From Start-Up to Grown-Up

Learning how to run a startup board is one of the most overlooked jobs a founder has, and most CEOs never treat it like one. If your board meetings feel like flipping through a deck sent the night before, or investors keep filling the silence with their own agenda, the problem may be that no one is leading the room. Your board wants to be led. When you set the norms early, choose aligned investors, and invite independent directors for real expertise, governance becomes a source of energy instead of dread.Alisa Cohn, named the Top Startup Coach in the World at the Thinkers50/Marshall Goldsmith Global Coaches Awards and host of From Start-Up to Grown-Up, sits down with Mike Seckler, CEO of Justworks, the payroll, benefits, and HR platform for small businesses. Mike shares the one-pager he gives every potential board member, the dinner-table advice from his 12-year-old daughter that pulled him from the Justworks board into the business, and Ann Winblad’s lesson on intellectual stamina. You’ll also hear the Wall Street Journal test he uses for hard decisions, the imagined retro exercise that built trust before the Via acquisition, and why Justworks pulled back from its IPO in 2022.You’ll learn:How to run a startup board well above the median: send materials a week early, expect everyone to read them, start on time, and put phones in a basket so meetings stay substantive.Why your board actually wants to be led, and how a leadership vacuum invites investors to fill the space in ways that feel bad for everyone in the room.What to tell a potential independent director up front, using Mike Seckler’s one-pager on the board’s mission, values, what success looks like, self-assessments, and the standards management commits to.Why early choices about co-founders, first investors, and how much capital you raise build a “self-inflicted wound quotient” that can narrow your options for years.How the Wall Street Journal front-page test helps leaders make hard decisions, like a reduction in force, in a way that builds the brand instead of eroding it.How a lifeline exercise and an imagined retro, picturing the deal failing 18 months out, helped Justworks and the Via founders build trust before the acquisition.Why being the calmest person in the room is a leadership superpower, and how stepping away for two weeks helped Mike’s team grow faster than when he was everywhere.We talk about:00:00 Why risk in your 20s has almost no downside06:10 Surviving the dot-com bust when 80 to 90% failed10:01 Ann Winblad’s lesson on intellectual stamina16:32 How his 12-year-old daughter helped him choose Justworks20:42 How to run a startup board people want to join25:54 What should you tell a new board member up front?30:41 Why values like grit can be weaponized35:45 The Wall Street Journal test for hard decisions45:45 The imagined retro exercise behind the Via acquisition56:09 Why did Justworks pull its IPO before going public?1:02:31 Why taking two weeks off made his team grow1:16:03 The self-inflicted wound quotient every founder carriesFollow Mike onJustworks: https://www.justworks.comLinkedIn: https://www.linkedin.com/in/mikeseckler/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

To build a media business as an independent journalist, you need more than a great newsletter. You need to see what your audience wants before anyone else does, then move fast. If you’ve ever talked yourself out of a big leap, waited for the perfect launch date, or wondered when your solo project becomes a real company, this conversation is for you. You’ll hear how a side event planned around a bachelor party became Cerebral Valley, an invite-only AI summit which has spawned numerous connections and deals, including the   $1.3 billion acquisition of MosaicML by DataBricks at its start.Alisa Cohn, named the Top Startup Coach in the World at the Thinkers50/Marshall Goldsmith Global Coaches Awards and host of From Start-Up to Grown-Up, sits down with Eric Newcomer, founder of Newcomer and a former Bloomberg tech reporter. Eric shares how he hired his first employee, why a RACI chart helped his team of four own their work, and what makes founders great storytellers. Alisa introduces the personal operating manual, a simple tool for telling your team how to work with you. Eric also explains why procrastination, not imposter syndrome, is his real challenge, and why he wishes he’d left Bloomberg a year sooner. You’ll learn:How to build a media business from a solo newsletter, and the moment Eric Newcomer realized Newcomer had become a real company with employees, contractors, and events.Why saying “I quit” out loud is the real act of leaving a secure job, and how Eric’s wife pushed him to stop rationalizing and finally go.How Cerebral Valley grew from a half-day event in a friend’s office into AI’s hottest ticket, with partners from Benchmark and Kleiner Perkins on board within 30 minutes.How to bring people together around an unmet need: know exactly who the event is for, book speakers people want to hear, and pick the topic before everyone else does.How a RACI chart and a personal operating manual help a small, remote media business team know who owns what and how to work with the founder.What makes founders great storytellers, from a reporter who has covered them for years: tell it truthfully, give the backstory, and tell it again and again with real enthusiasm.Why being decisive matters, from making the call on business decisions to leaving a job you’ve outgrown before you stay a year too long.We talk about:00:00 Why Eric Newcomer almost didn’t quit Bloomberg02:17 When does a newsletter become a media business?07:51 How a bachelor party became the Cerebral Valley AI Summit12:49 How do you spot opportunities before everyone else?15:18 Hiring the first employee for a one-person brand18:41 Using a RACI chart so everyone owns their work24:37 The personal operating manual and hearing the truth29:09 Journalist or influencer: can you be authentic online?39:12 What great founders and storytellers have in common44:03 Where the AI startup market is heading55:52 Why procrastination, not imposter syndrome, is Eric’s real struggle57:50 Why Eric wishes he’d left Bloomberg soonerFollow Eric onLinkedIn: https://www.linkedin.com/in/ericpnewcomer/ X: https://x.com/EricNewcomer Substack: https://www.newcomer.co/  YouTube: https://www.youtube.com/@newcomerpod  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

