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

Podcast: Moneywise

Published: 2025-09-30

Duration: 37 min

Summary

In this episode, Jacqueline Johnson shares her journey of building, selling, and eventually buying back her company, Create and Cultivate, emphasizing the importance of internal success and having a balanced approach to entrepreneurship.

What Happened

Jacqueline Johnson, a seasoned entrepreneur, discusses her career journey, beginning with the launch of her first company, No Subject, after being laid off at 23. This venture served as her crash course in entrepreneurship, leading to a successful agency that she eventually sold for a seven-figure sum, which she reinvested into her next project, Create and Cultivate. Despite her success, Jacqueline admits she struggled to enjoy her achievements as she quickly moved on to new ventures, including running a family office fund and launching a wine line.

By the end of 2022, feeling burnt out and having gone through a divorce, Jacqueline took a much-needed break in 2023. During this time, she focused on personal growth, traveling, and rediscovering joy in her life without the pressure of professional obligations. However, she soon felt a desire to re-engage with her entrepreneurial spirit, leading to a serendipitous opportunity to buy back Create and Cultivate. With a newfound perspective, Jacqueline embraced this challenge, applying lessons learned from her past experiences to rebuild the company with a focus on boundaries and support from operational partners.

Key Insights

Key Questions Answered

What led Jacqueline Johnson to start her first company?

Jacqueline Johnson started her first company, No Subject, after being laid off from her media job at the age of 23. She viewed this as an opportunity to embark on her entrepreneurial journey, which she describes as a crash course in entrepreneurship. The experience allowed her to learn from her mistakes and build a successful marketing events and influencer agency during the early days of social media.

What was Jacqueline's experience after selling No Subject?

After selling No Subject for an undisclosed amount in the seven-figure range, Jacqueline used her earnings to purchase a house in Los Angeles and invest in her next venture, Create and Cultivate. However, she felt the pressure to quickly move on to new projects, which prevented her from enjoying her financial success. She funneled much of her earnings into this new business, which was gaining significant momentum.

How did Jacqueline cope with burnout and personal challenges?

Jacqueline experienced burnout by the end of 2022, compounded by personal challenges including a divorce. She recognized the need for a break and spent much of 2023 focusing on herself, traveling, and engaging in activities that brought her joy. This period allowed her to step back from the pressures of entrepreneurship and reconnect with her personal interests, such as becoming a certified sommelier and practicing yoga.

What motivated Jacqueline to buy back Create and Cultivate?

Jacqueline's desire to buy back Create and Cultivate arose after she felt a renewed sense of purpose and readiness to return to the business world. The opportunity to reacquire the company came unexpectedly, and she interpreted it as a sign that it was meant to be. She embraced this new phase with a clearer vision of how to approach the business, putting systems in place to avoid past pitfalls.

What changes did Jacqueline implement after buying back her company?

After reacquiring Create and Cultivate, Jacqueline focused on establishing boundaries and collaborating with operational partners to manage the day-to-day operations. She recognized that this time around, the company was an established brand, requiring a different approach compared to her earlier experiences. By leveraging the strengths of her team, she aimed to rebuild the company while maintaining a sustainable work-life balance.