Explore every episode of the podcast From Start-Up to Grown-Up
| Title | Pub. Date | Duration | |
|---|---|---|---|
| 128: Ken Davenport Produces Broadway Hits. Here's the Startup Playbook Behind Them | 12 Oct 2026 | 00:44:58 | |
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:
We talk about: 00:00 Meet Tony Award-winning Broadway producer Ken Davenport Follow Ken on
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| 127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild | 21 Sep 2026 | 00:59:13 | |
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:
We talk about:
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
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| 126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE] | 07 Sep 2026 | 01:07:44 | |
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:
We talk about:
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
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| 125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch | 24 Aug 2026 | 01:04:52 | |
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:
We talk about:
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
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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 | |||
| 124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE] | 10 Aug 2026 | 01:03:40 | |
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:
We talk about:
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
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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 | |||
| 123: GiaNina Paolantonio Has Millions of Followers. Here’s the Business Behind Them | 27 Jul 2026 | 01:02:05 | |
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:
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
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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 | |||
| 122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed | 13 Jul 2026 | 00:47:47 | |
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:
We talk about:
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
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| 121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold | 29 Jun 2026 | 00:50:33 | |
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:
We talk about: 00:00 Why building on Bitcoin means you're riding two rollercoasters at once Follow Will on
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| 120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro | 15 Jun 2026 | 00:46:40 | |
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:
We talk about:
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
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| 119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit | 01 Jun 2026 | 00:48:51 | |
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:
We talk about: 00:00 Why Eric Ries says builders are “under siege” Follow Eric on
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| 118: Josh Reeves, Co-Founder and CEO of Gusto, The 3-Part Alignment Framework Every Founder Needs Before Their Next Hire [ENCORE] | 18 May 2026 | 01:06:06 | |
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:
We talk about:
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| 117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up | 04 May 2026 | 01:02:31 | |
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:
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| 116: Gina Bianchini, Founder of Mighty Networks, Stop Building an Audience. Build Community Instead [ENCORE] | 20 Apr 2026 | 01:01:14 | |
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:
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| #115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Leadership, Product, and the AI Revolution | 06 Apr 2026 | 01:05:26 | |
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:
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| #114 - Kim Scott, Radical Respect and Radical Candor: How to Build Teams That Challenge Directly and Care Personally [ENCORE] | 23 Mar 2026 | 01:18:36 | |
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:
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| #113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies | 09 Mar 2026 | 00:54:40 | |
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:
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| #112 - Sal Di Stefano, Co-Founder of Mind Pump Media, How Authenticity, Cofounder Alignment, and Physical Strength Shape Great Leadership [ENCORE] | 23 Feb 2026 | 01:22:51 | |
What actually drives long-term growth, in business, leadership, and life? In this replay episode, Alisa Cohn sits down with Sal Di Stefano, co-founder of Mind Pump Media, to explore what it really takes to build something that lasts. From turning a podcast into a multi-revenue media company to navigating cofounder relationships, conflict, and personal growth, Sal shares hard-earned lessons from nearly a decade of building Mind Pump without venture capital or shortcuts. This conversation goes beyond tactics. Sal breaks down why authenticity creates trust at scale, how to know you’ve chosen the right cofounders, and why being “right” is far less important than staying aligned. He also shares how prioritizing physical health and personal boundaries made him a stronger leader, not a weaker one. If you’re a founder, creator, or leader who wants sustainable growth without burnout, this episode offers a grounded, honest look at what actually works. You’ll learn:
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| #111 – Dr. Becky Kennedy on Why Great Leaders Stop Managing Feelings and Start Building Trust | 09 Feb 2026 | 00:51:39 | |
What does it actually mean to lead with authority and empathy, without burning out, people-pleasing, or losing yourself in the process? In this episode, Alisa Cohn sits down with clinical psychologist, parenting expert, and bestselling author Dr. Becky Kennedy to explore why the skills that make great parents also create the strongest leaders. Dr. Becky introduces the concept of sturdy leadership, a grounded approach that rejects both authoritarian control and emotional over-accommodation. Instead, it teaches leaders how to hold boundaries, stay regulated during conflict, and repair relationships when things go sideways. This conversation unpacks why leadership is not about managing everyone’s feelings, how guilt often disguises emotional over-responsibility, and why repair after rupture is more powerful than perfection. You’ll learn how to handle defensiveness, set boundaries without shame, navigate imposter syndrome, and build trust through consistency and self-leadership. You’ll learn:
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| #110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey [ENCORE] | 27 Jan 2026 | 01:04:11 | |
What does it actually take to build something that has never existed before? In this episode, Jim McKelvey, co-founder of Square (now Block), breaks down the real story behind building Square from scratch, not with a perfect plan, but through necessity, invention, and relentless problem-solving. Jim introduces the concept of the Innovation Stack, why innovation is rarely chosen willingly, and why copying “what worked before” fails when you’re solving a problem no one else has solved. He shares the moment Square felt real, the panic of Amazon launching a competing product, and the counterintuitive strategy that helped Square survive. You’ll learn:
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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 | |||
| #109 Robbie Bent cofounder of Othership— From Rock Bottom to Community Buildering Community | 12 Jan 2026 | 01:18:56 | |
In this episode, Robbie Bent,CEO and Co-founder of Othership shares his remarkable journey from addiction recovery to leading one of today’s most innovative wellness brands. Othership combines sauna, ice bath, and guided breathwork to help people regulate their emotions and connect in community. Robbie opens up about the evolution of his leadership, the challenges of scaling a purpose-driven business, and the importance of authenticity as a founder. From a small Toronto garage gathering during the pandemic to thriving studio locations in Toronto and New York (with more on the way), Robbie’s story is one of resilience, self-awareness, and growth. He and Alisa discuss creating spaces for emotional connection, navigating co-founder dynamics, and learning to lead through imperfection. Robbie’s approach to leadership is a powerful reminder that emotional wellness isn’t just personal, it’s foundational to how we build, lead, and grow.
