Explore every episode of the podcast From Start-Up to Grown-Up
| Title | Pub. Date | Duration | |
|---|---|---|---|
| #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, ph 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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| #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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| #6: Jeff Wald, WorkMarket | 15 Nov 2021 | 01:10:08 | |
Jeff Wald is a serial entrepreneur, Board Member, Best Selling author, Keynote speaker and investor. Jeff is co-founder and Chairman of two new technology startups, Bento Engine (toolkit for financial advisers) and Sonero (AI tool that provides summaries and action items from meetings). Jeff’s previous company, Work Market, an enterprise software platform that enables companies to manage freelancers was acquired by ADP in 2018, where he served on the Senior Leadership Team until 2020. Mr. Wald has founded several other technology companies, including Spinback, a social sharing platform (eventually purchased by salesforce.com). He began his career in finance, serving as Managing Director at activist hedge fund Barington Capital Group, a Vice President at venture capital firm GlenRock and various roles in the M&A Group at JP Morgan. Jeff has served on numerous public and private Boards of Directors including Steel Connect (NASDAQ: STCN), Costar Technologies (OTC: CSTI) and venture-backed TransfrVR. Mr. Wald serves as an adviser to several companies and entities including the X-Prize’s Rapid Reskilling Initiative. Jeff is the author of the #1 Amazon Best Seller, The End of Jobs: The Rise of On-Demand Workers and Agile Corporations and The Birthday Rules: A Fun and Flexible Framework for Raising Children in a Technology Enabled World. In this episode, Jeff talks about cofounder drama, his depression when his first startup failed, and what he said to his investors when they told him to get a coach, frameworks, and what he now looks for as an investor. [13:44] Sign of Weakness [20:37] Getting a Coach [27:33] Working Habit [37:28] Lifeline [45:05] Achievements [47:28] Jeff’s Imposter Syndrome [55:23] Advice [01:07:57] Conclusion To hear more from Alisa, sign up for her newsletter at alisacohn.com/5scripts Connect with Alisa! Follow Alisa Cohn on
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| #5: Sadie Lincoln, Barre3 | 08 Nov 2021 | 00:42:17 | |
Sadie Lincoln is the co-founder and CEO of the fitness franchise company, Barre3. In this episode, Sadie shares how their in-person business had to pivot during the pandemic, why she views running her business as a spiritual practice, the worst feedback she ever received, and the importance of having the right team around her. [2:17] Building business was a spiritual practice [5:14] Micro practices that bring her closer to her spiritual practices [7:46] Shifting into a more confident state [9:45] The founding story of Barre3 [16:39] During the pandemic [33:26] A circle in Sadie’s leadership group [37:41] Female leadership [39:55] What else does Sadie wish she had known earlier on her journey? [41:04] Sadie’s Advice
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| #4: Chris Hsu, Azibo | 01 Nov 2021 | 01:02:24 | |
Chris Hsu is the CEO & Co-Founder of Azibo, a VC-backed real estate fintech startup focused on simplifying the rental property experience. Prior to Azibo, Chris served as an Advisory Partner at a16z and previously was CEO of Micro Focus, a $4B enterprise software company. He also was COO of Hewlett Packard Enterprise, where he successfully led the largest corporate separation in history. Chris spent the earlier part of his career in leadership roles at top consulting firms, including KKR and McKinsey. A military veteran, Chris graduated as a Distinguished Cadet from the United States Military Academy at West Point and completed his U.S. Army tenure as a Captain. He also has an MBA from Northwestern’s Kellogg School of Management. [1:59] Chris’ Personal Life [7:33] Chris’ Experience on Ranger School [13:55] Azibo Founding Story [18:17] Co-Founding Azibo [22:02] Culture of the Company that Chris wrote down [33:40] Chris on Leadership [37:43]The Struggles of Chris in his journey [46:44] Chris as a CEO [54:09] Challenges in Talking to Employees and Executives [59:48] What Chris Wished He Had Known Earlier [1:02:02] Advice for other Founders To hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts Connect with Alisa! Follow Alisa Cohn on
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| #3: Jake Stein, Common Paper | 19 Oct 2021 | 01:01:27 | |
