From Start-Up to Grown-Up

Hosted by Alisa Cohn

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125

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Aug 2026

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EN-US

About the show

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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60 recent

August 10, 20261 hr 3 min

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 Brew Why early reader behavior revealed that the idea had real potential Why regret minimization helped him make a life-changing decision What happened behind the scenes during Morning Brew’s acquisition Why the $75 million exit felt different from what Alex expected How OCD and panic attacks affected Alex’s experience as a founder Why founders can struggle with identity after an exit or leadership transition How to build a “purpose portfolio” beyond your professional title How to choose an executive coach for your current challenges Why reflection is an essential part of growing from founder to leader We talk about: 00:00 Meet Morning Brew co-founder Alex Lieberman 01:08 How a college newsletter became Morning Brew 04:16 Finding a co-founder with complementary strengths 08:19 Leaving Morgan Stanley to build Morning Brew full time 10:31 Using worst-case scenarios and regret to make difficult decisions 19:18 Navigating Morning Brew’s acquisition during the pandemic 23:25 Why the $75 million exit felt surprisingly underwhelming 28:32 Realizing he was a builder CEO, not an operational CEO 31:34 Leading a growing company while managing OCD and panic attacks 36:01 Losing his identity after transitioning out of the CEO role 40:00 Rebuilding through reflection, experimentation, and connection 50:19 Why every founder needs a diversified “purpose portfolio” 57:27 Making mistakes as a strategy for entrepreneurial growth 01:00:45 What Alex wishes he had understood earlier Follow Alex on Instagram: https://www.instagram.com/alexlieb LinkedIn: https://www.linkedin.com/in/alex-lieberman/ Website: https://alexlieberman.com/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

July 27, 20261 hr 2 min

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 business Why one sold-out class became the foundation of a global teaching tour How she evaluates brand partnerships and confidently turns down lucrative deals Why refusing to stay in one niche may create greater career longevity What creators must understand about contracts, exclusivity, and content rights How she manages public criticism, overwhelm, and competing demands Why authenticity is the foundation of her brand and long-term strategy We talk about: 00:00 Meet GiaNina Paolantonio 01:40 Going from the couch to Broadway at nine years old 06:00 Turning social media momentum into a career 08:20 Why GiaNina refuses to be confined to one niche 11:45 Building multiple revenue streams around dance and content 14:51 Creating her own global dance tour 18:30 How an Instagram post revealed worldwide demand 23:35 Managing overwhelm while building a public career 28:23 Handling criticism from millions of followers 33:32 Negotiating partnerships and turning down brand deals 38:00 The hidden business behind being a content creator 45:24 Evolving beyond early success and trusting what comes next Follow GiaNina on Instagram: https://www.instagram.com/gianina TikTok: https://www.tiktok.com/@gianina YouTube: https://www.youtube.com/c/GiaNinaPaolantonio Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

July 13, 202647 min

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: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

June 29, 202650 min

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 underestimate The exact moment Will realized Fold was solving the wrong problem, and how the pivot unlocked real product-market fit and landed Visa as their first major partner. Why "growth at all costs" is uniquely dangerous for Bitcoin companies, and what it actually looks like to build a business for long-term survival What changed when Fold went public How to spot when an executive has stopped scaling with the company What imposter syndrome actually feels like from inside a public company CEO role We talk about: 00:00 Why building on Bitcoin means you're riding two rollercoasters at once 04:03 Is resilience something you're born with or something you build over time? 06:37 The advice Will gives founders on withstanding the startup journey day to day 09:32 How Fold realized it was solving the wrong problem, and what they did about it 13:22 How do you get your team on board when you've found a new direction? 15:04 What Bitcoin is really for: decentralization, inflation, and financial freedom 22:23 Why growth at all costs will destroy you when you're building on Bitcoin 24:41 Why Fold went public via SPAC and what that decision looked like from the inside 33:03 The painful lesson of replacing yourself as a founder CEO 39:18 The lowest lows and highest highs of building Fold 43:13 Have you ever experienced imposter syndrome? Will's honest answer 46:43 Advice for founders on building a company and a life at the same time Follow Will on LinkedIn: https://www.linkedin.com/in/will-reeves/ Website: https://foldapp.com/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

