From Start-Up to Grown-Up

What if the most valuable asset you can build as an entrepreneur is not your company, but your relationships?

Jayson Gaignard built one of Canada’s largest ticket-wholesaling businesses, only to realize he had created a company he hated. When circumstances left him approximately $250,000 in debt, with a six-month-old daughter and a new marriage, he began investing in the one thing no one could take from him: his relationships.

That decision eventually led Jayson to create MMT, an invite-only entrepreneurial community built around intentional connection, carefully curated experiences, and the belief that success should never be pursued alone.

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Jayson to explore how entrepreneurs can build meaningful professional relationships, make the most of conferences, overcome social anxiety, and develop the courage to enter rooms where they do not yet feel they belong.

Jayson also shares the story behind buying 4,000 copies of Tim Ferriss’s book, his “eight seconds of courage” strategy for doing intimidating things, and the leadership decision that put nearly $2 million at risk during the pandemic.

This is a candid conversation about entrepreneurial community, relationship building, leadership, discomfort, comparison, and why proximity to the right people can change the trajectory of your life.

You’ll learn:

• How Jayson turned a financial and personal crisis into a new entrepreneurial path
• Why meaningful relationships are among the safest investments a founder can make
• How to build an aspirational network before you have status or connections
• Why attending the right events can accelerate years of relationship building
• How to prepare for conferences and follow up before the excitement fades
• How “eight seconds of courage” can help you move through social anxiety
• Why MMT prioritizes character and connection over financial success
• How Jayson made an integrity-driven decision involving nearly $2 million
• Why comparison can quietly damage otherwise meaningful relationships
• How founders can balance ambition with their health and long-term well-being

We talk about:

00:00 Meet Jayson Gaignard, founder of MMT and author of Community Made

03:12 Building a successful business he ultimately hated

05:00 Facing $250,000 in debt and searching for what came next

06:00 Why Jayson began investing in relationships

07:00 Buying 4,000 copies of Tim Ferriss’s book

09:16 Using regret minimization to make difficult decisions

12:00 How the right room can change your life

16:06 Building an aspirational network from scratch

22:22 How to make the most of conferences and large events

28:15 Managing social anxiety through preparation

29:45 Using eight seconds of courage to do hard things

34:07 Why personal growth requires discomfort

37:47 Building MMT as an invite-only entrepreneurial community

42:48 Leading a community like a company

45:15 Making a nearly $2 million decision during the pandemic

47:19 Why leaders cannot avoid difficult conversations

49:06 Escaping comparison and jealousy around successful peers

55:20 The long-term cost of entrepreneurial stress

56:51 Jayson’s advice for founders growing into leaders

Follow Jayson on

• LinkedIn: https://www.linkedin.com/in/jaysongaignard/ 
• Instagram: https://www.instagram.com/jaysongaignard 
• Website: https://www.jaysongaignard.com/ 
• Read Community Made: The Truth About Success and the Relationships That Create It

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

How did Joe Thomas and his co-founders keep building Loom when they had maxed-out credit cards and only 14 days of runway left?

Before Loom became one of the most recognizable asynchronous video platforms, Joe Thomas, Vinay Hiremath, and Shahed Khan spent nine months testing ideas, making major pivots, and listening closely to early users. Their persistence eventually transformed a struggling user-feedback product into a new way for people to communicate at work.

In this encore episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Joe to explore Loom’s earliest days, the approximately 100 fundraising rejections that strengthened his pitch, and the leadership lessons he learned while scaling the company.

Joe also reveals why Loom defined its values when the team had only seven people, how meditation helped him make better decisions, and why founders must become comfortable doing the work they would naturally rather avoid.

This is a candid conversation about resilience, fundraising, company culture, asynchronous leadership, and what it takes to grow from founder to CEO.

