ChooseFI Podcast Episode Show Notes Episode Title: Unlocking Travel Rewards for Families **Episode Summary:**Travel rewards can significantly cut travel costs for families, allowing them to enjoy vacations without the burden of flight expenses. Lynn from Families Fly Free introduces the 80/20 principle for maximizing travel rewards, emphasizing efficient strategies for redeeming points. Families can leverage credit card sign-up bonuses to earn free flights, especially through the Southwest compa...
Nov 29, 2021•49 min•Ep. 353
You already know how to save, invest, and track your expenses — but when did you last map your entire financial ecosystem? Most DIY investors in the FI community can name their portfolio allocation, but ask them about beneficiary designations, tax-efficient asset location, or whether their spending actually reflects their values, and the answers get fuzzy fast. Cody Garrett, CFP and founder of Measure Twice Money, helps FI-minded people fill those gaps without the traditional advisor fee structu...
Nov 21, 2021•1 hr 9 min•Ep. 352
Congress is about to eliminate the backdoor Roth IRA — and you have until December 31st to act. Sean Mullaney returns to help you squeeze every last tax benefit out of 2021 before year-end deadlines slam shut. This year's tax landscape looks different: backdoor Roth conversions face a new deadline, modified adjusted gross income thresholds determine who qualifies for key tax credits, and early retirees have a shrinking window to optimize Roth conversions. Whether you're racing to max out 401(k) ...
Nov 15, 2021•59 min•Ep. 351
When 70% of your net worth suddenly lands in a single stock, you're not managing a portfolio anymore — you're gambling. Brad and Jonathan tackle the terrifying euphoria of runaway winners with Brian Feroldi, who walks through exactly when to take profits, how to stomach the volatility, and why your tax bill might be the least of your problems. As prices surge on holdings like Tesla, Bitcoin, or Ethereum, investors face an uncomfortable reality: what started as a balanced portfolio can morph into...
Nov 08, 2021•42 min•Ep. 350
The personal finance acronym you know could cost you thousands—but the one you don't know might cost you everything. Brad and Jonathan break down NGMI (Not Gonna Make It) and HFSP (Have Fun Staying Poor), two phrases exploding across crypto communities, while dissecting what they reveal about investor psychology and market dynamics. Timestamps & Key Topics [00:02:51] NGMI: Not Gonna Make It The acronym reflects a negative viewpoint on financial prospects, especially in investments. [00:03:09...
Nov 01, 2021•48 min•Ep. 349
You're convinced retirement planning is all spreadsheets and sacrifice—but what if the biggest wins come from understanding a few simple rules most people never learn? Jonathan and Brad break down how mastering the mechanics of the tax code, employer benefits, and spending strategies can accelerate your path to financial independence without requiring a finance degree. Key Topics and Takeaways Introduction to Financial Independence [00:01:21] Overview of the financial independence concept and th...
Oct 25, 2021•53 min•Ep. 348
Most investors think a 50% loss needs a 50% gain to recover. They're wrong — and that math mistake can destroy retirement plans. Brad and Jonathan unpack the deceptively simple mathematics of percentage returns and why statistical blind spots lead to massive financial miscalculations. The conversation centers on how losses hit harder than equivalent gains, why the sequence of returns matters more than average returns, and what safe withdrawal rates really mean when markets swing violently. They ...
Oct 17, 2021•49 min•Ep. 347
Most people think they understand their retirement accounts — until they try to figure out the tax bill. Brad and Jonathan break down the three main "buckets" of retirement savings and reveal why knowing the difference between tax-deferred and tax-free accounts could save you thousands in taxes you don't need to pay. Brad's father-in-law asked a deceptively simple question over the weekend: "I've got a 401k, IRAs, a brokerage account, and savings — how do I figure out what gets taxed and when?" ...
Oct 10, 2021•56 min•Ep. 346
Rethinking your career path doesn't mean starting over—it means building on what you already have. Brad and Jonathan break down how to navigate career transitions without sacrificing the financial independence you're working toward, while juggling the real demands of family life. The hosts share candid reflections on finding pockets of freedom as parents, including Brad's first solo breakfast with his wife after both kids started preschool. They explore how small budget decisions, like cooking a...
Oct 04, 2021•50 min•Ep. 345
Playing it safe with your money might feel smart — until you realize you're watching your savings shrink year after year while others build real wealth. Brad and Jonathan dissect how excessive caution in investing often backfires, costing you more than any market downturn ever could. Drawing from William Green's "Richer, Wiser, Happier" and Morgan Housel's "The Psychology of Money," they explore why trying to avoid all risk actually guarantees poor returns. The culprit? Opportunity cost and infl...
