What happens when authenticity becomes your superpower?

For Goldie Chan, she turned her authentic, vulnerable story into a personal brand everyone wants. She’s the founder of Warm Robots, a Forbes contributor, and the author of Personal Branding for Introverts, a guide to building influence without pretending to be someone you’re not.

Dubbed the “Oprah of LinkedIn,” Goldie built one of the most trusted voices in storytelling and leadership by doing something revolutionary in the age of algorithms: leading with heart.

In this episode, Healey Cypher sits down with Goldie to talk about how stories shape trust, why vulnerability is magnetic, and what it really takes to connect in a world run by metrics.

You’ll hear:

• How emotional intelligence beats IQ in leadership and influence

• The two versions of every great story (and when to use each)

• Why authenticity builds more trust than perfection ever could

• How to make one-to-many communication feel one-to-one

• Why “Yes, and…” might be the secret to better teams and conversations

• How Goldie’s cancer story became a masterclass in vulnerability

• The storytelling framework that every founder should steal

This conversation is equal parts strategy and soul. It’s about turning your humanity into your advantage and proving that empathy, not ego, is the real growth engine.

⏱️ EPISODE TIMESTAMPS

00:00 — The story behind Don’t Be a Jerk (and Adam Grant’s advice)

05:00 — Meet Goldie Chan: from poetry to the “Oprah of LinkedIn”

10:00 — Why storytelling is the most human skill we have left

14:30 — “Broetry,” bad writing, and how to actually hook your reader

19:00 — Vulnerability as a superpower: Goldie’s cancer story

22:00 — The two versions of every story: short vs. long

26:30 — Authenticity → Trust → Performance: the leadership loop

31:00 — The improv rule that transforms conversations

34:00 — How to make one-to-many feel one-to-one

40:00 — Confidence vs. ego — and why both are contagious

47:00 — Storytelling as a muscle: how to keep it strong

55:00 — Goldie’s final lesson: tell the story that resonates

🎧 Listen now to this episode of Don’t Be a Jerk wherever you get your podcasts.

Follow along for more conversations on leadership, empathy, and storytelling in the age of AI:

IG: @healeycypher

@dontbeajerkpodcast

LinkedIn:

Healey Cypher

What happens when life throws you something you can’t control?

For Lucy Aragon, the answer was to keep dancing.

She’s been to 105 countries, built a life around optimism and adventure, and faced her husband’s cancer diagnosis with humor, perspective, and a contagious belief that joy isn’t luck. It’s work.

In this episode, Healey Cypher sits down with Lucy to talk about the art of staying light when life gets heavy. From her solo travels through war zones to the lessons she learned about resilience, confidence, and perspective, Lucy’s story is a reminder that happiness isn’t something you find. It’s something you create.

You’ll hear:

- How travel rewires your empathy and your brain

- Why “the rules were invented by people way stupider than you”

- The moment in Yemen that changed how she sees courage

- How humor became her greatest survival tool

- Why optimism is a health advantage, not a personality trait

- The 50 Cent quote that helped her beat anxiety and depression

- What lighting poop on fire taught her about leadership and joy

This conversation is equal parts philosophy and laughter. It’s about choosing perspective over panic, humor over fear, and joy as a daily act of rebellion.

⏱️ EPISODE TIMESTAMPS

00:00 — How Healey and Lucy met (and why she lights up every room)

04:00 — Travel as a teacher: empathy, perspective, and the Yemen story

10:00 — “The rules were invented by people way stupider than you”

15:30 — Disneyland, the 8-year-old, and the moment Lucy realized most rules are fake

24:30 — Facing cancer with confidence, humor, and perspective

31:00 — Why optimism isn’t denial

35:45 — How comparison became the thief of modern joy

39:00 — Travel, gratitude, and the psychology of happiness

45:20 — “Depression is a luxury” from 50 Cent

49:00 — Anxiety, control, and the mental rewiring that joy requires

55:00 — The loneliness epidemic and how to fight it with connection

01:05:00 — The art of humor (even when life is serious)

01:10:00 — Lighting poop on fire (yes, really) and parenting through joy

01:17:00 — Why intention matters more than perfection

01:22:00 — Lucy’s final lesson: You can just be happy, without being rich or successful

—

🎧 Listen now to this episode of Don’t Be a Jerk wherever you get your podcasts.

Follow along for more conversations on leadership, kindness, and the science of joy:

IG: @healeycypher | @dontbeajerkpodcast

LinkedIn: https://www.linkedin.com/in/healeycypher/

What does it take to build a real community in a world that rewards hustle over humanity?