You’ll learn:

• How Joe Thomas and his co-founders discovered the idea for Loom
• How Joe improved his fundraising skills after approximately 100 rejections
• Why founders often avoid the responsibilities that make them uncomfortable
• How Loom defined its company values with only seven employees
• Why values become most important during difficult decisions
• How meditation helped Joe become less reactive as a leader
• Why giving difficult feedback can be an act of belief
• How leaders can protect their energy while building a company
• When to communicate asynchronously and when to hold a meeting
• Why discomfort is an unavoidable part of growing into a leader

We talk about:

00:00 Meet Joe Thomas, co-founder of Loom

01:27 The original idea behind video communication at work

04:20 Nine months of experimentation, customer conversations, and pivots

10:17 Starting the company with $25,000 and a mattress on the floor

12:20 Reaching the final 14 days of runway

16:17 Learning to fundraise after approximately 100 rejections

19:44 Choosing investors for a long-term relationship

22:01 Tracking time and prioritizing a founder’s responsibilities

31:43 Defining Loom’s values with only seven employees

42:13 How meditation improved Joe’s decision-making

46:13 Balancing empathy with difficult feedback

50:33 Becoming friends with hard times

51:28 Why taking care of yourself makes you a better CEO

57:10 When to use asynchronous communication instead of a meeting

01:01:04 Learning to live with imposter syndrome

01:03:28 What Joe wishes he had understood earlier

01:05:16 Joe’s advice for founders growing into leaders

Follow Joe on

• LinkedIn: https://www.linkedin.com/in/joethomasx/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What if the biggest mistake CEOs are making with AI is trying to improve the company they already have?

Seth Levine believes leaders need to ask a more radical question: If you were building your company from scratch today, how would you design it?

Seth is a founder, investor, author, and co-founder of Foundry, the venture capital firm he built alongside Brad Feld and their partners. After decades of working with founders, boards, and leadership teams, he has seen what separates businesses that adapt from those that remain anchored to the way things have always been done.

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Seth to explore how CEOs should approach AI transformation, why incremental efficiency is not enough, and what it takes to rethink an organization from the ground up.

Seth also shares the rarely told story behind Foundry’s creation, including the fifth founding partner who ultimately left the firm, the difficult conversation that ended a close friendship, and the months of rejection Seth and his partners endured while attempting to raise their first fund. At one point, Seth believed he had lost his family’s entire life savings. One pivotal yes changed everything, helping Foundry close a $225 million fund.

This is a candid conversation about building boldly, leading intentionally, and creating enough space to breathe along the way.

You’ll learn:

• The most important AI question every CEO and board should be asking
• Why using AI to improve productivity is not the same as becoming AI-native
• How legacy workflows prevent established companies from transforming
• Why CEOs need firsthand experience with emerging AI tools
• How Foundry used coaching to build a healthier partnership from the beginning
• How to prepare for a difficult leadership conversation
• Why Foundry’s first fund nearly failed before closing at $225 million
• How one significant yes can change the momentum of a fundraising process
• The three qualities Seth sees in the most successful founders
• How intentionality helps leaders remain bold without burning themselves out

We talk about:

00:00 Meet Foundry co-founder Seth Levine

01:25 The 25-year relationship between Seth Levine and Brad Feld

02:06 How boards should evaluate the opportunities and threats created by AI

04:19 Why most companies are still only dabbling with AI

08:50 The difference between improving a company and rebuilding it for the AI era

13:08 How CEOs can redesign their organizational structure from scratch

14:05 Why leaders need to experiment with AI tools themselves

18:00 How organizational coaching shaped Foundry from the beginning

21:44 Seth’s productivity system and morning planning routine

26:38 The untold story of Foundry’s original fifth partner

31:11 The words Seth used to begin a difficult leadership conversation

37:39 The pivotal yes that helped Foundry raise its first $225 million fund

41:32 How writing helped Seth build his reputation and personal brand

55:00 The difference between expressing company values and entering politics

57:21 The qualities Seth looks for in successful founders

59:19 What Seth wishes he had understood earlier in his career

01:03:48 Seth’s advice for founders growing into leaders

Follow Seth on

• LinkedIn: https://www.linkedin.com/in/sethjlevine/ 
• Books: https://sethlevine.com/books/ 
• Website: https://sethlevine.com/ 
• Foundry: https://foundry.vc/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What comes after you build and sell the company that has defined your entire adult life?

