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Kass and Mike Lazerow built two companies together, sold one for $25M… and the next for $745M. Along the way, they went bankrupt, survived dot-com busts and Facebook booms, and figured out how to build a business without destroying their marriage.

Here’s what we talk about:

What it’s actually like to sell your company for $745 million
The early Golf.com bankruptcy scare, and how Tiger Woods saved the business
Why their co-founder relationship works (and where it almost blew up entirely)
Mixing work and love: the brutal fights, trust, and one-liners from the delivery room
Full breakdown of their first splurge, and what “enough” money really means
Raising $50M without meaning to sell, and getting a surprise offer from Salesforce
The $12M flop that reminded Mike why Kass is the only co-founder he needs
Co-founder red flags, communication rules, and how they manage disagreements
Living rich vs. feeling rich: the moment they finally felt secure

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Kass and Mike https://kassandmike.com/
Kass and Mike's book: Shoveling $h!t: A Love Story https://www.amazon.co.uk/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W

Sponsors:

The modern way to run your business phone is https://www.quo.com/perks/moneywise
Achieve your dream body with https://www.dailybodycoach.com/moneywise
Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

(1:26) The $745M Buddy Media exit
(4:29) What people get wrong about working with a spouse
(6:22) How Kass and Mike met
(8:44) The Golf.com story
(15:33) Managing team dynamics as married co-founders
(23:17) Handling finances as a married couple
(28:18) What they did with the money after the exit
(32:33) Lessons learned and what they'd do differently
(36:58) Closing thoughts on finding the right co-founder

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

Ben Nadareski - Solstice