From Start-Up to Grown-Up

• #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.

  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.comNeedlepoint.comTimestamps:(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 wantsIn this episode, you’ll learn:How Red Hat became the first successful open source companyWhy control—not price—is the real value of open source softwareWhat makes transparency a business strategy, not just a virtueHow capitalism and idealism can actually alignWhy understanding customer needs matters more than their wantsThe difference between proprietary and democratic tech systemsHow to build culture that owns mistakes and learns out loudWhat it really means to commit to your co-founder and spouseHow to navigate failure, burnout, and your own limitations as a leaderWhat keeps Bob starting new companies in his third and fourth actsConnect 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

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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.

  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:Why Jonathan left the world of adtech in search of purposeHis sabbatical was a challenging period of self-discovery.The importance of relationships over ideas became clear to him.How he navigated the founder’s journeyThe scientific gaps in mainstream nutrition adviceWhat most people misunderstand about ultra-processed foodHow ZOE turned a research project into a product that helps millionsWhat coffee can reveal about your gut microbiomeWhy leadership gets easier when you stop trying to be likedHow Jonathan uses one key question to make sure he’s actually being heardWhy ZOE launched a free tool to put science into people’s handsHow to communicate clearly as a CEO without over-explainingWhy repeating your message 100 times is part of the jobHow to hire people who care more about the mission than the resumeWhat coaching and therapy taught Jonathan about being an effective leaderWhy ZOE’s shift to a free app was a strategic business decisionHow to scale without losing sight of your company’s purposeJonathan 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 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

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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.

  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:The dot-com crash that nearly killed Golf.com and how they raised money to buy it back from bankruptcyThe early bet they placed on Facebook that became Buddy MediaWhy did they choose Salesforce over a larger offer from GoogleHow they built a radically transparent culture that kept employees during a 3-month no-pay periodWhat it's really like to sell a company for hundreds of millions, then stay on as an employeeHow ego, secrecy, and shiny-object syndrome kill foundersWhat it takes to choose the right co-founder and build a business that lastsThey 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:The story behind Mike’s near-death health crisis and how it changed his entire mindsetWhy Kass believes in minivans and Mike believes in showing up for everythingThe advice they give to every founder they backedHow their kids learned more from watching than listeningTheir 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: Kass and Mike Lazerow are entrepreneurs and investors best known for building and selling Buddy Media, a leading social media marketing platform, to Salesforce for $745 million. They co-founded Golf.com early in their careers and have since supported more than 100 startups as investors and advisors. Notable investments include Scopely and Liquid Death. They are also sought-after speakers, writers, and podcast guests. Their book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success is out June 3, 2025.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

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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

  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.What you’ll learn:How David transitioned from gaming to healthcare through mission-driven insightThe real story behind Calm’s evolution from sleep and meditation to global mental healthWhy David uses “battery level” as a tool for checking in at workHow leaders can model vulnerability without sacrificing authorityWhy burnout stems from poor workload management, not just long hoursThe power of shared purpose in turbulent timesHow Calm uses rituals like Jay Shetty meditations and Zoom-free days to reinforce its cultureWhy sleep, diet, and presence are core to David’s leadership performanceHow transparency builds trust even when the news isn’t goodWhy the conversation around mental health needs to start at the topSome takeaways:➡️ Stress is not the problem. Unchecked, unacknowledged stress is. Good stress can fuel resilience and performance.➡️ “How’s your battery?” is a more meaningful check-in than “How are you?”➡️ Burnout often comes from lack of clarity and excessive task stacking, not too many hours.➡️ Leaders must explain the why behind priorities and remove as much as they assign. ➡️ Transparency about culture survey results builds psychological safety. ➡️ Rituals like 90-second meditations help reset and re-center teams. ➡️ Leadership can be lonely. Trusted colleagues make a critical difference. ➡️ Presence matters more than hours. Back-to-back meetings are not a badge of honor. ➡️ Sharing your own mental health journey is not weakness. It’s how resilient teams are built. ➡️ “We take better care of our phone batteries than our mental health batteries.” Time to change that.Where to find David Ko:LinkedIn: https://www.linkedin.com/in/daveko/ Calm: https://www.calm.comBook: Recharge: Boosting Your Mental Battery One Conversation at a TimePodcast: Recharge (available on major platforms)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

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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

  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:How Mike evolved from first-time founder to CEO of JustworksThe “self-inflicted wound quotient” every founder faces—and how to reduce itHow values shape Justworks’ culture and decision-makingThe impact of structured, intentional board leadershipWhy Justworks pulled its IPO and why it was the right callLessons from integrating a remote team post-acquisitionHow to stay adaptable without losing momentumWhy stepping back (even for vacation) makes you a stronger leaderBalancing in-person U.S. operations with global remote teamsThe importance of staying close to your end userKey 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. Where to find Mike Seckler:LinkedInJustworksConnect 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

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