Alex Lieberman co-founded Morning Brew as a college student after noticing that traditional business news felt dense, dry, and disconnected from the way young professionals wanted to consume information. What began as a Microsoft Word document emailed to a small group of students grew into one of the world’s most recognizable business media brands and ultimately led to a reported $75 million deal.

But the exit was not the end of Alex’s entrepreneurial journey. It became the beginning of a deeper conversation about identity, leadership, purpose, and what success is actually supposed to feel like.

Alex is now on his new entrepreneurial journey building Tenex, an AI transformation consulting firm. 

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Alex to unpack the decisions behind Morning Brew’s growth. Alex shares why he walked away from his dream job at Morgan Stanley, how he found a co-founder whose strengths complemented his own, and what he learned when the business needed him to evolve from a builder into an operational CEO.

This is an honest, thoughtful conversation about building something remarkable while remembering that your company is something you do, not the entirety of who you are.

You’ll learn:

• How Alex Lieberman transformed a college newsletter into Morning Brew
• Why early reader behavior revealed that the idea had real potential
• Why regret minimization helped him make a life-changing decision
• What happened behind the scenes during Morning Brew’s acquisition
• Why the $75 million exit felt different from what Alex expected
• How OCD and panic attacks affected Alex’s experience as a founder
• Why founders can struggle with identity after an exit or leadership transition
• How to build a “purpose portfolio” beyond your professional title
• How to choose an executive coach for your current challenges
• Why reflection is an essential part of growing from founder to leader

We talk about:

00:00 Meet Morning Brew co-founder Alex Lieberman

01:08 How a college newsletter became Morning Brew

04:16 Finding a co-founder with complementary strengths

08:19 Leaving Morgan Stanley to build Morning Brew full time

10:31 Using worst-case scenarios and regret to make difficult decisions

19:18 Navigating Morning Brew’s acquisition during the pandemic

23:25 Why the $75 million exit felt surprisingly underwhelming

28:32 Realizing he was a builder CEO, not an operational CEO

31:34 Leading a growing company while managing OCD and panic attacks

36:01 Losing his identity after transitioning out of the CEO role

40:00 Rebuilding through reflection, experimentation, and connection

50:19 Why every founder needs a diversified “purpose portfolio”

57:27 Making mistakes as a strategy for entrepreneurial growth

01:00:45 What Alex wishes he had understood earlier

Follow Alex on

• Instagram: https://www.instagram.com/alexlieb 
• LinkedIn: https://www.linkedin.com/in/alex-lieberman/ 
• Website: https://alexlieberman.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

GiaNina Paolantonio has spent most of her life in the spotlight. She made her Broadway debut in Matilda the Musical at nine, appeared in The Greatest Showman and Dance Moms, and built an online audience of millions. But behind the performances, viral videos, and global following is something much bigger: a multi-channel business built around dance, creativity, and authenticity.

Today, GiaNina’s business includes social content, brand partnerships, dance education, collaborations with artists and record labels, and a global teaching tour developed and managed alongside her family.

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with GiaNina to explore the business behind being a creator. GiaNina shares how one sold-out dance class became an international opportunity, why she refuses to let one niche define her career, and how she monetizes her audience without promoting products or partnerships she does not believe in.

This is an honest look at what it takes to turn creative talent and online influence into an enduring business without losing yourself along the way.

You’ll learn:

• How GiaNina transformed dance and social media into a multi-channel business
• Why one sold-out class became the foundation of a global teaching tour
• How she evaluates brand partnerships and confidently turns down lucrative deals
• Why refusing to stay in one niche may create greater career longevity
• What creators must understand about contracts, exclusivity, and content rights
• How she manages public criticism, overwhelm, and competing demands
• Why authenticity is the foundation of her brand and long-term strategy

We talk about:

00:00 Meet GiaNina Paolantonio

01:40 Going from the couch to Broadway at nine years old

06:00 Turning social media momentum into a career

08:20 Why GiaNina refuses to be confined to one niche

11:45 Building multiple revenue streams around dance and content

14:51 Creating her own global dance tour

18:30 How an Instagram post revealed worldwide demand

23:35 Managing overwhelm while building a public career

28:23 Handling criticism from millions of followers

33:32 Negotiating partnerships and turning down brand deals

38:00 The hidden business behind being a content creator

45:24 Evolving beyond early success and trusting what comes next

Follow GiaNina on

• Instagram: https://www.instagram.com/gianina 
• TikTok: https://www.tiktok.com/@gianina 
• YouTube: https://www.youtube.com/c/GiaNinaPaolantonio

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Justin Mares built Kettle & Fire into one of the best known bone broth brands in the country. Then he walked away from it to go after something a lot less exciting on paper: the red tape standing between Americans and the preventive health products that actually keep them well. 

