• Advice:

• Follow your energy when possible.

• If you're flowing creatively, go with it (unless there's an urgent deadline).

• You'll produce better work.

• She believes:

• The book is better because she created the musical.

• Musical helps during speaking engagements.

• Sometimes she sings during talks.

• Why music?

• Attention spans are short.

• Not just Gen Z — everyone is distracted.

• Music keeps people engaged.

• "I'm not just gonna tell you about the three ways to win at work. I'm gonna sing it for you too."

• Robin on capturing attention

• If you can hold attention of:

• Five-year-olds.

• Thirteen-year-olds.

• You can hold anyone's attention.

• Shares story:

• In Alabama filming for Department of Education.

• Interviewed Alabama Teacher of the Year (Katie).

• She has taught for 20 years (kindergarten through older students).

• Observed:

• High enthusiasm.

• High energy.

• Willingness to be ridiculous to capture attention.

• Key insight:

• Engagement requires energy and presence.

28:37 The Power of Music in Capturing Attention

• Mandy's part of a group called Mic Drop Workshop.

• Led by Lindsay (last name unclear in transcript) and Jess Tro.

• They meet once a month.

• Each session focuses on improving a different performance skill.

• The session she describes focused on facial expressions.

• Exercise they did:

• Tell a story with monotone voice and no facial expressions.

• Tell the story "over the top clown like, go really big, something that feels so ridiculous."

• Tell it the way you normally would.

• Result:

• Her group had four people.

• "Every single one of us liked number two better than one or three."

• Why version two worked best:

• When people are emotive and expressive:

• It's more fun to watch.

• It's more entertaining.

• It's more engaging.

• Connection to kids and storytelling:

• Think of how you tell stories to five-year-olds:

• Whisper.

• Get loud.

• Get soft.

• Use dynamic shifts.

• The same applies on stage.

• Musical integration:

• Music is another tool for keeping attention.

• Helps maintain engagement in a distracted world.

• Robin: Hiring for energy and presence

• Talks about hiring his colleague Zach Fish.

• Technical producer for:

• Responsive Conference.

• Snafu Conference.

• Freelancer Robin works with often.

• Why Robin hires Zach:

• Yes, he's technically excellent.

• But more importantly:

• "He's a ball of positive energy and delight and super capable and confident, but also just pleasant to be with."

• Robin's hiring insight:

• If he has a choice, he chooses Zach.

• Why?

• "I feel better."

• Energy and presence influence hiring decisions.

• Zach's background:

• Teaches weekly acrobatics classes for kids in Berkeley.

• He's used to engaging audiences.

• That translates into professional presence.

• Robin: Energy is learnable

• When thinking about:

• Who to hire.

• Who to promote.

• Who to give opportunities to.

• Traits that matter:

• Enthusiasm.

• Positivity.

• Big energy.

• Being "over the top" when needed.

• Important insight:

• This isn't necessarily a God-given gift.

• It can be learned.

• Like music or performance.

• Like anything else.

31:00 The Importance of Positive Work Relationships

• Mandy reflects on:

• The tension between loud voices and quiet voices.

• "Oftentimes the person who is the loudest is the one who gets to talk the most, but the person who's the quietest is the one who maybe has the best ideas."

• Core question:

• How do you exist in a world where both of those things are true?

• Parenting lens:

• One daughter is quieter than the other.

• Important to:

• Encourage authenticity.

• Teach the skill of using your voice loudly when needed.

• It's not about changing personality.

• It's about equipping someone to advocate for themselves when necessary

• Book is targeted at:

• Students about to enter the corporate world.

• Early-career professionals.

• Intentional writing decision:

• Exactly 100 pages.

• Purpose:

• "To the point, practical advice."

• Holds attention.

• Digestible.

• Designed for distracted readers.

• Emotional honesty:

• Excited but nervous to reconnect with students.

• Acknowledges:

• The world has changed.

• It's been a while since she was in college.

• Advice she's trying to live: Know your audience

• Core principle:

• "Get to know your audience. Like really get in there and figure out who they are."

• Pre-book launch tour purpose:

• Visiting universities (including her alma mater).

• Observing students.

• Understanding:

• Their learning environment.

• Their day-to-day experiences.

• The world they're stepping into.

• Communication principle:

• Knowing your audience is essential in communications.

• Also essential in career-building.

• If you have a vision of where you want to go:

• "Try to find a way to get there before you're there."

• Tactics:

• Meet people in those roles.

• Shake their hands.

• Have coffee.

• Sit in those seats.

• Walk those halls.

• See how it feels.

• Idea:

• Test the future before committing to it.

• Reduce uncertainty through proximity.

• What if you don't have a vision?

• Robin pushes back thoughtfully:

• What about people who:

• Don't know what they want to do?

• Aren't sure about staying at a company?

• Aren't sure about career vs. business vs. stay-at-home parent?

• Acknowledges:

• There's abundance in the world.

• Attention is fragmented.

• Implied tension:

• How do you move forward without clarity?

35:13 Mentorship and Career Guidance

• How to help someone figure out what's next

• Start with questions, not answers

• A mentor's primary job: ask questions from a place of curiosity

• Especially when someone is struggling with what they want to do or their career direction

• Key questions: What brings you joy? What gives you energy? What's the dream? Imagine retirement — what does that look like?

• Example: A financial advisor made Mandy and her husband define retirement vision; then work backwards (condo in New Zealand, annual family vacations)

• Clarify what actually matters

• Distinguish life priorities: Security → corporate job; Teamwork → corporate environment; Variety and daily interaction → specific roles

• Mentoring becomes a checklist: Joy, strengths, lifestyle, financial expectations, work environment preferences

• Then make connections: Introduce them to people in relevant environments, encourage informational interviews

• You don't know what you don't know

• Trial and error is inevitable

• Build network intentionally: Shadow people, observe, talk to parents' friends, friends of friends

• Even experienced professionals have untapped opportunities

• Stay curious and do the legwork

• Mixing personal and professional identity

• Confidence to bring personal interests into corporate work comes from strategy plus luck

• Example: Prologis 2021, senior leaders joked about forming a band; Mandy spoke up, became lead singer

• CEO took interest after first performance, supported book launch

• She didn't always feel this way

• Early corporate years: Feel like a "corporate robot," worrying about jargon, meetings, email etiquette, blending in

• Book explores blending in while standing out

• Advice for bringing full self to work

• Don't hide it, but don't force it; weave into casual conversation

• Find advocates: Amazing bosses vs terrible ones, learn from both

• Mentorship shaped her framework: Relationships, reputation, and resilience

• Resilience and rejection

• Theater as rejection bootcamp: Auditions, constant rejection

• Foundations of resilience: Surround yourself with supportive people, develop intrinsic self-worth, know you are worthy

• Creating conditions for success

• Age 11 audition story: Last-minute opportunity, director asked her to sing, she sang and got the part

• Why it worked: Connections (aunt in play), parent support, director willing to take a chance, she showed up

• Resilience is not just toughing it out: Have support systems, build self-worth, seek opportunity, create favorable conditions, step forward when luck opens a door

44:18 Overcoming Rejection and Building Resilience

• First show experiences

• Robin's first stage production is uncertain; she had to think carefully

• At 17, walked into a gymnastics gym after being a cross country runner for ten years, burnt out from running

• Cold-called gyms from the Yellow Pages; most rejected her for adult classes, one offered adult classes twice a week

• That led to juggling, circus, fencing, capa, rock climbing — a "Cambrian explosion" of movement opportunities

• About a year and a half later, walked into a ballet studio in corduroy and a button-up, no ballet shoes; first ballet teacher was Eric Skinner at Reed College, surrounded by former professional ballerinas

• First internal college production was his first show; ten years later performed as an acrobat with the San Francisco Opera in 2013, six acrobats among 200 people on stage, four-hour shows with multiple costume changes and backflips

• Relationship to AI and the evolving world of work

• Mandy never asks her daughters "What do you want to be?" because jobs today may not exist in the future

• Focus on interests: plants, how things are built, areas of curiosity for future generations

• Coaching her team: Highly capable, competent, invested in tools and technology for digital signage, webinars, emails, data-driven insights, videos

• Approach AI with cautious optimism: Adopt early, embrace technology, use it to enhance work rather than replace it

• Example: Uses a bot for scheduling efficiency, brainstorming; enhances job performance by integrating AI from day one

• Advice: Approach AI with curiosity, not fear; embrace tools to be smarter and more efficient, stay ahead in careers

53:05 Where to Find Mandy

• Mandy will be speaking at Snafu Conference on March 5, discussing rejection and overcoming it.

• Author and speaking information: mandymooney.com

• LinkedIn: Mandy Mooney

• Music available under her real name, Mandy Mooney, on streaming platforms.

Welcome back to Snafu with Robin P. Zander.

In this episode, I'm doing something a little different: I step into the guest seat for a conversation with one of my good friends, Andrew Bartlow, recorded for the People Leader Accelerator podcast alongside Jessica Yuen.

We dive into storytelling, identity, and leadership — exploring how personal experiences shape professional influence. The conversation begins with a reflection on family and culture, from the Moroccan textiles behind me, made by my mother, to the influence of my father's environmental consulting work. These threads of personal history frame my lifelong fascination with storytelling, persuasion, and coalition-building.

Andrew and Jessica guide the discussion through how storytelling intersects with professional growth. We cover how early experiences — like watching Lawrence of Arabia at a birthday sleepover — sparked curiosity about adventure, influence, and human connection, and how these interests evolved into a career focused on organizational storytelling and leadership.

We explore practical frameworks, including my four-part story model (Setup → Change → Turning → Resolution) and the power of "twists" to create momentum and memorability. The episode also touches on authentic messaging, the role of vulnerability in leadership, and why practicing storytelling in everyday life—outside high-stakes moments—builds confidence and executive presence over time.

Listeners will hear lessons from a lifetime of diverse experiences: running a café in the Mission District, collaborating with BJ Fogg on behavioral change, building Zander Media, and applying storytelling to align teams and organizations. We also discuss how authenticity and personal perspective remain a competitive advantage in an age of AI-generated content.

If you're curious about how storytelling, practice, and presence intersect with leadership, persuasion, and influence, this episode is for you. And for more insights on human connection, organizational alignment, and the future of work, check out Snafu, my weekly newsletter on sales, persuasion, and storytelling here, and Responsive Conference, where we explore leadership, work, and organizational design here.

Start (0:00) Storytelling & Identity

• Robin introduces Moroccan textiles behind him

• Made by his mother, longtime practicing artist

• Connects to Moroccan fiancée → double meaning of personal and cultural

• Reflection on family influence

• Father: environmental consulting firm

• Mother: artist

• Robin sees himself between their careers

• Early Fascination with Storytelling

• Childhood obsession with Morocco and Lawrence of Arabia

• Watched 4-hour movie at age 6–7

• Fascinated by adventure, camels, storytelling, persuasion

• Early exposure shaped appreciation for coalition-building and influence

• Identity & Names

• Jess shares preference for "Jess" → casual familiarity

• Robin shares professional identity as "Xander"

• Highlights fluidity between personal and professional selves

• Childhood Experiences & Social Context

• Watching Lawrence of Arabia at birthday sleepover

• Friends uninterested → early social friction

• Andrew parallels with daughters and screen preferences

• Childhood experiences influence perception and engagement

• Professional Background & Storytelling Application

• Robin's long involvement with PeopleTech and People Leader Accelerator

• Created PLA website, branding, documented events

• Mixed pursuits: dance, media, café entrepreneurship

• Demonstrates applying skills across domains

• Collaboration with BJ Fogg → behavioral change expertise

Storytelling as Connection and Alignment

• Robin: Storytelling pulls from personal domains and makes it relevant to others

• Purpose: foster connection → move together in same direction

• Executive relevance: coalition building, generating momentum, making the case for alignment

• Andrew: HR focus on connection, relationships, alignment, clarity

• Helps organizations move faster, "grease the wheels" for collaboration

• Robin's Credibility and Experience in Storytelling

• Key principle: practice storytelling more than listening

• Full-time entrepreneur for 15 years

• First business at age 5: selling pumpkins

• Organized neighborhood kids in scarecrow costumes to help sell

• Earned $500 → early lessons in coalition building and persuasion

• Gymnastics and acrobatics: love of movement → performance, discipline

• Café entrepreneurship: Robin's Cafe in Mission District, SF

• Started with 3 weeks' notice to feed conference attendees

• Housed within a dance studio → intersection of dance and behavioral change

• First experience managing full-time employees

• Learned the importance of storytelling for community building and growth

• Realized post-sale missed opportunity: storytelling could have amplified success

• Transition to Professional Storytelling (Zander Media)

• Lessons from cafe → focus on storytelling, messaging, content creation

• Founded Zander Media (2018)

• Distributed small team, specializes in narrative strategy and video production

• Works with venture-backed companies and HR teams to tell stories internally and externally

• Provides reps and depth in organizational storytelling

• Why Storytelling Matters for Organizations

• Connects people, fosters alignment

• Enables faster movement toward shared goals

• Storytelling as a "powerful form of connection"

• What Makes a Good Story

• Robin: frameworks exist, but ultimately humans want:

• Education, entertainment, attention

• Sustained attention (avoid drift to TikTok, distractions)

• Framework examples:

• Hero's Journey (Joseph Campbell) → 17 steps

• Dan Harmon's 8-part structure → simplified version of Hero's Journey

• Robin's preferred model: 4-part story structure (details/examples forthcoming)

The Power of the Twist, and Organizational Storytelling

• Robin's Four-Part Story Model

• Core idea: stories work best when they follow a simple arc

• Setup → Change → Turning (twist/reveal) → Resolution

• Goal: not rigid frameworks, but momentum, surprise, payoff

• The "Turning" (Twist) as the Sticky Moment

• Pixar example via Steve Jobs and the iPod Nano

• Setup: Apple's dominance, market context, long build-up

• Choice point:

• Option A: just reveal the product

• Option B (chosen): pause + curiosity

• Turning: the "tiny jeans pocket" question

• Reveal: iPod Nano pulled from the pocket

• Effect: entertainment, disruption, memorability

• Key insight:

• The twist creates pause, delight, and attention

• This moment often determines whether a story is remembered

• Why Flat Stories Fail

• Example (uninspiring):

• "I ran a cafe → wanted more marketing → now I run Xander Media"

• Improved arc with turning:

• Ran a cafe → wanted to do more marketing → sold it on Craigslist → built Xander Media

• Lesson:

• A reveal or risk creates narrative energy

• The Four Parts in Practice

• Setup

• The world as it is (Bilbo in the Shire)

• Change

• Something disrupts the norm (Gandalf arrives)

• Turning

• Twist, reveal, or surprise (the One Ring)

• Resolution

• Payoff and return (Bilbo back to the Shire)

• How to Use This as a Leader

• Don't force stories into frameworks

• Look at stories you already tell

• Identify where a disruption, surprise, or reveal could live

• Coalition-building lens

• Stories should move people into shared momentum

• Excitement → flow → aligned action

• Storytelling Mediums for HR & Organizations

• Employer brand ≠ separate from company brand

• Should be co-owned by HR and marketing

• Brand clarity attracts the right people, repels the wrong ones

• Strong brands are defined by:

• Who they are

• Who they are not

• Who they're for and not for

• HR vs Marketing: The Nuance

• Collaboration works only if:

