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, a seasoned entrepreneur and investor at Kleiner Perkins, shares invaluable insights from his impressive career. He recounts transforming a challenging interview with Neil Young into a success by ditching the script. Randy also discusses the influence of his gambler father on his ability to read people, and highlights crucial signs to detect lies in entrepreneurs. He emphasizes the importance of self-awareness and shares the three ‘whys’ every founder must answer: why this, why you, and why now. A must-listen for aspiring founders!

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, a Princeton professor and CEO of EnCharge AI, shares his journey from academia to entrepreneurship. He discusses rethinking energy-efficient AI computing and the limitations of traditional models. Naveen emphasizes the importance of co-founder alignment over titles and how failure shaped his empathetic leadership style. He also explores fundraising strategies as a professor-turned-founder and the significance of building a culture through actions. This conversation provides invaluable insights for anyone curious about merging research with real-world applications.

Craig Walker, Founder and CEO of Dialpad, shares his journey from door-to-door sales to leading a 1,500-person company. He discusses the pivotal acquisition of TalkIQ and the loneliness of leadership, revealing the toughest day of his career when four crucial deals hinged on one call. Craig emphasizes the significance of long-term trust in leadership and his unique approach to hiring, avoiding a COO. His insights into integrating AI into business strategies and maintaining company culture provide invaluable lessons for aspiring entrepreneurs.

Brad Feld, co-founder of Techstars and author of 'Give First', shares his transformative journey of introspection after turning 60. He discusses the importance of non-transactional generosity and leading with curiosity instead of ego. Feld reflects on Techstars' early struggles, emphasizing founder empathy gained from challenges. He humorously explores personal alter egos and articulates how vital random meetings can be for fostering relationships, all while redefining success and balancing personal purpose with entrepreneurship.