Episode Details

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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