Jake Stein is the cofounder and CEO of Common Paper. Previously, he was the co-founder of RJMetrics (acquired by Magento, then Adobe) and Stitch (acquired by Talend). Before RJMetrics, Jake worked in venture capital, started a landscaping business in high school, and was the 44th ranked table tennis player under 21 in New Jersey; achievements of which he is equally proud. In this episode, Jake discusses the pros and cons of distributed teams, the questions that he and his co-founder asked before they started their company, and the challenges he ran into once his former company was acquired. You'll also hear Jake's biggest mistake, how he invites company feedback parties, and all about Whale Wednesdays. [03:32] Aligning Company Plans [11:33] The Emotional Battle of Running a Business [28:03] Written Feedback vs. Verbal Feedback [33:23] Fostering Company Culture [45:36] Jake’s Biggest Professional Blunder [58:05] The Importance of Self-Care [58:51] Advice for New Business Owners To hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts Connect with Alisa! Follow Alisa Cohn on
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| #2: Zvi Band, Contactually | 15 Oct 2021 | 01:04:00 | |
Zvi Band is the co-founder and CEO of Contactually, which has been acquired by Compass. He is also the author of Success is In Your Sphere. His new venture is called Talk Social, which is focused on bringing humanity back together. In this episode, Zvi and I had a conversation about how he got onto the path of entrepreneurship, how he learned to see himself as the leader, and the limits of transparency. Zvi and I also get into a real talk discussion about co-founder dynamics, mental health, and his surprising advice to founders who are getting ready to sell their business. Connect with Alisa! Follow Alisa Cohn on
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| #1: Matt Blumberg, Bolster | 11 Oct 2021 | 01:13:21 | |
Matt Blumberg is the founder and CEO of Bolster, a new talent marketplace for on-demand executives launched in 2020. Before Bolster, he was the CEO of Return Path. He has authored two books, namely: The Startup CEO and The Startup CXO. In this episode, Matt will take us through his entrepreneurship journey. He will give us in-depth details on how they founded Return Path, how they built the company culture, as well as their exit from the company. Matt also shares how he creates a support system, learned to say ”no,” and became a two-time CEO. Matt is a founder and CEO of Bolster, a new talent marketplace for on-demand executives launched in 2020. Before Bolster, he was the CEO of Return Path. Also, he has authored two books, namely: The Startup CEO and The Startup CXO. In this episode, Matt will take us through his entrepreneurship journey. He will give us in-depth details on how they founded Return-path, how they built the company culture, and their exit from the company. Also, he will tell us how he creates a support system, his journey to learning to say, "no” and how he became a second-time CEO. Key Talking Points of the Episode: [01:36] Getting to know Matt [03:27] Matt’s growth path in leadership [09:30] How Matt learned to say NO [12:39] How to build a support system [13:23] What’s the difference between a coach and a mentor? [15:10] How Matt handles difficult conversations with his employees [21:20] Coaching someone is about to get fired [29:30] How Matt built the company culture at Return Path and how it evolved [40:16] How Matt deals with difficult setbacks and bad moments in his day-to-day life [41:57] Transparency and authenticity [43:27] Matt’s favorite failure [51:05] How Matt sold Return Path [56:25] What is it like to be a second-time CEO for Matt? [01:02:58] The most challenging role for Matt in his current role [01:04:42] Matt’s book, Startup CXO and why it is important [01:10:43] What Matt wishes he knew earlier on his journey [01:11:15] Matt’s message to other founders, as they embark on their journey to grow into leaders Quotes from the Episode: “You’re never done growing as a leader all of us are works in progress.” “The most important conversation to have with an employee or an executive who is not doing well is the conversation you have before the one you fire them.” “The best way to deal with a bad moment is to wait a few minutes. Something else is going to come along and replace it.” “When you make the hard conversation early, that means the later conversation is easier.” “Don’t be shy about asking for help. There are a lot of people around you who know a lot more than you do about a lot of things that you’re doing.” Grab Matt’s Books: Connect with Alisa! Follow Alisa Cohn on
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| #0: A Welcome Message from Alisa | 15 Jul 2021 | 00:01:28 | |
Learn about Alisa's new podcast, From Start-Up to Grown-Up, where she interviews founders about the journey from their beginnings as a fledgling business to thriving companies that are leading the way. 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 | |||
| #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
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 | |||
| #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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| #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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| #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
