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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 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 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 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

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

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

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

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

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

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

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

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

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

What if the thing you’ve been told to build… isn’t the thing that actually creates results? In this encore episode, Gina Bianchini joins Alisa Cohn to break down why community, not content, not audience size, not algorithms, is the real driver of transformation, retention, and long-term business growth. This conversation goes far beyond theory. It’s a masterclass in how communities actually work, why most founders get it wrong, and what it really takes to build something people don’t just follow… but belong to. Gina shares the exact frameworks behind thriving communities, the psychology of engagement, and the structure that turns passive consumers into active participants. This is also a raw look at entrepreneurship behind the scenes, from navigating dark moments and doubt, to leading with mission instead of ego, to building something that feels inevitable before it’s proven. If you’re building a brand, a business, or a movement, this episode will change how you think about growth. You’ll learn: Why community is the most powerful driver of transformation and resultsThe difference between an audience and a true community (and why it matters)The simple framework behind high-engagement communities that actually lastHow to structure your community for consistency, growth, and retentionWhy giving advice kills engagement and what to do insteadThe role of purpose in attracting and sustaining membersHow founders can navigate doubt, feedback, and uncertaintyWhy entrepreneurship is irrational, and how to stay grounded anywayThe real skill CEOs need to master, and it’s not what you thinkHow to manage energy, not just time, to lead effectivelyWe talk about: 00:00 Why community is the foundation of transformation02:30 The founding vision behind Mighty Networks05:00 Growing up in community and why it shaped everything12:30 Founder mental health and why it’s not for everyone14:00 Using mission to move through doubt and dark moments16:00 When investors don’t believe in your vision18:30 How to process feedback without losing your direction22:30 The core elements of building a powerful community29:30 The biggest mistake that kills community engagement31:00 Simple rituals that create deeper connection33:00 Why energy management matters more than time management36:00 The hidden cost of poor leadership energy38:00 Morning routines and protecting creative thinking time44:00 Agreements vs policies inside a company47:00 Building a human system, not a mechanical one50:00 What great leadership actually looks like in practice58:00 Advice for founders building something meaningfulFollow Gina on https://www.instagram.com/gbianchini/https://www.linkedin.com/in/ginabianchini/https://www.mightynetworks.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 does it actually take to lead when the stakes are real, the decisions are heavy, and people are counting on you? In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Tanay Kothari, Co-Founder and CEO of Wispr Flow, one of the most talked-about AI companies right now, to explore what it means to build, lead, and grow at a level most founders never reach. Tanay may be a young founder, but the way he thinks about leadership, people, and decision-making is anything but early-stage. This conversation goes deep into the realities of building a company, not just the strategy, but the responsibility, the trade-offs, and the emotional weight that comes with it. They unpack what founders often get wrong about vision versus execution, why the hardest decisions are usually the right ones, and how to lead teams through uncertainty without losing trust. Tanay also shares his approach to managing people more experienced than him, why understanding how each individual wants to be led changes everything, and how aligning on beliefs, not just decisions, can transform how teams operate. This is a conversation about leadership under pressure, building with intention, and becoming the kind of founder your company actually needs. You’ll learn: What founders get wrong about vision vs. execution, and how to separate the twoHow to navigate difficult decisions, including layoffs, without losing your integrityHow to lead and influence people who are more experienced than youThe power of aligning on beliefs instead of debating decisionsHow to build faster, more effective teams through shared frameworksWhat it really means to take responsibility as a founderThe trade-offs required to build a company, and how to choose them consciouslyHow emotional maturity becomes a leadership advantageWhy great leaders focus on how they show up, not just what they buildWe talk about: 00:00 Building from a young age and what drives Tanay03:00 Early product thinking and what makes great products work06:00 The difference between vision and execution in startups09:00 Making hard decisions and leading