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

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

Update: 2025-09-30
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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:

Sponsors:


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

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

Hampton