From Start-Up to Grown-Up

Alisa Cohn

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. 1d ago

    126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE]

    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 LoomHow Joe improved his fundraising skills after approximately 100 rejectionsWhy founders often avoid the responsibilities that make them uncomfortableHow Loom defined its company values with only seven employeesWhy values become most important during difficult decisionsHow meditation helped Joe become less reactive as a leaderWhy giving difficult feedback can be an act of beliefHow leaders can protect their energy while building a companyWhen to communicate asynchronously and when to hold a meetingWhy discomfort is an unavoidable part of growing into a leaderWe 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: @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

    126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE]
  2. Aug 24

    125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch

    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 askingWhy using AI to improve productivity is not the same as becoming AI-nativeHow legacy workflows prevent established companies from transformingWhy CEOs need firsthand experience with emerging AI toolsHow Foundry used coaching to build a healthier partnership from the beginningHow to prepare for a difficult leadership conversationWhy Foundry’s first fund nearly failed before closing at $225 millionHow one significant yes can change the momentum of a fundraising processThe three qualities Seth sees in the most successful foundersHow intentionality helps leaders remain bold without burning themselves outWe 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: @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

    125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch
  3. 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]
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
4.9
out of 5
68 Ratings

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.

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