• HR leads on audience and truth

• Marketing supports execution, not control

• Risk:

• Marketing optimizes for customers, not employees

• HR understands attraction, retention, culture fit

• Storytelling at the Individual Level

• No one is "naturally" good or bad at storytelling

• It's reps, not talent

• Practical advice:

• Know your ~15 core stories (career, company, turning points)

• Practice pauses like a comedian

• Notice when people lean in

• Opinionated Messaging = Effective Messaging

• Internal storytelling should:

• Be clear and opinionated

• Repel as much as it attracts

• Avoid:

• Corporate vanilla

• Saying a lot without saying anything

• Truth + Aspirational Truth

• Marketing and storytelling are a mix of:

• What is actually true

• What the organization is becoming

• Being "30% more honest" builds trust

• Including flaws and tradeoffs

• Example: budget brands, Southwest, Apple's office-first culture

• Why This Works

• Opinions create personality

• Personality creates stickiness

• Stickiness creates memory, alignment, and momentum

Authenticity as the last real advantage

• We're flooded with AI-generated content (video, writing, everything)

• Humans are extremely good at sensing what feels fake

• Inauthenticity is easier to spot than ever

• One of the few remaining advantages:

• Be true to the real story of the person or organization

• Not polished truth — actual truth

• What makes content feel "AI-ish"

• AI can generate volume fast

• Books, posts, stories in minutes

• What it can't replicate:

• Personal specificity

• Why a story matters to you

• What an experience felt like from the inside

• Lived moments

• Running a café

• Growing into leadership

• What lasts:

• Personal story

• lesson learned

• relevance to this reader

• relevance to this relationship

• What content will win long-term

• Vulnerability

• Not oversharing, but real experience

• Personal perspective

• Why this matters to me

• Relevance

• Why it should matter to you

• Outcome

• Entertainment

• Insight

• Shared direction

• The risk of vulnerability (it can backfire)

• Being personal doesn't guarantee buy-in

• Example: inspirational talk → employee openly disagrees

• Emotional deflation

• Self-doubt

• Early leadership lesson:

• You can do your best

• People will still push back

• Leadership at higher levels gets harder, not easier

• Bigger teams → higher stakes

• Better pay

• Benefits

• Real expectations

• First "real" leadership pain points:

• Bad hires

• Mismatched expectations

• Disgruntled exits

• Realization:

• Conflict isn't failure

• It's a sign you've leveled up

• "Mountains beyond mountains"

• Every new level comes with new challenges

• Entrepreneurship

• Executive leadership

• Organizational scale

• Reframe setbacks:

• Not proof you're failing

• Proof you're progressing

• Authenticity at the executive table

• Especially hard for HR leaders

• Often younger

• Often earlier in career

• Often underrepresented

• Anxiety is normal

• The table doesn't feel welcoming

• Strategy:

• Name it

• "This is new for me"

• "I'm still finding my voice"

• Own it

• Ask for feedback

• Speak anyway

• Authenticity ≠ no consequences

• Being honest can carry risk

• Not every organization wants change

• Hard truth:

• You can't change people who don't want to change

• Sometimes the right move is leaving

• Guiding advice:

• Find people who already want what you offer

• Help them move faster

• Vulnerability as a competitive advantage

• Almost any perceived weakness can be reframed

• New

• Nervous

• Different

• When named clearly:

• It builds trust

• It creates permission

• It signals confidence

• Getting better at storytelling (practical)

• It's not talent — it's reps

• Shyness → confidence through practice

• Start small

• Don't test stories when stakes are highest

• Practice specifics

• Your core stories

• Your pitch

• Energy matters

• Enthusiasm is underrated

• Tempo matters

• Pauses

• Slowing down

• Letting moments land

• Executive presence is built

• Incrementally

• Intentionally

Practice, Progress, and Learning That Actually Sticks

• Measure growth against yourself, not "the best"

• The real comparison isn't to others

• It's who you were yesterday

• MrBeast idea:

• If you're not a little uncomfortable looking at your past work

• You're probably not improving fast enough

• Important distinction:

• Discomfort ≠ shame

• Shame isn't a useful motivator

• Progress shows up in hindsight

• Looking back at past work

• "I'd write that differently now"

• Not embarrassment — evidence of growth

• Example:

• Weekly newsletter

• Over time, clearer thinking

• Better writing

• Stronger perspective

• Executive presence is a practice, not a trait

• Storytelling

• Selling

• Persuasion

• Presence

• Core question:

• Are you deliberately practicing?

• Or just repeating the same behaviors?

• Practice doesn't have to happen at work

• Low-stakes environments count

• Family

• Friends

• Everyday conversations

• Example:

• Practicing a new language with a dog

• Safe

• Repetitive

• No pressure

• Life skills = leadership skills

• One of the hardest lessons:

• Stop trying to get people to do what they don't want to do

• Daily practice ground:

• Family dynamics

• Respecting boundaries

• Accepting reality

• These skills transfer directly to work

• Influence

• Communication

• Leadership

• Why practice outside of high-stakes moments

• When pressure is high

• You default to habits

• Practicing in everyday life:

• Builds muscle memory

• Makes high-stakes moments feel familiar

• How to learn (without overengineering it)

• Follow curiosity

• Pick a thread

• A name

• A book

• An idea

• Pull on it

• See where it leads

• Let it branch

• Learning isn't linear

• It's exploratory

• Learning through unexpected sources

• Example:

• Reading a biography

• Leads to understanding an era

• Context creates insight

• The subject matters less than:

• Genuine interest

• Sustained attention

• Career acceleration (simple, not flashy)

• Always keep learning

• Find what pulls you in

• Go deeper

• Press the gas

Where to find Robin

• Ongoing work lives in:

• Snafu (weekly newsletter on sales, persuasion, and storytelling)

• https://joinsnafu.com

• Responsive Conference (future of work, leadership, and org design)

• https://responsiveconference.com

In this episode, I'm joined by Virginie Raphael — investor, entrepreneur, and philosopher of work — for a wide-ranging conversation about incentives, technology, and how we build systems that scale without losing their humanity.

We talk about her background growing up around her family's flower business, and how those early experiences shaped the way she thinks about labor, value, and operating in the real economy. That foundation carries through to her work as an investor, where she brings an operator's lens to evaluating businesses and ideas.

We explore how incentives quietly shape outcomes across industries, especially in healthcare. Virginie shares why telehealth was a meaningful shift and what needs to change to move beyond one-to-one, supply-constrained models of care.

We also dig into AI, venture capital, and the mistakes founders commonly make today — from hiring sales teams too early to raising too much money too fast. Virginie offers candid advice on pitching investors, why thoughtful cold outreach still works, and how doing real research signals respect and fit.

The conversation closes with a contrarian take on selling: why it's not a numbers game, how focus and pre-qualification drive better outcomes, and why knowing who not to target is just as valuable as finding the right people.

If you're thinking about the future of work, building with intention, or navigating entrepreneurship in an AI-accelerated world, this episode is for you. And for more conversations like this, join us at Snafu Conference 2026 on March 5th, where we'll keep exploring incentives, human skills, and what it really takes to build things that last.

Start (0:00) Reflections on Work, Geography, and AI Adoption

• Virginie shares what she's noticing as trends in work and tech adoption:

• Geographic focus: she's excited to explore AI adoption outside traditional tech hubs.

• Examples: Atlanta, Nashville, Durham, Utah, Colorado, Georgia, North Carolina, parts of the Midwest.

• Rationale: businesses in these regions may adopt AI faster due to budgets, urgency, and impatience for tech that doesn't perform.

• "There are big corporates, there are middle and small businesses in those geos that have budget that will need the tech… and/or have less patience, I should say, for over-hub technologies that don't work."

• She notes that transitions to transformational technology never happen overnight, which creates opportunities:

• "We always underestimate how much time a transition to making anything that's so transformational… truly ubiquitous… just tends to think that it will happen overnight and it never does."

• Robin adds context from her own experience with Robin's Cafe and San Francisco's Mission District:

• Observed cultural and business momentum tied to geography

• Mentions Hollywood decline and rise of alternative media hubs (Atlanta, Morocco, New Jersey)

• Virginie reflects on COVID's impact on workforce behaviors:

• Opened a "window" to new modes of work and accelerated change:

• "There were many preexisting trends… but I do think that COVID gave a bit of a window into what was possible."

• Emphasis on structural change: workforce shifts require multi-year perspective and infrastructure, not just trends.

Investor, Mission, and Capital Philosophy

• Virginie clarifies she is an investor, not a venture capitalist, resisting labels and prestige metrics.

• "I don't call myself a venture capitalist… I just say investor."

• Focuses on outcomes over categories, investing in solutions that advance the world she wants to see rather than chasing trendy tech sectors.

• "The outcome we want to see is everyone having the mode of work that suits them best throughout their lives."

• Portfolio themes:

• Access: helping people discover jobs they wouldn't otherwise know about.

• Retention / support: preventing workforce dropouts, providing appropriate healthcare, childcare, and caregiving support.

• "Anyone anywhere building towards that vision is investible by us."

• Critiques traditional venture capital practices:

• Raising VC money is not inherently a sign of success.

• "Raising from a VC is just not a sign of success. It's a milestone, not the goal."

• Concerned about concentration of capital into a few funds, leaving many founders unsupported.

• "There's a sense… that the work we do commands a lot less power in the world, a lot less effectiveness than holding the capital to hire that labor."

• Emphasizes structural, mission-driven investing over chasing categories:

• Invests in companies that prevent workforce dropouts, expand opportunity, and create equitable access to meaningful work.

• Portfolio strategy is diversified, focusing on infrastructure and long-term impact rather than quick wins.

• "We've tracked over time what type of founders and what type of solutions we attract and it's exactly the type of deal that we want to see."

• Reflects on COVID and societal trends as a lens for her investment thesis:

• "COVID gave a bit of a window into what was possible," highlighting alternative modes of work and talent distribution that are often overlooked.

Labor, Ownership, and Durable Skills

• Virginie reframes the concept of labor, wages, and ownership:

• "The word labor in and of itself… is something we need to change."

• Interested in agency and ownership as investment opportunities, especially for small businesses transitioning to employee ownership.

• "For a very long time… there's been a shift towards knowledge work and how those people are compensated. If you go on the blue-collar side… it's about wages still and labor."

• Emphasizes proper capitalization and alignment of funds to support meaningful exits for smaller businesses, rather than chasing massive exits that drive the VC zeitgeist.

• AI fits into this discussion as part of broader investment considerations.

• Childhood experience in family flower business shaped her entrepreneurial and labor perspective:

• Selling flowers, handling cash, and interacting with customers taught "durable skills" that persisted into adulthood.

• "When I think of labor, I think of literally planting pumpkin plants… pulling espresso shots… bringing a customer behind the counter."

• Observing her father start a business from scratch instilled risk-taking and entrepreneurial spirit.

• "Seeing my dad do this when I was seven… definitely part of that."

• Skills like sales acumen, handling money, and talking to adults were early lessons that translated into professional confidence.

• Non-linear career paths and expanding exposure to opportunity:

• Concerned that students often see only a narrow range of job options:

• "Kids go out of high school, they can think of three jobs, two of which are their parents' jobs… Surely because we do a poor job exposing them to other things."

• Advocates for creating more flexible and exploratory career pathways for young people and adults alike.

• Durable skills and language shaping work:

• Introduction of the term "durable skills" reframes how competencies are understood:

• "I use it all the time now… as a proof point for why we need to change language."

• Highlights the stigma and limitations of words like "soft skills" or "fractional work":

• Fractional roles are high-impact and intentional, not temporary or inferior.

• "Brilliant people who wanna work on a fractional basis… they truly wanna work differently… on a portfolio of things they're particularly good at solving."

• Work in Progress uses language intentionally to shift perceptions and empower people around work.

• Cultural significance of language in understanding work and people:

• Virginie notes that language carries stigma and meaning that shapes opportunities and perception.

• References Louis Thomas's essays as inspiration for attention to the nuance and power of words:

• He'll take the word discipline and distill it into its root, tie it back into the natural world."

• Robin shares a personal anecdote about language and culture:

• "You can always use Google Translate… but also it's somebody learning DIA or trying to learn dharia, which is Moroccan Arabic… because my fiance is Moroccan."

Human-Positive AI, Process, and Apprenticeship

• Virginie emphasizes the value of process over pure efficiency, especially in investing and work:

• "It's not about the outcome often, it's about the process… there is truly an apprenticeship quality to venture and investing."

• Using AI to accelerate tasks like investment memos is possible, but the human learning and iterative discussion is critical:

• "There's some beauty in that inefficiency, that I think we ought not to lose."

• AI should augment human work rather than replace the nuanced judgment, particularly in roles requiring creativity, judgment, and relationship-building:

• "No individual should be in a job that's either unsafe or totally boring or a hundred percent automatable."

• Introduces the term "human-positive AI" to highlight tools that enhance human potential rather than simply automate tasks:

• "How do we use it to truly augment the work that we do and augment the people?"

• Project selection and learning as a metric of value:

• Virginie evaluates opportunities not just on outcome, but what she will learn and who she becomes by doing the work:

• "If this project were to fail, what would I still learn? What would I still get out of it?"

• Cites examples like running a one-day SNAFU conference to engage people in human-centered selling principles:

• "Who do I become as a result of doing that is always been much more important to me than the concrete outcomes of this thing going well."

AI Bubble, Transition, and Opportunity

• Discusses the current AI landscape and the comparison to past tech bubbles:

• "I think we're in an AI bubble… 1999 was a tech bubble and Amazon grew out of it."

• Differentiates between speculative hype and foundational technological transformation:

• "It is fundamental. It is foundational. It is transformative. There's no question about that."

• Highlights the lag between technological introduction and widespread adoption:

• "There's always a pendulum swing… it takes time for massively transformative technology to fully integrate."

• AI as an enabler, not a replacement:

• Transition periods create opportunity for investment and human-positive augmentation.

• Examples from healthcare illustrate AI's potential when applied correctly:

• "We need other people to care for other people. Should we leverage AI so the doctor doesn't have to face away from the patient taking notes? Yes, ambient scribing is wonderful."

• Emphasizes building AI around real human use cases and avoiding over-automation:

• "What are the true use cases for it that make a ton of sense versus the ones we need to stay away from?"

• History and parallels with autonomous vehicles illustrate the delay between hype and full implementation:

• Lyft/Uber example: companies predicted autonomous vehicles as cost drivers; the transition opened up gig work:

• "I was a gig worker long before that was a term… the conversation around benefits and portability is still ongoing."

• AI will similarly require time to stabilize and integrate into workflows while creating new jobs.

Bias, Structural Challenges, and Real-World AI Experiments

• Discusses the importance of addressing systemic bias in AI and tech:

• Shares the LinkedIn "#WearThePants" experiment: women altered gender identifiers to measure algorithmic reach:

• "They changed their picture, in some cases changed their names… and got much more massive reach."

• Demonstrates that AI can perpetuate structural biases baked into systems and historical behavior:

• "It's not just about building AI that's unbiased; it's about understanding what the algorithm might learn from centuries of entrenched behavior."

• Highlights the ongoing challenge of designing AI to avoid reinforcing existing inequities:

• "Now you understand the deeply structural ingrained issues we need to solve to not continue to compound what is already massively problematic."

