I Sold My Company for $22M. Here’s Why I Bought It Back.
Moneywise
Hampton
4.7 • 701 Ratings
🗓️ 30 September 2025
⏱️ 36 minutes
🧾️ Download transcript
Summary
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.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Most founders agree the hardest part of scaling a business is not the product. It's the hiring. |
| 0:06.4 | You've got to find, interview, and vet the right people. And if you're growing, like Hampton, my company, |
| 0:11.7 | you're doing it almost all of the time. And that's why Oceans is so valuable for business owners. |
| 0:18.1 | They place U.S. level talent out of Sri Lanka. They're vetted, train, |
| 0:23.1 | and supported so you can stop spending months on the hiring grind. At Hampton, we've got a few |
| 0:29.1 | ocean hires in our team, including Myonie. They truly are part of our team. And so for our |
| 0:35.4 | all hands last week, they met up at our co-working spot in Sri Lanka just so they can be together for the Zoom call. Also, |
| 0:42.6 | Oceans can place talent across operations, finance, marketing, or EAs. Whether you need an |
| 0:50.0 | EA or an entire marketing team, they adapt to your stage of growth. If hiring is slowing you down, |
| 0:55.9 | check out oceanstalent.com. Mention money-wise and you'll get $500 off your first hire. Again, |
| 1:02.9 | oceans, talent.com. Founders don't burn out just from long hours or bad markets. A lot of the time, it's this invisible pressure and a constant need to prove yourself. |
| 1:16.6 | Underneath all the metrics and milestones is a human being who once had a wild idea and actually made it happen. |
| 1:22.6 | But when does that feeling go away, that scrappy, anxious energy? |
| 1:26.6 | When you stop chasing and start feeling successful? |
| 1:31.1 | Today's guest, Jacqueline Johnson, might be one of the rare few who actually does. |
| 1:36.0 | She's built and sold multiple businesses, including one for $22 million. |
| 1:39.7 | But what stands out isn't the exits, it's the quiet confidence that shows up when that voice of doubt finally dies down. |
| 1:46.0 | I don't have some big lofty goal to be like billionaire and have $50 million in the bank. |
| 1:53.0 | I'm not like big on having that much money in general, like as a person. |
| 1:57.0 | I definitely feel like I've completely lost FOMO. |
| 2:00.0 | I actually really enjoy missing out on stuff. |
| 2:01.6 | Like, I think it's actually really nice. |
... |
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