Timestamps: (00:00) Introduction to the Conversation (02:55) The Importance of Emotional Space (05:59) The Mechanics of OtherShip (08:56) The Backstory of OtherShip (12:01) Choosing New York as a Market (15:02) Building Community and Connection (18:01) Co-Founder Dynamics and Relationships (26:08) Navigating Difficult Conversations (31:40) Challenges of Expansion and Financial Strain (37:33) The Weight of Responsibility and Fear (39:42) Self-Awareness and Personal Growth (48:42) Balancing Excellence with Empathy (52:12) Creating Accessible Wellness Experiences (54:44) Building a Brand with Emotional Connection (57:19) The Evolution of Brand and Personal Experience (59:35) Learning from Mistakes and Trusting Your Gut (01:03:12) The Role of a CEO and Leadership Growth (01:10:07) Overcoming Imposter Syndrome and Embracing Authenticity Connect with Alisa! Follow Alisa Cohn on
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| #108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants | 30 Dec 2025 | 00:47:46 | |
Semyon Dukach, the Founding Partner at One Way Ventures, serial entrepreneur, and former leader of the famed MIT Blackjack team, joins me to share his extraordinary journey from arriving in the U.S. as a Soviet refugee to becoming one of New England’s top venture capitalists. We discuss his path from leading the MIT Blackjack team to startup founder to prolific investor. One Way Ventures invests only in immigrant founders and we discussed how he developed that thesis. We also talk about personal growth, overcoming imposter syndrome, and what it really takes to become an exceptional founder and leader. Where to find Semyon: Timestamps: (00:00) From Pacman to Blackjack: A Unique Journey (02:58) Lessons from the MIT Blackjack Team (05:54) Transitioning from Operator to Investor (08:52) The Immigrant Experience and Entrepreneurship (11:46) Building Trust in High-Stakes Environments (14:36) The Power of Immigrant Founders (17:44) Branding and Recognition in Venture Capital (28:18) Building a Strong Network for Deal Flow (31:39) Recognizing Undervalued Immigrant Founders (34:19) Traits of Extraordinary Founders (37:07) The Importance of Customer Focus (38:53) Growth Through Partnership and Experience (42:23) Navigating the Challenges of Venture Capital (44:56) Turning Disappointments into Opportunities (46:19) Dealing with Imposter Syndrome (47:32) Lessons Learned on the Entrepreneurial Journey (51:03) The Inner Drive of Entrepreneurship Connect with Alisa! Follow Alisa Cohn on
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| #107 Jonathan Wolf— Co-Founder and CEO of ZOE: The Growth of a Founder, the Most Important Leadership Skills, and How to Raise 7 Million Euros in 3 Weeks (Encore) | 15 Dec 2025 | 00:44:06 | |
Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins me to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think. ZOE’s origin story is as unconventional as it is inspiring. After scaling Critéo into a billion-dollar business, Jonathan stepped away with no plan and plenty of questions. That wandering period led him to microbiome researcher Tim Spector, and from there, to the bold idea of using AI and big data to personalize nutrition at scale. Eight years and 250,000 microbiome samples later, ZOE is running the world’s largest nutrition science study and has launched a free app to help people assess their food in real time. Where to find Jonathan: Timestamps: (00:01:30) Jonathan’s Path from Tech Operator to Founder Connect with Alisa! Follow Alisa Cohn on
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| #106 Kass and Mike Lazerow— Serial Married Founders Sold their Company to Salesforce for $750M on Loving the Journey (Encore) | 01 Dec 2025 | 01:28:55 | |
Kass and Mike Lazerow who are serial entrepreneurs, seasoned investors, and co-authors of Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success joined me for one of the most honest conversations I’ve had about what it really takes to build companies and build a life. They share the unvarnished truth about their journey: surviving the dot-com crash, buying Golf.com back from bankruptcy, founding and scaling Buddy Media (eventually acquired by Salesforce for $745 million), and raising three kids while raising capital. They talk about the choices that shaped them, including why they walked away from a bigger offer from Google and how radical transparency kept their team committed during a three-month period when they couldn’t make payroll. We also dive into the patterns they see in the 100+ startups they’ve backed like how ego, secrecy, and shiny-object syndrome derail founders along with the essential habits that help leaders stay grounded. And because they work together and live together, they open up about how they divide responsibilities, handle stress, and stay connected through exits, pivots, health scares, and everything in between. Their upcoming book distills 50 hard-earned lessons about leadership, resilience, and building a life that actually works. This episode gives you a powerful preview and a reminder that the entrepreneurial path is messy, human, and absolutely worth it. Where to find Kass and Mike:
(00:00) The beauty in the struggle: why entrepreneurship is a love story (01:10) Resilience as identity and getting punched 10 times for one win (19:19) Creating a workplace people stay in through loyalty and learning (20:16) Radical transparency: telling the team you might not make payroll (21:06) Bad news vs. surprises: the leadership rule that protects trust (22:21) Benevolent dictatorship vs. democracy: choosing decisive leadership (23:53) Honesty as the most valuable currency in a downturn (37:30) The pivot mindset: knowing when to throw things away (52:23) Life after a big exit and leaving ego at the door (53:45) Why working under others made Mike a stronger leader (58:26) Founders and the guilt tax: the emotional cost of ambition (01:08:45) The long-term power of paying it forward (01:10:01) When cofounding goes wrong: misalignment, fallout, and repair (01:12:50) Picking the right partner—in life and in business (01:13:29) Cofounder “prenup” talks: values, work ethic, commitment (01:14:05) No shortcuts: filtering for grit and willingness to shovel (01:15:16) Why overlapping founder roles create conflict (01:21:12) A simple lens for evaluating opportunities without the jargon (01:22:14) Imposter syndrome and grounding yourself under pressure (01:24:22) What they wish they’d known: focus, phases, and the myth of balance (01:26:32) Final advice for founders: transparency, confidence, intentional living Connect with Alisa! Follow Alisa Cohn on