Most people don’t know that producing a Broadway show is like building a startup. That’s what Tony Award-winning Broadway producer Ken Davenport has learned over his decades producing hits.  He has to find the product, raise the capital, build the team, and get 1,000 to 2,000 people through the door eight times a week, for years. And when founders tell him their business is different, he tells them every business runs on the same principles. Ken is a Tony and Olivier Award-winning producer whose credits include Once On This Island, Godspell, Oh, Mary!, and A Beautiful Noise: The Neil Diamond Musical. He was the first to use dial testing on a Broadway-bound musical, landing him on the front page of The New York Times, and he crowdfunded Godspell with $5 million from 737 investors before Kickstarter existed. In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Ken to explore how he sees the potential in an idea before anyone else does, what he did when investors refused to write checks for a show he believed in, and why he raised money to build a marketing army, not just a budget. This is a candid conversation about product development, fundraising, market research, taste, and leadership, with a rare look behind the curtain of Broadway.You’ll learn:Why Broadway producer Ken Davenport believes every business runs on the same principles Why audiences choose the devil they know, and what that means for launching something new How Ken develops his taste and keeps challenging it as audiences change What Ken did when investors couldn't see the vision for Once On This Island How dial testing and audience research shape a Broadway show before it reaches New York Why Ken crowdfunded Godspell to build a marketing army, not just raise money How Ken uses AI to find patterns in reviews and audience data without replacing the artist Why founders should seek out rooms where they are not the smartest person, and how Ken handles imposter syndromeWe talk about:00:00 Meet Tony Award-winning Broadway producer Ken Davenport 01:52 How seeing Les Mis at 16 changed everything 06:03 Why a Broadway producer is really a startup founder 07:07 How do you find a hit the market can't explain yet 11:13 Developing taste in the age of AI 16:41 What do you do when investors won't write the check 19:49 Market testing and the first dial test on Broadway 24:00 Crowdfunding Godspell to build a marketing army 27:08 Marketing stunts that match the artistic message 30:00 How Ken Davenport uses AI without replacing the artist 36:23 Growing into a leader as an introverted extrovert 40:43 Imposter syndrome, showing face, and advice for founders Follow Ken onLinkedIn: https://www.linkedin.com/in/kendavenport/ Facebook: https://www.facebook.com/KenDavenport/ Instagram: https://www.instagram.com/kendavenportbway YouTube: https://www.youtube.com/channel/UCSKlIEVE5mIEoyktgQVt0jA Website: https://kendavenport.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

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 pathWhy meaningful relationships are among the safest investments a founder can makeHow to build an aspirational network before you have status or connectionsWhy attending the right events can accelerate years of relationship buildingHow to prepare for conferences and follow up before the excitement fadesHow “eight seconds of courage” can help you move through social anxietyWhy MMT prioritizes character and connection over financial successHow Jayson made an integrity-driven decision involving nearly $2 millionWhy comparison can quietly damage otherwise meaningful relationshipsHow founders can balance ambition with their health and long-term well-beingWe talk about:00:00 Meet Jayson Gaignard, founder of MMT and author of Community Made03:12 Building a successful business he ultimately hated05:00 Facing $250,000 in debt and searching for what came next06:00 Why Jayson began investing in relationships07:00 Buying 4,000 copies of Tim Ferriss’s book09:16 Using regret minimization to make difficult decisions12:00 How the right room can change your life16:06 Building an aspirational network from scratch22:22 How to make the most of conferences and large events28:15 Managing social anxiety through preparation29:45 Using eight seconds of courage to do hard things34:07 Why personal growth requires discomfort37:47 Building MMT as an invite-only entrepreneurial community42:48 Leading a community like a company45:15 Making a nearly $2 million decision during the pandemic47:19 Why leaders cannot avoid difficult conversations49:06 Escaping comparison and jealousy around successful peers55:20 The long-term cost of entrepreneurial stress56:51 Jayson’s advice for founders growing into leadersFollow Jayson onLinkedIn: 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 ItConnect 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

