I Sold My Company for $22M. Here’s Why I Bought It Back.

64 snips

Sep 30, 2025

Jacqueline Johnson, a founder and serial entrepreneur, discusses her $22M exit from Create & Cultivate and her journey back after buying the company back. She shares her experience with burnout and divorce, which led her to take a year off for self-discovery. Jacqueline reveals how she turned $10K into $1.2M through angel investing while enjoying a lavish lifestyle. She talks about the scrutiny female founders face, the difference between wealth and status, and how she finally felt successful. Her insights on building community and future-focused wealth strategies are particularly inspiring.

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00:00 / 00:00

Selling, Buying Back, And Resetting

Jacqueline sold her first company, invested $50K into Create & Cultivate and later sold it for $22M.
She later bought it back for less and now runs it with stronger boundaries and operational partners.

00:00 / 00:00

Never Run Day-To-Day Again

Hire operational leaders and set firm boundaries so founders don't run day-to-day.
Use operators to focus on strategy while delegating execution and avoid burnout.

00:00 / 00:00

Small Bets Can Yield Massive Returns

Jacqueline built liquid wealth via real estate, stocks and angel investing into ~25 startups.
A $10K friends-and-family check into Away became a ~$1.2M payoff and hooked her on angel investing.

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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/

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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.