Parenting, Durable Skills, and Resilience

• Focus on instilling adaptability and problem-solving in children:

• "I refuse to problem solve for them. If they forget their homework, they figure it out, they email the teacher, they apologize the next day. I don't care. I don't help them."

• Emphasizes allowing children to navigate consequences themselves to build independence:

• "If he forgets his flute, he forgets his flute. I am not making the extra trip to school to bring him his flute."

• Everyday activities are opportunities to cultivate soft skills and confidence:

• "I let them order themselves at the restaurant… they need to look the waiter in the eye and order themselves… you need to speak more clearly or speak loudly."

• Cultural context and exposure shape learning:

• Practices like family meals without devices help children appreciate attention, respect, and communication:

• "No iPad or iPhone on our table… we sit properly, enjoy a meal together, and talk about things."

• Travel and cultural exposure are part of teaching adaptability and perspective:

• "We spent some time in France over the summer… the mindset they get from that is that meals matter, and people operate differently."

• Respecting individuality while fostering independence:

• "They are their own people and you need to respect that and step away… give them the ability to figure out who they are and what they like to do."

• Parenting as a balance of guidance and autonomy:

• "Feel like that was a handbook that you just offered for parenting or for management? Either one. Nobody prepares you for that… part of figuring out."

Future of Work and Technology Horizons

• Timeframes for predicting trends:

• Focus on a 5-year horizon as a middle ground between short-term unpredictability and long-term uncertainty:

• "Five years feels like this middle zone that I'm kind of guessing in the haze, but I can kind of see some odd shapes."

• Short-term (6–18 months) is more precise; long-term (10–15 years) is harder to anticipate:

• "I'm a breezy investor. Six months at a time max… deal making between two people still matters in 18 months."

• Identifying emerging technologies with latent potential:

• Invests in technologies that are ready for massive impact but haven't yet had a "moment":

• "I like to look at technologies that have yet to have a moment… the combo of VR and AI is prime."

• Example: Skill Maker, a VR+AI training platform for auto technicians, addressing both a labor shortage and outdated certification processes:

• "We are short 650,000 auto technicians… if you can train a technician closer to a month or two versus two years, I promise you the auto shops are all over you."

• Focuses on alignment of incentives, business model innovation, and meaningful outcomes:

• "You train people faster, even expert technicians can benefit… earn more money… right, not as meaningful to them and not as profitable otherwise."

• Principles guiding technology and investment choices:

• Solving enduring problems rather than temporary fads:

• "What is a problem that is still not going to go away within the next 10–15 years?"

• Ensuring impact at scale while creating economic and personal value for participants:

• "Can make a huge difference in the lives of 650,000 people who would then have good paying jobs."

Scaling, Incentives, and Opportunity

• Re-examining traditional practices and identifying opportunities for change:

• "If you've done a very specific thing the exact same way, at some point, that's prime to change."

• Telehealth is an example: while helpful for remote access, it hasn't fundamentally created capacity:

• "You're still in that one-to-one patient's relationship and an hour of your time with a provider is still an hour at a time."

• Next version of telehealth should aim to scale care beyond individual constraints:

• "Where do we take telehealth next… what is the next version of that that enables you to truly scale and change?"

• Incentives shape outcomes:

• "Thinking through that and all the incentives… if I were to change the incentives, then people would behave differently? The answer very often is yes, indeed."

• Paraphrasing Charlie Munger:

• "Look for the incentives and I can tell you the outcome."

Founders, Pitching, and Common Mistakes

• Pet peeves in founder pitches:

• Lack of research and generic outreach is a major turn-off:

• "I can really quickly tell if you have indeed spent a fraction of a minute on my site… dear sir, automatic junk. I won't even read the thing."

• Well-crafted, thoughtful cold inbound pitches get attention:

• "Take some time. A well crafted cold inbound will get my attention… you don't need to figure out an intro."

• Big mistakes entrepreneurs make:

• Hiring too early, especially in sales:

• "Until you have a playbook, like don't hire a sales team… if you don't have about a million in revenue, you're probably not ready."

• Raising too much capital too quickly:

• "You get into that, you're just gonna spend a lot more time fundraising than you are building a company."

• Comparing oneself to others:

• "You don't know if it's true… there's always a backstory… that overnight success was 15 years in the making."

Sales Strategy and Non-Sales Selling

• Approach is contrarian: focus on conversion, not volume:

• "It is not a numbers game. I think it's a conversion game… I would much rather spend more time with a narrower set of targets and drive better conversion."

• Understanding fit is key:

• "You gotta find your people… and just finding who is not or should not be on your list is equally valuable."

• Recognizes that each fund and business is unique, so a tailored approach is essential:

• "The pitch is better when I'm talking to the quote unquote right people in the right place about the right things."

Where to Find Virginie and Her Work

• Resources for listeners:

• Full Circle Fund: fullcirclefund.io

• Work in Progress: workinprogress.io

• LinkedIn: Virginie Raphael

Where to Access Snafu

• Go to joinsnafu.com and sign up for free.

Welcome back to Snafu with Robin Zander.

In this episode, I'm joined by Jeff Jaworsky, who shares his journey from a global role at Google to running his own business while prioritizing time with his children.

We talk about the pivotal life and career decisions that shaped this transition, focusing on the importance of setting boundaries—both personally and professionally. Jeff shares insights on leaving a structured corporate world for entrepreneurship and the lessons learned along the way.

We also explore the evolving landscape of sales and entrepreneurship, highlighting how integrating human connection and coaching skills is more important than ever in a tech-driven world. The conversation touches on the role of AI and technology, emphasizing how they can support—but not replace—essential human relationships.

Jeff offers practical advice for coaches and salespeople on leveraging their natural skills and hints at a potential future book exploring the intersection of leadership, coaching, and sales.

If you're curious about what's next for thoughtful leadership, entrepreneurship, and balancing work with life, this episode is for you. And for more conversations like this, get your tickets for Snafu Conference 2026 on March 5th here, where we'll continue exploring human connection, business, and the evolving role of AI.

Start (0:00) Early life and first real boundary

• Jeff grew up up in a structured, linear environment

• Decisions largely made for you

• Clear expectations, predictable paths

• Post–high school as the first inflection point

• College chosen because it's "what you're supposed to do"

• Dream: ESPN sports anchor (explicit role model: Stuart Scott)

• Reality check through research

• Job placement rate: ~3%

• First moment of asking:

• Is this the best use of my time?

• Is this fair to the people investing in me (parents)?

• Boundary lesson #1

• Letting go of a dream doesn't mean failure

• Boundaries can be about honesty, not limitation

• Choosing logic over fantasy can unlock unexpected paths

• Dropping out of college → accidental entry into sales

• Working frontline sales at Best Buy while in school

• Selling computers, service plans, handling customers daily

• Decision to leave college opens capacity

• Manager notices and offers leadership opportunity

• Takes on home office department

• Largest sales category in the store

• Youngest supervisor in the company (globally) at 19

• Early leadership challenges

• Managing people much older

• Navigating credibility, age bias, exclusion

• Learning influence without authority

• Boundary insight

• Temporary decisions can become formative

• Saying "yes" doesn't mean you're locked in forever

• Second boundary: success without sustainability

• Rapid growth at Best Buy

• Promotions

• Increasing responsibility

• Observing manager life up close

• 60-hour weeks

• No real breaks

• Lunch from vending machines

• Internal checkpoint

• Is this the life I want long-term?

• Distinguishing:

• Liking the work

• Disliking the cost

• Boundary lesson #2

• You can love a craft and still reject the lifestyle around it

• Boundaries protect the future version of you

• Returning to school with intention

• Decision to go back to college

• This time with clarity

• Sales and marketing degree by design, not default

• Accelerated path

• Graduates in three years

• Clear goal: catch up, not start over

• Internship at J. Walter Thompson

• Entry into agency world

• Launch of long-term sales and marketing career

• Pattern recognition: how boundaries actually work

• Ongoing self-check at every stage

• Have I learned what I came here to learn?

• Am I still growing?

• Is this experience still stretching me?

• Boundaries as timing, not rejection

• Experiences "run their course"

• Leaving doesn't invalidate what came before

• Non-linear growth

• Sometimes stepping down is strategic

• Demotion → education

• Senior role → frontline role (later at Google)

• Downward moves that enable a bigger climb later

• Shared reflection with Robin

• Sales as a foundational skill

• Comparable to:

• Surfing (handling forces bigger than you)

• Early exposure to asking, pitching, rejection

• Best Buy reframed

• Customer service under pressure

• Handling frustrated, misinformed, emotional people

• Humility + persuasion + resilience

• Parallel experiences

• Robin selling a restaurant after learning everything she could

• Knowing the next step (expansion) and choosing not to take it

• Walking away without knowing what's next

• Core philosophy: learning vs. maintaining

• "If I'm not learning, I'm dying"

• Builder mindset, not maintainer

• Growth as a non-negotiable

• Career decisions guided by curiosity, not status

• Titles are temporary

• Skills compound

• Ladders vs. experience stacks

• Rejecting the myth of linear progression

• Valuing breadth, depth, and contrast

• The bridge metaphor

• Advice for people stuck between "not this" and "not sure what next"

• Don't leap blindly

• Build a bridge

• Bridge components

• Low-risk experiments

• Skill development

• Small tests in parallel with current work

• Benefits

• Reduces panic

• Increases clarity

• Turns uncertainty into movement

Framing the modern career question

• Referencing the "jungle gym, not a ladder" idea

• Careers as lateral, diagonal, looping — not linear

• Growth through range, not just depth

• Connecting to Range and creative longevity

• Diverse experiences as a competitive advantage

• Late bloomers as evidence that exploration compounds

• Naming the real fear beneath the metaphor

• What if exploration turns into repeated failure?

• What if the next five moves don't work?

• Risk of confusing experimentation with instability

• Adding today's pressure cooker

• Economic uncertainty

• AI and automation reshaping work faster than previous generations experienced

• The tension between adaptability and survival

• The core dilemma

• How do you pursue a non-linear path without tumbling back to zero?

• How do you "build the bridge" instead of jumping blindly?

• How do you keep earning while evolving?

• The two-year rule

• Treating commitments like a contract with yourself

• Two years as a meaningful unit of time

• Long enough to:

• Learn deeply

• Be challenged

• Experience failure and recovery

• Short enough to avoid stagnation

• Boundaries around optional exits

• Emergency ripcord exists

• But default posture is commitment, not escape

• Psychological benefit

• Reduces panic during hard moments

• Prevents constant second-guessing

• Encourages depth over novelty chasing

• The 18-month check-in

• Using the final stretch strategically

• Asking:

• Am I still learning?

• Am I still challenged?

• Does this align with my principles?

• Shifting from execution to reflection

• Early exploration of "what's next"

• Identifying gaps:

• Skills to acquire

• Experiences to test

• Regaining control

• External forces aren't always controllable

• Internal planning always is

• Why most people get stuck

• Planning too late

• Waiting until:

• Layoffs

• Burnout

• Forced transitions

• Trying to design the future in crisis

• Limited creativity

• Fear-based decisions

• Contrast with proactive planning

• Calm thinking

• Optionality

• Leverage

• Extending the contract

• Recognizing unfinished business

• Loving the work

• Still growing

• Still contributing meaningfully

• One-year extensions as intentional choices

• Not inertia

• Not fear

• Conscious recommitment

• A long career, one organization at a time

• Example: nearly 13 years at Google

• Six different roles

• Multiple reinventions inside one company

• Pattern over prestige

• Frontline sales

• Sales leadership

• Enablement

• Roles as chapters, not identities

• Staying while growing

• Leaving only when growth plateaus

• Experience stacking over ladder climbing

• Rejecting linear advancement

• Titles matter less than skills

• Accumulating perspective

• Execution

• Leadership

• Systems

• Transferable insight

• What works with customers

• What works internally

• What scales

• Sales enablement as an example of bridge-building

• Transition motivated by impact

• Desire to help at scale

• Supporting many sellers, not just personal results

• A natural evolution, not a pivot

• Built on prior sales experience

• Expanded influence

• Bridge logic in action

• Skills reused

• Scope widened

• Risk managed

• Zooming out: sales, stigma, and parenting

• Introducing the next lens: children

• Three boys: 13, 10, 7

• Confronting sales stereotypes

• Slimy

• Manipulative

• Self-serving

• Tension between reputation and reality

• Loving sales

• Building a career around it

• Teaching it without replicating the worst versions

• Redefining sales as a helping profession

• Sales as service

• Primary orientation: benefit to the other person

• Compensation as a byproduct, not the driver

• Ethical center

• Believe in what you're recommending

• Stand behind its value

• Sleep well regardless of outcome

• Losses reframed

• Most deals don't close

• Failure as feedback

• Integrity as the constant

• Selling to kids (and being sold by them)

• Acknowledging reality

• Everyone sells, constantly

• Titles don't matter

• Teaching ethos, not tactics

• How you persuade matters more than whether you win

• Kindness

• Thoughtfulness

• Awareness of the other side

• Everyday negotiations

• Bedtime extensions

• Appeals to age, fairness, peer behavior

• Sales wins without good reasoning

• Learning opportunity

• Success ≠ good process

• Boundaries still matter

• Why sales gets a bad reputation

• Root cause: selfishness

• Focus on "what I get"

• Language centered on personal gain

• Misaligned value exchange

• Overselling

• Underdelivering

• The alternative

• Lead with value for the other side

• Hold mutual benefit in the background

• Make the exchange explicit and fair

• Boundaries as protection for both sides

• Clear scope

• What's included

• What's not

• Saying no as a service

• Preventing resentment

• Preserving trust

• Entrepreneurial lens

• Boundaries become essential

• Scope creep erodes value

• Clarity sustains long-term relationships

Value exchange, scope, and boundaries

• Every request starts with discernment, not enthusiasm

• What value am I actually providing?

• What problem am I solving?

• How much time, energy, and attention will this really take?

• The goal isn't just a "yes"

• Both sides need to feel good about:

• What's being given

• What's being received

• What's being expected

• What's realistically deliverable

• Sales as a two-sided coin

• Mutual benefit matters

• Overselling creates future resentment

• Promising "the moon and the stars" is how trust breaks later

• Boundaries as self-respect

• Clear limits protect delivery quality

• Good boundaries prevent repeating bad sales dynamics

• Saying less upfront often enables better outcomes long-term

• Transitioning into coaching and the SNAFU Conference

• Context for the work today

• Speaking at the inaugural SNAFU Conference

• Focused on reluctant salespeople and non-sales roles

• Why coaching became the next chapter

• Sales is everywhere, regardless of title

• Coaching emerged as a natural extension of sales leadership

• The origin story at Google

• Transition from sales leadership to enablement

• Core question: how do we help sellers have better conversations?