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| #105 Randy Komisar— Legendary Kleiner Perkins Investor Shares the 3 “Whys” Every Founder Must Answer (Encore) | 18 Nov 2025 | 01:09:46 | |
Randy Komisar is an entrepreneur and investor at Kleiner Perkins. Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law. Randy is a founding director of TiVo and serves on the Roadtrip Nation Advisory Board and Orrick’s Women’s Leadership Board. He is the author of the best-selling book,The Monk and the Riddle, as well as several articles on leadership and entrepreneurship. He is also the co-author of Straight Talk for Startups, the insider best practices for entrepreneurial success, Getting to Plan B, on managing innovation, and I F**king Love that Company, on building consumer brands. This conversation with Randy Komisar is just spectacular! We dive right into how he turned his interview with Neil Young from disaster to success, why growing up with a professional gambler sharpened his communication skills, the way that luck factors into your career, and the way to maximize your chances of serendipity coming your way. You’ll learn pearl after pearl of wisdom from Randy in our conversation, including a crucial question he asks as an investor to any entrepreneur to assess what they’re made of. Randy’s such a great storyteller, and this discussion is not to be missed! Where to find Randy:
(00:00) The Neil Young interview disaster—and how Randy saved it (02:00) Throwing away the script and learning to “follow the spark” (03:15) Reading people: Randy’s people-sense and street upbringing (04:00) Growing up with a salesman and professional gambler father (05:20) Lessons from watching gamblers: losing stories, tells, and ego (07:00) How his father’s instincts shaped Randy’s BS-detector in VC (12:35) Self-awareness, delusion, and Buddhism’s core teaching (13:40) Coaching as holding up a mirror (14:20) Randy’s winding path: from upstate NY to Brown University (15:55) Finding paradise at Brown: curiosity and lifelong learning (21:30) How meaningful small acts of encouragement can be (23:00) Enter Bill Campbell: how they met at Apple (34:00) The inner conflict: purpose vs. title (37:00) Managing through influence, not authority (39:30) Bringing the virtual-CEO model into venture capital (40:50) Success, skepticism, and earning trust at Kleiner (43:10) Why this? Why you? Why now? (44:30) “Is this worth failing at?”—the most important founder question (46:00) The gambler’s wisdom: inviting luck (48:30) How to make yourself luckier (excellence, flexibility, humility) (50:10) Most great companies succeed with Plan B, not Plan A (51:30) A painful miss: the Juicero story (53:00) PR mismatch, press backlash, and the fatal Bloomberg article Connect with Alisa! Follow Alisa Cohn on
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| #104 Issac Evans— How a Series D CEO Found Product-Market Fit, Stays Self-Aware, and Survived His Bank Melting Dow | 04 Nov 2025 | 01:08:46 | |
In this episode, Alisa Cohn interviews Isaac Evans, co-founder and CEO of Semgrep, a startup giving security tools directly to developers. Isaac shares his journey from conducting research at the U.S. Defense Department and MIT Lincoln Laboratory, where he explored binary exploitation bypasses, control-flow integrity, and novel hardware defenses on architectures like RISC-V, to founding and leading a fast-growing company at the forefront of developer security. A graduate of MIT with BS and MS degrees in EECS, Isaac also brings a deep curiosity for next-generation programming languages, secure-by-design frameworks, and the intersection of cryptography and public policy. Together, Alisa and Isaac dive into the realities of startup leadership, the evolution of Semgrep’s business model, the value of feedback, and the transition from founder to CEO. Isaac offers candid insights on managing a growing team, navigating change, and staying grounded through self-awareness. The conversation also explores how AI is reshaping software development, concluding with advice and reflections for aspiring founders building companies in today’s fast-moving world. Where to find Isaac: Timestamps: (00:00) Introduction to Deep Conversations (01:55) Exploring Love Languages in Relationships (06:00) The Founding Insight of Semgrep (10:06) Navigating Early Startup Challenges (13:45) The Evolution of Semgrep's Business Model (17:53) Handling Community Feedback and Criticism (21:54) Crisis Management and Personal Growth (25:46) The Importance of Feedback Culture (33:20) Embracing Feedback as a Gift (35:45) Shifting Leadership Styles (38:32) The A-Plus Responsibilities of a CEO (42:34) Navigating the Founder to CEO Transition (46:46) Learning Through Experience (50:32) The Challenge of Team Dynamics (54:31) The Future of AI and Security (59:28) Imposter Syndrome and Self-Awareness (01:03) 15 Advice for Aspiring Founders Connect with Alisa! Follow Alisa Cohn on
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| #103 Patrick Lee— Rotten Tomatoes Founder: The Secrets to Building an Enduring Business | 20 Oct 2025 | 01:16:58 | |
Patrick Lee is best known as the co-founder and founding CEO of Rotten Tomatoes, the groundbreaking review platform that reshaped how audiences connect with movies and television. What started as a side project born out of his love for film became a global authority that continues to influence critics, fans, and the entertainment industry. In this conversation, Patrick shares his journey from running a small web design firm to creating one of the most recognizable brands in pop culture. He opens up about navigating the chaos of the dot-com boom, the lessons learned from selling his company, and how he’s managed imposter syndrome and focus throughout his entrepreneurial career. Today, Patrick continues to merge storytelling, technology, and fandom through his latest venture, Fanverse, a curated community for passionate fans. His insights reveal what it truly takes to build something people love and to keep evolving long after success.