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| #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
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| #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
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| #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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| #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
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| #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
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| #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
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| #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
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| #78: Jake Schwartz, Co-Founder and former CEO of General Assembly—Navigating startup chaos, what a startup and the Beatles have in common, and the wisdom of looking back on the journey | 22 Oct 2024 | 01:13:13 | |
Jake Schwartz is a serial entrepreneur, investor and advisor. Until 2020, Jake Schwartz served at CEO of General Assembly (GA), the global leader in education and career transformation, which he co-founded in 2011. He grew GA to over 1,000 employees on five continents. In 2018, GA was acquired by The Adecco Group. Jake Schwartz co-founded and serves as Chair of Brave Health, a mission-driven company focused on expanding access to high-quality, affordable care for mental health and addiction. Jake Schwartz was named E&Y Entrepreneur of the Year in 2014 and one of Crain’s “40 under 40” in 2015. Jake holds a BA from Yale and an MBA from The Wharton School of Business at the University of Pennsylvania. He is a former CFA Charterholder. That the end was clear at the beginning and the founders held an unwavering gaze. We often think launching a successful company requires:
That's one way to do it! But what if there's another approach? What if building a successful startup isn't about following a strict formula, but about embracing serendipity and intuition? Jake Schwartz, Co-Founder and former CEO of General Assembly, didn't have a conventional playbook. Looking back a decade later, he felt like they were forming a band. Just get together, start creating, figuring things out as you go. What I took away from this discussion: Passion > perfect plan. Flexibility > rigidity early on. Evolution > clear vision. By following their intuition and leaning into serendipity, Jake and his co-founders discovered a unique formula for success. Connect with Alisa! Follow Alisa Cohn on
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| #77: Jake Kloberdanz, One Hope Winery Co-founder — Building “Girl Scout Cookies” for adults, building community, and scaling philanthropy | 08 Oct 2024 | 01:22:00 | |
Jake Kloberdanz is the founder of ONEHOPE, a pioneering wine brand with a mission to create a positive social impact. Under his leadership, ONEHOPE has donated tens of millions of dollars to over 40,000 non-profits and grown from zero to producing over one million bottles per year. The company boasts a world-class vineyard in Napa Valley and has garnered more than 30 wines with 90+ point ratings. Recognized as one of the fastest-growing private companies by Inc. Magazine, ONEHOPE has raised over $100 million in funding. Jake has been honored as a "Top 40 Under 40" by Wine Enthusiast and a "Top 30 Under 30" by Forbes. He serves on the boards of 8VC and After the Fire, and is a sought-after speaker, having presented at the UN Global Summit, TED, and leading universities like Stanford and MIT. A graduate of UC Berkeley's Haas School of Business and a two-time national rugby champion, Jake is an advocate for "Cause-centric Commerce," integrating purpose into business models. From selling wines out of a U-Haul to building a company that’s donated over $10 million to meaningful causes, Jake's story is nothing short of inspiring. Jake talks about his original idea to create “Girl Scout Cookies for adults” and how that evolved over time. He also talks about his evolution as a leader as the company overcame turbulence, how he learned the importance of clarity and how he developed his frameworks for communication. Learn more about One Hope Winery | Website 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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| #76: Susan McPherson, Founder and CEO of McPherson Strategies — Investing in dormant ties, networking superpowers, and converting nerves into strength | 24 Sep 2024 | 00:41:19 | |