Sep 27, 2021•44 min•Ep. 344
Settling for "good" might be the very thing blocking your path to greatness. Brad and Jonathan examine how autopilot living keeps us comfortable but stagnant, and why breaking out requires confronting uncomfortable truths about where we actually stand. Drawing from Jim Collins' Good to Great , they introduce the Stockdale Paradox: maintain unwavering faith in a positive outcome while simultaneously facing the brutal facts of your current reality. This balance—not blind optimism, not crushing pes...
Sep 13, 2021•40 min•Ep. 342
Spending $50 more on the right Airbnb location can transform an entire vacation—but most people in the FI community would never consider it. Jonathan and Brad share their experiences from Red X month, a dedicated period where they completely disconnected from work to focus on family and personal priorities. They challenge the scarcity mindset that often dominates personal finance discussions and explore how strategic splurges—from better-located accommodations to services that free up mental ene...
Sep 06, 2021•55 min•Ep. 341
That aging baseball card collection gathering dust in your closet might be worth more than your entire investment portfolio. Brad and Jonathan examine a listener's surprising discovery about the real value of their childhood sports cards — and why the same market forces driving up stocks and real estate have quietly transformed the collectibles market. The conversation reveals how grading systems, artificial scarcity, and changing demand can turn nostalgic keepsakes into serious financial assets...
Aug 30, 2021•42 min•Ep. 340
Most people obsess over cutting expenses, but there's a floor to how much you can save — and no ceiling to how much you can earn. Brad and Jonathan team up with Alan Donegan from Rebel Business School to flip the script on traditional personal finance advice, mapping out ten concrete strategies to increase your income without sacrificing what makes life worth living. Key Insights Financial Independence Is Not About Deprivation True financial independence should enhance your life, not restrict it...
Aug 16, 2021•1 hr 9 min•Ep. 338
Most people dream of making every day feel like vacation—yet struggle to inject spontaneity into rigid family routines. Heidi Dusik, host of the Ordinary Sherpa podcast, reveals how families can design their lifestyles around accessible adventure, meaningful experiences, and joy—without draining the bank account. From conducting a "joy audit" to practicing untourism, she offers practical frameworks for enriching family connections through everyday adventures. Key Topics: Adventure Mom Lifestyle ...
Aug 09, 2021•1 hr 2 min•Ep. 337
Most side hustle advice tells you to mow lawns. Nick Loper found 99 other ways to make your first $1,000 — and some of them are delightfully weird. Brad and Jonathan sit down with the Side Hustle Show host to explore everything from mobile notary work to professional grilled cheese chefs, focusing on why that first thousand dollars matters more than you might think. Whether you're building a crisis fund or flexing entrepreneurial muscles for the first time, this episode breaks down three core bu...
Aug 02, 2021•50 min•Ep. 336
What if the life you're building—the one everyone says you're "supposed" to want—isn't actually yours? Jonathan and Brad dissect the autopilot choices most people make from college to career to retirement, questioning why we follow paths we never consciously chose. The episode unpacks the "standard lifecycle narrative" and challenges listeners to reclaim time now instead of deferring fulfillment to some distant golden years. Through discussions on career flexibility, alternative education models...
Jul 26, 2021•52 min•Ep. 335
Jonathan thought he'd save money growing his own vegetables. After tallying up garden boxes, soil, and tools, his homegrown zucchini might be the most expensive produce he's ever eaten. Brad and Jonathan explore this and other listener questions in today's mashup episode, from tracking inflation's real impact on your budget to protecting your family's wealth through estate planning. Experiments in Financial Independence Jonathan shares his gardening experiment, breaking down initial investments ...
Jul 19, 2021•56 min•Ep. 334
Most people dream of retirement as a single distant finish line. What if you could cross it multiple times—starting now? Brad and Jonathan explore how mini retirements reframe the entire concept of taking time off. Instead of deferring adventure and personal growth until age 65 (or 85, in the Suze Orman scenario), mini retirements let you inject intentional breaks into your working years. Guest Jillian Johnsrud shares how she's woven multiple extended breaks into her journey toward financial ind...
Jul 12, 2021•1 hr 2 min•Ep. 333
Most people treat their tax refund like hitting the lottery—exciting, but they never stop to question why the government had their money in the first place. Sean Mullaney walks Jonathan Mendonsa and Brad Barrett through what your tax return actually reveals about your finances and where you might be leaving money on the table. The conversation covers capital gains distributions that silently erode returns, the strategic use of HSAs beyond basic medical expenses, and how adjusted gross income det...