Timestamps: (00:00) Founding Rotten Tomatoes (02:57) Transitioning to a Business (07:50) Selling Rotten Tomatoes (25:29) Entrepreneurial Spirit (30:58) Other Business Ventures (37:46) The Importance of Product Focus (39:04) Dealing with Failure and Self-Doubt (40:12) The Impact of Company Culture (41:31) Lessons Learned from Zombie Companies (42:46) The Importance of Company Growth and Culture (43:27) Creating a Curated Community at Fanverse (50:28) Learning from Other Communities (51:57) Building Community and Bonding (55:06) Learning from Other Communities and Models (01:00:58) Dealing with Imposter Syndrome and Self-Doubt (01:05:01) The Importance of Focus and Network (01:06:44) Advice for Founders on Growing into Leaders Connect with Alisa! Follow Alisa Cohn on
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| #102 Robert Glazer — Serial Entrepreneur on the Most Important Tool for Success | 07 Oct 2025 | 01:07:21 | |
Robert Glazer is the founder of Acceleration Partners, a serial entrepreneur, bestselling author, and a leading voice on how values shape leadership. In this episode, Bob shares why stepping down from the company he built triggered a surprising crisis of meaning, how that experience led him to write The Compass Within, and how helping people clarify their core values has become his new personal mission. Bob opens up about the link between pain and passion, the power of writing and brand-building for impact, and why success often leaves high achievers feeling empty until they redefine what it means. He also discusses parenting through a values-first lens, the danger of protecting kids from disappointment, and what happens when founders skip the inner work. Whether you're a founder, leader, or someone navigating your next chapter, this episode offers a clear, grounded path toward meaning, alignment, and better decision-making.
Timestamps: (00:00) Redefining success after stepping down as CEO Connect with Alisa! Follow Alisa Cohn on
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| #101 Nick Huber — Building Wealth in “Boring” Businesses | 22 Sep 2025 | 01:10:30 | |
Nick Huber is an entrepreneur and real estate investor who resides in Athens, Georgia, with his wife and three children. He owns Somewhere.com, Bolt Storage, RE Cost Seg, and several other businesses. His real estate portfolio currently includes sixty-eight self-storage properties, covering two million square feet. His portfolio of companies employs over 325 people and makes over $35 million annually. He’s the author of “The Sweaty Startup: How to Get Rich Doing Boring Things.” Where to find Nick: Timestamps: (00:00) Introduction to Boring Businesses (02:46) The Value of Boring Startups (05:59) The Journey of Entrepreneurship (08:58) Understanding Stress in Entrepreneurship (11:53) Sales as a Core Skill (14:57) Building Resilience in Kids and Employees (17:57) Effective Delegation and Decision Making (20:50) The Importance of Self-Awareness in Leadership 23:59) Navigating Employee Dynamics (26:44) The Role of Mentorship in Growth (29:37) Sales Strategies for Entrepreneurs (36:07) Mastering Sales Through Practice (40:56) Hiring Strategies for Entrepreneurs (49:20) Understanding Financial Goals (55:05) Balancing Ambition and Personal Life (01:00:12) Building Your Brand on Social Media (01:07:41) Advice for Aspiring Founders
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| #100 Arvind Jain, Founder of Glean — From Technical Leader to First-Time CEO, the Business Case for Culture and Selling as a Founder’s Superpower | 08 Sep 2025 | 00:53:28 | |
Arvind Jain is the founder and CEO of Glean, the Work AI platform that connects to all your company’s data so you can find, create, and automate anything. In this episode, Arvind shares his journey as a second-time founder and first-time CEO, reflecting on the challenges of moving from a deeply technical role into leading an organization. He talks about why selling is one of the most important skills for founders, the importance of hiring for desire and cultural fit, and how company culture and values shape everything from attracting talent to making tough decisions. Arvind also shares how persistence helps founders push through moments of market indifference, and why self-reflection is one of the most powerful tools for becoming an effective leader. Whether you’re a first-time founder, a seasoned operator, or simply curious about the human side of leadership, this episode offers a grounded look at what it takes to grow both a company and yourself along the way. Where to find Naveen: In this episode, you’ll learn:
Timestamps: (00:00) Introduction and Context Setting (01:32) Transitioning from Founder to CEO (05:47) Learning to Sell and Collaborate (10:08) Hiring for Growth and Culture (18:18) The Vision Behind Glean and AI Integration (25:19) The Importance of Company Culture (26:40) The Challenges of the Startup Journey (31:02) Building a Strong Company Culture (37:51) Navigating Early Struggles and Market Challenges (44:43) Self-Reflection and Leadership Growth (53:26) Lessons Learned and Advice for Founders Connect with Alisa! Follow Alisa Cohn on
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| #99 Naveen Verma — From Princeton Professor to Venture-Backed CEO, Fundraising Without a Network, and Leading Firmly and Empathetically | 25 Aug 2025 | 01:07:51 | |