Susan McPherson is a serial connector, angel investor, and corporate responsibility expert. As the founder and CEO of McPherson Strategies, a communications consultancy focused on brands and social impact, she brings over 30 years of experience in marketing, PR, and sustainability communications. Susan is the author of The Lost Art of Connecting and a sought-after speaker at major events like the Massachusetts Conference for Women and Techonomy. She has contributed to outlets like Harvard Business Review and Fast Company and has appeared in NPR, CNN, and USA Today. Susan invests in and advises women-led startups and is involved in several boards and advisory groups, including The 19th News and Just Capital. Susan shares her insights on the significance of rekindling dormant ties, the benefits of dormant connections, and the importance of proactive outreach in networking. Susan started her company at the bold age of 48, reaching out to a staggering 500 people in her network, demonstrating the power of asking for help and the value in promoting others. She's full of practical tips - including hosting your own events collaboratively and keeping the conversation focused on what others need. We'll also hear about her smart approach to follow-up after events, employing the "ten touches rule" to keep her contacts engaged. Prepare to be inspired as Susan discusses her entrepreneurial journey, overcoming personal and professional low points, and the joy she finds in team growth and recognition. Stay tuned as we learn that it's never too late to start, it’s okay to be afraid of failure, and that, at times, success is serendipitous – often resulting from seeds we plant long before they bear fruit. Learn more about Susan | Website Connect with Alisa! Follow Alisa Cohn on
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| #75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping your company, and how to hire senior executives | 10 Sep 2024 | 01:09:48 | |
Jeff Shiner is the CEO of 1Password, a leader in human centric security and privacy. Since joining in 2012, Jeff has grown the company from 20 people to a 900-employee global organization with a $6.8 billion valuation. Today, 1Password enables over 100,000 businesses and millions of individuals to navigate the digital world without fear or friction when logging in – and in less time. The company has been recognized on the Forbes Cloud 100 list and Quartz’s Best Companies for Remote Workers. Prior to joining 1Password, Jeff held leadership roles at IBM Canada and Rosetta and has a demonstrated history of growing technology companies. Jeff also currently serves on the Board of Directors of GenomOncology, a company that provides the healthcare community with data-driven insights to improve cancer care. This episode is particularly valuable for first-time founders, as Jeff covers how to mitigate the lonely job as a founder by making smart hires, what you can do to cultivate a strong team through reflective hiring practices, and the activities that can ground you and give perspective. This is such a powerful and practical episode that will bolster all founders and leaders with resolve! Learn more about 1Password | Website Connect with Alisa! Follow Alisa Cohn on
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| #74: Seth Godin, Author and Marketing Strategist — showing up for yourself, creating conditions for your best work, and how to deal with massive rejection (Repost) | 27 Aug 2024 | 00:48:57 | |
Seth is an entrepreneur, best-selling author, and speaker. In addition to launching one of the most popular blogs in the world, he has written 20 best-selling books, including The Dip, Linchpin, Purple Cow, Tribes, and What To Do When It's Your Turn (And It's Always Your Turn). His book, This is Marketing, was an instant bestseller in countries around the world. Though renowned for his writing and speaking, Seth also founded two companies, Squidoo and Yoyodyne (acquired by Yahoo!). By focusing on everything from effective marketing and leadership, to the spread of ideas and changing everything, Seth has been able to motivate and inspire countless people around the world. In 2013, Seth was one of just three professionals inducted into the Direct Marketing Hall of Fame. In an astonishing turn of events, in May 2018, he was inducted into the Marketing Hall of Fame as well. He might be the only person in both. Imagine a world where people work where they are respected, where the work - not the employee - is thoughtfully criticized, and where managers create the conditions for employees to do the best work of their lives. Seth Godin does a deep dive on all of these and so much more in our conversation, sharing concepts from his brand new book The Song of Significance that reimagines what work and leadership can be. Find out more about Seth | Website Connect with Alisa! Follow Alisa Cohn on
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| #73: David Savage, Group Technology Evangelist at Nash Squared and host of TechTalks podcast — How to become an "intrapreneur," the importance of consistent behavior over vanity metrics, and how to learn to trust yourself | 13 Aug 2024 | 01:01:20 | |
David is Nash Squared's Group Technology Evangelist. He crafts podcasts, hosts video debates, speaks, moderates conferences, and chairs keynote stages. He's a passionate advocate for technology, dissecting its challenges and opportunities. In addition to learning about trusting yourself, you’ll also hear from David how to become an “intrapreneur,” the importance of establishing consistent behavior, and how that applies to strengthening our personal branding. Learn more about David and Tech Talks | Website Connect with Alisa! Follow Alisa Cohn on