June 15, 202646 min

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 again How AI is changing the future of collaboration and teamwork What "day one thinking" means and why founders need it The difference between experimentation in scaling versus reinvention Why conviction matters more than consensus in zero-to-one innovation How founders can communicate vision when they can't fully articulate it yet The biggest mistake leaders make when trying to innovate inside large organizations Why founder mode and CEO mode are both essential leadership skills How AI is reshaping management, teams, and organizational design The surprising reason culture becomes weaker as companies scale Why entrepreneurial talent is becoming more valuable than specialized expertise How to create startup energy inside an established business The role of trust, feedback, and productive conflict in high-performing teams Why leadership chemistry matters more than most executives realize The mindset shift required to survive rapid technological disruption We talk about: 00:00 How Miro evolved from a digital whiteboard to an AI-powered collaboration platform 04:00 Day One Thinking, AI disruption, and why every company must reinvent itself 06:00 Leading with conviction when the vision isn't fully formed yet 10:00 Finding product-market fit again inside a 1,600-person company 13:00 Founder Mode vs. CEO Mode and the leadership skills required for both 16:00 Learning faster, staying entrepreneurial, and adapting in the AI era 19:00 Culture Growth Trips, founder fit, and building a mission-driven company 24:00 Rebuilding startup energy, ownership, and accountability at scale 26:00 AI, organizational design, and the future of management 29:00 Leadership coaching, team chemistry, and creating a culture of trust 35:00 Why productive conflict beats politeness and how great teams challenge each other 42:00 The hardest lesson about company transformation and Andrey's advice for founders Follow Andrey on LinkedIn: https://www.linkedin.com/in/khusid/ Website: https://miro.com/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

June 1, 202648 min

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 destroying What Eric Ries means by “financial gravity” How companies lose their mission after founders lose control Why Costco became one of the strongest governance models in business The hidden danger of shareholder primacy Why trustworthiness may be the most underrated asset in business How Lean Startup was misunderstood by most founders The real purpose behind MVPs and rapid experimentation Why principles create faster companies, not slower ones How aligned teams move faster with less management overhead What Anthropic is doing differently with AI governance Why constraints often create breakthrough innovation The leadership lesson Eric learned from nearly compromising his own principles How founders can build companies their grandchildren will be proud of We talk about: 00:00 Why Eric Ries says builders are “under siege” 02:00 The hidden problem with modern business “best practices” 05:00 Why shareholder primacy destroys long-term companies 08:00 The untold Costco and Sol Price story 12:00 How Costco built a governance fortress 16:00 Understanding “financial gravity” inside organizations 19:00 Why Costco shareholders defended leadership decisions 22:00 The problem with management entrenchment 24:00 Why corporations should function more like balanced systems 26:00 Anthropic’s governance structure and AI leadership 30:00 Why checks and balances do not kill innovation 32:00 The real philosophy behind Lean Startup 35:00 Why principles create speed inside organizations 38:00 The overlooked role of trust and alignment 40:00 Why great leaders intentionally make things harder 42:00 The danger of compromising on core values 44:00 Eric’s hardest leadership decision 46:00 What founders misunderstand about success and power 47:00 How to build companies designed to last generations Follow Eric on LinkedIn: https://www.linkedin.com/in/eries/ Website: https://theleanstartup.com/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

May 18, 20261 hr 6 min

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

What if you have been hiring wrong this entire time? In this episode, Josh Reeves, Co-Founder and CEO of Gusto, a $10B people platform serving over 300,000 businesses, joins Alisa Cohn for one of the most practical and deeply human conversations about building teams that actually work. This is not a generic leadership talk. This is a masterclass in how to hire people who genuinely care, how to scale a values-driven culture without losing it, and how to lead through the kind of uncertainty that breaks most founders. Josh shares the three-part alignment framework Gusto uses at every level of hiring, why the skills conversation gets too much attention, how he fires himself from jobs as fast as possible, and what the Platinum Rule taught him about giving feedback that actually lands. You’ll learn: Why values and motivation alignment matter more than skills in the startup hiring process How to scale a hiring process so culture stays intact past 50, 150, and 2,500 employees What the Platinum Rule is and why it will transform how you give feedback The difference between a builder and a manager (and why it matters enormously in a startup) How to recognize when a leader is in over their head before it costs you too much Why great talent sometimes fails at the wrong stage company What Josh learned from a previous startup that shaped everything about how Gusto was built The one question to ask yourself before committing to any startup idea We talk about: 00:00 Introduction to Josh Reeves and Gusto 02:00 The founding story and what problem Gusto was built to solve 08:00 The three-part hiring alignment framework: values, motivation, and skill 17:00 How Gusto scaled their hiring culture to 2,500 employees 19:00 How the CEO role evolved across 12 years 24:00 Symptoms of a leader who is outpacing their role vs. one who came from too large a company 29:00 The difference between builders and managers in a startup 33:00 Situational leadership and why directive leadership is not the opposite of empowerment 37:00 The Platinum Rule and how it changed the way Josh gives feedback 48:00 Highs, lows, and leading through uncertainty as a founder 59:00 The lesson from his previous startup that shaped everything about Gusto 01:03:00 Final advice for founders: imagine describing your company for the 10,000th time Follow Josh on LinkedIn: https://www.linkedin.com/in/joshuareeves/ Website: https://gusto.com/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