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 Loom01:27 The original idea behind video communication at work04:20 Nine months of experimentation, customer conversations, and pivots10:17 Starting the company with $25,000 and a mattress on the floor12:20 Reaching the final 14 days of runway16:17 Learning to fundraise after approximately 100 rejections19:44 Choosing investors for a long-term relationship22:01 Tracking time and prioritizing a founder’s responsibilities31:43 Defining Loom’s values with only seven employees42:13 How meditation improved Joe’s decision-making46:13 Balancing empathy with difficult feedback50:33 Becoming friends with hard times51:28 Why taking care of yourself makes you a better CEO57:10 When to use asynchronous communication instead of a meeting01:01:04 Learning to live with imposter syndrome01:03:28 What Joe wishes he had understood earlier01:05:16 Joe’s advice for founders growing into leadersFollow Joe onLinkedIn: 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

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 Levine01:25 The 25-year relationship between Seth Levine and Brad Feld02:06 How boards should evaluate the opportunities and threats created by AI04:19 Why most companies are still only dabbling with AI08:50 The difference between improving a company and rebuilding it for the AI era13:08 How CEOs can redesign their organizational structure from scratch14:05 Why leaders need to experiment with AI tools themselves18:00 How organizational coaching shaped Foundry from the beginning21:44 Seth’s productivity system and morning planning routine26:38 The untold story of Foundry’s original fifth partner31:11 The words Seth used to begin a difficult leadership conversation37:39 The pivotal yes that helped Foundry raise its first $225 million fund41:32 How writing helped Seth build his reputation and personal brand55:00 The difference between expressing company values and entering politics57:21 The qualities Seth looks for in successful founders59:19 What Seth wishes he had understood earlier in his career01:03:48 Seth’s advice for founders growing into leadersFollow Seth onLinkedIn: 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

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 Lieberman01:08 How a college newsletter became Morning Brew04:16 Finding a co-founder with complementary strengths08:19 Leaving Morgan Stanley to build Morning Brew full time10:31 Using worst-case scenarios and regret to make difficult decisions19:18 Navigating Morning Brew’s acquisition during the pandemic23:25 Why the $75 million exit felt surprisingly underwhelming28:32 Realizing he was a builder CEO, not an operational CEO31:34 Leading a growing company while managing OCD and panic attacks36:01 Losing his identity after transitioning out of the CEO role40:00 Rebuilding through reflection, experimentation, and connection50:19 Why every founder needs a diversified “purpose portfolio”57:27 Making mistakes as a strategy for entrepreneurial growth01:00:45 What Alex wishes he had understood earlierFollow Alex onInstagram: 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

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 Paolantonio01:40 Going from the couch to Broadway at nine years old06:00 Turning social media momentum into a career08:20 Why GiaNina refuses to be confined to one niche11:45 Building multiple revenue streams around dance and content14:51 Creating her own global dance tour18:30 How an Instagram post revealed worldwide demand23:35 Managing overwhelm while building a public career28:23 Handling criticism from millions of followers33:32 Negotiating partnerships and turning down brand deals38:00 The hidden business behind being a content creator45:24 Evolving beyond early success and trusting what comes nextFollow GiaNina onInstagram: 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

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 mission00:29 Why Kettle and Fire exposed how expensive prevention really is02:37 The red tape problem hiding inside health savings accounts04:43 Why Justin pivoted from consumer products into fintech07:39 What Truemed tested before writing a line of code09:54 Why an ugly MVP still proved real customer demand14:21 How Truemed built its first team around mission alignment19:37 Why Justin chose venture capital over staying bootstrapped24:39 What Andreessen Horowitz brought beyond the check29:00 Why the MAHA movement matters for chronic disease39:38 How Justin worked through his hardest founder decisions43:57 What Justin wishes he had known earlier as a founderFollow Justin onLinkedIn: 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

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 timeFollow Will onLinkedIn: 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