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| #72: Kim Scott, Author of Radical Respect and Radical Candor — Building your team’s muscles to address discomfort, cutting through workplace politics, and why you need a purple flag | 30 Jul 2024 | 01:22:47 | |
Kim Scott is the author of Radical Respect and Radical Candor. Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. My next guest on From Start-Up to Grown-Up is Kim Scott, bestselling author of Radical Candor and her new book, Radical Respect. Kim delivers a masterclass in building respect and kindness as the foundation of a company’s DNA with several strategies you’re going to want to use immediately. You’ll learn how to create an environment where employees feel safe. You’ll also learn that empowering yourself and your employees to challenge openly and diplomatically can lead to building a successful company. Connect with Alisa! Follow Alisa Cohn on
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| #71: Matt Reustle, CEO of Colossus — Lessons from a first-time CEO, how to analyze a career pivot, and the art of a great question | 16 Jul 2024 | 01:16:38 | |
Matt Reustle is currently the CEO of Colossus, a business that creates, curates, and distributes top-quality content for investors and entrepreneurs. He is the primary host of the Business Breakdowns podcast. Prior to Colossus, Matt worked in institutional investing. Most recently on the investment team at Raven Capital Management. Matt spent the first decade of his career at Goldman Sachs splitting his time between the Sales & Trading and Research divisions. If you’re thinking about a career pivot, if you’re trying to be a great leader in your company, or if you’re interested in podcasting, check out this great episode of From Start-up to Grown-up with Matt Reustle. Matt is the CEO of Colossus Media and host of the podcast Business Breakdowns. Matt shares so honestly why leadership isn’t just about wins but about creating sustainable systems of growth and communication, how empathy is foundational for meaningful connections, and why there is an unlimited amount of friction running a company and how to find balance. Connect with Alisa! Follow Alisa Cohn on
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| #70: Mike Michalowicz, Author and Entrepreneur — The right way to hire; practical exercises for team retention; and how to come back from rock bottom | 02 Jul 2024 | 01:11:04 | |
Mike Michalowicz is the entrepreneur behind three multimillion-dollar companies and is the author of several business books, including Profit First, Clockwork, The Pumpkin Plan and his newest book, All In. Mike is a great story-teller and you’ll laugh out loud and come away with some great wisdom. Mike shares practical exercises for team retention, how to come back from rock bottom, and the right way to hire people - interviews are over rated! You’ll also learn from his personal stories about the value and power of having an array of mentors, why companies thrive when leadership focuses on the human experience for both clients and employees, and how to build stamina to succeed as an entrepreneur. Learn more about Mike at Website | mikemichalowicz.com Connect with Alisa! Follow Alisa Cohn on
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| #69, Rahul Vohra, Co-Founder and CEO of Superhuman — How to craft core values, tactics for implementing culture to help you achieve company goals, and the importance of moving quickly | 18 Jun 2024 | 00:51:41 | |
Rahul Vohra is the Co-Founder and CEO of Superhuman. He is also a Technical Advisor at Boldstart Ventures, an investor and advisor at Partender, and an investor of sendwithus and Easy Post. He received his bachelor of arts in Computer Science at the University of Cambridge. Rahul shares the lessons he learned from being a serial entrepreneur, how and why he learned to meditate, what he does to build trust with his team, and the pros and cons of being a celebrity founder. This time we’re taking a deep dive on instilling powerful values and culture within a rapidly growing company. We talked about: ✅ How and why to create values in your company at the start: A step by step practical process you can use immediately. ✅ The need to evolve your leadership: As a founder and CEO you should always be identifying your highest and best use and using that as your guide. ✅ The importance of asking hard questions: It can be awkward, but it’s essential to be rigorous with yourself and your team as your company grows. Learn more about Superhuman | Website Connect with Alisa! Follow Alisa Cohn on
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| #68, Gina Bianchini, Co-Founder and CEO of Mighty Networks — The secret to building communities, managing self-worth as a CEO, and why humor is a leadership superpower | 04 Jun 2024 | 01:06:30 | |
