From Start-Up to Grown-Up

Alisa Cohn
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One of the top startup coaches in the world, Alisa Cohn, talks to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in growing from Start-up to Grown-up.

  1. Aug 10

    124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE]

    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 BrewWhy early reader behavior revealed that the idea had real potentialWhy regret minimization helped him make a life-changing decisionWhat happened behind the scenes during Morning Brew’s acquisitionWhy the $75 million exit felt different from what Alex expectedHow OCD and panic attacks affected Alex’s experience as a founderWhy founders can struggle with identity after an exit or leadership transitionHow to build a “purpose portfolio” beyond your professional titleHow to choose an executive coach for your current challengesWhy reflection is an essential part of growing from founder to leaderWe 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: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE]

  2. Jul 27

    123: GiaNina Paolantonio Has Millions of Followers. Here’s the Business Behind Them

    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 businessWhy one sold-out class became the foundation of a global teaching tourHow she evaluates brand partnerships and confidently turns down lucrative dealsWhy refusing to stay in one niche may create greater career longevityWhat creators must understand about contracts, exclusivity, and content rightsHow she manages public criticism, overwhelm, and competing demandsWhy authenticity is the foundation of her brand and long-term strategyWe 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/GiaNinaPaolantonioConnect with Alisa! Follow Alisa Cohn on  Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    123: GiaNina Paolantonio Has Millions of Followers. Here’s the Business Behind Them

  3. Jul 13

    122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed

    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: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed

  4. Jun 29

    121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold

    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 underestimateThe 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 survivalWhat changed when Fold went public How to spot when an executive has stopped scaling with the companyWhat imposter syndrome actually feels like from inside a public company CEO roleWe 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: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold

  5. Jun 15

    120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro

    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 againHow AI is changing the future of collaboration and teamworkWhat "day one thinking" means and why founders need itThe difference between experimentation in scaling versus reinventionWhy conviction matters more than consensus in zero-to-one innovationHow founders can communicate vision when they can't fully articulate it yetThe biggest mistake leaders make when trying to innovate inside large organizationsWhy founder mode and CEO mode are both essential leadership skillsHow AI is reshaping management, teams, and organizational designThe surprising reason culture becomes weaker as companies scaleWhy entrepreneurial talent is becoming more valuable than specialized expertiseHow to create startup energy inside an established businessThe role of trust, feedback, and productive conflict in high-performing teamsWhy leadership chemistry matters more than most executives realizeThe mindset shift required to survive rapid technological disruptionWe 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: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro

  6. Jun 1

    119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit

    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 destroyingWhat Eric Ries means by “financial gravity”How companies lose their mission after founders lose controlWhy Costco became one of the strongest governance models in businessThe hidden danger of shareholder primacyWhy trustworthiness may be the most underrated asset in businessHow Lean Startup was misunderstood by most foundersThe real purpose behind MVPs and rapid experimentationWhy principles create faster companies, not slower onesHow aligned teams move faster with less management overheadWhat Anthropic is doing differently with AI governanceWhy constraints often create breakthrough innovationThe leadership lesson Eric learned from nearly compromising his own principlesHow founders can build companies their grandchildren will be proud ofWe 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: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit

  7. May 18

    118: Josh Reeves, Co-Founder and CEO of Gusto, The 3-Part Alignment Framework Every Founder Needs Before Their Next Hire [ENCORE]

    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 processHow to scale a hiring process so culture stays intact past 50, 150, and 2,500 employeesWhat the Platinum Rule is and why it will transform how you give feedbackThe 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 muchWhy great talent sometimes fails at the wrong stage companyWhat Josh learned from a previous startup that shaped everything about how Gusto was builtThe one question to ask yourself before committing to any startup ideaWe talk about: 00:00 Introduction to Josh Reeves and Gusto02:00 The founding story and what problem Gusto was built to solve08:00 The three-part hiring alignment framework: values, motivation, and skill17:00 How Gusto scaled their hiring culture to 2,500 employees19:00 How the CEO role evolved across 12 years24:00 Symptoms of a leader who is outpacing their role vs. one who came from too large a company29:00 The difference between builders and managers in a startup33:00 Situational leadership and why directive leadership is not the opposite of empowerment37:00 The Platinum Rule and how it changed the way Josh gives feedback48:00 Highs, lows, and leading through uncertainty as a founder59:00 The lesson from his previous startup that shaped everything about Gusto01:03:00 Final advice for founders: imagine describing your company for the 10,000th timeFollow Josh on LinkedIn: https://www.linkedin.com/in/joshuareeves/Website: https://gusto.com/ Connect with Alisa! Follow Alisa Cohn on  Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    118: Josh Reeves, Co-Founder and CEO of Gusto, The 3-Part Alignment Framework Every Founder Needs Before Their Next Hire [ENCORE]

  8. May 4

    117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up

    What happens after you “make it”… and realize money was never the point? In this episode, Jyoti Bansal, Founder & CEO of Harness and founder of AppDynamics (sold for $3.7B), sits down with Alisa Cohn for a conversation that cuts deeper than typical startup playbooks. This is not just about building companies. It’s about what happens when the finish line disappears… and you have to decide who you are without it. Jyoti shares the unexpected identity crisis that hit after his exit, why he chose to build again anyway, and what most founders misunderstand about success, sales, and staying relevant in a world that’s changing faster than your roadmap can keep up. From the brutal reality of startup milestones to the urgency of the AI transformation, this episode is a masterclass in how to think, move, and lead when the stakes are real. You’ll learn: Why a worse product can still beat you (and how to prevent it)The hidden identity crisis founders face after a big exitHow to think of entrepreneurship as a craft, not a one-time eventWhy startup growth is about milestones, not perfectionThe real reason most companies fall behind during major tech shiftsHow to operate in “founder mode” when speed is everythingThe difference between product differentiation and go-to-market dominanceHow to build a scalable sales machine (not just hire “charismatic closers”)The hiring framework Jyoti uses to spot elite sales talentHow to align a company fast during high-pressure transformationThe “startup within a startup” model that creates ownership at scaleWhy transparency in numbers builds accountability across the entire orgWe talk about: 00:00 The uncomfortable truth after a billion-dollar exit02:00 Why Jyoti came back to build again05:00 The founder identity crisis no one prepares you for08:00 Entrepreneurship as a craft, not a single shot11:00 The milestone framework for building successful companies15:00 The AI transformation and why most companies will lose18:00 Founder mode, speed, and making decisions in real time22:00 Aligning teams when everything is changing fast26:00 Why revenue is the only truth in business29:00 Sales as a competitive advantage 32:00 The myth of “relationship-based” selling35:00 Building a scalable, structured go-to-market machine38:00 How to hire great sales leaders (and avoid getting sold in the interview)41:00 The onboarding mistake most founders make44:00 Transparency, numbers, and company-wide accountability47:00 The “startup within a startup” model explained52:00 Ownership, incentives, and building multiple winning products Follow Jyoti on LinkedIn: https://www.linkedin.com/in/jyotibansalWebsite:  ​https://www.harness.io/Connect with Alisa! Follow Alisa Cohn on  Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload 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

    117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up
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About

One of the top startup coaches in the world, Alisa Cohn, talks to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in growing from Start-up to Grown-up.

Information

  • Creator
    Alisa Cohn
  • Years Active
    2021 - 2026
  • Episodes
    125
  • Rating
    Clean
  • Copyright
    © 2026 From Start-Up to Grown-Up
  • Show Website
    From Start-Up to Grown-Up

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