• Result: building Google's global sales coaching program

• Grounded in practice and feedback

• Designed to prepare for high-stakes conversations

• The hidden overlap between sales and coaching

• Coaching as an underutilized advantage

• Especially powerful for sales leaders

• Shared core skills

• Deep curiosity

• Active listening

• Presence in conversation

• Reflecting back what's heard, not what you assume

• The co-creation mindset

• Not leading someone to your solution

• Guiding toward their desired outcome

• Why this changes everything

• Coaching improves leadership effectiveness

• Coaching improves sales outcomes

• Coaching reshapes how decisions get made

• A personal inflection point: learning to listen

• Feedback that lingered

• "Jeff is often the first and last to speak in meetings"

• The realization

• Seniority amplified his voice

• Being directive wasn't the same as being effective

• The shift

• Stop being the first to speak

• Invite more voices

• Lead with curiosity, not certainty

• The result

• More evolved perspectives

• Better decisions

• Sometimes realizing he was simply wrong

• The parallel to sales

• Talking at customers limits discovery

• Pre-built pitch decks obscure real needs

• The "right widget" only emerges through listening

• What the work looks like today

• A synthesis of experiences

• Buyer

• Seller

• Sales leader

• Enablement leader

• Executive coach

• How that shows up in practice

• Executive coaching for sales and revenue leaders

• Supporting decision-making

• Developing more coach-like leadership styles

• Workshops and trainings

• Helping managers coach more effectively

• Building durable sales skills

• Advisory work

• Supporting sales and enablement organizations at scale

• The motivation behind the shift

• Returning to the core questions:

• Am I learning?

• Am I growing?

• Am I challenged?

• A pull toward broader impact

• A desire to test whether this work could scale beyond one company

• Why some practices thrive and others stall

• Observing the difference

• Similar credentials

• Similar training

• Radically different outcomes

• The uncomfortable truth

• The difference is sales

• Entrepreneurship without romance

• Businesses don't "arrive" on their own

• Clients don't magically appear

• Visibility, rejection, iteration are unavoidable

• Core requirements

• Clear brand

• Defined ICP

• Articulated value

• Credibility to support the claim

• Debunking "overnight success"

• Success is cumulative

• Built on years of unseen experience

• Agency life + Google made entrepreneurship possible

• Sales as a universal survival skill

• Especially now

• Crowded markets

• Economic uncertainty

• Increased competition

• Sales isn't manipulation

• It's how value moves through the world

• Avoiding the unpersuadable

• Find people who already want what you offer

• Make it easier for them to say yes

• For those who "don't want to sell"

• Either learn it

• Or intentionally outsource it

• But you can't pretend it doesn't exist

• The vision board and the decision to leap

• December 18, 2023

• 45th birthday

• Chosen as a forcing function

• Purpose of the date

• Accountability, not destiny

• A moment to decide: stay or go

• Milestones on the back

• Coaching certification

• Experience thresholds

• Personal readiness

• Listening to the inner signal

• The repeated message: "It's time"

• The bridge was already built

• Skills stacked

• Experience earned

• Risk understood

• Stepping forward without full certainty

• You never know what's on the other side

• You only learn once you cross and look around

Decision-making and vision boards

• Avoid forcing yourself to meet arbitrary deadlines

• Even if a date is set for accountability (e.g., a 45th birthday milestone), the real question is: When am I ready to act?

• Sometimes waiting isn't necessary; acting sooner can make sense

• Boundaries tie directly into these decisions

• They help you align personal priorities with professional moves

• Recognizing what matters most guides the "when" and "how" of major transitions

• Boundaries in the leap from corporate to entrepreneurship

• Biggest boundary: family and presence with children

• Managing a global team meant constant connectivity and messages across time zones

• Transitioning to your own business allowed more control over work hours, clients, and priorities

• The pro/con framework reinforced the choice

• Written lists can clarify trade-offs

• For this example, the deciding factor was: "They get their dad back"

• Boundaries in entrepreneurship are intertwined with opportunity

• More freedom comes with more responsibility

• You can choose your hours, clients, and areas of focus—but still must deliver results

• Preparing children for a rapidly changing world

• Skill priorities extend beyond AI and automation

• Technology literacy is essential, but kids will likely adapt faster than adults

• Focus on human skills

• Building networks

• Establishing credibility

• Navigating relationships and complex decisions

• Sales-related skills apply

• Curiosity, empathy, observation, and problem-solving help them adapt to change

• These skills are timeless, even as roles and tools evolve

• Human skills in an AI-driven world

• AI is additive, not replacement

• Leverage AI to complement work, not fear it

• Understand what AI does well and where human judgment is irreplaceable

• Coaching and other human-centered skills remain critical

• Lived experience, storytelling, and nuanced judgment cannot be fully replaced by AI

• Technology enables scale but doesn't replace complex human insight

• The SNAFU Conference embodies this principle

• Brings humans together to share experiences and learn

• Demonstrates that face-to-face interaction, stories, and mutual learning remain valuable

• Advice for coaches learning to sell

• Coaches already possess critical sales skills

• Curiosity, active listening, presence, problem identification, co-creating solutions

• These skills, when applied to sales, still fall within a helping profession

• Key approach

• Use your coaching skills to generate business ethically

• Reframe sales as an extension of support, not self-interest

• For salespeople

• Learn coaching skills to improve customer conversations

• Coaching strengthens empathy, listening, and problem-solving abilities, all core to effective selling

• Book and resource recommendations

• Non-classical sales books

• Setting the Table by Danny Meyer → emphasizes culture and service as a form of sales

• Unreasonable Hospitality by Will Guidara → creating value through care for people

• Coaching-focused books

• Self as Coach, Self as Leader by Pam McLean

• Resources from the Hudson Institute of Coaching

• Gap in sales literature

• Few resources fully integrate coaching with sales

• Potential upcoming book: The Power of Coaching and Sales

Welcome back to Snafu with Robin Zander.

In this episode, I'm joined by Melissa Painter, founder of Breakthru – a platform bringing movement, mindfulness, and behavior change into workplaces around the world.

We talk about how Melissa uses movement as a tool to improve focus, resilience, and well-being, and how her background in dance and creative movement informs her approach to human performance. We explore the science and art of helping people move more, think better, and feel more connected to their work and each other.

Melissa shares how she designs short, immersive experiences for employees, what it takes to change workplace culture, and why small, intentional shifts in movement can unlock big changes in thinking and performance.

We also dive into the intersection of creativity, neuroscience, and technology, and how thoughtful, human-centered design can make work feel more alive and meaningful.

If you're curious about how movement, mindfulness, and behavior change can transform your work and life, this episode is for you. And for more conversations like this, stay tuned for Responsive Conference 2026, where we'll be continuing the dialogue on human connection, creativity, and thriving in the modern workplace.

I'm so glad and honored to have Melissa joining us in this talk. If you're interested in her work, take a look at Breakthru – you can try it and share it with your team here: Take your first Breakthru! https://breakthru.me/

Welcome back to Snafu with Robin Zander.

In this episode, I'm joined by Kevan Lee and Shannon Deep, co-founders of Bonfire – a creative studio reimagining what it means to build brands, tell stories, and live meaningful lives.

We talk about how Bonfire began as a "Trojan horse" – a branding agency on the surface, but really a vehicle for deeper questions: What does fulfilling work look like? How do we find meaning beyond our careers? And how can business become a space for honesty, connection, and growth?

Kevan and Shannon share how their partnership formed, what it takes to build trust as co-founders, and how vulnerability and self-awareness fuel their collaboration. We explore their path from tech and theater to building Bonfire, hosting creative retreats, and helping founders tell more authentic stories.

We also dive into how AI is changing storytelling, the myth of "broetry" on LinkedIn, and why transparency is the future of marketing.

If you're curious about what's next for creativity, leadership, and meaningful work, this episode is for you. And for more conversations like this, stay tuned for Responsive Conference 2026, where we'll be continuing the dialogue on human connection, business, and the evolving role of AI.

Start (0:00) How Bonfire Started (14:25)

• Robin notes how transparent and intentional they've been building their business and community

• Says Bonfire feels like a 21st-century agency – creative, human, and not traditional

• Invites them to describe what they're building and their vision for it

• Kevan's response:

• Admits he feels imposter syndrome around being called an "entrepreneur"

• Laughs that it's technically true but still feels strange

• Describes Bonfire as partly a traditional branding agency

• They work with early-stage startups

• Help with brand strategy, positioning, messaging, and differentiation.

• But says the heart of their work is much deeper

• "We create spaces for people to explore what a fulfilling life looks like – one that includes work, but isn't defined by it."

• Their own careers inspired this – jobs that paid well but felt empty, or jobs that felt good but didn't pay the bills

• Bonfire became their way to build something more meaningful

• A space to have these conversations themselves

• And to invite others into it

• This includes community, retreats, and nontraditional formats

• Jokes that the agency side is a Trojan horse – a vehicle to fund the work they truly care about

• Shannon adds:

• They're agnostic about what Bonfire "does"

• Could be a branding agency, publishing house, even an ice cream shop

• "Money is just gas in the engine."

• The larger goal is creating spaces for people to explore their relationship to work

• Especially for those in transition, searching for meaning, or redefining success

• Robin reflects on their unusual path

• Notes most marketers who start agencies chase awards and fame

• But Shannon and Kevan built Bonfire around what they wished existed

• Recalls their past experiences

• Kevan's path from running a publication (later sold to Vox) to Buffer and then Oyster

• Shannon's shared time with him at Oyster

• Mentions their recent milestone – Bonfire's first live retreat in France

• 13 participants, including them

• Held in a rented castle

• For a two-year-old business, he calls it ambitious and impressive

• Asks: "How did it go? What did people get out of it?"

• Shannon on the retreat

• Laughs that they're still processing what it was

• They had a vibe in mind – but not a fixed structure

• One participant described it as "a wellness retreat for marketers"

• Not wrong – but also not quite right

• Attendees came from tech and non-tech backgrounds

• The focus: exploring people's most meaningful relationship to work

• Who you are when you're not at your desk

• How to bring that awareness back to real life — beyond castles and catered meals

• People came at it from different angles

• Some felt misaligned with their work

• Others were looking for something new

• Everyone was at a crossroads in their career

• Kevan on the space they built

• The retreat encouraged radical honesty

• People shared things like:

• "I have this job because I crave approval."

• "I care about money as a status symbol."

• "I hate what I do, but I don't know what else I'd be good at."

• They didn't force vulnerability, but wanted to make it safe if people chose it

• They thought deeply about values – what needed to be true for that kind of trust

• Personally, Kevan says the experience shifted his identity

• From "marketer" to something else – maybe "producer," maybe "creator"

• The retreat made him realize how many paths are possible

• "Now I just want to do more of this."

• Robin notes there are "so many threads to pull on"

• Brings up family business and partnerships

• Shares his own experience growing up in his dad's small business

• Talks about lessons from Robin's Cafe and the challenges of partnerships

• Says he's fascinated by co-founder dynamics – both powerful and tricky

• Asks how Shannon and Kevan's working relationship works

• What it was like at Oyster

• Why they decided to start Bonfire together

• And how it's evolved after the retreat

• Kevan on their beginnings

• He hired Shannon at Oyster – she was Editorial Director, he was SVP of Marketing

• Worked together for about a year and a half

• Knew early on that something clicked

• Shared values

• Similar worldview

• Trusted each other

• When Oyster ended, partnering up felt natural – "Let's figure out what's next, together."

• Robin observes their groundedness

• Says they both seem stable and mature, which likely helps the partnership

• Jokes about his own chaos running Robin's Café – late nights, leftover wine, cold quinoa

• Asks Shannon directly: "Do you still follow Kevan's lead?"

• Shannon's laughs and agrees they're both very regulated people

• But adds that it comes from learned coping mechanisms

• Says they've both developed pro-social ways to handle stress

• People-pleasing

• Overachievement

• Perfectionism

• Intellectualizing feelings instead of expressing them

• "Those are coping mechanisms too," she notes, "but at least they keep us calm when we talk."

Building Trust and Partnership (14:54–23:15)

• Shannon says both she and Kevan have done deep personal work.

• Therapy, reflection, and self-inquiry are part of their toolkit.

• That helps them handle a relationship that's both intimate and challenging.

• They know their own baggage.

• They try not to take the other person's reactions personally.

• It doesn't always work—but they trust they'll work through conflict.

• When they started Bonfire:

• They agreed the business world is unpredictable.

• So they made a pinky swear:

• Friends first, business second.

• The friendship is the real priority.

• When conflict comes up, they ask: "Is this really life or death—or are we just forgetting what matters?"

• Shannon goes back to the question and clarifies

• Says they lead in different ways.

• Each has their "zone of genius."

• They depend on each other's strengths.

• It's not leader and follower – it's mutual reliance.

• Shannon explains:

• Kevan's great at momentum:

• He moves things forward and ships projects fast.

• Shannon tends to be more perfectionist:

• Wants things to be fully formed before releasing.

• Kevan adds they talk often about "rally and rest."

• Kevan rallies, he thrives on pressure and urgency.

• Shannon rests, she values slowing down and reflection.

• Together, that creates a healthy rhythm.

• Robin notes lingering habits

• Wonders if any "hangovers" from their Oyster days remain.

• Kevan reflects

• At first, he hesitated to show weakness.

• Coming from a manager role, vulnerability felt risky.

• Shannon quickly saw through it.

• He realized openness was essential, not optional.

• Says their friendship and business both rely on honesty.

• Robin agrees and says he wouldn't discourage co-founders—it's just a big decision.

• Like choosing a spouse, it shapes your life for years.

• Notes he's never met with one of them without the other.

• "That says something," he adds.

• Their partnership clearly works—even if it takes twice the time.

Rethinking Marketing (23:19)

• Kevan's light moment:

• Asks if Robin's comment about their teamwork was feedback for them.

• Robin's observation

• Notes how in sync Shannon and Kevan are.

• Emails one, gets a reply CC'd with the other.

• Says the tempo of Bonfire feels like their collaboration itself.

• Wonders what that rhythm feels like internally.

• Kevan's response

• Says it's partly intentional, partly habit.

• They genuinely enjoy working together.

• Adds they don't chase traditional agency milestones.

• No interest in Ad Age lists or Cannes awards.

• Their goal: have fun and make meaningful work.

• Robin pivots to the state of marketing (24:04)

• Mentions the shift from Madison Avenue's glory days to today's tech-driven world.

• Refers to Mad Men and the "growth at all costs" startup era.

• Notes how AI and tech are changing how people see their role in work and life.

• Kevan's background

• Came from startups, not agencies.

• Learned through doing, not an MBA.

• Immersed in books like Hypergrowth and Traction.

• Took Reforge courses—knows the mechanics of scaling.

• Before that, worked as a journalist.

• Gained curiosity and calm under pressure, but also urgency.

• Admits startup life taught him both good and bad habits.

• Robin notes

• Neither lives the Madison Avenue life.

• Kevan's in Boise.

• Shannon's in France.

• Shannon's background

• Started in theater – behind the scenes as a dramaturg and producer.

• Learned how to shape emotion and tell stories.

• Transitioned into brand strategy in New York.

• Worked at a top agency, Siegel+Gale.

• Helped global B2B and B2C clients define mission, values, and design.

• Competed with big names like Interbrand and Pentagram.

• Later moved in-house at tech startups.

• Saw how B2B marketing often tries to "act cool" like B2C.

• Learned to translate creative ideas into language that convinces CFOs.

• Says her role often meant selling authentic storytelling to risk-averse execs.

• Admits she joined marketing out of necessity.

• "I was 27, broke in New York, and needed a parking spot for my storytelling skills."

• Robin connects the dots

• Notes how Silicon Valley's "growth" culture mirrors old ad-world burnout.

• Growth at all costs.

• Not much room for creative autonomy.

• Adds most big agencies are now owned by holding companies.

• The original Madison Avenue independence is nearly gone.

• Robin's reflection

• Mentions how AI-generated content is changing video and storytelling.

• Grateful his clients still value human connection.

• Asks how Bonfire helps brands tell authentic stories now that the old model is fading.