Gina Bianchini is the CEO & founder of Mighty Networks, a digital business platform that powers what it calls people magic. People magic is advanced technology and AI that connects the most relevant and interesting people to each other in the context of community, courses, events, and paid memberships.She’s also the author of the 2022 Wall Street Journal best selling book, Purpose: Design a Community & Change Your Life. Mighty is trusted by brands from TED to Tony Robbins, Mindbody, LAUNCH by Mel Robbins, Esther Perel, Matthew Hussey, Jim Kwik, BODi, Gym Launch, and Fortune. Gina Bianchini is the visionary Co-Founder and CEO of Mighty Networks, and my latest guest on From Start-up to Grown-up. Gina’s life has been devoted to building communities, and in this episode she describes the important nuances you can use to build your own communities as well as simply improve your relationships. Gina also shares what she’s learned on her journey as an entrepreneur and a leader. Learn more about Mighty Networks | Website Connect with Alisa! Follow Alisa Cohn on
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| #67, 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 | 21 May 2024 | 00:29:36 | |
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 new book, Day Trading Attention | Website 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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| #66, Mary-Catherine Lader, COO of Uniswap Labs — How you know you're ready to take on more risk, why you should create anti-values, and the importance of community | 07 May 2024 | 01:05:14 | |
Mary-Catherine Lader is the Chief Operating Officer of Uniswap Labs. She previously was a Managing Director at BlackRock, and Chief Operating Officer of the firm’s Digital Wealth business and head of its climate tech business, Aladdin Sustainability. She began her career as an investment analyst with Goldman Sachs’ Special Situations Group and served on the staff of the World Economic Forum’s Davos gatherings for a decade. ➡️ The Uniswap Approach: How they balance the drive for building public infrastructure with the demands of running an equity-focused business, all while maintaining a hands-off approach to the governance community. ➡️ Cultivating Company Culture: Rituals, Transparency, and Empowerment. Learn how Uniswap Labs is fostering a learning-rich environment and driving employee engagement through university sessions and regular updates. Connect with Alisa! Follow Alisa Cohn on
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| #65, Gregory Galant, Co-Founder and CEO of Muck Rack — Pros and cons of bootstrapping, building a scrappy culture, the importance of building a network | 23 Apr 2024 | 01:20:23 | |
Gregory Galant is the co-founder and CEO of Muck Rack, a platform enabling PR teams to work together to find the right journalists for their stories, send customized pitches, build meaningful relationships with the media, monitor news and quantify their impact. It’s used by thousands of organizations, including Taco Bell, Pfizer, Golin, International Committee of the Red Cross, Knight Foundation, Kauffman Foundation and Penguin Random House. Muck Rack is also the solution of choice for journalists, who use Muck Rack’s free, automatically updated portfolios to showcase their work and provide information about what stories they’re looking for. Greg is also the co-creator and executive producer of The Shorty Awards, which honor the best of social media. After being rejected by countless secret societies, Greg secured membership in Twitter and Instagram's exclusive first name club -- follow him at @gregory on both platforms. Listen to our conversation to learn all about: ➡️ Co-founder dynamics: The power of complementary skills and the dangers of too much similarity. ➡️ Hiring: How to know when it’s time to hire someone and what to look for when you’re running lean. ➡️ Managing challenges: How to handle the stress that comes with building a startup - or doing anything challenging. Learn more about Greg's company Muck Rack | 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 | |||
| #64, Kristi Herold, Founder and CEO of JAM — Pivoting during a crisis, leading through playfulness, and creating joy in the workplace | 09 Apr 2024 | 00:56:54 | |
