Juggling Family and Entrepreneurship: Real Talk with Jesse Jackson on Building an 8 Figure Empire

Juggling Family and Entrepreneurship: Real Talk with Jesse Jackson on Building an 8 Figure Empire

June 1, 2026 · 29 min

About this episode

Tiffani Higgins interviews Jesse Jackson about balancing family life with entrepreneurship while building a successful business.

Let’s be honest - none of us grew up dreaming about running payroll or juggling receipts. What we did dream about? More freedom, more time with family, and the chance to carve our own path. Today on the Stay-at-Home Bookkeeper Podcast, we sit down with Jesse Jackson—a powerhouse entrepreneur who jumped from environmental engineering to software, and finally into owning eight (!) automotive shops, all while raising seven kids. If you’re someone who wants more flexibility or you’re tired of bu...

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