How to Money
iHeartPodcasts
Best friends Joel and Matt are the co-hosts of How to Money which is all about providing the knowledge & tools that normal folks need to thrive in areas like debt payoff, DIY investing, and crucial money tricks that will provide continuous help along your journey. We believe that access to unbiased and jargon-free personal finance guidance is more necessary than ever before. When you handle your money in a purposeful, thoughtful way that works for your lifestyle, you can really start living a rich life.
Episodes
Mentioned books
22 snips
Mar 11, 2026 • 57min
Are Teachers Doomed to a Broke Retirement? w/ Shaun Morgan #1112
Shaun Morgan, a full-time teacher and creator of the Teacher Money Show who advises educators on retirement and pensions. He discusses teacher pay cycles and budgeting, Public Service Loan Forgiveness and student loan strategies, pensions versus 403(b)/457 plans, stopping out-of-pocket classroom spending, and smart side hustles and career moves to boost retirement prospects.
16 snips
Mar 9, 2026 • 58min
Ask HTM - Debating a Raise vs WFH Flexibility, Investing in Nvidia, & Digital Hygiene Frugal or Cheap #1111
Listeners ask about choosing a big pay raise versus keeping full remote flexibility. A huge single-stock stake in Nvidia and strategies for rebalancing and tax-aware selling come up. They debate frugality versus cheapness, whether to let medical bills go to collections, and how to shop auto insurance through agents. Quick book picks for a 25-year-old and a beer tasting wrap things up.
18 snips
Mar 6, 2026 • 41min
Friday Flight - Jump at the Pump, Lessening Leverage, & Tapping Too Soon #1110
Quick takes on a sudden gas price spike tied to global oil risks. A look at the most fuel-efficient and cheapest new cars and total cost tradeoffs. Why remote roles are harder to land and job-hopping pay boosts have faded. Rising 401k hardship withdrawals and the pros and cons of tapping home equity. Trends in small business 401k access, pricey performance apparel, and budget Apple laptops.
18 snips
Mar 4, 2026 • 56min
Bouncing Back from Bankruptcy & Business Failure w/ Phil Sanders #1109
Phil Sanders, serial entrepreneur and founder of Multiply who helps business owners sharpen strategy and financial operations. He shares stories of rebuilding after business failure and bankruptcy. Conversations touch on profitability from day one, testing demand before scaling, managing debt and ego, stress-testing plans, and practical steps for recovery and sustainable growth.
18 snips
Mar 2, 2026 • 56min
Ask HTM - Housing Rule of Thumb, Axing a Boat Payments, & Making Bank on the World Cup #1108
Listeners ask practical finance questions about keeping mortgage payments manageable and simple rules to follow. They cover the nuts and bolts of 401(k) rollovers and when to use trustee-to-trustee transfers. Debate if paying off a boat loan or preserving emergency savings makes sense. Learn how short-term rentals for the World Cup can boost income and what tax rules to watch.
24 snips
Feb 27, 2026 • 41min
Friday Flight - Tariff Turmoil, Winning So Much, & Border-Hopping for Bargains #1107
A rapid roundup of tariff rulings and how unpredictable trade policy hits small businesses. Discussion of a new retirement-match proposal for workers without employer plans. Practical talk on home maintenance costs, DIY repairs, and timing the spring mortgage market. Strange tech headlines about AI after death, plus tips on medical tourism, grocery pantry planning, and smarter meat and seafood buys.
37 snips
Feb 25, 2026 • 49min
Die with Zero w/ Bill Perkins #1106
Bill Perkins, investor and author of Die With Zero, champions intentional spending to trade time and health for meaningful experiences. He discusses why time beats money, splurging on travel and shared memories, the idea of memory dividends, timing peak net worth earlier, and balancing saving with living now. Short, provocative takes on making life richer through deliberate choices.
Feb 23, 2026 • 58min
Ask HTM - High Net Worth but still Paycheck to Paycheck, Better Investing for Freelancers, & the Necessity of Amazon Prime #1105
Listener questions drive a fast-paced Q&A on student loan rescue strategies and beating toxic interest. They tackle living off investments despite steady net worth and how to model long-term sustainability. Freelance retirement planning meets Solo 401(k) tradeoffs versus taxable accounts. Practical takes on canceling Amazon Prime, using Fire TV, and top online business banking picks.
20 snips
Feb 20, 2026 • 42min
Friday Flight - 401k Mullets, Crappy Coffee, & Bitcoin Bashing #1104
Quick takes on quirky financial culture, from 401k mullets and solo 401(k) tips to the rise of surveillance pricing. A debate over cheap vs better home coffee gear pops up. They flag soaring credit card debt, collections rights, and high babysitting rates. The conversation also touches on an aging-driven spending shift, prediction-market gambling, and recent Bitcoin volatility.
22 snips
Feb 18, 2026 • 55min
Why Being “Good With Money” Still Feels So Hard w/ Shannah Game #1103
Shannah Game, a CFP and money therapist who helps people untangle emotions behind financial behavior. She talks about how hormones and past money trauma shape spending, why shame keeps people stuck, exercises to notice bodily money signals, and ways couples can share money histories to build better systems. Short, practical strategies for calming money stress and redefining what ‘enough’ feels like.