• Kevan's take

• Says people now care less about "moments" and more about audiences.

• It's not about one viral hit—it's about building consistency.

• Brands need to stand for something, and keep showing up.

• People want that outcome, even if they don't want the hard work behind it.

• Shannon adds

• Notes rising skepticism among audiences.

• Most content people see isn't from who they follow, it's ads and algorithms.

• Consumers are subconsciously filtering out the noise.

• Says that's why human storytelling matters more than ever.

• People crave knowing a real person is behind the message.

• AI can mimic tone but not authenticity.

• Adds it's hard to convince some clients of that.

• Authentic work isn't fast or easily measured.

• It requires belief in the process and a value system to match.

• That's tough when your client's investors only want quick returns.

• Robin agrees

• "Look at people's incentives and I'll tell you who they are."

• Shannon continues

• Wonders where their responsibility ends.

• Should they convince people of their values?

• Or just do the work and let the right clients come?

• Kevan says they've found a sweet spot with current clients.

• Mostly bootstrapped founders.

• Work with them long-term instead of one-off projects.

• Says that's the recipe that fits Bonfire's values and actually works.

The Quarter Analogy (35:36)

• Robin quotes BJ Fogg:

• "Don't try to persuade people of your worldview. Look for people who already want what you can teach, and just show them how."

• He compares arguing with people who don't align to "an acrobat arguing with gravity – gravity will win 100% of the time."

• The key: harness momentum instead of fighting resistance. Even a small, aligned audience is better than chasing everyone.

• Kevan shares Bonfire's failed experiment with outbound sales:

• They tried reaching out to recently funded AI companies.

• "It got us nowhere," he admits.

• That experience reminded him how much old startup habits – growth at all costs, scale fast – still shape thinking.

• "I thought success meant getting as big as possible, as fast as possible. That meant doing outbound, even if it felt inauthentic."

• But that mindset just added pressure.

• Realizing there were other ways to grow – slower, more intentional – was a relief.

• Now they've stopped outbound entirely.

• Focused instead on aligned clients who find them naturally.

• Robin connects it to a MrBeast quote.

• "If I'm not ashamed of the video I put out last week, I'm not growing fast enough."

• He says he doesn't love the "shame" part but relates to the evolution mindset –

• Looking back at work from six months ago and thinking, I'd do that differently now.

• Growth as a visible, measurable journey.

• Robin shifts to storytelling frameworks:

• Mentions Kevan and Shannon's analogies about storytelling and asks about "the quarter analogy."

• Kevan explains the "quarter" story:

• A professor holds up two quarters: "Sell me the one on the right."

• No one can – until someone says, "I'll dip it in Marilyn Monroe's purse."

• That coin now has emotional and cultural value.

• Marketing can be the same – alchemy that turns something ordinary into something meaningful.

• Robin builds on that:

• You can tell stories about a coin's history – "Lincoln touched it," etc.

• But Kevan's version is different: adding new meaning in the present.

• "How do you imbue something with value now that makes it matter later?"

• Shannon's take:

• It's about values and belonging.

• "Every story implicitly says: believe this."

• That belief also says: we don't believe that – defining who's in your tribe.

• Humans crave that – community, validation, connection.

• That belonging is intangible but real.

• "Try selling that to a CFO who just wants ROI. Impossible — but it's real."

• Kevan adds:

• Values are one piece – authenticity is another.

• Some brands already have a genuine story; others want to create one.

• "We get asked to dip AI companies into Marilyn Monroe's purse," he jokes.

• The real work is uncovering what's true or helping brands rediscover it.

• The challenge: telling that story consistently and believably.

• Robin mentions Shannon's storytelling framework of three parts –

• Purpose → Story frameworks → Touch points.

• Shannon breaks it down:

• Clients usually come in with half-baked "mission" or "vision" statements.

• She uses Ogilvy's "Big Ideal" model:

• Combine a cultural tension (what's happening in the world) with your brand's best self.

• Then fill in the blank:

• "We believe the world would be a better place if…"

• That single sentence surfaces a company's "why us" and "why now."

• It's dramaturgy, really — same question as in theater:

• "Why this play now?"

• "Why us?"

• Bonfire's own version (in progress):

• "We believe the world would be a better place if people and brands had more room to explore their creativity."

• Kevan adds: it's evolving, like them.

• Robin relates it back to his own story:

• After selling Robin's Café, he started Zander Media to tell human stories.

• He wanted to document real connections — "the barista-customer relationships, the neighborhood changing."

• That became his north star: storytelling as a tool for change and human connection.

• "I don't care about video," he says. "I care about storytelling, helping people become more of who they want to be."

• Kevan closes the loop:

• A good purpose statement is expansive.

• It can hold video, podcasts, even a publishing house.

• "Maybe tomorrow it's something else. That's the beauty — it allows room to grow."

Against the Broetry (49:01)

• Kevan reflects on transparency and values at Bonfire

• He and Robin came from Buffer, a company known for radical transparency — posting salaries, growth numbers, everything.

• Says that while Bonfire isn't as extreme about it, the spirit is the same.

• "It just comes naturally to invite people in."

• Their openness isn't a tactic – it's aligned with their values and mission.

• They want to create space for people to explore – new ideas, new ways of working, more fulfilling lives.

• Sharing their journey publicly felt like the obvious, authentic thing to do.

• "It wasn't even a conversation – just who we are."

• Shannon jumps in with a critique of business culture online

• Says there's so much terrible advice about "how to build a business."

• Compliments Robin for cutting through the noise – being honest through Snafu and his newsletter.

• "You're trying to be real about what selling feels like and what it says about you."

• Calls out the "rise and grind" nonsense dominating LinkedIn:

• "Wake up at 4 a.m., protein shake at 4:10, three-hour workout…"

• Robin laughs – "I'll take the three-hour workout, but I'll pass on the protein shake."

• Shannon and Kevan call it "broetry"

• The overblown, performative business storytelling on social media.

• "I went on my honeymoon and here's what I learned about B2B sales."

• Their goal with building in public is the opposite:

• To admit mistakes.

• To share pivots and moments of doubt.

• To remind people that everyone is figuring it out.

• "But the system rewards the opposite – gatekeeping, pretending, keeping up the facade."

• Shannon says she has "no patience for it."

• She traces that belief back to a story from college

• Producer Paula Wagner once told her class:

• "Here's the secret: nobody knows anything."

• That line stuck with her.

• Gave her permission to question authority.

• To show up confidently even when others pretend to know more.

• After years of watching powerful men "fail upward," she realized:

• "The emperor has no clothes."

• So she might as well take up space too.

• Transparency, for her, is a form of connection and courage –

• "When people raise their eyes from their desks and actually meet each other, that's power."

• Robin thanks Shannon for the kind words about Snafu.

• Says their work naturally attracts people who want that kind of realness.

• Then pivots to a closing question:

• "If you had one piece of advice for founders – about storytelling or business building – what would it be?"

• Kevan's advice:

• "Look beyond what's around you."

• Inspiration doesn't have to come from your industry.

• Learn from other fields, other stories, other worlds.

• It builds curiosity, empathy, and creativity.

• Robin sums it up: "Get out of your silos."

• Shannon's advice:

• "Make the thing you actually want to see."

• Too many founders copy what's trendy or "smart."

• Ask instead: What would I genuinely love to consume?

• Remember your audience is human, like you.

• And remember, building a business is a privilege.

• You get to create a small world that reflects your values.

• You get to hire people, pay them, shape a culture.

• "That's so cool, and it should make you feel powerful."

• With that power comes responsibility.

• "Everyone says it's about making the most money. But what if the goal was to make the coolest world possible, for as many people as possible?"

Where to find Kevan and Shannon (57:16)

• Points listeners to aroundthebonfire.com/experiences.

• That's where they host their retreats.

• Next one is April 2026.

• "We'd love to see you there."

Companies/Organizations

• Bonfire

• Buffer

• Oyster

• Vox

• Zander Media

• Siegel+Gale

• Interbrand

• Pentagram

• Reforge

• Robin's Café

Books / Frameworks / Theories

• Traction

• BJ Fogg's behavioral model

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• David Ogilvy

Newsletters

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Welcome back to Snafu with Robin Zander.

In this episode, I'm joined by Miki Johnson – coach, facilitator, and co-founder of Job Portraits, a creative studio that helped companies tell honest stories about their work and culture.

Today, Miki leads Leading By Example, where she supports leaders and teams through moments of change – whether that's a career shift, new parenthood, or redefining purpose. We talk about how to navigate transition with awareness, why enjoying change takes practice, and what it means to lead with authenticity in uncertain times.

Miki shares lessons from a decade of coaching and storytelling – from building human-centered workplaces to bringing more body and emotion into leadership. We also explore creativity in the age of AI, and how technology can either deepen or disconnect us from what makes us human.

And if you're interested in these kinds of conversations, we'll be diving even deeper into the intersection of leadership, creativity, and AI at Responsive Conference 2026.

If you're interested, get your tickets here! https://www.responsiveconference.com/

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00:00 Start 01:20 Miki's Background and Reservations about AI

• Miki hasn't used AI and has "very serious reservations."

• She's not anti-AI – just cautious and curious.

• Her mindset is about "holding paradox", believing two opposing things can both be true.

• Her background shapes that approach.

• She started as a journalist, later ran her own businesses, and now works as a leadership coach.

• Early in her career, she watched digital technology upend media and photography – industries "blown apart" by change.

• When she joined a 2008 startup building editable websites for photographers, it was exciting but also unsettling.

• She saw innovation create progress and loss at the same time.

• Now in her 40s with two sons, her focus has shifted.

• She worries less about the tools and more about what they do to people's attention, empathy, and connection – and even democracy.

• Her concern is how to raise kids and stay human in a distracted world.

• Robin shares her concerns but takes a different approach.

• He notes that change now happens "day to day," not decade to decade.

• He looks at technology through systems, questioning whether pre-internet institutions can survive.

• "Maybe the Constitution was revolutionary," he says, "but it's out of date for the world we live in."

• He calls himself a "relentless optimist," believing in democracy and adaptability, but aware both could fail without reform.

• Both worry deeply about what technology is doing to kids.

• Robin cites The Anxious Generation by Jonathan Haidt and says, "I don't believe social media is good for children."

• He and his fiancée plan to limit their kids' screen time, just as Miki already does.

• They see it as a responsibility: raising grounded kids in a digital world.

• Robin sees AI as even more transformative – and risky – than anything before.

• "If social media is bigger than the printing press," he says, "AI is bigger than the wheel."

• He's amazed by its potential but uneasy about who controls it.

• He doubts people like Sam Altman act in the public's best interest.

• His concern isn't about rejecting AI but about questioning who holds power over it.

• Their difference lies in how they handle uncertainty.

• Miki's instinct is restraint and reflection – question first, act later, protect empathy and connection.

• Robin's instinct is engagement with vigilance – learn, adapt, and reform systems rather than retreat.

• Miki focuses on the human and emotional.

• Robin focuses on the structural and systemic.

• Both agree technology is moving faster than people can process or regulate.

• Miki uses curiosity to slow down and stay human.

• Robin uses curiosity to move forward and adapt.

• Together, they represent two sides of the same challenge: protecting what's most human while building what's next.

10:05 Navigating the Tech Landscape

• Miki starts by describing how her perspective has been shaped by living in two very different worlds.

• She spent over a decade in the Bay Area, surrounded by tech and startups.

• She later moved back to her small hometown of Athens, Ohio—a progressive college town surrounded by more rural areas.

• She calls it "a very small Austin", a blue dot in a red state.

• She loves it there and feels lucky to have returned home.

• Robin interrupts briefly to highlight her background.

• He reminds listeners that Miki and her husband, Jackson, co-founded an employer branding agency called Job Portraits in 2014, the same year they got married.

• Over eight years, they grew it to around 15 full-time employees and 20 steady contractors.

• They worked with major startups like DoorDash, Instacart, and Eventbrite when those companies were still small—under 200 employees.

• Before that, they had started another venture in Chicago during Uber's early expansion beyond San Francisco.

• Their co-working space was right next to Uber's local team setting up drivers, giving them a front-row seat to the tech boom.

• Robin points out that Miki isn't coming at this topic as a "layperson."

• She deeply understands technology, startups, and how they affect people.

• Miki continues, explaining how that background informs how she sees AI adoption today.

• Her Bay Area friends are all-in on AI.

• Many have used it since its earliest days—because it's part of their jobs, or because they're building it themselves.

• Others are executives leading companies developing AI tools.

• She's been watching it unfold closely for years, even if she hasn't used it herself.

• From her position outside the tech bubble now, she can see two clear camps:

• Those immersed in AI, excited and moving fast.

• And those outside that world—more cautious, questioning what it means for real people and communities.

• Living between those worlds—the fast-paced tech culture and her slower, more grounded hometown—gives her a unique vantage point.

• She's connected enough to understand the innovation but distant enough to see its costs and consequences.

16:39 The Cost of AI Adoption

• Miki points out how strange it feels to people in tech that she hasn't used AI.

• In her Bay Area circles, the idea is almost unthinkable.

• Miki understands why it's shocking.

• It's mostly circumstance—her coaching work doesn't require AI.

• Unlike consultants who "all tell leaders how to use AI," her work is based on real conversations, not digital tools.

• Her husband, Jackson, also works at a "zero-technology" K–12 school he helped create, so they both exist in rare, tech-free spaces.

• She admits that's partly luck, not moral superiority, just "tiny pockets of the economy" where avoiding AI is still possible.

• Robin responds with his own story about adopting new tools.

• He recalls running Robin's Café from 2016 to 2019, when most restaurants still used paper timesheets.

• He connected with two young founders who digitized timesheets, turning a simple idea into a company that later sold to a global conglomerate.

• By the time he sold his café, those founders had retired in their 20s.

• "I could still run a restaurant on paper," he says, "but why would I, if digital is faster and easier?"

• He draws a parallel between tools over time—handwriting, typing, dictation.

• Each serves a purpose, but he still thinks best when writing by hand, then typing, then dictating.

• The point: progress adds options, not replacements.

• Miki distills his point: if a tool makes life easier, why not use it?

• Robin agrees, and uses his own writing practice as an example.

• He writes a 1,000-word weekly newsletter called Snafu.

• Every word is his, but he uses AI as an editor—to polish, not to create.

• He says, "I like how I think more clearly when I write regularly."

• For him, writing is both communication and cognition—AI just helps him iterate faster.

• It's like having an instant editor instead of waiting a week for human feedback.

• He reminds his AI tools, "Don't write for me. Just help me think and improve."

• When Miki asks why he's never had an editor, he explains that he has—but editors are expensive and slow.

• AI gives quick, affordable feedback when a human editor isn't available.

• Miki listens and reflects on the trade-offs.

• "These are the cost-benefit decisions we all make," she says—small, constant choices about convenience and control.

• What unsettles her is how fast AI pushes that balance.

• She sees it as part of a long arc—from the printing press to now—but AI feels like an acceleration.

• It's "such a powerful technology moving so fast" that it's blowing the cover off how society adapts to change.

• Robin agrees: "It's just the latest version of the same story, since writing on cave walls."

20:10 The Future of Human-AI Relationships

• Miki talks about the logical traps we've all started accepting over time.

• One of the biggest, she says, is believing that if something is cheaper, faster, or easier – it's automatically better.