Naveen Verma is a professor of electrical and computer engineering at Princeton and the co-founder and CEO of EnCharge AI, a startup building radically energy-efficient computers for artificial intelligence. In this episode, Naveen shares how his academic research into in-memory computing evolved over six years into a venture-backed company that’s rethinking the physical limits of AI computers. Naveen explains why traditional computing models can’t keep up with the energy demands of AI, how in-memory architectures unlock new efficiency, and what it means to transition from professor to startup CEO. He also opens up about how failure shaped his leadership style, why co-founder alignment is more important than titles, and what academia taught him about being an empathetic manager. Whether you’re in deep tech, academia, or just curious how foundational innovation becomes a company, this episode offers a grounded and honest look at what it takes to build from the lab up. Where to find Naveen: In this episode, you’ll learn:
Timestamps: (00:00) Why Naveen almost quit engineering Connect with Alisa! Follow Alisa Cohn on
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| #98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship | 11 Aug 2025 | 01:02:09 | |
Craig Walker is the founder and CEO of Dialpad, a business communications platform powered by AI. A former M&A lawyer turned serial entrepreneur, Craig previously co-founded GrandCentral (acquired by Google and relaunched as Google Voice) and sold his prior company to Yahoo. In this episode, Craig shares how his career unfolded from door-to-door dictation sales to running a 1,500-person company, and how AI became central to Dialpad’s strategy long before the hype cycle. Craig opens up about the loneliness of leadership, his bet-the-company acquisition of TalkIQ, and the hardest day of his career when four high-stakes deals all hinged on one phone call. He also explains why he still avoids hiring a COO, how he evaluates executive talent, and why long-term trust is his leadership superpower. Whether you’re building in AI, navigating founder-operator transitions, or learning to scale without burning out, Craig’s story is packed with hard-earned lessons and honest insights. Where to find Craig: Timestamps: (00:00) Starting in door-to-door sales In this episode, you’ll learn:
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| #97 Brad Feld, Founder of Techstars - Lessons from Techstars, why you should have “random” meetings, and the value of the “Give First” mentality. | 29 Jul 2025 | 01:08:01 | |
Brad Feld has spent over 40 years building companies, mentoring founders, and investing in the startup ecosystem. He’s the co-founder of Techstars, a prolific venture capitalist, and the author of nine books. In this episode, Brad opens up about the mental reset that came with turning 60, why he stopped chasing “more,” and what led him to dust off a book draft about mentorship that had been sitting on the shelf. We go deep into his new book Give First, his belief in non-transactional generosity, and why he thinks founders should lead from curiosity, not ego. Brad also shares what went wrong at Techstars, what it taught him about founder empathy, and how he thinks about legacy in a world where everything is temporary. Where to find Brad: Timestamps: In this episode, you’ll learn:
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| #96: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers (Repost) | 17 Jul 2025 | 01:20:28 | |
David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man. He writes regularly on HEY World and speaks on The REWORK Podcast. Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web framework he created in 2003, and continues to develop to this day. Some of the more famous include Github, Shopify, Airbnb, Square, Coinbase, and Zendesk. For my newest episode of From Start-Up to Grown-Up, I talk with David Heinemeier Hansson, Co-Founder of 37signals, to explore his journey of innovation, remote work, and unconventional management. Learn more about DHH | Website Connect with Alisa! Follow Alisa Cohn on
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| #95: From Startup to Grown-Up: Bob Young, co-founder of Red Hat - The origin of Open Source; the key to life and startup success, and how failure can fuel you. | 01 Jul 2025 | 01:15:47 | |
Bob Young co-founded Red Hat, the first company to build a successful business around open source software, and helped shape the modern internet in the process. In this episode, Bob shares the story of how Red Hat went from a CD in a Ziploc bag to a billion-dollar business that inspired GitHub, Coinbase, and much of the cloud infrastructure we use today. But this conversation is about more than just software. Bob opens up about betting his family’s finances on Red Hat, the moment he realized he wasn’t meant to be a public company CEO, and why he believes capitalism, when done right, can be a powerful force for good. He also shares what he's building now (including a needlepoint company), how he thinks about failure, and the one principle he thinks every founder should live by. Where to find Bob: Lulu.com Needlepoint.com Timestamps: (00:00) The challenge of fragmented attention and overbooked schedules (05:09) Red Hat’s founding story and the philosophy behind open source (08:56) Why the internet is the world’s largest open source project (13:34) From newsletter publishing to reinventing Linux (19:49) Why customers chose Red Hat: control, not cost (22:12) The business model insight that changed everything (24:44) How IBM’s services model inspired Red Hat’s structure (27:36) Scaling Linux for enterprise and dealing with constant updates (36:24) Proprietary software as a modern feudal system (43:33) Racking up $50K in credit card debt to keep Red Hat alive (49:01) Trust, marriage, and startup risk (55:05) Leaving Red Hat and why Bob stepped down as CEO (59:23) What sleep taught Bob about optimism and recovery (01:06:10) Red Hat’s culture of ownership and accountability (01:14:24) Why Bob still builds: making the world a better place through business (01:15:02) The importance of discipline and organization (01:17:08) Founders’ advice: serve customer needs, not just wants In this episode, you’ll learn:
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| #94: From Startup to Grown-Up: Jonathan Wolf, co-founder and CEO of ZOE - The growth of a founder, the most important leadership skills, and how to raise 7 million euros in 3 weeks. | 17 Jun 2025 | 01:15:37 | |
Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins Alisa to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think. ZOE’s origin story is as unconventional as it is inspiring. After scaling Critéo into a billion-dollar business, Jonathan stepped away with no plan and plenty of questions. That wandering period led him to microbiome researcher Tim Spector, and from there, to the bold idea of using AI and big data to personalize nutrition at scale. Eight years and 250,000 microbiome samples later, ZOE is running the world’s largest nutrition science study and has launched a free app to help people assess their food in real time. In this episode:
Jonathan also shares the emotional and psychological journey of leadership: learning to make hard calls without sugarcoating, building teams that stick, and staying grounded while leading a fast-growing company. ZOE’s new free app is now available in the US. It uses AI to analyze any food item or meal for its processing risk and nutritional quality, helping people make smarter choices instantly. If you care about your energy, mood, and long-term health, this episode will change how you think about food and leadership. Connect with Alisa! Follow Alisa Cohn on
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| #93: From Startup to Grown-Up: Kass and Mike Lazerow, Serial founders; co-founders of Buddy Media (sold to Salesforce for $750M) - How to survive a failed acquisition, stay married to your co-founder, and enjoy the journey of entrepreneurship. | 03 Jun 2025 | 01:28:55 | |
Kass and Mike Lazerow are serial entrepreneurs, seasoned investors, and co-authors of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. They join Alisa to share an unfiltered look at what it really takes to build companies, navigate chaos, and stay married through it all. Known for founding Golf.com and Buddy Media, which they sold to Salesforce for $745 million, Kass and Mike have also backed more than 100 early-stage startups. Their portfolio includes Scopely, acquired for $5 billion, and Liquid Death. In this conversation, they recount the wild highs and lows of startup life, from raising three kids while raising capital to walking away from a higher offer because it came with too much risk. You’ll hear about:
They also share what it's like to run companies as a married couple, including how they divide responsibilities, handle stress, and maintain date nights through multiple exits and pivots. Also in this episode:
Their new book, Shoveling Sh!t, hits shelves on June 3, 2025. It captures 50 hard-earned lessons that can help any founder become a better leader and build a life that actually works. About Kass & Mike: Connect with Alisa! Follow Alisa Cohn on
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| #92: From Startup to Grown-up: David Ko, CEO of Calm — from gaming to mental health, tools to combat burnout, and the rituals you can use in your own meetings | 19 May 2025 | 00:52:06 | |
David Ko is the CEO and board member of Calm, the #1 app for sleep, meditation, and mindfulness. A former healthcare executive and tech operator, David previously served as COO of Zynga, held senior roles at Yahoo!, and founded a healthtech company acquired by Calm. He is the bestselling author of Recharge, and has been recognized by TIME, LinkedIn, RockHealth, and NYU Stern for his leadership in digital health.
Some takeaways: Where to find David Ko:
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| #91: From Startup to Grown-up: Mike Seckler, CEO of Justworks — how to run a great board process, how to avoid self-inflicted wounds, and the value of taking big risks early in your career | 06 May 2025 | 01:21:58 | |
Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hybrid world, and why mission-driven support for small businesses matters now more than ever. What You’ll Learn:
Key Takeaways: ➡️ Minimize your “self-inflicted wounds”: Founders often make early decisions—co-founder choices, board composition, capital structure—that can hinder growth. Mike calls this your “self-inflicted wound quotient.” Keep it low. ➡️ Good governance starts with leadership: Don’t wait for your board to self-organize. Set norms, prep materials early, and lead it the way you’d lead your exec team. ➡️ Clarity beats comfort: From acquisitions to layoffs, Mike emphasizes over-communicating the why and making decisions that would “look good on the front page of the Wall Street Journal.” ➡️ Culture isn’t what you say—it’s what you do: Values like “comradery” and “grit” must be defined through behavior and reinforced through recognition, awards, and storytelling. ➡️ Board building is strategic: Justworks’ board includes domain-specific experts—from healthcare to global payments. Choose members like you’d build your C-suite. ➡️ Hard decisions made early pay off later: Fix the roof when it’s sunny. The cost of delay is always higher. ➡️ Remote vs. in-person is not either/or: Justworks combines in-office culture in the U.S. with distributed international teams, intentionally designing for both. ➡️ Real leadership means managing your energy: Mike learned from parenting that being the calmest person in the room is often your superpower. ➡️ Mission attracts the right people: Employees at Justworks are deeply motivated by its purpose—to serve small businesses as heroes of the economy.
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| #90: From Startup to Grown-Up: Jeff Byers, Co-founder and CEO of Momentous — Transitioning from NFL player to CEO, managing cultural clashes during a merger, and navigating the high-pressure world of growth-stage leadership | 21 Apr 2025 | 01:11:40 | |
Jeff Byers is the co-founder and CEO of Momentous, a high-performance wellness company delivering science-backed products used by elite athletes, military operators, and high-performers worldwide. A former NFL player and two-time USC football captain, Jeff brings both personal and professional insight to optimizing performance and building values-driven companies. What you’ll learn:
Takeaways:
Find Jeff: In this episode: Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #89: From Startup to Grown-Up: Kevin Evers, author of There’s Nothing Like This: The Strategic Genius of Taylor Swift — unpacking Taylor Swift’s rise to the top; when to take big risks; and how to build a rabid fan base | 08 Apr 2025 | 00:54:46 | |
Kevin Evers is a Senior Editor at Harvard Business Review, where he shapes groundbreaking research and develops award-winning and bestselling books on high performance, creativity, innovation, marketing, and digital disruption. He’s also written popular essays on brain science, persuasion, unpredictability, and the power of storytelling. Kevin holds degrees in English and Film Studies, and his forthcoming book with HBR Press, There’s Nothing Like This, offers a strategic analysis of Taylor Swift’s unmatched ability to evolve her brand without losing her audience. Episode Highlights & Timestamps
Resources & References 📖 There’s Nothing Like This: The Strategic Genius of Taylor Swift (Preorder) Connect with Kevin Evers Instagram: @there_is_nothing_like_this Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #88: From Startup to Grown-Up: Eddie Kim, Co-founder and CTO of Gusto - Wearing different “hats” as a leader; learning to get his hands off the keyboard and enable others instead; and how to build a growth mindset | 25 Mar 2025 | 00:43:08 | |
Eddie Kim is the CTO and cofounder of Gusto, which serves 400,000+ small and medium-sized businesses nationwide by helping them onboard, pay, insure, engage, and provide benefits for their teams, in one integrated, friendly, and easy-to-use platform. Eddie’s career has been shaped by chance encounters, a passion for software, and a deep commitment to growth. Before Gusto, he launched his first company—an experience that ultimately led him to reconnect with his future co-founder, Josh Reeves. In this episode, Eddie opens up about co-founder dynamics, leadership struggles, scaling a company, and the surprising tools he uses to stay aligned with his team. Episode Highlights & Timestamps 🔹 [00:00] - The Decision-Making Process of a Leader Resources & References 📖 Mindset: The New Psychology of Success – Carol Dweck 🎙️ Listen to my previous conversation with Gusto Co-Founder & CEO Josh Reeves (Episode 58) Where to Find Eddie Kim 🌍 Website: www.gusto.com Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #87: How Daniel Yanisse Scaled Checkr to $700M+ and Overcame the Post-Hypergrowth Crisis | 11 Mar 2025 | 00:42:11 | |
In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Daniel Yanisse, co-founder and CEO of Checkr, to discuss the exhilarating rise and the challenges of sustaining a high-growth company. Checkr revolutionized the background check industry, scaling from a $1M revenue run rate in just three months to processing millions of background checks annually. But with hypergrowth came intense operational, cultural, and leadership challenges. Daniel shares how he navigated:
This episode is packed with real-world lessons for founders, CEOs, and startup leaders facing the challenges of rapid growth, leadership transitions, and market shifts. 🎧 Listen now and learn how to build and sustain a high-growth company.
00:00 – Introduction 02:30 – The Early Days of Checkr 06:20 – The Downside of Hypergrowth 08:45 – Facing Leadership Challenges & Executive Turnover 15:30 – Hiring and Managing Executives 21:00 – Redefining Checkr’s Mission: Fairness vs. Safety 28:00 – Leadership Lessons & Overcoming Challenges 39:00 – Confidence, Imposter Syndrome & Founder Loneliness 45:00 – Final Advice for Founders Connect with Alisa! Follow Alisa Cohn on
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| #86: Peter Attia, MD, Founder of Early Medical — improving your lifespan and healthspan, the centenarian decathlon, and the process of making major life changes (Repost) | 25 Feb 2025 | 00:44:29 | |
Peter Attia, MD, is the founder of Early Medical, a medical practice that applies the principles of Medicine 3.0 to patients with the goal of lengthening their lifespan and simultaneously improving their healthspan. He is the host of The Drive, one of the most popular podcasts covering the topics of health and medicine. Dr. Attia received his medical degree from the Stanford University School of Medicine and trained for five years at the Johns Hopkins Hospital in general surgery, where he was the recipient of several prestigious awards, including resident of the year. He spent two years at the National Institutes of Health as a surgical oncology fellow at the National Cancer Institute, where his research focused on immune-based therapies for melanoma. Learn more about Peter here | Website Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #85: Isabelle Freidheim, Founder of Athena Capital — The benefits of being an only child, creating opportunities for women in finance, and unlocking hidden talent | 11 Feb 2025 | 01:09:33 | |
Isabelle Freidheim is the founder and managing partner of Athena Capital. She is the youngest chairman of a publicly traded company in the U.S. In her role as managing partner of Athena Capital, Freidheim oversees the company's strategic direction and leads its efforts in identifying and investing in technology companies. Find out more about Athena Capital | Website https://www.athenacap.com/ Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #84: Ethan Evans, Executive Mentor and Former Amazon VP — Managerial myths debunked, how to create a safety net for your career, and why everyone should write online | 28 Jan 2025 | 00:51:06 | |
