Jess Jackson grew up believing she was solidly middle class. But once she arrived at college, she realized many of her peers came from far wealthier backgrounds. Determined to keep up, she borrowed more than she should have—decisions that later became a heavy financial burden. 

Her journey has been one of jumping into new opportunities and learning through trial and error. She bought her first home at a young age, navigating plenty of financial growing pains along the way. Over time, those lessons fueled her growth into a successful business built around real estate investment. 

As her career has evolved, Jess has had to reinvent herself more than once. The path hasn’t been easy, but her persistence and resilience continue to drive her forward—and inspire her to create a better world for those around her. 

2:40 Jess reflects on how being around people of different financial means influenced her. 

7:09 When she attends the University of Michigan, she feels pressure to keep up with the Joneses. 

11:42 Her credit score prevents her from getting approved for housing while in a teaching program. 

12:56 She optimizes available resources as she gets her MBA. 

14:52 Jess buys her first house and learns a lot along the way. 

19:26 She learns a financial lesson related to her business and taxes. 

20:43 She balances her savings goals and student loan repayment goals. 

23:09 She discusses shame and ego and how this contributed to her stress. 

24:58 She experiences job loss and a subsequent mental breakdown but emerges in a better place. 

28:58 Jess shares some practical money tips. 

35:18 Our co-hosts reflect on the themes from Jess’ story.  

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