Espree Devora has spent over a decade answering that question.

She’s the founder of We Are LA Tech and host of Women in Tech, where she’s spent thousands of hours connecting entrepreneurs, creators, and founders (and learning the hard way what it means to lead with empathy).

In this episode, Healey Cypher sits down with Espree to explore the science and soul of connection. From raising venture capital with no introduction to Sequoia, to learning the power of boundaries, breathwork, and burnout recovery, Espree shares how to build communities that last, starting with yourself.

You’ll hear:

- Why community is a human survival tool, not a marketing strategy

- The simple mindset shift that made Espree fall in love with herself

- How to set boundaries without shutting people out

- Why “curious compassion” can fix almost any conflict

- The real reason most founders burn out

- What Tony Hsieh taught her about culture and core values

- How to build belonging without losing yourself in the process

This conversation is equal parts tactical and deeply human. It’s about self-worth, leadership, and why the most successful communities are built on something simple but radical: love.

🎧 Listen now to this episode of Don’t Be a Jerk on Spotify, Apple Podcasts, or wherever you get your shows.

Follow along for more conversations on empathy, leadership, and the art of human connection:

@healeycypher | @dontbeajerkpodcast

What happens when you build a $400 million startup and then lose it all?

For James Beshara, the answer wasn’t another company. It was a complete rewiring of how to live.

In this episode, Healey Cypher sits down with the founder of Tilt (acquired by Airbnb) and Magic Mind to talk about the unseen side of ambition: the waves you catch, the ones you miss, and the peace that comes when you stop fighting the current.

James shares how public failure became the best thing that ever happened to him, why stillness is the ultimate competitive advantage, and how a decade of studying philosophy (Advaita Vedanta) reshaped his definition of success.

You’ll hear:

- How to build mental wealth the same way you build physical health

- Why “we don’t see the world as it is; we see it as we are”

- The founder trap of external validation and how to escape it

- The 90-minute morning ritual that keeps him calm in chaos

- Why work without attachment is a form of worship

- The story behind my $100 million mistake and what it taught him about ego

- The simple, radical truth that changed his life: “It’s not out there.”

This conversation is a rare blend of practicality and philosophy. It’s about ambition without anxiety, growth without ego, and finding meaning in the middle of the mess.

🎧 Listen now to this episode of “Don’t Be a Jerk” on your favorite podcast platform.

What if telling the truth faster could make your company more profitable, your culture stronger, and your life easier?

Robert Yuen, CEO of Monograph, believes it can. He has built an entire business around it.

In this episode of Don’t Be a Jerk, Healey sits down with Robert to unpack what radical transparency really looks like in practice. They discuss everything from open dashboards and revenue lines visible to every employee, to investor meetings where Robert leads with the hard stuff first.

Together, Healey and Robert explore:

- Why transparency is the ultimate trust accelerant and the only sustainable culture strategy

- How to communicate bad news without breaking morale

- When to hold back information and how to do it without eroding trust

- Why asking for help early saves startups from silent collapse

- How Monograph uses visual dashboards, revenue transparency, and consistent cadences to eliminate surprises

- The money conversation script architects and founders should use to make pricing fair, firm, and drama-free

- How transparency with investors flips power dynamics and attracts the right partners faster

- The surprising reason radical honesty is also a form of self-care

Robert’s leadership philosophy is simple but bold: “Transparency might backfire sometimes, but it always nets positive.”

This episode is part tactical playbook, part therapy session for founders who are tired of carrying everything alone. If you have ever wondered how to build a company that runs on trust rather than politics, this conversation is your blueprint.

Listen and subscribe wherever you get your podcasts!

Empathy is one of the most powerful tools we have for survival, leadership, and connection.

In this episode of Don’t Be a Jerk, Healey Cypher sits down with Jamil Zaki — Stanford psychology professor, empathy researcher, and author of The War for Kindness — to explore why empathy is under siege and how we can build it back, stronger than ever.

Jamil shares:

• Why empathy has declined 40% in the past few decades and why that’s reversible.

• How reading fiction can be a “gateway drug” for empathy.

• A simple tactic to de-escalate conflict (marriage fights included): list what you don’t know and what you already agree on.

• Why organizations that lead with empathy have lower turnover, more innovation, and stronger profits.

• How to move from a “warrior mentality” to a guardian mentality in leadership.

• Why nobody says hi… but everybody says hi back (and what that reveals about loneliness).

• The contagious nature of kindness and how to spark a ripple effect in your team.

