The Tumultuous Journey of Entrepreneurship

Episode Description:

James reconnects with entrepreneurs Michael and Kass Lazerow, whose journey spans selling Golf.com for $24 million, launching and pivoting Buddy Media into a $700 million Salesforce acquisition, and now investing in breakout brands like Liquid Death. This episode isn’t about startup clichés—it’s about emotional resilience, firing with kindness, how marriage can (barely) survive co-founding, and how to spot a trend before the world does.

They break down their “Go Gauge,” the six-part test they use before investing in a company. They talk about the trauma of being betrayed by family. And they reveal the surprisingly simple cheat codes they’ve used to keep building—and keep loving each other—across decades of risk. Whether you're building a business, looking for one good idea, or wondering what failure really feels like behind closed doors—this episode will give you a few new answers.

What You’ll Learn:

• Why transparency—not optimism—is a founder’s best crisis tool
• The six traits every idea needs to pass their “Go Gauge”
• How to fire someone with empathy and still tell them the truth
• What to do when your startup fails and the investors vanish
• Why the best startup strategy might be launching a pizza shop

Timestamped Chapters:

• [00:00] Bacon, milkshakes, and a first meeting
• [03:00] The Golf.com collapse and family betrayal
• [07:30] The psychology of failure and the will not to quit
• [12:00] Buddy Media’s pivot: from Facebook games to SaaS
• [15:00] Why failure sucks—but trends are your friend
• [21:00] Surviving marriage while surviving a startup
• [26:00] Emotional awareness, therapy, and not “shining the turd”
• [33:00] The $500M pizza truck startup fail
• [38:00] The truth about hiring, firing, and reorganizing
• [44:00] The death of venture capital—and rise of bootstrapping
• [50:00] Investing in pets, ice cream, and par-3 golf
• [54:00] Why Liquid Death is a billion-dollar brand
• [57:00] The Go Gauge: 6 filters for a fundable idea
• [01:02:00] Friendship, failure, and why they finally wrote the book

Additional Resources:

• 📘 Shoveling Sh*t: A Love Story About the Entrepreneur’s Messy Path to Success by Michael and Kass Lazerow
• 💧 Liquid Death – The canned water startup redefining beverage branding
• 🧾 Slice – Supporting independent pizza shops with tech
• 🐎 Commonwealth – Fractional ownership of racehorses and athletes
• 🍦 Van Leeuwen Ice Cream – The indie creamery with 70+ locations

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