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 bankruptcy
  
  
• The early bet they placed on Facebook that became Buddy Media
  
  
• Why did they choose Salesforce over a larger offer from Google
  
  
• How they built a radically transparent culture that kept employees during a 3-month no-pay period
  
  
• What it's really like to sell a company for hundreds of millions, then stay on as an employee
  
  
• How ego, secrecy, and shiny-object syndrome kill founders
  
  
• What it takes to choose the right co-founder and build a business that lasts
  
  

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:

• The story behind Mike’s near-death health crisis and how it changed his entire mindset
  
  
• Why Kass believes in minivans and Mike believes in showing up for everything
  
  
• The advice they give to every founder they backed
  
  
• How their kids learned more from watching than listening
  
  

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:
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.

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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 insight
• The real story behind Calm’s evolution from sleep and meditation to global mental health
• Why David uses “battery level” as a tool for checking in at work
• How leaders can model vulnerability without sacrificing authority
• Why burnout stems from poor workload management, not just long hours
• The power of shared purpose in turbulent times
• How Calm uses rituals like Jay Shetty meditations and Zoom-free days to reinforce its culture
• Why sleep, diet, and presence are core to David’s leadership performance
• How transparency builds trust even when the news isn’t good
• Why the conversation around mental health needs to start at the top

Some 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.com
• Book: Recharge: Boosting Your Mental Battery One Conversation at a Time
• Podcast: Recharge (available on major platforms)

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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 Justworks
• The “self-inflicted wound quotient” every founder faces—and how to reduce it
• How values shape Justworks’ culture and decision-making
• The impact of structured, intentional board leadership
• Why Justworks pulled its IPO and why it was the right call
• Lessons from integrating a remote team post-acquisition
• How to stay adaptable without losing momentum
• Why stepping back (even for vacation) makes you a stronger leader
• Balancing in-person U.S. operations with global remote teams
• The importance of staying close to your end user
  
  

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.

Where to find Mike Seckler:

• LinkedIn
• Justworks
  
  

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• Website: http://www.alisacohn.com

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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:

• Why Jeff says effort and attitude are the only things you can control—and how they ground him in tough moments
• The cultural clash behind merging two wellness companies
• How “speed over consensus” became a core value at Momentous
• Why returning to in-person work cost talent but aligned culture
• How EOS helped reset their operating rhythm
• Building high-integrity partnerships with leaders like Huberman and Starrett
• Lessons from Pete Carroll on consistency and energy
• Why growth-stage CEOs must “reset the scoreboard” and stay curious

Takeaways:

• Control what you can: Effort and attitude define how you show up
• Merge carefully: “Equals” often clash without clear direction
• Culture lives in person: Jeff prioritized cohesion over convenience
• Decide fast on people: Delays around misfits create drag
• Earn trust: Authenticity attracted elite advisors
• Balance roles: EOS clarified vision vs. execution
• You define you: Not your title—your choices

Find Jeff:

• LinkedIn
• Momentous

In this episode:

(00:00:00) Expectations in growth-backed companies
(00:00:23) Intro to Jeff
(00:02:00) NFL to CEO journey
(00:03:52) Life as a pro athlete
(00:05:28) Teamwork, rhythm, winning
(00:09:10) Athletic mindset in startups
(00:11:06) Stress rituals, effort & attitude
(00:14:02) Purpose-driven leadership
(00:19:15) Founding Momentous
(00:30:51) Merger lessons
(00:35:25) Cultural alignment
(00:42:27) In-person work benefits
(00:48:38) Standing out in supplements
(00:54:20) Partnering with leaders
(00:57:59) Co-founder dynamics
(01:02:23) Imposter syndrome
(01:10:22) Curiosity = leadership growth

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• LinkedIn: https://www.linkedin.com/in/alisacohn/
• Website: http://www.alisacohn.com

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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

• 00:00 - Introduction
  • Alyssa Cohn introduces Kevin Evers and the topic of Taylor Swift's strategic genius.
• 00:01:55 - Building Intimacy with Fans
  • Discussion on how Taylor Swift creates a close relationship with her fans.
• 00:02:04 - Controversies and Success
  • Overview of Taylor's famous fights and controversies and their impact on her career.
• 00:03:04 - The Idea Behind the Book
  • Kevin explains the inspiration for his book on Taylor Swift.
• 00:13:05 - Inner Compass and Drive
  • Exploration of Taylor's determination and her "killer instinct."
• 00:20:25 - The Kanye West Incident
  • Analysis of the infamous VMA moment with Kanye West and its implications.
• 00:34:14 - Collaboration and Growth
  • Discussion on Taylor's collaborations with producers and her evolution as an artist.
• 00:39:34 - The Importance of Risk
  • Kevin shares insights on the importance of taking calculated risks in business.
• 00:44:37 - Re-recording Old Music
  • Discussion on Taylor's strategy to re-record her old albums and its significance.
• 00:48:34 - Antifragility Concept
  • Kevin explains the concept of antifragility and how it applies to Taylor's career.
• 00:53:25 - Advice for Founders
  • Kevin offers advice to startup founders based on insights from Taylor's career.
• 00:54:10 - Conclusion

Resources & References

📖 There’s Nothing Like This: The Strategic Genius of Taylor Swift (Preorder)
Amazon Link

Connect with Kevin Evers

Instagram: @there_is_nothing_like_this
LinkedIn: Kevin Evers

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• Website: http://www.alisacohn.com

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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
🔹 [02:00] - The Origin Story of Gusto: A Half Marathon That Changed Everything
🔹 [06:00] - Co-Founder Dynamics: How Eddie, Josh, and Tomer Divided Leadership Roles
🔹 [10:00] - Managing Ego: Accepting the CTO Role Instead of CEO
🔹 [12:00] - Hands Off the Keyboard: How Eddie Transitioned from Engineer to Leader
🔹 [15:00] - The Role of Mentors: Lessons from Jeremy Stoppelman (Yelp) & Drew Houston (Dropbox)
🔹 [17:00] - Breaking Stereotypes: Being an Asian Founder of a Unicorn Startup
🔹 [20:00] - The Role of Company Values in Decision-Making & Hiring
🔹 [24:00] - Encouraging Debate in an Organization & Aligning the Team
🔹 [32:00] - Wearing Multiple Hats: The Skill Every Leader Must Master
🔹 [38:00] - The Highs and Lows of Hiring Executives
🔹 [40:00] - Gusto’s AI Initiatives: How AI is Revolutionizing Payroll & HR for Small Businesses
🔹 [45:00] - Eddie’s #1 Advice for Founders: The Power of a Growth Mindset

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
🐦 Twitter: @edawerd
💼 LinkedIn: Edward Kim

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• Website: http://www.alisacohn.com

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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 Topics

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

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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

https://www.peterattiamd.com/

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• Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

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