27: Leadership Lessons from a CEO: Denise Conroy's Road to the Top

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 passed away at 38, leaving behind a wife and young child with no coverage, and no financial protection. It’s a harsh wake-up call and a reminder that life can change in an instant. Here’s what you’ll le...

3 Sep 27min

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 hidden financial risks that can last for decades. In this episode, Jess & Brandon explore: How career gaps impact your resume and earning powerWhy retirement savings and Social Security shrink when you’re out of the workforceThe power imbalances that can emerge in single-...

27 Aug 31min

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 in Nigeria, Bola absorbed early money lessons from her parents and watched her mother’s determination change the trajectory of their family. After being dismissed by a financial advisor who questio...

20 Aug 1h 2min

In this episode, Jess and Brandon tackle the misconception of taxes, corporate greed and the new twist in retirement planning: cryptocurrency in your 401(k). The path to financial security lies in addressing the real economic challenges: demanding fair compensation, understanding the true value of your work, and sticking with sound, proven financial principles. If you want to stop falling behind and start building real financial security, this episode is your wake-up call. Watch this ep...

13 Aug 21min

Your income and investment returns matter—but nothing predicts your financial freedom more than your savings rate. Yet, most Americans save only 3–5% of their income, a level that almost guarantees they’ll have to work far longer than they’d like. In this episode, Jess & Brandon reveal why your savings rate is the true driver of wealth and how it works regardless of income level. They share real examples of modest earners who retired as millionaires—and why high-income professionals often...

6 Aug 24min

Money secrets can wreck marriages—and cost you everything in divorce. In this episode, Forensic Accountant, Tracy Coenen, reveals how spouses hide assets (think offshore accounts, hidden income, even billionaires fighting over private jets) and how she uncovers the truth. Tracy’s 25+ year career as a forensic accountant gives her a unique lens into corporate fraud, white-collar crime, and high-stakes divorce battles. In this episode she shares: How to spot signs your partner might be hi...

30 Juli 46min

Ever wonder how politicians like Nancy Pelosi and Marjorie Taylor Greene grow millionaire-level wealth while you're getting hit with overdraft fees? In this episode, Jess and Brandon expose the shady world of insider stock trades, slap-on-the-wrist fines, and the double standards baked into the system. Then they’re coming for out-of-touch celebrity financial “advice” that sounds more like satire. If you’re tired of money tips that ignore real-life struggles, this one’s for you. Let’s ta...

23 Juli 35min

Still swiping your debit card? You could be earning serious rewards instead. In this episode, Jessica and Brandon unpack how they use credit cards as intentional tools to build value—whether that’s free travel, cashback, or everyday perks that actually make life easier. They explain how to choose cards based on what you’ll actually use, not what sounds flashy. For Jessica and Brandon, travel rewards are the priority—like the $1,500 they saved on a family trip to Panama using points from just ...

16 Juli 20min