Planning for Exit Before You’re Ready to Exit

Jesse Jackson, founder of Mango Automotive, reveals how she built an eight-location auto repair empire from scratch—despite having no prior experience in the industry—by embracing discomfort, learning relentlessly, and strategically partnering with experts. Her journey began after helping a software company exit to private equity, where she saw a massive opportunity in the automotive sector: six in ten owners were planning to retire within a decade. What made her success possible wasn’t industry expertise, but her ability to question everything, hire people better than herself, and act decisively—even when it meant boarding the wrong plane. She shares a pivotal lesson: as businesses grow, the cost of decisions escalates, and the ability to slow down and think through consequences becomes critical. Balancing a seven-child family with an eight-figure business, Jesse admits her life is held together by 'a hair tie and two broken bobby pins,' but she thrives on the struggle, embracing the chaos as proof she’s growing. Her core philosophy? 'You have to be willing to eat glass' and set audacious goals—because real growth happens when you’re uncomfortable and committed to evolving. The episode underscores that scaling a business isn’t about doing more—it’s about doing less, better, by delegating, learning, and making bold but thoughtful moves.