His new company, Truemed, gives people a simple way to use money they already have set aside for health on things like workouts, better food, and sleep, instead of letting it sit unused or only get spent once they're already sick.

Alisa Cohn, executive coach and author of From Start-up to Grown-up, sits down with Justin to talk about why he left a thriving consumer brand to go build something in one of the most regulated, paperwork heavy industries there is. You'll hear how he tests ideas before he feels ready, how he hires for real mission alignment, why he chose venture capital this time around after largely bootstrapping Kettle & Fire, and how he still wrestles with imposter syndrome four companies in.

You’ll learn:

• Justin Mares walked away from Kettle & Fire, one of the best known bone broth brands in the country, to go build Truemed instead.
• Launching an imperfect product, like Justin's ghost landing page for Kettle and Fire built on $500 of ads, beats waiting for a perfect one.
• Justin chose venture capital over bootstrapping Truemed after growing Kettle and Fire to hundreds of millions in revenue on less than $10 million raised.
• Hiring your first five to ten people purely for mission alignment shapes every hire that follows, including Truemed's best employee, who found the company through Justin's newsletter.
• Andreessen Horowitz brought Truemed access to founders and operators that a bootstrapped CEO could never reach cold, well beyond the capital itself.
• Justin still deals with imposter syndrome after twelve years and four companies, and uses a specific reframe to move from doubt into action.
• Justin believes startups are fundamentally momentum games, and wishes he had learned to trust his own judgment earlier in his career.

We talk about:

00:00 Justin Mares introduces Truemed and its preventive health mission

00:29 Why Kettle and Fire exposed how expensive prevention really is

02:37 The red tape problem hiding inside health savings accounts

04:43 Why Justin pivoted from consumer products into fintech

07:39 What Truemed tested before writing a line of code

09:54 Why an ugly MVP still proved real customer demand

14:21 How Truemed built its first team around mission alignment

19:37 Why Justin chose venture capital over staying bootstrapped

24:39 What Andreessen Horowitz brought beyond the check

29:00 Why the MAHA movement matters for chronic disease

39:38 How Justin worked through his hardest founder decisions

43:57 What Justin wishes he had known earlier as a founder

Follow Justin on

• LinkedIn: https://www.linkedin.com/in/justinmares/ 
• Instagram: https://www.instagram.com/justin.mares 
• Website: https://justinmares.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Building a startup on Bitcoin means you're not riding one rollercoaster, you're riding two at once. The volatility of launching a company is hard enough. Layer on top of that a protocol still finding its own product-market fit, and you get a compounding effect that will break founders who aren't prepared for it. 

Will Reeves knows this firsthand. He co-founded Fold, lived through deep bear markets with no investor interest in sight, made a critical pivot after realizing he was building the wrong solution, and took Fold public on Nasdaq in February 2025 as the first Bitcoin financial services company on the exchange. 

In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Will Reeves, Co-Founder and CEO of Fold, to explore the real cost of building on Bitcoin, why "growth at all costs will destroy you," how a Starbucks line changed everything for Fold, what shifts the moment you go public, and the one truth about imposter syndrome most founders will never admit. 

You’ll learn:

• Why building a company on top of Bitcoin creates a compounding risk that most founders and investors seriously underestimate
• The exact moment Will realized Fold was solving the wrong problem, and how the pivot unlocked real product-market fit and landed Visa as their first major partner. 
• Why "growth at all costs" is uniquely dangerous for Bitcoin companies, and what it actually looks like to build a business for long-term survival
• What changed when Fold went public 
• How to spot when an executive has stopped scaling with the company
• What imposter syndrome actually feels like from inside a public company CEO role

We talk about:

00:00 Why building on Bitcoin means you're riding two rollercoasters at once 
04:03 Is resilience something you're born with or something you build over time? 
06:37 The advice Will gives founders on withstanding the startup journey day to day 
09:32 How Fold realized it was solving the wrong problem, and what they did about it 
13:22 How do you get your team on board when you've found a new direction? 
15:04 What Bitcoin is really for: decentralization, inflation, and financial freedom 
22:23 Why growth at all costs will destroy you when you're building on Bitcoin 
24:41 Why Fold went public via SPAC and what that decision looked like from the inside 
33:03 The painful lesson of replacing yourself as a founder CEO 
39:18 The lowest lows and highest highs of building Fold 
43:13 Have you ever experienced imposter syndrome? Will's honest answer 
46:43 Advice for founders on building a company and a life at the same time

Follow Will on

• LinkedIn: https://www.linkedin.com/in/will-reeves/ 
• Website: https://foldapp.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What happens when you've already built a company used by more than 100 million people, and suddenly the world changes again?

In this episode, Alisa Cohn sits down with Andrey Khusid, Founder and CEO of Miro, to explore one of the biggest leadership challenges founders face: reinventing a successful company while it's still growing.

As AI transforms the way teams work, Andrey shares how Miro evolved from a digital whiteboard into a collaborative platform where humans and AI agents create together. He explains why founders must embrace "day one thinking," how to build startup energy inside a 1,600-person organization, and why many leaders struggle when shifting between founder mode and CEO mode.

The conversation dives deep into innovation, company culture, organizational transformation, leadership chemistry, experimentation, and what it really takes to stay relevant when technology changes faster than ever.

If you're a founder, CEO, executive, or entrepreneur navigating growth, change, or AI disruption, this episode offers a masterclass in adapting without losing your mission.

You’ll learn:

• Why Andrey believes every company is now searching for product-market fit again
• How AI is changing the future of collaboration and teamwork
• What "day one thinking" means and why founders need it
• The difference between experimentation in scaling versus reinvention
• Why conviction matters more than consensus in zero-to-one innovation
• How founders can communicate vision when they can't fully articulate it yet
• The biggest mistake leaders make when trying to innovate inside large organizations
• Why founder mode and CEO mode are both essential leadership skills
• How AI is reshaping management, teams, and organizational design
• The surprising reason culture becomes weaker as companies scale
• Why entrepreneurial talent is becoming more valuable than specialized expertise
• How to create startup energy inside an established business
• The role of trust, feedback, and productive conflict in high-performing teams
• Why leadership chemistry matters more than most executives realize
• The mindset shift required to survive rapid technological disruption

We talk about:

00:00 How Miro evolved from a digital whiteboard to an AI-powered collaboration platform

04:00 Day One Thinking, AI disruption, and why every company must reinvent itself

06:00 Leading with conviction when the vision isn't fully formed yet

10:00 Finding product-market fit again inside a 1,600-person company

13:00 Founder Mode vs. CEO Mode and the leadership skills required for both

16:00 Learning faster, staying entrepreneurial, and adapting in the AI era

19:00 Culture Growth Trips, founder fit, and building a mission-driven company

24:00 Rebuilding startup energy, ownership, and accountability at scale

26:00 AI, organizational design, and the future of management

29:00 Leadership coaching, team chemistry, and creating a culture of trust

35:00 Why productive conflict beats politeness and how great teams challenge each other

42:00 The hardest lesson about company transformation and Andrey's advice for founders

Follow Andrey on

• LinkedIn: https://www.linkedin.com/in/khusid/
• Website: https://miro.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What if the biggest threat to your company is not competition, but the systems everyone told you to trust?

In this episode, Alisa Cohn sits down with Eric Ries, creator of the Lean Startup methodology and bestselling author of The Lean Startup, The Startup Way, and Incorruptible, for a conversation about leadership, corporate governance, innovation, and why so many modern companies lose their way as they grow.

Eric unpacks the dangerous side of “best practices,” why shareholder primacy often destroys long-term value, and how financial pressure quietly reshapes company culture from the inside out. He also shares the untold story behind Costco’s governance model, why Anthropic’s structure matters in the AI race, and what founders misunderstand about speed, alignment, and leadership integrity.