Jul 04, 2021•1 hr 1 min•Ep. 332
The Federal Reserve is projecting 3.4% inflation, but the Consumer Price Index is already hitting 5%. That gap matters more to your portfolio than you might think. Brad and Jonathan sit down with Karsten Jeske (Big ERN) from Early Retirement Now to dissect what rising inflation means for your investment strategy—and whether you need to change course. With costs rising across sectors and media coverage intensifying, the core question is simple: Is this a temporary spike, or a sustained shift that...
Jun 28, 2021•1 hr 2 min•Ep. 331
Home prices shooting to the moon while your friends bid $100,000 over asking and still get rejected—sound familiar? The current housing market has a shortage of inventory creating fierce competition among buyers, a stark contrast to the 2006 surplus that led to the last crash. Real estate expert Paula Pant breaks down why this frenzy is fundamentally different from past crises and shares concrete strategies for navigating it without losing your shirt. Current Market Dynamics [00:01:00] Bidding w...
Jun 21, 2021•1 hr 15 min•Ep. 330
Stock prices soar and plummet while the underlying businesses barely budge. ARK's latest struggles and Zoom's wild ride reveal a fundamental truth most investors miss: short-term stock movements have little to do with actual business performance. Brian Feroldi breaks down how to separate market noise from real value. High-profile funds like ARK and companies such as Zoom Video Communications have shown extreme volatility despite strong business performance. Brian explains how to evaluate a compa...
Jun 07, 2021•50 min•Ep. 328
Your skills can't sell themselves—and neither can a résumé alone. Brad and Jonathan dismantle outdated job-search tactics and show why identifying your "talent stack"—the unique combination of experiences that make you valuable—matters more than ever. Rather than relying on canned cover letters and keyword-stuffed résumés, the hosts argue for a diagnostic approach: map your abilities, learn to articulate them clearly, and use networking to get in front of hiring managers before your résumé does....
May 29, 2021•49 min•Ep. 326
Your kids won't remember another Netflix binge — they'll remember the Saturday you taught them to ride bikes, made pancakes together, or built a backyard fort. Jonathan and Brad tackle an overlooked truth about family life: the most memorable moments rarely cost money, and the financial habits you model now will echo for decades. The conversation spans the importance of prioritizing quality time with family, recognizing value in everyday experiences rather than expensive outings, and the signifi...
May 28, 2021•48 min•Ep. 325
Most people drift through their finances on autopilot until something forces them to wake up. Jonathan and Brad map the journey from that first "hair on fire" moment of financial awareness through specific milestones that turn abstract goals into achievable wins. The hosts break down financial independence into distinct stages: hair on fire (urgent financial awakening), drift (financial stagnation), and key checkpoints like net worth zero, coast FI, half FI, and fat FI. They emphasize tracking p...
May 24, 2021•1 hr 5 min•Ep. 324
Cryptocurrency is not the casino you think it is — it's far more dangerous because it feels legitimate. Brad and Jonathan explore pump and dump schemes through the cryptocurrency lens, dissecting the psychological forces that drive irrational investor behavior. Using recent gasoline shortages as an example of scarcity-driven panic, they examine how fear, social media influence, and hype create perfect conditions for market manipulation. The conversation distinguishes speculation from investing, ...
May 21, 2021•1 hr 5 min•Ep. 323
Most people wait until a crisis to rethink their finances. Dennison's pandemic disruption forced him to rebuild from scratch—and what he discovered changed everything. When his plans fell apart, he learned that the real path to financial independence wasn't following a rigid blueprint, but mastering adaptability itself. Dennison's journey began with his immigrant parents from the Philippines, who worked multiple jobs while instilling a powerful work ethic. Their frugality and dedication laid the...
May 17, 2021•44 min•Ep. 322
The pandemic forced millions to confront a question they'd been avoiding: Why am I doing this? For many high earners on the path to financial independence, the answer suddenly became uncomfortably vague. Jonathan and Brad explore how the past year's workplace upheaval has exposed cracks in traditional career thinking—and created rare opportunities to renegotiate the terms of work itself. They examine "one more year syndrome," the tendency to defer personal fulfillment for one more bonus, one mor...
May 10, 2021•44 min•Ep. 320
A single Roth IRA contribution made when your child is young could grow to over a million dollars by the time they retire. That's the power of time and compounding working together—and it costs far less than you'd think. Equipping children with financial independence tools starts with teaching them the importance of saving and investing. The episode emphasizes using vehicles like Roth IRAs to encourage early wealth building. Children with earned income can contribute to these accounts, and even ...
May 07, 2021•42 min•Ep. 319
