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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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — http://www.joinhampton.com/exit-report

Jaclyn Johnson sold Create & Cultivate for $22 million. Then she hit pause – burned out, got divorced, and took a year off to figure out what she actually wanted. Now? She’s back, running the same company she sold, after buying it back for less.

Here’s what we talk about:

• Flipping real estate, investing in 25 startups, and turning $10K into $1.2M
• Spending $17K/month on rent – and not caring
• The number where she actually felt rich: $4–5M liquid
• Her full wealth breakdown: real estate, stocks, startups, and “a little” crypto
• Why angel investing works for her, and the returns that keep her going
• How burnout and divorce forced her to take a full year off
• What it’s like buying back the company you sold – for less
• Why she’ll never run day-to-day again (and how operators changed everything)
• Female founder scrutiny, and why being the face of the brand gets brutal
• Why she’s done chasing status, and how FOMO just disappeared

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jaclyn Johnson https://jaclynrjohnson.com/

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• 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:

• (0:25) How Jacqueline Johnson built and sold businesses for millions
• (1:43) The three kinds of success every founder chases
• (7:04) What it actually feels like to have $15M in the bank
• (15:29) How Create & Cultivate became a brand women rally behind
• (18:37) The double standard: What it’s really like being a female CEO
• (23:18) The moments that made Jacqueline feel like she’d “made it”
• (25:37) What happens after you stop chasing FOMO
• (29:38) The money mistakes founders make after a big exit
• (32:04) What Jacqueline wishes every founder knew before selling

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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://www.joinhampton.com/exit-report

Jordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he left too much money on the table.

Here’s what we talk about:

• Why Jordan left a lucrative investment banking path to chase startups
• How the Rainmaking model let him share risk (and reward) with fellow founders
• The downside of passion-led business: no investment thesis, millions wasted
• Why he believes he could’ve made way more money doing less exciting work
• What he thinks about his $4M liquid net worth — and why it doesn’t feel like enough
• The moment he realized private equity is a better game than startups
• How he’s now trying to turn around a $10M beauty business without raising capital
• What it really costs to live well in London as a founder with a family
• Why he regrets chasing the “cool” startup dream instead of playing it safe
• What true wealth means to him today: help, time, and optionality

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174

Sponsors:

• Tam your taxes today at https://olarry.com/
• 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:

• (0:49) Breaking Down the Rainmaking Model
• (2:08) Jordan’s Pivot from Investment Banking to Startups
• (4:15) Why He Couldn’t Stay Away from Startups
• (5:43) The Origins & Vision Behind Rainmaking
• (8:48) Biggest Challenges in the Rainmaking Model
• (10:57) Costly Mistakes & Lessons Learned Along the Way
• (13:00) Why Jordan Stepped Away from VC
• (17:05) Taking Over as CEO of a Beauty Brand
• (18:23) Jordan’s Current Finances & Where He Stands Today
• (20:23) Lifestyle Adjustments & Financial Struggles
• (24:32) Life Before Family vs. Life After
• (29:04) What He Wishes He’d Done Differently

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.