• She pushes further: just because something is more efficient doesn't mean it's better than work.

• There are things you gain from working with humans that no machine can replicate, no matter how cheap or convenient it becomes.

• But we rarely stop to consider the real cost of trading that away.

• Miki says the reason we overlook those costs is capitalism.

• She's quick to clarify – she's not one of those people calling late-stage capitalism pure evil.

• Robin chimes in: "It's the best of a bunch of bad systems."

• Miki agrees, but says capitalism still pushes a dangerous idea:

• It wants humans to behave like machines—predictable, tireless, cheap, and mistake-free.

• And over time, people have adapted to that pressure, becoming more mechanical just to survive within it.

• Now we've created a tool—AI—that might actually embody those machine-like ideals.

• Whether or not it reaches full human equivalence, it's close enough to expose something uncomfortable:

• We've built a human substitute that eliminates everything messy, emotional, and unpredictable about being human.

• Robin takes it a step further, saying half-jokingly that if humanity lasts long enough, our grandchildren might date robots.

• "Two generations from now," he says, "is it socially acceptable—maybe even expected—that people have robot spouses?"

• He points out it's already starting—people are forming attachments to ChatGPT and similar AIs.

• Miki agrees, noting that it's already common for people under 25 to say they've had meaningful interactions with AI companions.

• Over 20% of them, she estimates, have already experienced this.

• That number will only grow.

• And yet, she says, we talk about these changes as if they're inevitable—like we don't have a choice.

• That's what frustrates her most:

• The narrative that AI "has to" take over—that it's unstoppable and universal—isn't natural evolution.

• It's a story deliberately crafted by those who build and profit from it.

• "Jackson's been reading the Hacker News comments for 15 years," she adds, hinting at how deep and intentional those narratives run in the tech world.

• She pauses to explain what Hacker News is for anyone unfamiliar.

• It's one of the few online forums that's still thoughtful and well-curated.

• Miki says most people there are the ones who've been running and shaping the tech world for years—engineers, founders, product leaders.

• And if you've followed those conversations, she says, it's obvious that the people developing AI knew there would be pushback.

• "Because when you really stop and think about it," she says, "it's kind of gross."

• The technology is designed to replace humans—and eventually, to replace their jobs.

• And yet, almost no one is seriously talking about what happens when that becomes real.

• "I'm sorry," she says, "but there's just something in me that says—dating a robot is bad for humanity. What is wrong with us?"

• Robin agrees.

• "I don't disagree," he says. "It's just… different from human."

• Miki admits she wrestles with that tension.

• "Every part of me says, don't call it bad or wrong—we have to make space for difference."

• But still, something in her can't shake the feeling that this isn't progress—it's disconnection.

• Robin expands on that thought, saying he's not particularly religious, but he does see humanity as sacred.

• "There's something fundamental about the human soul," he says.

• He gives examples: he has metal in his ankle from an old injury; some of his family members are alive only because of medical devices.

• Technology, in that sense, can extend or support human life.

• But the idea of replacing or merging humans with machines—of being subsumed by them—feels wrong.

• "It's not a world I want to live in," he says plainly.

• He adds that maybe future generations will think differently.

• "Maybe our grandkids will look at us and say, 'Okay boomer—you never used AI.'"

24:14 Practical Applications of AI in Daily Life

• Robin shares a story about a house he and his fiancée almost bought—one that had a redwood tree cut down just 10 feet from the foundation.

• The garage foundation was cracked, the chimney tilted—it was clear something was wrong.

• He'd already talked to arborists and contractors, but none could give a clear answer.

• So he turned to ChatGPT's Deep Research—a premium feature that allows for in-depth, multi-source research across the web.

• He paid $200 a month for unlimited access.

• Ran 15 deep research queries simultaneously.

• Generated about 250 pages of analysis on redwood tree roots and their long-term impact on foundations.

• He learned that if the roots are alive, they can keep growing and push the soil upward.

• If they're dead, they decompose, absorb and release water seasonally, and cause the soil to expand and contract.

• Over time, that movement creates air pockets under the house—tiny voids that could collapse during an earthquake.

• None of this, Robin says, came from any contractor, realtor, or arborist.

• "Even they said I'd have to dig out the roots to know for sure," he recalls.

• Ultimately, they decided not to buy that house—entirely because of the data he got from ChatGPT.

• "To protect myself," he says, "I want to use the tools I have."

• He compares it to using a laser level before buying a home in earthquake country: "If I'll use that, why not use AI to explore what I don't know?"

• He even compares Deep Research to flipping through Encyclopedia Britannica as a kid—hours spent reading about dinosaurs "for no reason other than curiosity."

• Robin continues, saying it's not that AI will replace humans—it's that people who use AI will replace those who don't.

• He references economist Tyler Cowen's Average Is Over (2012), which described how chess evolved in the early 2000s.

• Back then, computers couldn't beat elite players on their own—but a human + computer team could beat both humans and machines alone.

• "The best chess today," Robin says, "is played by a human and computer together."

• "There are a dozen directions I could go from there," Miki says.

• But one idea stands out to her:

• We're going to have to choose, more and more often, between knowledge and relationships.

• What Robin did—turning to Deep Research—was choosing knowledge.

• Getting the right answer.

• Having more information.

• Making the smarter decision.

• But that comes at the cost of human connection.

• "I'm willing to bet," she says, "that all the information you found came from humans originally."

• Meaning: there were people who could have told him that—just not in that format.

• Her broader point: the more we optimize for efficiency and knowledge, the less we may rely on each other.

32:26 Choosing Relationships Over AI

• Robin points out that everything he learned from ChatGPT originally came from people.

• Miki agrees, but says her work is really about getting comfortable with uncertainty.

• She helps people build a relationship with the unknown instead of trying to control it.

• She mentions Robin's recent talk with author Simone Stolzoff, who's writing How to Not Know—a book she can't wait to read.

• She connects it to a bigger idea: how deeply we've inherited the Enlightenment mindset.

• "We're living at the height of 'I think, therefore I am,'" she says.

• If that's your worldview, then of course AI feels natural. It fits the logic that more data and more knowledge are always better.

• But she's uneasy about what that mindset costs us.

• She worries about what's happening to human connection.

• "It's all connected," she says—our isolation, mental health struggles, political polarization, even how we treat the planet.

• Every time we choose AI over another person, she sees it as part of that drift away from relationship.

• "I get why people use it," she adds. "Capitalism doesn't leave most people much of a choice."

• Still, she says, "Each time we pick AI over a human, that's a decision about the kind of world we're creating."

• Her choice is simple: "I'm choosing relationships."

• Robin gently pushes back.

• "I think that's a false dichotomy," he says.

• He just hosted Responsive Conference—250 people gathered for human connection.

• "That's why I do this podcast," he adds. "To sit down with people and talk, deeply."

• He gives a personal example.

• When he bought his home, he spoke with hundreds of people—plumbers, electricians, roofers.

• "I'm the biggest advocate for human conversations," he says.

• "So why not both? Why not use AI and connect with people?"

• To him, the real question is about how we use technology consciously.

• "If we stopped using AI because it's not human," he asks,

• "should we stop using computers because handwriting is more authentic?"

• "Should we reject the printing press because it's not handwritten?"

• He's not advocating blind use—he's asking for mindful coexistence.

• It's also personal for him.

• His company relies on AI tools—from Adobe to video production.

• "AI is baked into everything we do," he says.

• And he and his fiancée—a data scientist—often talk about what that means for their future family.

• "How do we raise kids in a world where screens and AI are everywhere?"

• Then he asks her directly: "What do you tell your clients? Treat me like one—how do you help people navigate this tension?"

• Miki smiles and shakes her head.

• "I don't tell people what to do," she says. "I'm not an advisor, I'm a coach."

• Her work is about helping people trust their own intuition.

• "Even when what they believe is contrarian," she adds.

• She admits she's still learning herself.

• "My whole stance is: I don't know. I don't know. I don't know."

• She and her husband, Jackson, live by the idea of strong opinions, loosely held.

• She stays open—lets new conversations change her mind.

• "And they do," she says. "Every talk like this shifts me a little."

• She keeps seeking those exchanges—with parents, tech workers, friends—because everyone's trying to figure out the same thing:

• How do we live well with technology, without losing what makes us human?

37:16 The Amish Approach to Technology

• Miki reflects on how engineers are both building and being replaced by AI.

• She wants to understand the technology from every angle—how it works, how it affects people, and what choices it leaves us with.

• What worries her is the sense of inevitability around AI—especially in places like the Bay Area.

• "It's like no one's even met someone who doesn't use it," she says.

• She knows it's embedded everywhere—Google searches, chatbots, everything online.

• But she doesn't use AI tools directly or build with them herself.

• "I don't even know the right terminology," she admits with a laugh.

• Robin points out that every Google search now uses an LLM.

• Miki nods, saying her point isn't denial—it's about choice.

• "You can make different decisions," she says.

• She admits she hasn't studied it deeply but brings up an analogy that helps her think about tech differently: the Amish.

• "I call myself kind of 'AI Amish,'" she jokes.

• She explains her understanding of how the Amish handle new technology.

• They're not anti-tech; they're selective.

• They test and evaluate new tools to see if they align with their community's values.

• "They ask, does it build connection or not?"

• They don't just reject things—they integrate what fits.

• In her area of Ohio, she's seen Amish people now using electric bikes.

• "That's new since I was a kid," she says.

• It helps them connect more with each other without harming the environment.

• They've also used solar power for years.

• It lets them stay energy independent without relying on outside systems that clash with their values.

• Robin agrees—it's thoughtful, not oppositional.

• "They're intentional about what strengthens community," he says.

• Miki continues:

• What frustrates her is how AI's creators have spent the last decade building a narrative of inevitability.

• "They knew there would be resistance," she says, "so they started saying, 'It's just going to happen. Your jobs won't be taken by AI—they'll be taken by people who use it better than you.'"

• She finds that manipulative and misleading.

• Robin pushes back gently.

• "That's partly true—but only for now," he says.

• He compares it to Uber and Lyft: at first, new jobs seemed to appear, but eventually drivers started being replaced by self-driving cars.

• Miki agrees.

• "Exactly. First it's people using AI, then it's AI replacing people," she says.

• What disturbs her most is the blind trust people put in companies driven by profit.

• "They've proven over and over that's their motive," she says.

• "Why believe their story about what's coming next?"

• She's empathetic, though—she knows why people don't push back.

• "We're stressed, broke, exhausted," she says.

• "Our nervous systems are fried 24/7—especially under this administration."

• "It's hard to think critically when you're just trying to survive."

• And when everyone around you uses AI, it starts to feel mandatory.

• "People tell me, 'Yeah, I know it's a problem—but I have to. Otherwise I'll lose my job.'"

• "Or, 'I'd have bought the wrong house if I didn't use it.'"

• That "I have to" mindset, she says, is what scares her most.

• Robin relates with his own example.

• "That's how I felt with TikTok," he says.

• He got hooked early on, staying up until 3 a.m. scrolling.

• After a few weeks, he deleted the app and never went back.

• "I probably lose some business by not being there," he admits.

• "But I'd rather protect my focus and my sanity."

• He admits he couldn't find a way to stay on the platform without it consuming him.

• "I wasn't able to build a system that removed me from that platform while still using that platform."

• But he feels differently about other tools.

• For example, LinkedIn has been essential—especially for communicating with Responsive Conference attendees.

• "It was our primary method of communication for 2025," he says.

• So he tries to choose "the lesser of two evils."

• "TikTok's bad for my brain," he says. "I'm not using it."

• "But with LLMs, it's different."

• When researching houses, he didn't feel forced into using them to "keep up."

• To him, they're just another resource.

• "If encyclopedias are available, use them. If Wikipedia's available, use both. And if LLMs can help, use all three."

41:45 The Pressure to Conform to Technology

• Miki challenges that logic.

• "When was the last time you opened an encyclopedia?"

• Robin pauses. "Seven years ago."

• Miki laughs. "Exactly. It's a nice idea that we'll use all the tools—but humans don't actually do that."

• We gravitate toward what's easiest.

• "If you check eBay, there are hundreds of encyclopedia sets for sale," she says. "No one's using them."

• Robin agrees but takes the idea in a new direction.

• "Sure—but just because something's easy doesn't mean it's good," he says.

• He compares it to food:

• "It's easier to eat at McDonald's than cook at home," he says.

• But easy choices often lead to long-term problems.

• He mentions obesity in the U.S. as a cautionary parallel.

• Some things are valuable because they're hard.

• "Getting in my cold plunge every morning isn't easy," he says. "That's why I do it."

• "Exercise never gets easy either—but that's the point."

• He adds a personal note:

• "I grew up in the mountains. I love being at elevation, off-grid, away from electricity."

• He could bring Starlink when he travels, but he chooses not to.

• Still, he's not trying to live as a total hermit.

• "I don't want to live 12 months a year at 10,000 feet with a wood stove and no one around."

• "There's a balance."

• Miki nods, "I think this is where we need to start separating what we can handle versus what kids can."

• "We're privileged adults with fully formed brains," she points out.

• "But it's different for children growing up inside this system."

• Robin agrees and shifts the focus.

• Even though you don't give advice professionally," he says, "I'll ask you to give it personally."

• "You're raising kids in what might be the hardest time we've ever seen. What are you actually practicing at home?"

45:30 Raising Children in a Tech-Driven World

• Robin reflects on how education has shifted since their grandparents' time

• Mentions "Alpha Schools" — where

• AI helps kids learn basic skills fast (reading, writing, math)

• Human coaches spend the rest of the time building life skills

• Says this model makes sense:

• Memorizing times tables isn't useful anymore

• He only learned to love math because his dad taught him algebra personally — acted like a coach

• Asks Miki what she thinks about AI and kids — and what advice she'd give him as a future parent

• Miki's first response — humility and boundaries

• "First off, I never want to give parents advice."

• Everyone's doing their best with limited info and energy

• Her kids are still young — not yet at the "phone or social media" stage

• So she doesn't pretend to have all the answers

• Her personal wish vs. what's realistic

• Ideal world:

• She wishes there were a global law banning kids from using AI or social media until age 18

• Thinks it would genuinely be better for humanity

• References The Anxious Generation

• Says there's growing causal evidence, not just correlation, linking social media to mental health issues

• Mentions its impact on children's nervous systems and worldview

• It wires them for defense rather than discovery

• Real world:

• One parent can't fight this alone — it's a collective action problem

• You need communities of parents who agree on shared rules

• Example: schools that commit to being zero-technology zones

• Parents and kids agree on:

• What ages tech is allowed

• Time limits

• Common standards

• Practical ideas they're exploring

• Families turning back to landlines

• Miki says they got one recently

• Not an actual landline — they use a SIM adapter and an old rotary phone

• Kids use it to call grandparents

• Her partner Jackson is working on a bigger vision:

• Building a city around a school

• Goal: design entire communities that share thoughtful tech boundaries

• Robin relates it to his own childhood

• Points out the same collective issue — "my nephews are preteens"

• It's one thing for parents to limit screen time

• But if every other kid has access, that limit won't hold

• Shares his own experience:

• No TV or video games growing up

• So he just went to neighbors' houses to play — human nature finds a way

• Says individual family decisions don't solve the broader problem

• Miki agrees — and expands the concern

• Says the real issue is what kids aren't learning

• Their generation had "practice time" in real-world social interactions

• Learned what jokes land and which ones hurt

• Learned how to disagree, apologize, or flirt respectfully

• Learned by trial and error — through millions of small moments

• With social media and AI replacing those interactions:

• Kids lose those chances entirely

• Results she's seeing:

• More kids isolating themselves

• Many afraid to take social or emotional risks

• Fewer kids dating or engaging in real-life relationships

• Analogy — why AI can stunt development

• "Using AI to write essays," she says,

• "is like taking a forklift to the gym."

