Courtney (40) and Ray (41) have spent their entire adult lives in the structure of military life—but with retirement on the horizon, they’re about to face a future filled with choices for the first time.
For Ray, that means walking away from the rank, routine, and pension he’s built for over 20 years and entering a civilian job market he knows little about. ... Show More
Oct 7
229. “I’m almost 50 and have nothing to show for my life”
Christine (47) and Thad (57) have been together for more than six years, but instead of building wealth, they’re buried under nearly $340,000 of debt. Christine, the self-appointed “CFO,” is exhausted from tracking every bill, while Thad avoids the details and spends freely. Thei ... Show More
1h 44m
Sep 30
228. “I’m 30, broke, and tired of budgeting”
Kristen (30) and Josh (36) married just last year, but their honeymoon phase is buried under $40,000 of debt and a sense of being “trapped.” Kristen is meticulous, tracking every dollar and carrying deep guilt around spending—even on herself. Josh, meanwhile, shrugs off the stres ... Show More
1h 38m
Sep 23
227. “We bought our dream house. Now we’re drowning”
Jason (38) and Katie (36) thought buying their dream home in Minnesota would be the start of a new chapter. Instead, they’re buried in debt, daycare bills, and the pressure of raising a new baby while working demanding creative jobs in an industry threatened by AI. Despite earnin ... Show More
1h 20m
Jul 30
Mini Retirements: How to Take a Break Sooner That Could Also Boost Your Career and Income with Jillian Johnsrud
#239: Why wait until you're 65? It's feasible for almost anyone to take a mini retirement and when done right, it can also fast-track your career and income. Learn how to plan one, negotiate time off, manage costs, avoid pitfalls, and make it work if you’re self-employed. Plus, w ... Show More
1 h
Aug 2024
Navigating Your Twenties: How to Stop People Pleasing, Take Control of Your Bad Habits, Find What Makes You Happy & *ACTUALLY* Follow Your Dreams
This week's episode Kenzie sits down with Twenty Whatever to record another episode on navigating your twenties. The girls are talking financial literacy, relieving stress, following your dreams, taking the harder path, how to stop people pleasing, and following your dreams. ENJO ... Show More
51m 26s
Jul 29
Your Future Self is Begging You To Listen to This Episode (Let's Talk How Much Super You'll Really Need)
Trying to figure out how much super you actually need? Yep, it’s confusing. With all the numbers, charts, and retirement buzzwords flying around, it’s no wonder most of us throw it in the “deal with it later” pile. But future you? They’re going to be so glad you tuned in. This we ... Show More
39m 58s
Apr 2025
227. How to Stop Caring What People Think with Mel Robbins
You know that little voice in your head that says, “What will they think?” The one that’s held you back from hitting publish, setting a boundary, or even just being yourself? Yeah, we’re done with that. In this episode, I sit down with the iconic Mel Robbins to talk about how to ... Show More
1h 25m
Jan 2025
#896 - 3.25M Q&A - Marriage Plans, Beautiful Women & Chris Bumstead
I hit 3.25 million Subscribers on YouTube!!To celebrate, I asked for questions from YouTube, Twitter and Instagram, so here’s another 90ish minutes of me trying to answer as many as possible.Expect to learn my thoughts on the Fin vs The Internet episode, what my favorite band I’m ... Show More
1h 44m
Apr 2025
228. The Most Important Financial Decision You'll Ever Make (That NO ONE Talks About)
Worried about the stock market or a possible recession? Register for our FREE 'Don't Panic' workshop for your 3-step plan for financial security in 2025: herfirst100k.com/SOS We spend so much time stressing over budgets, investments, credit scores—basically, all the numbers. But ... Show More
48m 56s