Episode Description
Jaclyn Johnson built her company, Create & Cultivate, from nothing - and later sold it for a $22 million exit!
But life changed completely when she was diagnosed with breast cancer in 2025. The success she worked for left her burned out, depressed, and forced to start over.
What followed was a total reset. Divorce. Moving cities alone. Hiring a dating coach. Rebuilding her identity at 40…
Today, Jaclyn has successfully bought her original business back, has launched 2 more and continues her work as a longtime angel investor, having backed and championed female founders throughout her career. She reveals how she spots winning startups, why staying bootstrapped was her biggest business mistake, and how money changed the way people treated her.
Jaclyn Discusses:
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Your Body Keeps the Receipts: How her breast cancer diagnosis made her realise health is her real wealth and what she wishes she’d understood earlier.
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Reinventing Yourself: How she rebuilt her identity at 40 and how you can do the same when the life you’ve built no longer fits.
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Angel Investing Wins: How she approaches angel investing, what she looks for in founders, and why one small check can change everything.
Timestamps
00:00:00 Intro
00:02:57 Why Starting Over At 40 Felt Like A Gamble
00:05:35 Dating Again At 40 “I Was Too In My Masculine”
00:07:29 Lessons From A Dating Coach - From Anxious Attachment To Secure
00:10:24 I Sold My Company… And My Life Fell Apart
00:13:44 The Strange Sadness After Selling A Business
00:14:53 Can You Build A Huge Business Without Sacrificing Your Life?
00:16:36 Growing Up With Entrepreneur Parents
00:18:47 “You Won’t Build Real Wealth From A 9-5” Jaclyn's Money Rules
00:20:37 The $12,000 Angel Investment That Paid Out Millions
00:22:39 beehiiv Ad
00:24:01 What The Perfect Employee Actually Looks Like Today
00:27:12 I Sold My Company - Then What?
00:33:45 Why Jaclyn Refused To Be CEO Again
00:35:01 Some People Are Built For Stress - Others Aren’t
00:36:29 Jaclyn’s Biggest Regret - Not Raising Venture Capital
00:38:12 Why Women Must Talk About Money Openly
00:40:45 The Money Rules Jaclyn Lives By
00:44:48 How Men And Women Think About Money Differently
00:46:46 How To Pitch Investors Without Selling A Fantasy
00:48:05 Cozy Earth Ad
00:49:11 Should You Start Angel Investing? Here’s How To Know
00:51:29 How To Spot Winning Startups Early
00:52:45 The Smallest And Biggest Cheques She’s Ever Written
00:53:25 How To Break Into Angel Investing Without Capital
00:56:14 Getting Equity By Advising Instead Of Investing
00:57:10 Jaclyn’s Breast Cancer Diagnosis
01:02:41 How Cancer Changed Her Relationship With Money And Success
01:03:53 When Your Body Forces You To Pay Attention
01:05:28 The Advice She Says Could Save Your Life
01:08:18 How To Stop Falling Back Into Dark Periods
01:09:30 Rapid Fire: Credit Cards, Therapy & First Class Flights
01:12:21 Where To Find Jaclyn Online
Episode Sponsors:
. Cozy Earth - http://cozyearth.com with code HSR
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Follow Jaclyn Johnson:
Instagram: https://www.instagram.com/jaclynrjohnson
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