• Sure, you lift more weight — but you're not getting stronger

• Warns this is already visible in workplaces:

• Companies laying off junior engineers

• AI handles the entry-level work

• But in 5 years, there'll be no trained juniors left to replace seniors

• Concludes that where AI goes next "is anybody's guess" — but it must be used with intention

54:12 Where to Find Miki

• Invites others to connect

• Mentions her website: leadingbyexample.life

• Visitors can book 30-minute conversations directly on her calendar

• Says she's genuinely open to discussing this topic with anyone interested

Welcome back to Snafu with Robin Zander.

In this episode, I'm talking with Bobby Podesta, longtime Pixar animator and storyteller.

We dig into why storytelling and art matter, and why finding your own voice is more important than copying anyone else.

Bobby opens up about his journey as an artist, the imposter syndrome he's faced, and how he learned to create art in a style that's truly his.

We talk about how he turned a written novel into a graphic novel, translating dialogue and descriptions into illustrations along the way.

He shares lessons from his college design teacher about noticing the art all around us—not just in museums or galleries.

We also explore how design and storytelling balance function and emotion, in ways you might not even realize in everyday life.

Bobby's story shows that creativity isn't about perfection – it's about showing up and being authentic.

He gives a fresh perspective on how storytelling shapes the way we see the world and connect with others.

This episode is full of insights for anyone who cares about art, design, and telling stories that matter.

00:00 Start 03:13 The Importance of Human Connection in Storytelling

• Bobby on storytelling

• Background: 30 years in film, always thinking about story structure.

• Drama is about "what you're both keeping back and what you're waiting to surprise your audience with."

• Steve Jobs anecdote

• Jobs builds suspense with "one more thing."

• On stage, he asks: "Has anyone ever wondered what this small pocket is for?" (the tiny jeans pocket).

• Instead of something expected like a coin, he pulls out "the world's smallest iPod and people flip out."

• Why it works: audience knows the pocket's size → no need to explain iPod's dimensions.

• Structure: setup → familiar norm → question → twist → payoff.

• Bobby's takeaway: "That's really good storytelling, man. It's really good storytelling."

• "People call him a salesperson. Like he's a great salesman. He's a great storyteller. If you can tell a good story, you're pulling people in. That's the key."

• Robin on storytelling & AI

• His work is making commercials and mini-docs for startups.

• Says video itself doesn't matter as much as impact: "What I care about is changing human behavior and changing human emotion."

• Believes the value of human storytelling is timeless: "The value of sitting at Homer's feet and listening to him recite the Iliad is never going to go away."

• Bobby on storytelling & art

• Storytelling = fundamental way to convey and connect.

• Sees it like art: "Art is a way to express your opinion and how you process the world around you in a manner that hopefully other people can experience and relate to."

• Calls art his "oldest friend, who I've probably treated the worst… neglected, starved, and then expect it to show up and perform."

• Believes everyone can create: "Art is not a zero-sum game… art is ultimately subjective because art is an opinion about how you see the world."

• Goal of art/storytelling: help others "find some relationship to the world around them through it."

06:01 Art as a Form of Expression

• Robin's setup

• Grew up between an artist mother and entrepreneur father – "perfect intersection" of art + business.

• Distinguishes museum art ("old, on walls") from art that's "around us all the time."

• Points out modern communicators (Musk, Trump) as powerful storytellers/branders – even if you disagree with the content, "that is great art in the form of good communication."

• Asks: why do we separate "high" art (Iliad, museums) from everyday, cultural storytelling (Pixar, branding)?

• Art is everywhere

• Bobby uses the car-buying analogy to explain awareness:

• "You're looking for a midsize pickup and suddenly you see them everywhere. They didn't just appear. You're just paying attention."

• Art works the same way – once you start noticing, you realize it's all around you.

• Lesson from a design teacher:

• "If it wasn't dug up or grown, it's designed."

• Everything man-made carries intention – and therefore, art.

• Pushes back on the museum-only view of art:

• "Saying art is only in museums is like saying there are only cars at dealerships. There are cars everywhere. There's art everywhere."

• Examples of art woven into daily life:

• Clothing, headphones, glasses

• Desks, chairs, pottery, textiles

• Buildings, skylines, sidewalk prints

• Freeway dividers, lamps

• Even tools: "Go get a hammer. The handle's probably painted a color. It may be a penny's worth of art, but it's art, man."

• Definition of art:

• "All these things are working with that balance between functionality and making you feel something."

• Even branding choices – a color, a shape – are designed to evoke feeling.

• Perspective shift:

• Once you adjust your lens, "there's a lot of art out there. It's really, really amazing."

12:04 The Relationship Between Artist and Art

• Bobby compares practice to a relationship:

• "It's like the people that love you the most, sometimes you treat the worst."

• Practice is like a loyal friend or character always waiting:

• Wants to be fed, but often ignored.

• Always ready to show up again.

• "It's like that little character that shows up and is always there to help you out."

• Robin asks if practice is a character on his shoulder.

• Bobby: "It probably is… but I love it. If there's a napkin, I'll doodle."

• Art as a shared childhood language:

• Everyone starts out drawing: "Have you ever met an adult who didn't draw as a kid? Everyone says yes."

• Drawing is how children interpret the world.

• Family encouragement made "the artist" part of his identity.

• Becoming a writer:

• Took a UC Berkeley Extension class called "Finishing the Novel."

• Professor's advice: "You're all taking classes. None of you are professionals. Go form a writers' group."

• Writers' group provided accountability → led to a first draft.

• Draft → literary agent → graphic novel → published book.

• "Flash forward all these years later and I have a book that comes out… I guess I'm an author."

• Lessons on growth and identity:

• Identity comes from practice and persistence, not instant recognition.

• Progress isn't linear: "The road is not a straight line."

• Common trap: believing "I should have been there already."

• Bobby reframes time:

• "You can often have what you want, or you can have something when you want it. But you can rarely have what you want when you want it."

• Letting go of rigid timelines gives a better chance of arriving.

18:01 The Process of Creating a Graphic Novel

• Robin asks why this story, why now, and why as a debut novel.

• Bobby admits he had played with different story ideas before.

• Thought to himself: "If I only have one chance to do this, what story do I want to tell?"

• Origin spark: a daydream while driving.

• "What if an animal just jumped out in front of me?"

• What if it leapt into the air and flew away?

• "What if that animal was a reindeer?"

• Question: what would a reindeer be doing here?

• That "what if" became the seed of the story.

• Bobby folded parts of himself into the idea.

• Loves holiday stories and movies → wanted to write one.

• Describes storytelling as crafting from a "pantry of experiences."

• Not autobiography or documentary, but infused with pieces of his life.

• Details of the novel:

• Protagonist is an 11-year-old girl in 1955 Colorado.

• Bobby: "I was neither alive in 1955, nor have I ever been an 11-year-old girl, nor have I found a flying reindeer — spoiler alert."

• Still, fragments of his own experiences and emotions shape the narrative.

• Goal as an author:

• To blend reality with imagination.

• To create something unique, fresh, and able to stand on its own.

20:58 Visual Storytelling vs. Written Storytelling

• Robin asks about storytelling: what's similar between Steve Jobs' two-minute iPod reveal and a 350-page graphic novel?

• Bobby: scale is different, but fundamentals are the same.

• Both are about introducing an idea, building drama, and pulling the audience in.

• Events and books both follow arcs: setup → build → climax → resolution.

• "He doesn't start the event with that, he ends the event with that. That's the climax."

• Storytelling has shape across mediums:

• Characters introduced → audience grows to care → surprises and turns → payoffs.

• Example: Steve Jobs' coin pocket reveal → set up, then payoff.

• In a book, the payoff may come 100 pages later instead of 30 seconds.

• Analogy: whether you play 30 seconds of a song or an hour-long concert, you're still using the same fundamentals of music.

• Robin shifts to Bobby's background as a visual storyteller.

• As an animator of 30 years, Bobby is comfortable with visual stories, while Robin is more comfortable with written ones.

• Robin compares Bobby's graphic novel to The Bone Compendium (which he revisits often) and contrasts with Heinlein novels he might attempt.

• Robin: making comics doesn't have to be like "my mother's artwork she slaved over for years." It can be like newspaper comics compiled into story.

• Asks Bobby for advice on where to begin if he wanted to try sketching a visual story.

• Bobby's advice:

• Many people don't think visual storytelling is possible for them.

• Shares personal story:

• On his first post-college date with his wife (now 25 years married), he said he wanted to write a book.

• It took him 25 years to actually write one.

• Never thought of doing a graphic novel because his drawing style didn't look like Marvel or X-Men.

• Even as a professional artist, felt imposter syndrome

• Realization: it's not about imitating Spider-Man — it's about drawing in your own style.

• Art is your opinion expressed visually.

• Stick figures can work if they serve the story.

• Doesn't have to be polished airbrushed paintings.

• How his graphic novel came about:

• Originally wrote the story as a regular novel.

• Sent to publishers with just a few illustrations.

• All said no — except one, who said: "I love the illustrations. Would you consider making this a graphic novel?"

• Bobby: "All right." Treated it as an invitation. Decided to draw in his own style.

• Practical process:

• Took all the dialogue he had already written.

• Turned descriptions into drawings.

• Book was already written in close third person, without inner thoughts → made translation easier.

• First pass: dialogue in speech bubbles, description drawn.

• Realized: "I guess this works."

• Takeaway:

• You don't have to start by drawing an entire book from scratch.

• You can begin with writing, then translate description into visuals.

28:10 Resilience in the Face of Rejection

• Robin points out the sheer amount of work Bobby went through: writing a book, getting rejected repeatedly, reinventing it with illustrations, then turning it into a graphic novel only to be rejected again.

• Robin: "It's almost the literal definition of courage… getting back up and trying again."

• Notes that outsiders might think: "30-year Pixar animator, easy for you." But the reality was rejection after rejection.

• Asks: how do you come back? What is your relationship with practice that allows you to face no 50 times and keep going?

• Bobby on optimism and imagination:

• "I'm lucky that I happen to be what myself and other people probably call an optimistic person."

• Describes himself as "an optimist with a vivid imagination" → always assuming, "Yeah, we'll figure this out."

• Loves being middle-aged because experience gives perspective: you've seen enough to know you can recover.

• The arc of a career/life:

• Beginning stage: fearless.

• "I can do anything because I cannot die."

• Willing to leap into anything: start a company, go broke, jump off a cliff → "We'll figure it out."

• Middle stage: awareness of consequences.

• Relationships, responsibilities, failures and successes → "I don't know if I should do anything."

• Weight of awareness can freeze you.

• Later stage: resilience.

• "I'm still here, I figured it out."

• Confidence comes not from avoiding mistakes but from knowing: "I can recover from anything."

• Personal examples:

• Bobby's two kids are both in college. He reflects on their application process: multiple schools, multiple options.

• His own experience was the opposite:

• Applied to only one school (CalArts).

• Barely got in.

• Supported by his single mother, who let him pursue art school.

• That early challenge taught him persistence and how to "figure it out."

• The practice of persistence:

• Life and career filled with moments of trial and error.

• "That didn't work. Okay, maybe this. Well, that didn't work. Maybe this."

• Sometimes progress feels like moving backwards before going forward again.

• Analogy: like a Roomba.

• Hits an obstacle → bounces, changes direction, keeps moving.

• "I don't know that equating myself to a robot vacuum is the best thing, but it eventually gets the whole job done."

33:33 Storytelling Frameworks and Structures

• Bobby on classical story structure in his book:

• Book follows a traditional arc: opening, inciting incident (

• Includes a twist based on early-foreshadowed elements: "Think you have a solution and then have a hard turn… different solution planted 100 pages earlier."

• Early readers said it felt cinematic → Bobby wrote a movie as a book.

• References classic movie structures repeatedly during drafting, checking chapter progression, hooks, resolutions, and cliffhangers: "Do I end this chapter with a feeling of resolution or with a question… do I want you to turn the page?"

• Notes that creating the book strengthened his skills at Pixar and vice versa: "They have a symbiotic relationship."

• Robin asks about attention to structure:

• Bobby used a mix of planning and improvisation ("planners vs. pantsers").

• Laid out large story "tentpoles" first, then wrote chapter by chapter without immediate rewrites.

• After finishing, he reviewed for surprises, alignment with tentpoles, and adjustments → iterative back-and-forth process.

• Bobby on why people don't create:

• Humans face fatigue, distraction, and constant small friction points: "It's like mini marshmallow tests all the time… the barriers of resistance to start can seem so overwhelming in the moment."

• The promise of completion feels distant and foggy → can prevent starting.

• Practice builds momentum: "It's momentum… sometimes it's having someone to be your advocate… sometimes it's accountability."

• Big projects (books, movies) require an internal well of energy: "You can't count on someone else to always be there to say, 'Keep going.' You have to push yourself daily."

• Daily discipline = mental exercise: getting out of bed, starting small tasks → builds resilience.

• On avoiding writer's block:

• Robin: "Writer's block is trying to edit while in the process of creation… you can't do both simultaneously."

• Bobby: Agrees, emphasizes creation first, editing later.

• Early experience with comic strips in high school: studied Charles Schulz's process, learned professionals set deadlines → no excuses for "writer's block."

• On practical daily routine and momentum:

• Bobby wrote his book for ~1 hour a day while managing family, work, and marriage.

• Morning routine: 5–5:30 a.m. start, kettle and coffee prepped the night before → eliminates friction to starting work.

• Hardest step: moving from bed to floor → must commit, no complaining.

• Momentum principle: start creating first, quality comes later. "By the time I've sat down and portioned my coffee… here we go, just start. Start writing, start drawing, start doing whatever."

46:42 Overcoming Resistance and Building Momentum

• Bobby on moving yourself before moving others:

• Don't try to manipulate the audience's emotions: "Try to move yourself to emotion. If you try to move someone else… you're trying to tap into someone else's experience."

• Authenticity first: "Write, draw, create, tell a story that is as authentic to your own voice as it can be."

• Art as personal expression: putting your own emotion and opinion into the work.

• Bobby on why authenticity resonates:

• People relate most to what feels real and personal: "The stuff we relate to the most are the things that artists… seem to be really trying to tell from the inside out."

• Trying to make someone happy or sad is normal, but the deeper work comes from creating for yourself first.

• Bobby on the process of creating large works:

• Long projects require self-focus: "You kind of have to do it for yourself… in the hopes that someone else will see it like that."

• Early reviews affirmed authenticity: "I was reading some early reviews… and I was like, my gosh, they got it. They got it."

• The work doesn't have to resonate with everyone, just someone: "If it can make you smile, it probably is gonna make someone else smile."

• Bobby on art as perspective:

• Artists share how they see the world: "If it is a painting that your parents took you to in the museum… that painter was trying to say, this is how I saw the world."

• Audience connection = seeing through the artist's lens: "If you looked at that painting and said, I see that. I see that. That's great. That's the lens, man. That's the lens."