May 4, 20261 hr 2 min

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

What happens after you “make it”… and realize money was never the point? In this episode, Jyoti Bansal, Founder & CEO of Harness and founder of AppDynamics (sold for $3.7B), sits down with Alisa Cohn for a conversation that cuts deeper than typical startup playbooks. This is not just about building companies. It’s about what happens when the finish line disappears… and you have to decide who you are without it. Jyoti shares the unexpected identity crisis that hit after his exit, why he chose to build again anyway, and what most founders misunderstand about success, sales, and staying relevant in a world that’s changing faster than your roadmap can keep up. From the brutal reality of startup milestones to the urgency of the AI transformation, this episode is a masterclass in how to think, move, and lead when the stakes are real. You’ll learn: Why a worse product can still beat you (and how to prevent it) The hidden identity crisis founders face after a big exit How to think of entrepreneurship as a craft, not a one-time event Why startup growth is about milestones, not perfection The real reason most companies fall behind during major tech shifts How to operate in “founder mode” when speed is everything The difference between product differentiation and go-to-market dominance How to build a scalable sales machine (not just hire “charismatic closers”) The hiring framework Jyoti uses to spot elite sales talent How to align a company fast during high-pressure transformation The “startup within a startup” model that creates ownership at scale Why transparency in numbers builds accountability across the entire org We talk about: 00:00 The uncomfortable truth after a billion-dollar exit 02:00 Why Jyoti came back to build again 05:00 The founder identity crisis no one prepares you for 08:00 Entrepreneurship as a craft, not a single shot 11:00 The milestone framework for building successful companies 15:00 The AI transformation and why most companies will lose 18:00 Founder mode, speed, and making decisions in real time 22:00 Aligning teams when everything is changing fast 26:00 Why revenue is the only truth in business 29:00 Sales as a competitive advantage 32:00 The myth of “relationship-based” selling 35:00 Building a scalable, structured go-to-market machine 38:00 How to hire great sales leaders (and avoid getting sold in the interview) 41:00 The onboarding mistake most founders make 44:00 Transparency, numbers, and company-wide accountability 47:00 The “startup within a startup” model explained 52:00 Ownership, incentives, and building multiple winning products Follow Jyoti on LinkedIn: https://www.linkedin.com/in/jyotibansal Website: https://www.harness.io/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

April 20, 20261 hr 1 min

116: Gina Bianchini, Founder of Mighty Networks, Stop Building an Audience. Build Community Instead [ENCORE]

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 results The difference between an audience and a true community (and why it matters) The simple framework behind high-engagement communities that actually last How to structure your community for consistency, growth, and retention Why giving advice kills engagement and what to do instead The role of purpose in attracting and sustaining members How founders can navigate doubt, feedback, and uncertainty Why entrepreneurship is irrational, and how to stay grounded anyway The real skill CEOs need to master, and it’s not what you think How to manage energy, not just time, to lead effectively We talk about: 00:00 Why community is the foundation of transformation 02:30 The founding vision behind Mighty Networks 05:00 Growing up in community and why it shaped everything 12:30 Founder mental health and why it’s not for everyone 14:00 Using mission to move through doubt and dark moments 16:00 When investors don’t believe in your vision 18:30 How to process feedback without losing your direction 22:30 The core elements of building a powerful community 29:30 The biggest mistake that kills community engagement 31:00 Simple rituals that create deeper connection 33:00 Why energy management matters more than time management 36:00 The hidden cost of poor leadership energy 38:00 Morning routines and protecting creative thinking time 44:00 Agreements vs policies inside a company 47:00 Building a human system, not a mechanical one 50:00 What great leadership actually looks like in practice 58:00 Advice for founders building something meaningful Follow 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: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

April 6, 20261 hr 5 min

#115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Leadership, Product, and the AI Revolution

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 two How to navigate difficult decisions, including layoffs, without losing your integrity How to lead and influence people who are more experienced than you The power of aligning on beliefs instead of debating decisions How to build faster, more effective teams through shared frameworks What it really means to take responsibility as a founder The trade-offs required to build a company, and how to choose them consciously How emotional maturity becomes a leadership advantage Why great leaders focus on how they show up, not just what they build We talk about: 00:00 Building from a young age and what drives Tanay 03:00 Early product thinking and what makes great products work 06:00 The difference between vision and execution in startups 09:00 Making hard decisions and leading through uncertainty 12:00 The emotional reality of layoffs and responsibility as a founder 16:00 The weight of leadership and the trade-offs of building a company 23:00 Managing and leading people more experienced than you 26:00 Why personalization matters in leadership (“love languages” for teams) 29:00 Aligning on beliefs vs relying on authority 35:00 Building decision-making frameworks that scale with your team 41:00 How small systems unlock massive team productivity 46:00 Why entry-level roles are disappearing and what replaces them 49:00 Advice for young professionals in an AI-first world 55:00 Creating fast feedback loops to build better products 58:00 Why most companies build too many products too soon 01:01:00 Imposter syndrome and the hidden pressure of leadership 01:04:30 Final lessons on leadership, people, and building something that lasts Follow Tanay on LinkedIn: https://www.linkedin.com/in/tankots/ Website: https://wisprflow.ai/ Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon