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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Follow Alisa Cohn on

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• Website: http://www.alisacohn.com

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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
  
  

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