“I want you to go buy a house or I want you to go, you know, pay off your student loans or your debt and to be tangible about what you're doing. And if you can't say it in an authentic way, I think that's where things kind of fall apart.”
In this episode of the Entreprenista Podcast, we sit down with Kass Lazerow—serial founder, investor, and New York Times bestselling author of Shoveling $hit: A Love Story About the Entrepreneur’s Messy Path to Success. Kass shares the unfiltered reality of building companies from the ground up, from selling websites in the late ’90s when people were still asking “what’s the internet?” to building and scaling iconic businesses like Golf.com and Buddy Media, the latter reaching $50M in ARR in just three years.

Kass takes us behind the scenes of the highs and devastating lows of entrepreneurship, including surviving the dot-com crash, going months without paying herself or her team, rebuilding after bankruptcy, and betting on radical transparency as her defining leadership principle. She dives deep into how and why she structured companies where everyone owned a piece of the pie, her unconventional approach to scaling (including why she sometimes laid people off after raising capital), and what most founders get wrong about incentives, focus, and growth.

What we talked about:
The First Business [6:57]
The Rollercoaster of Entrepreneurship [9:31]
Scaling Secrets [17:28]
Know Your Employees [24:38]
About the Book! [30:24]

Connect with Kass:

Instagram

Website

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Kass Lazerow, Shoveling $hit: The Founder Lessons She Had to Learn the Hard Way