I Sold My Company for $22M. Here’s Why I Bought It Back.
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this Money Wise episode, Harry Morton sits down with serial entrepreneur Jacqueline Johnson, who built and sold multiple businesses including Create & Cultivate for $22 million. (01:36) The conversation explores three distinct categories of success: financial, external recognition, and internal fulfillment. Johnson shares her journey from being laid off at 23 to building a marketing agency, then creating the influential Create & Cultivate brand that she eventually sold and later bought back at a lower price. (07:18) With a current net worth of $30-40 million and $15 million liquid, Johnson discusses the psychology of wealth, the pressure of being a female founder, and that pivotal moment when the drive to prove yourself finally quiets down. (02:02)
- Main Theme: Exploring the different dimensions of entrepreneurial success and when external achievements translate into internal fulfillment for ambitious founders
Speakers
Jacqueline Johnson
Jacqueline Johnson is a serial entrepreneur who founded and sold multiple companies, with her most notable exit being Create & Cultivate for $22 million. She started her entrepreneurial journey at 23 after being laid off from a media job, launching No Subject, a marketing and influencer agency in the early days of social media. Johnson has since built a diverse investment portfolio including 25 angel investments, with her first investment in Away luggage returning nearly $1.2 million on a $10,000 initial investment. She's also the author of "Work Party" and serves on the board of Half the Story, a charity addressing social media's impact on mental health.
Harry Morton
Harry Morton is the host of Money Wise podcast and founder of Lower Street, a podcast production company. He's also associated with Hampton, a private community for high-growth entrepreneurs doing over $3 million in annual revenue. Morton focuses on exploring the financial and psychological aspects of entrepreneurial success through conversations with founders who have achieved significant exits.
Key Takeaways
Build Your Financial Advisory Team Before You Need It
Johnson emphasizes the critical importance of establishing relationships with wealth advisors, private bankers, and tax specialists well before any major liquidity event. (33:37) When her first potential $40 million exit was in progress, her banker asked who she had lined up from Goldman Sachs or UBS, and she had no one. This taught her that founders, especially those who aren't venture-backed, often lack the network to make proper introductions to wealth management professionals. The tax implications alone can be devastating if not properly planned - especially in high-tax states like California. She now refers to her wealth advisor as "the CFO of my life," highlighting how crucial proper financial infrastructure becomes once you achieve significant wealth.
The Sweet Spot for Financial Happiness is Lower Than You Think
Despite having $15 million liquid and $30-40 million total net worth, Johnson believes the optimal amount for financial peace of mind is around $4-5 million. (16:25) Her reasoning centers on having enough money that "your money is making you money without you having to do a thing." This threshold provides the psychological cushion of financial security while avoiding the complexity and stress that can come with managing excessive wealth. She maintains what she calls a "mini bar mentality" - being mindful of spending despite her wealth - which has served her well in building sustainable financial habits.
Angel Investing Success Requires Diversification and Founder-First Thinking
Johnson's angel investing approach centers on building a personal venture fund of 25 companies with a founder-first philosophy. (10:42) While her Away luggage investment returned nearly $1.2 million on $10,000, she emphasizes this isn't normal. Of her 25 investments, only three have exited successfully, two have gone under, and the rest remain in play. Her strategy focuses on how she can help founders navigate exits since she's been through the process multiple times. She views angel investing as both giving back to the founder community and building her own diversified portfolio, treating each investment as part of a larger strategic approach rather than hoping for individual home runs.
Female Founders Face Disproportionate Personal Scrutiny
Johnson reveals a stark difference in how male versus female founders are covered in business media and held accountable for company performance. (20:32) When Amazon faces issues, headlines focus on the company, but when Create & Cultivate had problems, media coverage directly named her personally. This creates intense pressure for female founders to maintain a perfect public image across social media, events, and business performance. The scrutiny extends beyond professional decisions to personal appearance and behavior, creating an "unattainable level of perfection." Johnson actively works to counter this by openly discussing founder depression, business struggles, and the isolating aspects of entrepreneurship to provide a more realistic perspective.
True Success Means Losing FOMO and Choosing Selective Participation
The most profound shift in Johnson's relationship with success came when she stopped chasing external validation and recognition. (29:39) She no longer feels compelled to attend every high-profile event, travel to glamorous locations, or maintain the Instagram-worthy lifestyle that many successful entrepreneurs showcase. Instead, she "actually really enjoys missing out on stuff" and has lost the fear of missing out entirely. This mental shift allows her to focus energy on building and creating rather than maintaining appearances or networking for status. She describes this as moving from constantly chasing "the next big thing" to recognizing when "you've already arrived" and can build from a place of fulfillment rather than need.
Statistics & Facts
- Johnson sold Create & Cultivate for $22 million and later bought it back for less than the sale price. (07:18) This demonstrates the volatility of business valuations and the strategic opportunity that can arise from market downturns.
- Her first angel investment was $10,000 in Away luggage during the friends and family round, which eventually returned close to $1.2 million. (10:20) This represents a 120x return on investment over approximately seven to eight years.
- Of her 25 angel investments, only 3 have successfully exited with returns, 2 have completely failed, and the remaining 20 are still active. (11:23) This portfolio performance illustrates the typical risk distribution in angel investing where most returns come from a small number of winners.
