Wilson (46) and Shannon (35) have built a strong financial foundation—owning a vacation rental, maxing out Roth IRAs, and earning solid incomes. But when it comes to their next move, they’re at odds.
Wilson wants to tap into their home equity to invest in stocks, believing they’re too heavily weighted in real estate. Shannon, more risk-averse, worries 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 38m
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
Feb 2025
Ask HTM - Birth Now Pay Later, Forcing Home Equity with a Basement Build, & Saving vs Paying Credit Cards #946
Let’s dive into the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guid ... Show More
54m 2s
Sep 29
Should You Pay Off Debt or Invest First? The Answer Might Surprise You (Money Q&A)
In this episode of the Personal Finance Podcast, we are going to do a Money Q&A about should you pay off debt or invest first. Today we are going to answer these questions: Question 1: Should I build my emergency fund to $20,000 first, or start paying down my mortgage and investi ... Show More
37m 34s