The Messy Parts with Maryam Banikarim

Episode: Kass & Mike Lazerow: The Billion Dollar Burnout

Date: June 23, 2025

Episode Overview

In this candid conversation, Maryam Banikarim welcomes Kass and Mike Lazerow—serial entrepreneurs, married partners, and authors of Shoveling Shit—to explore the unvarnished realities behind their headline-making business successes. Together, they discuss the grinding work, high personal costs, lessons learned, and the ongoing quest for meaning beyond monetary wins. With humor and unfiltered honesty, the Lazerows reflect on marriage, parenting, health, and redefining purpose in the "second chapter" after a billion-dollar exit.

Main Discussion Points & Insights

1. The Unglamorous Reality of Entrepreneurship

• Everyday Struggles:

  • “The messy parts are just every single day, the hard little fights, the annoying stuff, the hard stuff that you do. Because there's very little glamour in being an entrepreneur. There's lots of freedom, but there's little glamour.”
    — Cass Lazaro [00:00]

• Freedom Redefined:

  • The couple highlights the difference between being free from a boss’s idea versus true autonomy: "The freedom is that we're not chained to someone else's idea."
    — Cass Lazaro [03:09]

• Success is Not Always Joyous:

  • Reaching an outcome like selling Buddy Media for nearly $1B left them numb, not jubilant:
    "It should have been the greatest day week of our life...And we were relatively numb."
    — Mike Lazaro [00:16], [21:48]

2. Transparency and Resilience Amid Failure

• Losing it All — Together:

  • Early in their career, after selling Golf.com to a company that went bankrupt, they lost friends and family investors’ money:
    “We thought before the call that we were very rich...Then it's like, wow...we have lost all of our investors' money. And our investors were...family members.”
    — Mike Lazaro [03:36-04:33]

• Sticking With the Team:

  • Radical honesty saved their company culture:
    "Every single person did [stay]. The crazy part is that we learned that if you are transparent and you share the bad...there's no surprises."
    — Cass Lazaro [05:33]

• Lesson:

  • Transparency becomes the glue holding a company together through crises and pivots [06:04].

3. Marriage, Partnership, and the Off-Button Myth

• Working and Living Together:

  • They've been business partners as long as they've been married. Division of roles and respect are key.
    “It's our love language, and it's like shoveling shit. A love story...it's miserable and awesome.”
    — Mike Lazaro [06:44-07:09]

• Turning Off Is Hard:

  • "I don't have an off button unless I have to have an off button. Being a mom requires me to not have an off button."
    — Cass Lazaro [07:24]

• Strategy:

  • The cheat code: Regular date nights (Wednesday and Saturday)—sometimes just for crashing on the couch [07:45].

4. Identity, Suffering, and the Need to Build

• Entrepreneurial Drive:

  • The Lazerows and host ponder if founders are “broken” like comedians, always seeking to prove something.
    "To me, it’s more about suffering...That's really the difference with entrepreneurs, is that we like that suffering."
    — Cass Lazaro [09:10]

• Boredom with ‘Retirement’:

  • Mike tried retirement and painting—fun, until it wasn't:
    “It was fun until it wasn't. There are things called hobbies, which are things you love but aren't good at.”
    — Mike Lazaro [09:53]

• Joy and Misery from Building:

  • “We find our purpose in building...and it's where we find our misery and your joy.”
    — Mike Lazaro [31:35]

5. Impact of Dysfunctional Childhoods & Competitive Nature

• Origin of Drive:
  • Both Cass and Maryam attribute their relentless drive and competitive edge to challenging upbringings.
    “I believe that you can improve on something every single day, period.”
    — Cass Lazaro [17:38]

6. Parenting & Passing on Grit

• Modeling vs. Teaching:

  • They note how hard it is to teach resilience, but children do model adult behavior more than obey explicit advice [19:46-20:55].

