From Start-Up to Grown-Up

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.

David Heinemeier Hansson, co-owner of 37signals and creator of Ruby on Rails, shares insights on embracing creativity over traditional financing in tech startups. He discusses the importance of a first principles mindset in business strategy and how to navigate the complexities of modern remote work. The guest also reflects on evolving vacation policies and the challenges of authentic leadership. By advocating for flexibility and trust in decision-making, he encourages entrepreneurs to embrace mistakes as part of their innovative journey.

Bob Young, co-founder of Red Hat and a pioneer of open source software, shares insights from his entrepreneurial journey. He discusses how Red Hat evolved from a simple CD to a billion-dollar enterprise, emphasizing the importance of customer problem-solving. Young reflects on the financial risks he took, including racking up credit card debt, and stresses that failure can be a stepping stone to success. He also advocates for capitalism as a force for good and explores the significance of personal relationships in navigating the ups and downs of entrepreneurship.

Jonathan Wolf, co-founder and CEO of ZOE, transitioned from tech to health, focusing on personalized nutrition. He shares his inspiring journey from disillusionment to purpose, highlighting the importance of relationships in entrepreneurship. Jonathan discusses the challenges of nutrition science, the impact of processed foods, and the innovative app ZOE launched to democratize nutrition insights. He also reveals key leadership lessons learned along the way and the surprising insights about coffee and gut health.

Kass and Mike Lazerow are serial entrepreneurs, seasoned investors, and co-authors of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. They join Alisa to share an unfiltered look at what it really takes to build companies, navigate chaos, and stay married through it all.Known for founding Golf.com and Buddy Media, which they sold to Salesforce for $745 million, Kass and Mike have also backed more than 100 early-stage startups. Their portfolio includes Scopely, acquired for $5 billion, and Liquid Death. In this conversation, they recount the wild highs and lows of startup life, from raising three kids while raising capital to walking away from a higher offer because it came with too much risk.You’ll hear about:The dot-com crash that nearly killed Golf.com and how they raised money to buy it back from bankruptcyThe early bet they placed on Facebook that became Buddy MediaWhy did they choose Salesforce over a larger offer from GoogleHow they built a radically transparent culture that kept employees during a 3-month no-pay periodWhat it's really like to sell a company for hundreds of millions, then stay on as an employeeHow ego, secrecy, and shiny-object syndrome kill foundersWhat it takes to choose the right co-founder and build a business that lastsThey also share what it's like to run companies as a married couple, including how they divide responsibilities, handle stress, and maintain date nights through multiple exits and pivots.Also in this episode:The story behind Mike’s near-death health crisis and how it changed his entire mindsetWhy Kass believes in minivans and Mike believes in showing up for everythingThe advice they give to every founder they backedHow their kids learned more from watching than listeningTheir new book, Shoveling Sh!t, hits shelves on June 3, 2025. It captures 50 hard-earned lessons that can help any founder become a better leader and build a life that actually works.About Kass & Mike: Kass and Mike Lazerow are entrepreneurs and investors best known for building and selling Buddy Media, a leading social media marketing platform, to Salesforce for $745 million. They co-founded Golf.com early in their careers and have since supported more than 100 startups as investors and advisors. Notable investments include Scopely and Liquid Death. They are also sought-after speakers, writers, and podcast guests. Their book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success is out June 3, 2025.Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

David Ko is the CEO and board member of Calm, the #1 app for sleep, meditation, and mindfulness. A former healthcare executive and tech operator, David previously served as COO of Zynga, held senior roles at Yahoo!, and founded a healthtech company acquired by Calm. He is the bestselling author of Recharge, and has been recognized by TIME, LinkedIn, RockHealth, and NYU Stern for his leadership in digital health.What you’ll learn:How David transitioned from gaming to healthcare through mission-driven insightThe real story behind Calm’s evolution from sleep and meditation to global mental healthWhy David uses “battery level” as a tool for checking in at workHow leaders can model vulnerability without sacrificing authorityWhy burnout stems from poor workload management, not just long hoursThe power of shared purpose in turbulent timesHow Calm uses rituals like Jay Shetty meditations and Zoom-free days to reinforce its cultureWhy sleep, diet, and presence are core to David’s leadership performanceHow transparency builds trust even when the news isn’t goodWhy the conversation around mental health needs to start at the topSome takeaways:➡️ Stress is not the problem. Unchecked, unacknowledged stress is. Good stress can fuel resilience and performance.➡️ “How’s your battery?” is a more meaningful check-in than “How are you?”➡️ Burnout often comes from lack of clarity and excessive task stacking, not too many hours.➡️ Leaders must explain the why behind priorities and remove as much as they assign. ➡️ Transparency about culture survey results builds psychological safety. ➡️ Rituals like 90-second meditations help reset and re-center teams. ➡️ Leadership can be lonely. Trusted colleagues make a critical difference. ➡️ Presence matters more than hours. Back-to-back meetings are not a badge of honor. ➡️ Sharing your own mental health journey is not weakness. It’s how resilient teams are built. ➡️ “We take better care of our phone batteries than our mental health batteries.” Time to change that.Where to find David Ko:LinkedIn: https://www.linkedin.com/in/daveko/ Calm: https://www.calm.comBook: Recharge: Boosting Your Mental Battery One Conversation at a TimePodcast: Recharge (available on major platforms)Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Mike Seckler, CEO of Justworks and seasoned entrepreneur, shares insightful lessons from his journey through the dot-com boom and bust. He discusses the importance of minimizing 'self-inflicted wounds' in decision-making and how values shape company culture. Mike highlights effective board governance and maintaining a customer connection, especially in a hybrid work environment. He also emphasizes adaptability in leadership while reflecting on the strategic pause of Justworks' IPO, showcasing resilience in the face of uncertainty.

Jeff Byers, co-founder and CEO of Momentous, shares his inspiring journey from NFL player to wellness entrepreneur. He discusses the importance of focusing on effort and attitude in challenging times and how cultural clashes can surface during company mergers. Jeff emphasizes the value of in-person work for fostering culture and the principle of 'speed over consensus' in decision-making. He also touches on lessons learned from sports on leadership and maintaining a curious mindset amid growth, proving that your choices define you beyond your title.

Kevin Evers, Senior Editor at Harvard Business Review and author of 'There’s Nothing Like This', shares insights on Taylor Swift’s strategic rise and her unique brand evolution. He discusses Swift’s 'productive paranoia' and Day One mindset, illustrating how she effectively balances authenticity with innovation. The conversation delves into her bold decisions, fan engagement tactics, and the importance of emotional connections, offering entrepreneurs crucial lessons on resilience and navigating controversy for growth.