Kristi Herold is the CEO of JAM, a global business connecting people through play, and one of the largest recreational sports leagues in the world. Since 2020, JAM has produced 3,500+ corporate team-building events in over 30 countries. Kristi consults and speaks on how to move a culture from surviving to thriving. Her bestselling book, "It Pays to PLAY," is a rich resource to help organizations playfully connect with their teams and improve retention, engagement, and overall workplace culture. Here are three takeaways from our talk: - Pivot with Purpose When faced with adversity, like the 18-month revenue hit from the pandemic, Jam Group's shift to virtual events and culture consulting didn't just salvage the business. It highlighted how play can create bridges and bolster morale even in the toughest times. - Create Joy at Work Kristi’s entrepreneurial wisdom reminds us that injecting playfulness into the workplace—be it through music sessions, sports teams, or creative meetings—can significantly uplift employee engagement and translate into happier customers and improved profitability. - Lessons in Leadership Embracing vulnerability, from owning up to mistakes to combating imposter syndrome, Kristi's approach underscores the power of radical candor and the significance of building social connections within teams for a stronger and more resilient organization. Learn more about Kristi | 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 | |||
| #63, Matt Abrahams, Author and Lecturer at Stanford University — Embracing vulnerability in leadership, the art of feedback, and how to personalize your pitch | 26 Mar 2024 | 01:05:46 | |
If you've ever found yourself stumbling over words in a high-stakes presentation or wondering how to turn a dinner party into a deeper connection, this is the conversation you need to hear. Plus, for all the leaders out there, we have expert insights on managing emotional reactions to feedback and fostering a culture of open dialogue for transformative organizational growth. Prepare to enrich your entrepreneurial toolkit and communicate with confidence, empathy, and a little bit of small talk finesse. Matt Abrahams is a leading expert in communication with decades of experience as an educator, author, podcast host, and coach. As a Lecturer in Organizational Behavior at Stanford University’s Graduate School of Business, he teaches popular classes in strategic communication and effective virtual presenting. He received Stanford GSB’s Alumni Teaching Award in recognition of his teaching students around the world. 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 | |||
| #62, Sal Di Stefano, Co-Founder of Mind Pump Media — How authenticity drives growth, how you know you have the right cofounders, why being right is not the goal, and how physical strength drives your leadership | 12 Mar 2024 | 01:26:29 | |
Get pumped for this episode of From Start-Up to Grown-Up! I sat down with Sal Di Stefano, the co-founder of Mind Pump Media. You’ll learn how he and his co-founders propelled a fitness podcast into a multifaceted business empire. I loved his perspective on embracing the journey, how authenticity drives growth, and the importance of NOT being right. 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 | |||
| #61, Rob Ryan, Co-Founder of Ascend Communications — Embracing a bootstrap mentality, picking the right spouse, and handling the mental and physical toll of entrepreneurship | 24 Feb 2024 | 01:11:35 | |
My guest for the latest episode of From Start-Up to Grown-Up is Rob Ryan, Co-Founder of Ascend Communication. Ascend was acquired by Lucent Technologies in 1999 by Lucent Technologies. Rob is a fount of knowledge about entrepreneurship and courageous leadership. He’s also a great story teller and a hoot! Check out this clip for a sneak peek into our talk where Rob talks about something important for your company’s long term success: profits. As an early internet pioneer, Rob Ryan served as principal architect in developing the V.32 Modem. He also developed the ethernet blue book standards for the first ethernet chips used in server farms as well as establishing the first decentralized network while working at DECNET. 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 | |||
| #60, David Meltzer, Co-Founder of Sports 1 Marketing, and Peter Goldstein, Entrepreneur and author of The Entrepreneur's IPO — The surprising way money impacts your life, the three forms of ignorant arrogance, and how to prepare to take your company publi | 13 Feb 2024 | 00:32:58 | |
This new episode of From Start-Up to Grown-Up features a dynamic tag team of David Meltzer, the Co-Founder of Sports 1 Marketing, and Peter Goldstein, entrepreneur and the author of “The Entrepreneur’s IPO”! You’ll hear about David’s complete rebirth in his life and career journey as he shares the surprising ways that money impacts your life, and Peter shares solid gold advice about how you can prepare to take your company public. David Meltzer is the Co-Founder of Sports 1 Marketing, and a legendary sports executive. He formerly served as CEO of the renowned Leigh Steinberg Sports & Entertainment agency, which was the inspiration for the movie Jerry Maguire. He is one of the world's top Entrepreneurs, Investors and Business coaches. David has been recognized by Variety Magazine as their Sports Humanitarian of the Year and awarded the Ellis Island Medal of Honor. 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 | |||
| #59, Jim McKelvey, Co-Founder of Block (formerly Square)— Building a team of missionaries, what true innovation takes, and the importance of timing | 30 Jan 2024 | 01:08:51 | |
How do you find your new idea? 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 | |||