• Guilt and Trade-Offs:

  • Despite successful careers, their children see them as strong and present when needed.
    “All three of my kids think I’m very strong, very dedicated, and I show up when I need to.”
    — Cass Lazaro [25:45]

7. Physical and Emotional Health Costs

• Personal Toll:

  • Both suffered after their big exit: Mike was overweight, Cass had severe migraines.
    "It took me a full year to get my nervous system back after we sold the company, like, to get it, like, recalibrated."
    — Cass Lazaro [22:31-22:53]

• Defining a Life Worth Living:

  • “It's not just about how to excel at work, but how do you do it and create a life worth living?”
    — Mike Lazaro [22:53]

8. Giving Back, The Book, and Lasting Lessons

• Motivation for Writing Shoveling Shit:**

  • “To help as many entrepreneurs as possible...why am I saying the same messages over and over again five to ten times a week to all the entrepreneurs? Why can't I say it more?”
    — Cass Lazaro [28:33]

• Radical Generosity:

  • “The more we give, the more we get.”
    — Mike Lazaro [28:53]

• Scaling Wisdom:

  • The book encapsulates their “cheat codes” for entrepreneurship and life [30:03].

9. Examining Legacy: Tech, Social Media, and Regret

• Reflections on Social Media's Impact:
  • They candidly reckon with the unintended costs of the tech they helped build:
    “We really believed that when you connect the world...it was going to help democracy...And we didn't know that these platforms were only going to optimize for engagement...they have destroyed democracy and people's mental health, especially kids.”
    — Mike Lazaro [35:09–36:21]

10. Advice, Favorite Rituals, and Rapid-Fire Fun

• Actionable Takeaways:

  • “Do the right thing. Regardless what the contract says or what the social pressure or investors say, do the right thing and things will work out.”
    — Mike Lazaro [40:34]

  • “Be radically transparent with everything you do.”
    — Cass Lazaro [41:03]

• Rituals:

  • Plan date nights and time with friends—if you don’t, relationships and connections decay [24:08].

• Quirks and Surprises:

  • Mike is a self-admitted crier: “I'm a crier. I'm actually very emotional.” [39:15]
  • Cass loves fly fishing for its meditative, single-focus quality [40:02]
  • Potluck picks: marinated flank steak (Mike), Lipton onion dip (Cass) [37:14–37:38]
  • Karaoke: “Say You, Say Me” (Mike), “In Your Eyes” by Peter Gabriel (Cass) [36:55–37:10]

Notable Quotes

• “It's miserable and awesome.” — Mike Lazaro [07:09]
• “Transparency becomes a glue, a sticky glue in a company when you’re going through pivots and changes.” — Cass Lazaro [06:04]
• “We find our purpose in building...and it's where we find our misery and your joy.” — Mike Lazaro [31:35]
• "If you don't prioritize things, they will decay and you'll be left wondering." — Mike Lazaro [24:08]
• “The more we give, the more we get.” — Mike Lazaro [28:53]
• “Be radically transparent with everything you do.” — Cass Lazaro [41:03]
• “Do the right thing.” — Mike Lazaro [40:34]
• “We really believed that when you connect the world through these platforms, people had access...and it was going to help democracy. And we didn't know...they have destroyed democracy and people's mental health, especially kids.”
  — Mike Lazaro [35:29–36:21]
• “There's very little ROI on kids... you get these little moments.”
  — Cass Lazaro [20:22]
• “I believe that you can improve on something every single day. Period.”
  — Cass Lazaro [17:38]

Timestamps for Key Segments

• Entrepreneurship’s Realities: [00:00–03:18]
• Lessons from Failure: [03:22–06:14]
• Marriage & Work Partnership: [06:14–08:16]
• The Drive Beneath Success: [09:10–10:47]
• Mental & Physical Health Challenges: [11:13–13:19], [21:48–22:53]
• Parenting and Role Modeling: [18:27–20:55]
• Selling Buddy Media—Personal Fallout: [21:48–23:04]
• Purpose After Exit: [23:04–24:24], [31:35–32:37]
• Giving Back and Writing the Book: [27:31–30:03]
• Social Media Regrets: [35:09–36:39]
• Rapid Fire Fun: [36:46–40:09]
• Final Advice: [40:34–41:18]

Summary Takeaways

• Success is messy, even when it looks like a highlight reel.
• Radical transparency and honest communication build trust and loyalty, in business and in life.
• Building and creating, with all its challenges, is often the true source of joy—and sometimes pain—for lifelong entrepreneurs.
• Relationships, health, and purpose can be eclipsed by ambition—prioritize them or risk losing them.
• Give generously: wisdom, time, and kindness multiply.
• Don’t be afraid to openly discuss your struggles—those are the real teachable moments.
• Even after a billion-dollar exit, a life worth living comes from connection, learning, and impact, not just financial success.