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Health insurance costs are climbing, and this year’s open enrollment feels tougher than ever. Premiums are up, deductibles are higher, and plans seem designed to confuse you. In this episode, Jess and Brandon walk through how...
In this powerful episode, Jess and Brandon sit down with Ange Matthews, a first-generation investor and founder of The Happy Happy Method, who went from making $40K a year and battling six-figure debt to building seven-figure...
Confused about Roth vs Traditional IRAs? You're not alone. In this episode, Jess and Brandon break down the pros, cons, and real-world impact of choosing a Roth IRA versus a Traditional IRA for your retirement game plan. Learn how taxes, income levels, and long-term growth factor into the decision,…
In this episode, Jessica and Brandon dive into a tricky but essential question: How soon should you bring up money when you're dating? They unpack why money often feels taboo, share tips to start the conversation without tens...
What If You Could Completely Transform Your Finances in Just 180 Days? Forget overnight success stories and overwhelming budgets, this episode is about real, lasting change. Jess and Brandon are breaking down a six-month financial reset plan that shows you exactly how to take control of your money,…
Feel like investing is only for finance bros and math nerds? You’re not alone and this episode is about to change that. We’re joined by Chloé Daniels, the powerhouse behind Clobare Money, who’s helped over 300,000 people ditc...
GoFundMe should never be your family’s financial plan. In this episode Jess & Brandon break down why life insurance is a non-negotiable part of smart financial planning, no matter your age, income, or relationship status. They share a powerful, heartbreaking story of a brilliant friend who pass…
For many families, the decision to become a stay-at-home parent isn’t really a choice, it’s the result of America’s broken childcare system. Daycare costs can swallow an entire paycheck, but leaving the workforce carries hidd...
What does true financial freedom look like for women? Bola Sokunbi, founder of Clever Girl Finance, shares her journey from witnessing women in crisis—arriving at her family’s doorstep with nothing but suitcases—to building one of the largest personal finance platforms for women in the U.S. Raised …
Choosing between a Roth IRA and a Traditional IRA seems simple on the surface—pay taxes now or pay taxes later—but the details shape your real after-tax wealth. This episode explores the basics and the nuance: how each account treats tax…
When it comes to dating, we often focus on chemistry, shared interests, and physical attraction. But there's one critical topic that too many couples avoid until it's too late: money. In today's relationship landscape, understanding your partner's f…
In today's fast-paced world, financial stress can feel overwhelming. Many people believe that transforming their finances requires years of sacrifice or drastic lifestyle changes. However, what if you could completely reset your financial trajectory…
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.
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