• Why Jamil believes the empathy deficit is less about supply, and more about demand.

This is empathy with receipts: science, data, and tactical frameworks you can use today. Whether you’re running a company, managing a team, or just trying to argue better with your spouse, this episode is for you.

When you think about “service,” you might picture a volunteer day with matching T-shirts or a line on a résumé. But for Shakirah Simley, service is deeper. It’s generational. It’s survival. And it’s the force that has guided her life and leadership.

Shakirah grew up in Harlem and the South Bronx, raised by a family of Black women leaders, social workers, and activists. Today, she’s the Executive Director of the Booker T. Washington Community Service Center in San Francisco, where she’s quintupled the budget, quadrupled the staff, and transformed the center into a thriving hub of housing, education, food justice, and wellness.

In this conversation, Shakirah and Healey explore:

- Why research shows service makes us healthier, happier, and even live longer

- The difference between “resume service” and service that truly transforms communities

- Why low-income and marginalized communities are often the most generous

- How to prevent burnout when your job is helping others

- Shakirah’s framework for service: time, treasure, and talent

- The connection between service, empathy, and stronger democracies

- Why humility isn’t optional if you want to lead with impact

This conversation is about building trust, resilience, and joy through the act of giving back.

If you’ve ever thought “I’m too busy to volunteer” or wondered how to make service a real part of your life, this episode will change how you think.

When I first met Young Han, he wasn’t coming on my podcast. He was stepping in as a fractional CFO to help me lead through one of the hardest stretches of my career.

Within 15 minutes of our first meeting, he scrapped his entire plan and said: “We’re meeting three nights a week at 7pm until we get through this.” And then he did. Night after night, Young sat down with me and helped me push through. That’s who he is.

Today, Young is a serial founder, fractional COO/CFO, coach, and host of The Girl Dad Show. He’s on a mission to build 20 businesses to $1M ARR each. But more importantly, he’s built an operating system for human connection.

In this episode we cover:

- Why Starbucks taught him that relationships can outweigh even product quality

- His 4-step framework for building trust instantly

- The Rule of 100 and how it increases your surface area for luck

- Why the future belongs to the emotionally fluent, not just the technically brilliant

- Why diversity is a competitive advantage

- How to prepare for interactions without being transactional

Young’s story is part playbook, part inspiration, and all high-energy. If you want to learn how to scale not just your business but your relationships, this one’s for you.

Full episode is live now on Spotify, Apple Podcasts, and YouTube.

Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai, helping 100+ brands land in inboxes instead of spam. But ask anyone who’s worked with him, and they’ll tell you his real superpower isn’t just building businesses. It’s building people.

In this conversation, we dig into:

- Why sharing problems faster leads to better solutions (and stronger relationships).

- The inner circle of advisors that Aaron has relied on for years, and how you can build one too.

- His personal framework for paying it forward without burning out.

- Why he only advises founders he’d be willing to work for himself.

- The surprising ROI of generosity (including the story of how a casual meeting in Bryant Park turned into co-founding Orita).

- How to be authentic without oversharing, and the boundaries that protect trust.

- Balancing the weight of being a founder with the realities of family, guilt, and joy.

- The books Aaron rereads to stay focused and grounded when life gets loud.

This one’s about generosity, luck, boundaries, and the human side of building. I walked away with a new perspective on who I help, how I help, and what I say yes to. And I think you will too.

Full episode is live now on Spotify, Apple Podcasts, and YouTube.

This one’s different. No guests, no interviews. Just me, your questions, and a few stories from the trenches.

Over the last few weeks of Don’t Be a Jerk, I’ve had incredible conversations with founders, VCs, coaches, and comedians. But behind the scenes, I’ve also been getting a flood of DMs, texts, and Slack messages with questions about leadership, empathy, and what it actually means to “not be a jerk” at work.

So in this special solo episode, I sit down to answer them. We get into:

- Why I started this podcast in the first place

- How to be conflict-seeking without being an asshole

- The #1 mistake early leaders make that kills credibility

- How to repair when you realize you were the jerk

- The difference between expectations and agreements

- How to fire someone without being cruel

- The art of debriefs and BLUFs (bottom line up front)

- Two things you can do tomorrow to become a better person

- How to rebuild trust once it’s been broken

This episode is part playbook, part confession, part experiment, but at the core it’s about the same idea that launched this whole show: kindness in leadership isn’t weakness. It’s strategy.

If you’ve got more questions you want me to tackle in a future solo episode, drop them in the comments, DM me, or send a carrier pigeon. You never know, maybe your question makes the next one.