466: We Sold a Company for $745M - Here’s the Reality Behind The Scenes: A Raw Conversation with Kass + Mike Lazerow

the bossbabe podcast

Natalie Ellis

Education, Entrepreneurship, Marketing, Business, Self-improvement

4.9 • 2.3K Ratings

🗓️ 5 June 2025

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

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Summary

Kass and Mike Lazerow are serial entrepreneurs and investors, best known as the co-founders of Golf.com and Buddy Media, the leading social media marketing platform that sold to Salesforce for $745 million. In this episode, they join Natalie for a raw, unfiltered conversation on the messy reality of building billion-dollar businesses, raising a family, navigating marriage, and staying focused through it all. They don’t hold back. From the tough lessons they’ve learned as partners and parents to the playbook they’ve developed for building a business that lasts, you’ll walk away with the inside scoop on what it really takes to build a wildly successful business… and stay married while doing it. TIMESTAMPS 00:00 - Introduction to Mike and Kass Lazerow 01:22 - Why co-founder partnerships succeed, or fail 02:38 - How to navigate working together as a couple 05:11 - The must-ask questions before choosing a business partner 07:28 - Equity splits, work ethic, and setting expectations 12:03 - The reality of balance for entrepreneurial families 14:27 - Building businesses during early parenting years 21:18 - The V2MOM framework for focus and decision-making 29:17 - Identifying the key levers that drive business growth 32:34 - Common mistakes in hiring and building a team 36:18 - Scripts and frameworks for difficult conversations 40:20 - Legal foundations every founder should know 45:41 - The emotional side of entrepreneurship and building wealth 49:42 - Rethinking money, freedom, and legacy 55:24 - What success really looks like in business and life RESOURCES + LINKS Grab Kass + Mike’s New Book Shoveling Shit Here: kassandmike.com/the-book Get The Small Business Planner Here - The Tool Every Founder Needs To Organize + Run Every Detail Of Their Business, From Legal Documents + Contracts To Systems, SOPs, + Essential Operations. Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More. Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).

Transcript

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0:00.0	Welcome back to the Boss Babe podcast. So today's episode, we have Mike and Cass Lazaro who are
0:06.1	serial entrepreneurs and investors, best known as the co-founders of golf.com and buddy media,
0:11.8	which is the leading social media marketing platform that sold to Salesforce for $745 million.
0:20.3	This episode was one of my favorites in a really, really long time.
0:24.9	And the reason was it was so real and tactical about what it truly takes to build a wildly
0:32.1	successful business.
0:33.6	And they give so many insights on finding the right partner, on having hard conversations,
0:39.8	on hiring and firing team members, just really diving into the tactical.
0:45.7	And they even shared about the book process that they're in and how they're focusing,
0:49.9	what they're focusing on and what their day-to-day looks like.
0:52.7	And I think it's quite rare to be
0:54.7	able to have these conversations with really successful, really established entrepreneurs
0:59.3	who are so willing to be honest about the realness. They have a brand new book out shoveling
1:04.8	shit. So you can kind of guess by the title that they are not sugar-coating any of this. And it
1:09.8	really is just such a great conversation.
1:12.4	It's one that I'm going to listen to again because I pulled so much from it. So with that,
1:17.2	let's dive into the episode. I know you're really going to love it. Mike and Cass, welcome to the
1:23.9	podcast. I'm so excited that you're here. Thanks for having us. Thank you so much.
1:28.7	Big fans and can't wait to get started. So I have to ask, I ask everyone this who comes to the podcast on a book tour. Where's the energy at right now? How are you guys feeling?
1:38.6	I think we're tired, but we know this grind. We're serial entrepreneurs and this is kind of given us a different
1:47.2	purpose, which is awesome to help as many entrepreneurs as possible. So energy is still there.
1:52.3	I love hearing that. So diving into the serial entrepreneur piece, you don't say that lightly.
	...

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