From Start-Up to Grown-Up

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:InstagramFacebookMike's LinkedIn Kass’ LinkedInTimestamps:(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 kConnect 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

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:Kleiner and PerkinsTimestamps:(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 articleConnect 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

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:SemgrepXLinkedInTimestamps:(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 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

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.Where to find Patrick:XInstagramLinkedInTimestamps:(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 LeadersConnect 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

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.Where to find Bob:robertglazer.comThe Compass Within (book)XInstagramLinkedInFacebookTimestamps:(00:00) Redefining success after stepping down as CEO (04:00) Why overachievement never feels like enough (05:20) Lessons from Strength to Strength by Arthur Brooks (06:30) Building a life around one core value (08:18) The ripple effect of leadership (10:24) Bob’s daily dashboard and time-blocking system (13:45) How to focus in a world full of distraction (15:32) Why building a platform matters (17:00) Imposter syndrome and the long game of brand-building (19:06) Parenting with purpose and avoiding overprotection (22:26) A story of failure, transfer, and self-advocacy (26:52) Bob’s new book, The Compass Within (29:37) Making the big three life decisions with values in mind (32:45) The power of identifying your values through pain (35:35) Trust, self-awareness, and leading from values (38:30) The six questions to uncover your personal core values (41:34) Why one-word values fall short (43:43) Bonus question: tracing childhood roots of values (47:23) Company values that are lived, not laminated (49:26) Mission to Mars and value DNA extraction (52:22) Behavioral interviews that screen for culture fit (55:48) Rituals and rewards that reinforce company values (57:43) The J&J Tylenol recall and values in hard decisions (58:32) What Bob hopes readers take from The Compass Within (01:00:22) What Bob wishes he knew earlier (01:02:59) Founders need mentors, masterminds, and a few steps aheadConnect 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

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:Sweaty StartupLinkedInXInstagramTimestamps:(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 Leadership23:59) 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 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

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