Kass and Mike Lazerow sold their company for nearly $1 billion—and felt completely numb. In this episode of The Messy Parts, they share the brutal reality behind entrepreneurial success: kids struggling, health failing, friendships lost. Together with Maryam, they explore what radical transparency actually looks like when you strip away the corporate mask. It's a conversation about the hidden costs of achievement, the messiness of working with your spouse, and why showing your failures might be the most powerful leadership tool you have.
Guests: Kass and Mike Lazerow -- Entrepreneurs, Investors, Authors
https://kassandmike.com/
Follow Kass and Mike on Instagram: https://www.instagram.com/kassandmike and LinkedIn: https://www.linkedin.com/company/kassandmike/
Topics Covered:
- Personal stories of failure, discomfort, and growth
- The hidden cost of success
- Working with your life partner
- The parenting paradox
- What "radical transparency" actually looks like in practice
- The emotional and cultural risk of telling the full truth
- Creating a work culture where "messy" is normalized
- Why leaders are still afraid of vulnerability
- The power of being honest before the outcome is clear
- How storytelling can be a leadership tool—not just a communications tactic
- The difference between transparency and oversharing
- When to hold back (and how to do it without losing trust)
Mentioned:
- Kass & Mike’s book, Shoveling $h!t: A Love Story
- Mark Benioff (Salesforce CEO)
- Gary Vaynerchuk
- Phish (band)
- eToro
- Northwestern University
- Buddy Media
- Golf.com
Further Reading:
- Radical Candor by Kim Scott
- The Power of Vulnerability – TED Talk by Brené Brown
- Psychological Safety in Teams – Google’s Project Aristotle – Research on why speaking up matters at work.
- The Tell by Amy Griffin
- Articles about Cambridge Analytica
- Dying for Sex documentary
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