From Start-Up to Grown-Up

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

Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hybrid world, and why mission-driven support for small businesses matters now more than ever.What You’ll Learn:How Mike evolved from first-time founder to CEO of JustworksThe “self-inflicted wound quotient” every founder faces—and how to reduce itHow values shape Justworks’ culture and decision-makingThe impact of structured, intentional board leadershipWhy Justworks pulled its IPO and why it was the right callLessons from integrating a remote team post-acquisitionHow to stay adaptable without losing momentumWhy stepping back (even for vacation) makes you a stronger leaderBalancing in-person U.S. operations with global remote teamsThe importance of staying close to your end userKey Takeaways: ➡️ Minimize your “self-inflicted wounds”: Founders often make early decisions—co-founder choices, board composition, capital structure—that can hinder growth. Mike calls this your “self-inflicted wound quotient.” Keep it low. ➡️ Good governance starts with leadership: Don’t wait for your board to self-organize. Set norms, prep materials early, and lead it the way you’d lead your exec team. ➡️ Clarity beats comfort: From acquisitions to layoffs, Mike emphasizes over-communicating the why and making decisions that would “look good on the front page of the Wall Street Journal.” ➡️ Culture isn’t what you say—it’s what you do: Values like “comradery” and “grit” must be defined through behavior and reinforced through recognition, awards, and storytelling. ➡️ Board building is strategic: Justworks’ board includes domain-specific experts—from healthcare to global payments. Choose members like you’d build your C-suite. ➡️ Hard decisions made early pay off later: Fix the roof when it’s sunny. The cost of delay is always higher. ➡️ Remote vs. in-person is not either/or: Justworks combines in-office culture in the U.S. with distributed international teams, intentionally designing for both. ➡️ Real leadership means managing your energy: Mike learned from parenting that being the calmest person in the room is often your superpower. ➡️ Mission attracts the right people: Employees at Justworks are deeply motivated by its purpose—to serve small businesses as heroes of the economy. Where to find Mike Seckler:LinkedInJustworksConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.

Eddie Kim, Co-founder and CTO of Gusto, shares his inspiring journey of building a platform for small businesses. He discusses the nuances of co-founder dynamics and the importance of communication in leadership. Eddie reveals how he transitioned from a technical role to a leader, embracing a hands-off approach to enable his team. He also addresses the unique challenges faced by Asian founders and emphasizes a growth mindset. Bonding traditions among co-founders showcase how friendship fosters stronger professional relationships.

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:Hiring at hyperspeed—and why some employees quit on day one.The "hangover" after hypergrowth—losing key executives and investor pressure.How to hire and retain top executives—and avoid common leadership hiring mistakes.Revising a company mission to balance fairness and safety while scaling.The "Fly High, Fly Low" leadership approach—balancing strategy and deep operational insights.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. Timestamps & Key Topics00:00 – Introduction02:30 – The Early Days of Checkr06:20 – The Downside of Hypergrowth08:45 – Facing Leadership Challenges & Executive Turnover15:30 – Hiring and Managing Executives21:00 – Redefining Checkr’s Mission: Fairness vs. Safety28:00 – Leadership Lessons & Overcoming Challenges39:00 – Confidence, Imposter Syndrome & Founder Loneliness45:00 – Final 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

Dr. Peter Attia, founder of Early Medical and host of The Drive, dives deep into the interplay of health and wealth. He explores how daily habits can significantly boost longevity and healthspan. Attia discusses the evolution from Medicine 2.0 to 3.0, advocating for a new paradigm to tackle chronic illnesses. He highlights the concept of the 'centenarian decathlon,' encouraging fitness goals for maintaining capabilities as we age. Additionally, he addresses mental health challenges in entrepreneurship, emphasizing the need for compassion and timely intervention.

Isabelle Freidheim, founder of Athena Capital and the youngest chairman of a publicly traded company in the U.S., shares her inspiring journey. She discusses the unique challenges women face in finance and the importance of creating opportunities through SPACs. Freidheim emphasizes the benefits of empowering women in leadership roles and shares personal anecdotes of overcoming self-doubt. Her early entrepreneurial experiences shaped her innovative approach to investment, highlighting the value of resilience and collaboration in building successful, women-led teams.

Ethan Evans, former Amazon VP and executive mentor, shares his extensive experience in helping leaders level up their careers. He discusses the importance of self-promotion and strategic relationships in navigating managerial roles. Listeners learn to tackle career challenges by seeing them as puzzles, and Ethan emphasizes the value of mentorship in professional growth. He also addresses overcoming imposter syndrome and highlights the role of self-confidence in fostering career success, encouraging everyone to embrace their unique journey.

Chip Conley, founder of the Modern Elder Academy, offers rich insights as a leading voice at the intersection of psychology and business. He shares how to turn regret into future fuel and the necessity for founders to embrace identity shifts. Chip also discusses strategies for managing older team members and reflects on vital lessons learned from mentorship. Plus, he reveals his favorite interview question that uncovers deeper cultural fits—proof that wisdom truly transcends age in the workplace!