I Sold My Company for $22M. Here’s Why I Bought It Back.
Moneywise
Intro
Host and sponsor introductions framing the episode about founders, exits, and success, plus sponsor Oceanstalent message.
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com
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.
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