(49:59) Where to Find Bobby

• Website: bobbypedesta.com – easy to remember and navigate.

• Bobby on finding North for the Winter:

• Available anywhere books are sold.

• Website provides a direct link to purchase at your preferred retailer.

• Local bookstores can order it within a couple of days if they don't have it in stock.

Books / Works

• The Iliad

• North for the Winter

• The Bone Compendium

• Heinlein novels (Robert A. Heinlein)

People

• Steve Jobs

• Homer (epic poet)

• Elon Musk

• Donald Trump

• Charles Schulz

• Robert A. Heinlein

• Jeff Smith

Hi everyone, welcome back to Snafu with Robin Zander.

This episode is a little different - instead of me hosting, I was actually the guest on my good friend Josh Levine's podcast, Great Mondays Radio.

Josh and I went deep on a topic I care about a lot: why soft skills are the hard currency of the future. We explored what really sets humans apart in an age of rapid innovation, the rise of AI, and all the talk about machines taking over jobs. We dug into the skills that can't be automated, the value we bring that AI can never replicate, and why those human capabilities will only matter more in the years ahead.

We also touched on leadership, creativity, and how we can all prepare ourselves - and our organizations - for the changes still to come.

Please take a moment to subscribe to Josh's show, Great Mondays Radio. It would mean a lot to both of us, and I know you'll enjoy the incredible conversations he's hosting.

I'm also excited that Josh will be joining us at Responsive Conference 2025 as a guest - so this won't be the last time you hear from him in our orbit.

Welcome back to Snafu w/ Robin Zander.

In this episode, I'm joined by Simone Stolzoff – author of The Good Enough Job and the upcoming How to Not Know – and our opening keynote speaker at Responsive Conference 2025.

We explore what it means to have an identity beyond your job title, why rest is essential for high performance, and how ritual and community offer grounding in an age of uncertainty. Simone shares how Judaism and Shabbat have shaped his views on balance, the role of "guardrails" over boundaries, and how we can build more durable lives – personally and professionally. We talk about the future of religion, the risks and opportunities of AI, and why books still matter even in a tech-saturated world. Simone also offers practical writing advice, previews his next book, and explains why embracing uncertainty may be the most valuable skill of all.

Simone will be speaking live at Responsive Conference 2025, September 17–18, and I can't wait for you to hear more.

If you haven't gotten your tickets yet, get them here.

Start (00:00) Identity Beyond Titles (01:07.414)

• What identities do you hold that aren't listed on your LinkedIn?

• Simone's Answer:

• Ultimate frisbee player – "the entirety of my adult life"

• Aspiring salsa dancer – taking intro classes with his wife

• Former spoken word poet – "It was the most important thing to me when I was 19 years old."

• New father – navigating life with a five-month-old

• "I encourage people to ask: what do you like to do, as opposed to what do you do?"

Shabbat as a Sanctuary in Time (01:58.831)

• Robin references Simone's TED Talk, focusing on Shabbat as a metaphor for boundary-setting and presence.

• Simone expands:

• Shabbat offers a weekly rhythm to separate work from rest.

• Emphasizes the idea of "sacred time" and intentional disconnection from screens.

• Shabbat is a "sanctuary in time," paralleling physical sanctuaries like churches or synagogues.

• Relates this to work-life balance, noting that intentions alone aren't enough – infrastructure is needed.

• "We have intentions… but what actually leads to balance is structural barriers."

Boundaries vs. Guardrails (04:44.32)

• Cites Anne Helen Petersen's metaphor:

• Boundaries = painted lane lines

• Guardrails = physical barriers that actually keep you on the road

• There are calls for more guardrails (structural protections) in modern life.

• Examples:

• Airplane mode during playtime with his kid

• Attending yoga or activities where work can't creep in

• "Individually imposed boundaries often break down when the pressures of capitalism creep in."

Religion, Ritual & Community (06:48.57)

• Robin asks how Judaism has shaped Simone's thinking around work and life.

• Simone reflects:

• Religion offers a "container" with a different value system than capitalism.

• As organized religion declined, people turned to work for identity, meaning, and community.

• Religion can offer rituals to process uncertainty — e.g., mourning rituals like sitting shiva.

• Religious or community spaces offer contrast: they don't care about your career success.

• "Religion is sort of like a container… with a value system that isn't just about growth charts."

• "It can be refreshing to say: Day 1, do this. Day 7, go for a walk."

• Personal journey:

• Simone reconnected with Judaism in his 30s as he built his own family.

• Once, went out of obligation, then rejected it, and now see beauty in ritual and intergenerational wisdom.

The Future of Religion & Community (09:12.454)

• Robin theorizes a future rise in spiritual and communal gatherings:

• Predicts new spiritual movements or evolutions of old ones

• Notes a hunger for meaningful in-person connection, especially post-AI and amid tech saturation

• "There's a hunger... as AI and screens define how we relate, people want to gather in person."

• "I don't tend to make predictions, but I think this one's inevitable."

• Simone agrees... but offers data as contrast:

• Cites the decline in religious affiliation in the U.S.

• 1950s: 3–4% unaffiliated

• Today: Nearly 1 in 3 identify as "Nones" (no religion)

• Notes reasons:

• Rising wealth tends to increase secularism

• The internet creates alternate identity spaces

• "I do believe there is inevitability in the growth [of spirituality]... But the data points the opposite way."

• Simone reflects on the factors behind declining religious affiliation:

• Doubt now builds community – the internet has enabled people to connect around leaving religion as much as practicing it.

• Political entanglement – many young Americans, especially, are alienated by the perceived overlap between right-wing politics and Christianity.

• Yet despite this secular trend, the need for meaning, ritual, and purpose remains universal.

• "There still is this fundamental need to find meaning, to find purpose, to find ritual… even if it's not in the forms we're used to."

A Church in the Mission (13:07.182)

• Robin shares a formative experience from 2016:

• That year, he launched both Robin's Café and the first Responsive Conference.

• When he walked into the theater space that would become his café, he encountered a young, diverse Christian revival group – live music, dancing, and energetic worship happening in a Mission District theater.

• This juxtaposition – a traditional spiritual gathering inside a modern, "hip" venue – left a lasting impression.

• "It felt like a revival meeting in the South… except it was full of people my age and younger, partying on a Saturday morning – and it just happened to be church."

You Are More Than Your Work (14:51.182)

• Robin segues into the idea of multiple identities:

• He recalls how reading The 4-Hour Work Week helped him embrace not defining himself solely by his entrepreneurial work.

• Even on tough days running a business, movement and fitness have been a grounding force – something he does daily, independent of career performance.

• Quotes from Simone's TED Talk:

• "Some people do what they love for work; others work so they can do what they love. Neither is more noble."

• Robin asks Simone to share the origin of this line and how it connects to the poet Anis Mojgani.

• Simone recounts a pivotal conversation during college:

• As a poetry and economics double major, he was wrestling with career path anxiety.

• He interviewed his favorite poet, Anis Mojgani, asking: "Do you believe in the idea, 'Do what you love and never work a day in your life'?"

• Mojgani's response:

• "Some people do what they love for work. Others do what they have to so they can do what they love when they're not working. Neither is more noble."

• This countered Simone's expectations and left a deep impression. He highlights two cases for cultivating a broader identity beyond work:

• Business Case:

• High performance requires rest.

• People with "greater self-complexity" — more identities outside of work — are more creative, more resilient, and more emotionally stable.

• Moral Case:

• Investing in other parts of ourselves makes us better citizens, community members, and humans.

• Singular identity (especially career-based) is fragile and susceptible to collapse — e.g., pandemic layoffs.

• Solely work-based identity also sets unrealistically high expectations that can lead to disappointment.

• "You're balancing on a very narrow platform… You're susceptible to a large gust of wind."

• Robin reflects on how the Responsive Manifesto intentionally avoids prescribing one path:

• It's not anti-work or anti-grind.

• Recognizes that sometimes hard work is necessary, especially in entrepreneurship.

• Shares how his friend's newsletter, Just Go Grind, embraces the idea that seasons of hustle are sometimes required.

• "Everyone figuring out their own boundaries is actually the goal."

Work Isn't Good or Bad – It's Complex (18:34.436)

• Simone adds that society tends to polarize the narrative around work:

• Some say "burn it all down", that work is evil.

• Others say, "Do what you love, or it's not worth doing."

• His book The Good Enough Job argues for a middle way:

• It's not hustle propaganda.

• It's not a slacker's manifesto.

• It's about recognizing that we spend a huge portion of our lives working, so it matters how we approach it, but also recognizing we're more than just our jobs.

• He introduces the concept of temporal balance:

• "There's a natural seasonality to work."

• Sometimes, long hours are necessary (e.g., startup mode, sales targets).

• But it should be a season, not a permanent lifestyle.

What's the Role of Books in the Age of AI? (22:41.507)

• Robin poses a forward-looking question:

• In an age when AI can summarize, synthesize, and generate information rapidly, what's the role of books?

• Especially nonfiction, where facts are easier to reproduce.

• Simone responds with both uncertainty and hope:

• Human storytelling as a moat:

• His work relies on reporting, profiling, and character studies — something LLMs can't yet replicate with nuance.

• He doesn't know how long this will remain defensible, but will continue to lean into it.

• Books are more than information:

• Books have utility beyond facts: they are entertainment, physical objects, and cultural symbols.

• Quotes the vibe of being surrounded by books: there's even an untranslatable word (possibly German or Japanese) about the comfort of unread books.

• A vinyl-record future:

• Books may become more niche, collectible, or artisanal, similar to vinyl.

• But they still hold society's most well-formed, deeply considered ideas.

• The human touch still matters:

• A typed note that looks handwritten isn't the same as a note that is handwritten.

• People will crave authenticity and human creation, especially in a tech-saturated world.

• "You can appreciate when something has a level of human touch, especially in an increasingly tech-powered world."

• He closes with a self-aware reflection:

• "I don't claim to know whether my career will still exist in five years… which is why I picked this topic for my second book."

"Created by Humans" (25:49.549)

• Robin references a conversation with Bree Groff, who imagined a world where creative work carries a "Created by Human" tag, like organic food labeling.

• "I think we'll see that [kind of labeling] in the next few decades – maybe even in the next few years."

• As AI-generated content floods the market, human-made work may soon carry new cultural cachet.

• Simone shares a turning point: after submitting an op-ed to The New York Times, his editor flagged a bad metaphor. En route to a bachelor party, he opened ChatGPT, asked for new metaphors, chose one, and it made the print edition the next day.

• "Maybe I've broken some law about journalism ethics... but that was the moment where I was like: whoa. This sh*t is crazy."

The Home-Buying Crash Course Powered by AI (27:57)

• Robin's breakthrough came while navigating the chaos of buying a house. He used ChatGPT to upskill rapidly:

• Structural questions (e.g., redwood roots and foundation risk)

• Zoning and legal research

• Negotiation tactics

• "The rate of learning I was able to create because of these tools was 10 to 100 times faster than what I could've done previously."

How to Live Without Knowing (29:41.498)

• Simone previews his next book, How to Not Know, a field guide for navigating uncertainty. In an age of instant answers, our tolerance for the unknown is shrinking, while uncertainty itself is growing.

• "We're trying to find clarity where there is none. My hope is that the book offers tools to live in that space."

• The "Three Horsemen of Delusion":

• Comfort – we crave the ease of certainty.

• Hubris – we assume we know more than we do.

• Control – we believe certainty gives us power over the future.

• Robin asks how Simone finds his stories. His answer: chase change. Whether internal (doubt, transformation) or external (leaving a cult, facing rising seas), he seeks tension and evolution.

• Examples:

• A couple questioning their marriage

• An employee leading dissent at work

• A man leaving his religious identity behind

• A nation (Tuvalu) confronting its own disappearance

• "The story you find is always better than the one you seek."

Want to Be a Writer? Start Writing. (36:50.554)

• Robin asks for writing advice. Simone offers two pillars:

• Ask These Four Questions:

• What's the story?

• Why should people care?

• Why now?

• Why you?

• "Only you can tell the story of buying a café and selling it on Craigslist."

• Build the Practice:

• Writing is not just inspiration—it's routine.

• Schedule it. Join a group. Set deadlines.

• "Writing is the act of putting your ass in the chair."

• Robin applauds Simone's book title, How to Not Know, for its playfulness and relevance. He asks how Simone's own relationship with uncertainty has evolved through his research.

• Simone reflects on how writing his first book, The Good Enough Job, softened his stance, from a hot take to a more nuanced view of work's role in life. Similarly, with his new book, his thinking on uncertainty has shifted.

• "Uncertainty is uncomfortable by design. That discomfort is what makes us pay attention."

• Simone once championed uncertainty for its spontaneity and freedom. But now, he sees a more complex dance between certainty and uncertainty.

• "Certainty begets the ability to become more comfortable with uncertainty."

• He gives the example of a younger self traveling with no plan, and the maturity of seeing how some people use uncertainty to avoid depth and commitment.

Durable Skills for an Unstable Future (43:57.613)

• Robin shifts to the practical: In a world where stability is fading, what should we teach future generations?

• Simone shares three core "durable skills":

• Learn how to learn – Adaptability beats certainty.

• Tell compelling stories – Human connection never goes out of style.

• Discern control from chaos – Use a mental decision tree:

• What can I control?

• If I can't control it, can I prepare?

• If I can't prepare, can I accept?

• "Often we're more uncomfortable with uncertainty than with a certain bad outcome."

• He cites research showing people are stressed more by maybe getting shocked than actually getting shocked.

AI as Editor, Not Author (47:23.765)

• Robin circles back to AI. Simone explains how his relationship with it has evolved:

• He never uses it for first drafts or ideation.

• Instead, AI serves as a "sparring partner" in editing – great at spotting drag, less useful at solving it.

• "People are often right about something being wrong, but not about the solution. I treat AI the same way."

• Simone defends creative friction as essential to craft: rewriting, deleting, struggling – that's the work.

The Chinese Farmer & the Fallacy of Forecasts (50:27.215)

• Robin expresses cautious optimism – but also fears AI will widen inequality and erode entry-level jobs. He asks what gives Simone hope.

• Simone counters with the "Parable of the Chinese Farmer," where events can't be judged good or bad in real time. His conclusion: we don't know enough to be either pessimistic or optimistic.

• "Maybe AI ushers in civil unrest. Maybe a golden age. Maybe yes, maybe no."

• He's most hopeful about the growing value of human touch – gifts of time, love, and effort in an increasingly automated world.

Where to Find Simone (53:44.845)

• Website: thegoodenoughjob.com

• Newsletter: The Article Book Club (monthly articles not written by him, thousands of subscribers)

• Robin reminds listeners that Simone will be the opening speaker at Responsive Conference 2025, September 17–18.

People Mentioned:

• M'Gilvry Allen

• Anne Helen Petersen

• Anis Mojgani

• Bree Groff

• Tim Ferriss

• Steven Pressfield

• Ernest Hemingway

• Justin Gordon

Organizations Mentioned:

• Responsive Conference

• Zander Media

• Asana, Inc

• X, The Moonshot Factory (formerly Google X)

• Waymo,

• Jewish Community Centers (Boulder & Denver)

• Robin's Cafe

• Amazon

• Google / Alphabet

Books & Newsletters

• The Good Enough Job

• How to Not Know (upcoming book)

• The 4‑Hour Workweek

• Just Go Grind

• Article Book Club