Exit Negotiations, Timing, and the Importance of Advisors

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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/
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• 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.