through uncertainty12:00 The emotional reality of layoffs and responsibility as a founder16:00 The weight of leadership and the trade-offs of building a company23:00 Managing and leading people more experienced than you26:00 Why personalization matters in leadership (“love languages” for teams)29:00 Aligning on beliefs vs relying on authority35:00 Building decision-making frameworks that scale with your team41:00 How small systems unlock massive team productivity46:00 Why entry-level roles are disappearing and what replaces them49:00 Advice for young professionals in an AI-first world55:00 Creating fast feedback loops to build better products58:00 Why most companies build too many products too soon01:01:00 Imposter syndrome and the hidden pressure of leadership01:04:30 Final lessons on leadership, people, and building something that lastsFollow Tanay on LinkedIn: https://www.linkedin.com/in/tankots/Website: https://wisprflow.ai/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 does it actually mean to care about someone at work? In this encore episode, Alisa Cohn sits down with Kim Scott, former Apple and Google executive and bestselling author of Radical Candor and Radical Respect, to explore the real cost of silence, bias, and avoidance inside teams. This episode is not theoretical. It is deeply practical. From how to solicit feedback effectively, to how to “disrupt bias without disrupting the meeting,” to how to move through shame and defensiveness, Kim offers a roadmap for leaders who want high standards without losing humanity. If you care about building strong teams, giving better feedback, or creating a culture where people can actually do their best work, this conversation will challenge you in the best way. You’ll learn: Why Radical Candor works and how leaders often misapply itThe hidden damage caused by ruinous empathyWhy silence at work is more costly than discomfortHow to solicit feedback without triggering defensivenessThe difference between bias, prejudice, and bullyingHow to “disrupt bias without disrupting the meeting”How leaders can build psychological safety through vulnerabilityWhy upstanders matter and how to be oneWe talk about: 00:00 The painful story behind Radical Candor and why silence cost more than honesty03:00 The Radical Candor framework explained: care personally + challenge directly08:00 Ruinous empathy and the real consequences of avoiding feedback12:00 Why soliciting feedback is the first leadership move18:00 How to ask for feedback without getting fake reassurance24:00 From Radical Candor to Radical Respect: what prompted the new book28:00 The two definitions of respect and why they matter31:00 Bias, prejudice, and bullying, simple definitions leaders can use35:00 How to disrupt bias without disrupting the meeting44:00 Managing shame and defensiveness when your bias is flagged51:00 The cost of silence and the power of being an upstander57:00 Why discomfort is the price of real collaboration Follow Kim on Instagram: https://www.instagram.com/radicalcandorofficialLinkedIn: https://www.linkedin.com/in/kimm4/Medium: https://kimmalonescott.medium.com/ Website: https://kimmalonescott.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 does it really take to evolve from first-time founder to public company CEO without losing conviction, culture, or clarity? In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Matt Oppenheimer, Co-Founder and CEO of Remitly, the global financial services company serving customers in more than 170 countries. Matt shares the leadership evolution behind building Remitly from an early-stage startup into a publicly traded company. From spotting the broken experience of international money transfers while living in Kenya, to navigating executive transitions, IPO readiness, board dynamics, and imposter syndrome, Matt reflects on the real work of founder to CEO leadership growth. This conversation explores how conviction differs from stubbornness, why great founders fall in love with the problem rather than the solution, and how culture must evolve alongside strategy. If you are building, scaling, or leading a growth-stage company, this episode offers a practical and deeply human roadmap. You’ll learn: Why founders must apply grit to the problem, not the solutionHow to balance curiosity with decisiveness as a leaderThe difference between startup execution and public company leadershipHow to design culture intentionally and evolve it over timeWhy executive transitions are about stage-fit, not loyaltyWhat IPO readiness really requires behind the scenesHow to manage imposter syndrome and board pressureWhy psychological safety with investors mattersHow “towering strengths” create leadership shadowsWhat it means to grow into the CEO your company needsWe talk about: 00:00 The origin of Remitly and identifying a global problem03:00 Grit, flexibility, and falling in love with the problem06:00 Growth mindset, curiosity, and listening to feedback10:00 Global perspective and customer centricity14:00 Designing culture from day one18:00 Evolving values as strategy evolves23:00 Hiring executives for stage, not sentiment28:00 Managing leadership transitions thoughtfully33:00 Founder development plans and 360 reviews36:00 Moving from “doing” to leading at scale42:00 IPO preparation and avoiding IPO as the sole goal46:00 Becoming a public company CEO49:00 Imposter syndrome and board dynamics53:00 Advice for founders scaling their leadershipFollow Matt on LinkedIn: https://www.linkedin.com/in/mattoppenheimer/Website: https://www.remitly.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