You’ll learn:

• Why many “best practices” are actually value destroying
• What Eric Ries means by “financial gravity”
• How companies lose their mission after founders lose control
• Why Costco became one of the strongest governance models in business
• The hidden danger of shareholder primacy
• Why trustworthiness may be the most underrated asset in business
• How Lean Startup was misunderstood by most founders
• The real purpose behind MVPs and rapid experimentation
• Why principles create faster companies, not slower ones
• How aligned teams move faster with less management overhead
• What Anthropic is doing differently with AI governance
• Why constraints often create breakthrough innovation
• The leadership lesson Eric learned from nearly compromising his own principles
• How founders can build companies their grandchildren will be proud of

We talk about:

00:00 Why Eric Ries says builders are “under siege”
02:00 The hidden problem with modern business “best practices”
05:00 Why shareholder primacy destroys long-term companies
08:00 The untold Costco and Sol Price story
12:00 How Costco built a governance fortress
16:00 Understanding “financial gravity” inside organizations
19:00 Why Costco shareholders defended leadership decisions
22:00 The problem with management entrenchment
24:00 Why corporations should function more like balanced systems
26:00 Anthropic’s governance structure and AI leadership
30:00 Why checks and balances do not kill innovation
32:00 The real philosophy behind Lean Startup
35:00 Why principles create speed inside organizations
38:00 The overlooked role of trust and alignment
40:00 Why great leaders intentionally make things harder
42:00 The danger of compromising on core values
44:00 Eric’s hardest leadership decision
46:00 What founders misunderstand about success and power
47:00 How to build companies designed to last generations

Follow Eric on

• LinkedIn: https://www.linkedin.com/in/eries/
• Website: https://theleanstartup.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What if you have been hiring wrong this entire time?

In this episode, Josh Reeves, Co-Founder and CEO of Gusto, a $10B people platform serving over 300,000 businesses, joins Alisa Cohn for one of the most practical and deeply human conversations about building teams that actually work.

This is not a generic leadership talk. This is a masterclass in how to hire people who genuinely care, how to scale a values-driven culture without losing it, and how to lead through the kind of uncertainty that breaks most founders.

Josh shares the three-part alignment framework Gusto uses at every level of hiring, why the skills conversation gets too much attention, how he fires himself from jobs as fast as possible, and what the Platinum Rule taught him about giving feedback that actually lands.

You’ll learn:

• Why values and motivation alignment matter more than skills in the startup hiring process
• How to scale a hiring process so culture stays intact past 50, 150, and 2,500 employees
• What the Platinum Rule is and why it will transform how you give feedback
• The difference between a builder and a manager (and why it matters enormously in a startup)
• How to recognize when a leader is in over their head before it costs you too much
• Why great talent sometimes fails at the wrong stage company
• What Josh learned from a previous startup that shaped everything about how Gusto was built
• The one question to ask yourself before committing to any startup idea

We talk about:

• 00:00 Introduction to Josh Reeves and Gusto
• 02:00 The founding story and what problem Gusto was built to solve
• 08:00 The three-part hiring alignment framework: values, motivation, and skill
• 17:00 How Gusto scaled their hiring culture to 2,500 employees
• 19:00 How the CEO role evolved across 12 years
• 24:00 Symptoms of a leader who is outpacing their role vs. one who came from too large a company
• 29:00 The difference between builders and managers in a startup
• 33:00 Situational leadership and why directive leadership is not the opposite of empowerment
• 37:00 The Platinum Rule and how it changed the way Josh gives feedback
• 48:00 Highs, lows, and leading through uncertainty as a founder
• 59:00 The lesson from his previous startup that shaped everything about Gusto
• 01:03:00 Final advice for founders: imagine describing your company for the 10,000th time

Follow Josh on

• LinkedIn: https://www.linkedin.com/in/joshuareeves/
• Website: https://gusto.com/ 

Connect with Alisa!

Follow Alisa Cohn on 

• Instagram: @alisacohn
• Twitter: @alisacohn
• Facebook: facebook.com/alisa.cohn
• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better) 

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon