From Start-Up to Grown-Up

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:GleanXLinkedInIn this episode, you’ll learn:How a CEO needs to adapt The crucial skill for founders. The most important traits to look for when hiring. How company culture leads to attracting talent.Self-reflection is vital for effective leadership.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 FoundersConnect 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

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:EnCharge AIXLinkedInIn this episode, you’ll learn:How to turn academic research into a real-world companyHow to find and align with the right co-foundersWhat good conflict looks like in early-stage teamsHow to fundraise as a professor-turned-founderWhy being self-aware matters more than fitting a roleHow to build culture through actions, not statementsWhat it means to lead with empathy in high-stakes environmentsTimestamps:(00:00) Why Naveen almost quit engineering (03:50) From PhD to professor to founder (07:04) What EnCharge actually builds (10:56) The six-year journey to a spinout (13:20) Why incubation matters in deep tech (15:53) Inspiration, practicality, and real-world impact (17:28) Choosing the right co-founders (20:33) Why Naveen became CEO (23:00) Conflict as a strength (24:21) Vision, perspective, and pushing back (25:49) Advice on co-founder relationships (27:59) Fundraising lessons from a first-time founder (34:19) Growing to 70+ people (35:51) Hiring for culture and long-term vision (37:01) Talking about culture without naming it (38:16) Letting go and empowering the team (41:41) Hiring non-technical leaders (43:17) What Naveen found easy and hard as a manager (45:56) How he learned to give difficult feedback (48:56) Managing stress through abstraction and presence (51:23) Academic mentors who shaped his thinking (53:08) Leadership as enabling others (55:08) Impostor syndrome and comfort with failure (58:00) Early rejections and how he bounced back (01:01:00) What everyone should know about AI (01:02:43) What Naveen wishes he knew earlier (01:04:27) Final advice to founders: normalize failureConnect 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

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:DialpadLinkedInTimestamps:(00:00) Starting in door-to-door sales (02:54) What Craig learned about grit from early sales jobs (04:42) From Apple to law school to M&A at Wilson Sonsini (07:22) How Cisco influenced his approach to acquisitions (08:32) The founding of GrandCentral and acquisition by Google (09:12) Leaving Google to build again (13:22) Why Craig couldn’t stay a middle manager (14:53) What Dialpad is and how it started (17:36) Google Ventures’ support and early Dialpad funding (21:03) What startup life looked like in the pool house (24:17) Family trade-offs and how Craig stayed connected (28:23) Acquiring TalkIQ and the AI unlock (33:37) Why Dialpad was years ahead in AI (35:09) Lessons from integrating an early-stage acquisition (37:43) What tech reveals about culture (39:39) How Craig grew from scrappy founder to CEO (42:20) Delegating to operators while staying strategic (43:30) Why hiring executives is so hard (47:23) How he evaluates cultural fit and long-term potential (49:26) Loyalty, longevity, and building a trusted leadership team (50:57) Craig’s moment of truth and the most stressful day of his career (55:48) What he wishes he knew earlier (57:46) His advice for founders in the AI eraIn this episode, you’ll learn:How to evaluate and integrate an early-stage acquisitionWhy trust and long-term relationships build company resilienceWhat most founders get wrong about hiring senior executivesWhy naivete is an advantage in fast-changing marketsHow to stay optimistic in the face of startup volatilityWhy Craig empowers teams with autonomy, not layersHow a founder mindset helps navigate economic shocksWhat it takes to lead through multiple tech transitionsHow to pick colleagues  and partners you can grow with for decadesConnect 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

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:feld.comGive First (book) Timestamps: (00:00) Why Brad chose to go into hibernation (03:36) How stepping back gave him a 9-to-5 for the first time (06:58) Returning to code and reading 3 books a week (08:05) The four things Brad actually loves (10:11) Not striving, not optimizing: a new mindset for a new decade (13:14) The messy journey of writing Give First (15:08) Feedback that reshaped the book (17:34) Techstars’ awkward teenage years (19:59) Coming out of hibernation, temporarily (23:32) Alter egos: Brad the Book Salesman, Vlad, and Spike (29:14) The pain of watching Techstars struggle publicly (34:30) How founder empathy deepened after Techstars’ turbulence (36:28) What Give First really means and what it does not (38:49) Positive-sum, multi-turn thinking (41:34) Why tennis is the perfect metaphor for long-term success (45:00) Give First as the startup community engine (48:21) Mentorship without expectations (50:07) Socratic questioning and the five whys (54:00) Diagnosing startup fundraising problems (56:32) Being open to randomness (58:57) The power of short assignments and low-stakes access (01:04:28) Why Brad keeps writing: to learn (01:07:14) What he wishes he knew earlier (01:10:34) Advice for founders stepping into leadership (01:12:38) Mortality, meaning, and option valueIn this episode, you’ll learn:How Give First evolved from a Techstars mantra into a movementThe difference between mentorship and adviceWhy and how being a giver pays off How to set boundaries while still being responsiveWhat makes founder relationships thrive or breakWhy being open to randomness can change everythingHow to navigate difficult company phases with empathyWhat Brad believes really matters in the third act of lifeConnect 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

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 | Websitehttps://dhh.dk/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

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

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

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

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

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