During his 15+ years at Amazon, Ethan Evans helped invent Prime Video, Amazon Video, Amazon Appstore, Merch by Amazon, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. He led global teams of over 800 and holds more than 70 patents. Ethan has reviewed 10,000+ resumes, conducted 2,500+ interviews, made 1,000+ hires, and was an Amazon Bar Raiser and Bar Raiser Core Leader, responsible for training and maintaining Amazon's group of interview outcome facilitators. Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #83: Chip Conley, Founder at Modern Elder Academy — Using regret as fuel; how and why founders need to shift their identities; how to manage people older than you; and his favorite interview question (Repost) | 31 Dec 2024 | 01:14:32 | |
Chip is the founder of the Modern Elder Academy (MEA), where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico, and forthcoming campuses in Santa Fe, NM. His five books have made him a leading authority at the intersection of psychology and business. Love the show? Subscribe, Rate, Review, Like, and Share! Resources Mentioned
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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 | |||
| #82, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media (Repost) | 17 Dec 2024 | 00:30:27 | |
Gary Vaynerchuk, also known as "GaryVee," is a serial entrepreneur, the Chairman of VaynerX, and 5x New York Times Best Selling Author. He is a leading global mind on what's next in culture, relevance, and the internet. Gary possesses an uncanny ability to recognize trends and patterns early to help others understand how these shifts impact consumer behavior. He is one of the most forward-thinkers in business. Gary's approach sits at the intersection of business and culture. He keenly understands how to bring brand relevance to the forefront. That’s one of the wisdom bombs from my latest guest on From Start-up to Grown-up, the legendary Gary Vaynerchuk- Chairman of Vayner X and the author of his brand new book, Day Trading Attention. Here are a few more of the many great takeaways Gary offered during our discussion: “Chasing the short-term is the number one strategy that makes people fail.” “Entrepreneurship is a constant game of losing with occasional wins.” “There’s nothing that happens on earth that doesn’t start with attention.” Learn more about his book, Day Trading Attention | Website Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #81: Colin Bryar, Co-Author of "Working Backwards;" former Chief of Staff to Jeff Bezos — How Amazon built its processes, the birth of the 6-page memo, and how to instill psychological safety in a competitive culture | 03 Dec 2024 | 01:22:24 | |
Colin Bryar is a business advisor and technology leader whose career has focused on optimizing business strategy, technology, and operations. He is a former top-level executive at Amazon, where he spent more than 12 years – much of it in the early aughts during the company’s period of unmatched innovation – serving as a tech VP, leading the operations for IMDb.com, as well as shadowing and working directly with Amazon CEO Jeff Bezos to help with all aspects of Amazon's business including strategy, technology, and operations. Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #80: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers | 19 Nov 2024 | 01:20:28 | |
David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man. He writes regularly on HEY World and speaks on The REWORK Podcast. Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web framework he created in 2003, and continues to develop to this day. Some of the more famous include Github, Shopify, Airbnb, Square, Coinbase, and Zendesk. For my newest episode of From Start-Up to Grown-Up, I talk with David Heinemeier Hansson, Co-Founder of 37signals, to explore his journey of innovation, remote work, and unconventional management. Learn more about DHH | Website Connect with Alisa! Follow Alisa Cohn on
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 | |||
| #79, Shegun Otulana, Founder and CEO of Harmony Venture Labs—From Nigeria to unicorn founder; bootstrapping a profitable business; learning to embrace feedback | 05 Nov 2024 | 01:11:14 | |
Shegun Otulana is a seasoned entrepreneur, advisor, mentor and investor. Drawing from his experience as a bootstrapped startup founder who found incredible success, his mission is to empower the next generation of builders by sharing his lessons learned to guide their entrepreneurial journeys. In addition to mentoring founders in his community – many of whom have gone on to launch successful companies – he also enjoys sharing his insight with startup leaders, business associations, academic institutions and other growth-minded groups. In 2013, Shegun founded TheraNest and its parent company, Therapy Brands, a software platform for mental, behavioral, substance and physical rehab providers and organizations. In 2021, he exited the business for $1.25 billion, the largest software exit on record in the state of Alabama. Prior to establishing Therapy Brands, Shegun founded Zertis Technologies, a computer software consultancy company. Today, he continues his “idea lab” approach as the Founder of Harmony Venture Labs (HVL), an idea and growth studio that owns and operates a family of technology companies. What struck me most about Shegun's journey? ➡️ The power of constraints as blessings - limited funding forced profitable growth from day one ➡️ Culture needs rituals - it's not enough to have values, you must memorialize and celebrate them ➡️ Leadership growth requires vulnerability - others see you differently than you see yourself One of my favorite insights: "Your nature is your nature, but you need to find people who complement what you don't bring to the table." Shegun openly shared how he learned to build strong remote teams by finding cultural champions when that wasn't his natural strength. When Shegun could only raise $250,000 in 10 months for his healthcare SaaS company, he turned that constraint into motivation. Without the luxury of burning cash, he had to build profitably from day one. Rather than seeing limited capital as a barrier, he viewed it as a blessing that forced disciplined growth - a mindset that ultimately led to a billion-dollar exit. It's about intentionally designing incentive structures that make your team feel safe to experiment and learn. Learn more about Shegun | Website Connect with Alisa! Follow Alisa Cohn on
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 | |||