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Oct. 30, 2025
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Send a text If you feel like homeownership is out of reach, you’re not imagining it. In this episode, we break down why buying a home today is drastically harder than it was for previous generations and why this has nothing to do with lattes, avocado toast, or bad budgeting. We walk through real nu…
Send us a text If you've ever been confused about mutual funds, ETFs, and individual stocks, this episode is your beginner-friendly breakdown. Jessica and Brandon cut through the noise to explain what each investment type really is, how they work, and how to choose what’s right for your goals. From…
Send us a text A woman finds out she’s still the beneficiary on her ex-husband’s life insurance policy, years after their divorce. He’s since remarried and had a child. When he passes away unexpectedly, she’s notified she’ll receive $100,000. Now the new wife is asking for the money… for their chil…
Send us a text Are you managing money together, or living in two separate financial worlds? In this episode, Jessica and Brandon get real about a problem nearly every couple faces: one partner handling finances while the other stays out of the loop. That disconnect causes confusion, stress, and eve…
Financial planning isn’t a one-size-fits-all game. Life happens in seasons, and your money should move with them. In this episode, Jessica and Brandon break down the 4 major financial seasons, Building, Stability, Stretch, an...
Start the new year off right with a clear, actionable financial plan. In this episode, Jessica and Brandon walk you through five key money moves to make in January, from setting financial goals and reviewing your budget to bu...
Before you set another New Year’s resolution or budget goal, hit pause and reflect. In this episode, Jessica and Brandon walk you through the exact steps to do a personal money audit that sets you up to win in 2026. Whether y...
Most people think their money problems come from a lack of budgeting. But what if the real issue is emotional? In this powerful episode, Jessica and Brandon sit down with Aja Evans, LMHC , a licensed financial therapist and a...
Most couples don’t break up because of infidelity — they break up over money. And worse? They never saw it coming. In this episode, we’re breaking down the 5 biggest money mistakes that silently sabotage relationships… and ho...
Co-Host
Jessica works in sales enablement and IT strategy. A former classroom teacher, she is also the author of the award winning Your Hair is Magic line of children’s books. “Your Hair is Magic: Bed Head” was featured on LIVE with Kelly and Ryan on ABC in 2021. She has been featured on WRAL, Spectrum News, Fox 46 and more. Jessica is a dynamic and inspirational speaker, but her favorite job title is "mama."
Co-Host
Brandon is an award winning licensed financial planner, and owner of Oak City Financial, with over a decade of experience and millions of dollars managed for his clients all over the United States. He began his career at Fidelity, later moving to New York Life, before starting his own firm. Brandon is also an adviser with the startup, WhiteFlag Inc., a mental health app that provides immediate customized peer support. He believes that no two clients are the same, and personalizes all of his financial planning to the goals of the individual. His ideal clients are elder millennials who want to live their best lives... whatever that means for them.