How Shoveling $h!t Built a $745 Million Startup (And What It Really Cost)

Negotiate Anything

American Negotiation Institute

Education, Careers, Business

4.8 • 659 Ratings

🗓️ 4 August 2025

⏱️ 67 minutes

🔗️ Recording | iTunes | RSS

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Summary

What does it really take to build a $745 million startup from the ground up? Hint: It’s messy, painful, and nothing like the glamorous success stories you’ve heard. In this raw, unfiltered conversation, Kwame Christian sits down with Cas and Mike Lazerow—the entrepreneurial power couple behind the massive success of Golf.com, which they sold to Time Warner for $745 million. But behind the impressive exit lies a story of relentless struggle, countless pivots, and emotional battles most founders never talk about. Cas and Mike pull back the curtain on entrepreneurship’s harshest realities, sharing: How embracing brutally tough conversations transformed their business (and marriage). The secret mindset shifts that separate those who rise from those who burn out. Why falling in love with the hardest parts of your journey can become your ultimate competitive edge. This isn’t just another success story. It’s an honest look at the intense emotional cost that comes with high-stakes entrepreneurship—and a masterclass in how to survive the darkest moments of building something great. If you’re grinding day after day, wondering why success still feels impossibly far away, this episode offers the reset and insights you never knew you needed. Welcome to the real journey. It’s time to start shoveling. Hit play now, and discover what success truly costs. Buy The Book: Shoveling $h!t: A Love Story About the Entrepreneur’s Messy Path to Success Contact ANI ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Request A Customized Workshop For Your Company⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Kwame Christian on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠negotiateanything.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click here to buy your copy of Finding Confidence in Conflict: How to Negotiate Anything and Live Your Best Life!

Transcript

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0:00.0	Hey, I want you to listen to me very carefully for a second, because what I'm about to say
0:04.5	can change the way you look at success. The difference between staying stuck and finally breaking
0:10.2	through isn't just talent. It's learning how to fall in love with the hard parts of the journey.
0:16.6	And that's exactly what we're getting into today. I'm chatting with Cass and Mike Lazaro, the powerhouse couple who built and sold their company,
0:24.5	golf.com, to Time Warner, for $745 million.
0:30.1	They're sharing the real secrets to success in their new book and prepare for some profanity.
0:36.1	Their new book, which is titled Shoveling Shit, the Messy Truth of
0:40.8	Entrepreneurship. Today they're going to talk about how to have the tough conversations that
0:45.4	actually build trust, the mental cheat codes that keep you locked in, and the mindset shift
0:51.1	that separates the people who burn out from the ones who rise.
0:55.1	And if you've been grinding, pushing, and wondering why it still feels so hard,
1:00.3	this conversation is the reset that you didn't know that you needed.
1:04.7	I know you're going to get a lot out of this one.
1:06.6	So without further ado, let's jump into the interview.
1:13.2	Mike, you said something really interesting just now
1:16.4	because you said we can talk about difficult conversations
1:19.7	and you said Cass is really good at that.
1:22.3	And I found that fascinating.
1:26.2	So why didn't you say we are good at that? Let's start there. Well, the key to being
1:33.2	a great entrepreneur, which I don't know if I am, but we've had some success, is to be self-aware.
1:39.2	And it's very difficult for me to have those tough conversations. I've gotten better over the years,
1:46.7	and Cass has really been my rabbi and Sherpa there. The first time I went to lay someone off,
	...

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