2020 brought lower incomes for millions — but that also created a rare window for tax-savvy Roth conversions at historically low rates. Brad and Jonathan team up with tax expert Sean Mulaney to break down the year-end tax strategies that can save you thousands, from Roth conversions and tax-loss harvesting to strategic charitable giving and small business expense timing. With key deadlines looming, this episode walks through the specific moves you need to make before December 31st to optimize yo...
Nov 30, 2020•54 min•Ep. 274
Most people think a Roth IRA is just for retirement—but what if you could access the money right now, tax-free? Brad and Jonathan team up with tax expert Sean Malaney to explore how the Roth IRA functions as both a retirement vehicle and a flexible emergency fund. Contributions can be withdrawn anytime without taxes or penalties, making it a powerful dual-purpose tool for financial independence seekers. They break down backdoor Roth strategies for high earners, explain the tax rules you need to ...
Nov 27, 2020•49 min•Ep. 273
A $1,000 investment earning 10% can either make you $5,500 or $72,890 over 45 years — the only difference is whether you understand compound interest. Brad and Jonathan tackle one of the most fundamental concepts in personal finance, breaking down why compound interest truly deserves its reputation as the "eighth wonder of the world." Understanding compound interest is crucial when contrasting it with simple interest. The hosts emphasize how compound interest builds wealth over time, creating a ...
Nov 23, 2020•39 min•Ep. 272
Nine-year-old Annalise runs her own business, Creative Card Designs, navigating pricing decisions, marketing strategies, and business model pivots—skills most adults struggle with. Future-proofing isn't just about preparing for an uncertain world; it's about equipping both ourselves and the next generation with the entrepreneurial mindset to thrive regardless of what comes next. The conversation centers on how parents can nurture entrepreneurial thinking in children through programs like Simple ...
Nov 20, 2020•1 hr 7 min•Ep. 271
At 26, Amy had $150,000 to her name — despite starting at just $15 an hour through a temp agency. Her secret wasn't luck or a trust fund. It was treating her twenties like a launchpad instead of a waiting room. Amy shares how she tripled her salary to $93,000 by mastering LinkedIn networking and building a "skill stack" that made her impossible to ignore. With dual degrees in communications and international relations but zero job offers at graduation, she turned fear into fuel. She reveals the ...
Nov 09, 2020•49 min•Ep. 268
You can't predict the stock market's next move, but you can control what drowns out your peace of mind. Brad and Jonathan tackle multiple listener questions about staying sane during volatile times — from election anxiety to the temptation of market timing — by revisiting the alligator-and-kitten philosophy: eliminate the negative noise first, then focus on what builds you up. Key Topics Discussed Introduction to Alligators and Kittens [00:00:54] The metaphor illustrates how to prioritize mental...
Nov 06, 2020•47 min•Ep. 267
A Brown University graduate with over $21,000 in credit card debt—this isn't a cautionary tale about bad decisions, it's a story about a system that never taught her how money actually works. Yanelli, known as Miss Be Helpful, grew up in a low-income household where financial education didn't exist, and college only deepened the gap. One pivotal moment forced her to choose: keep swiping or break the generational cycle of poverty that had defined her family. She chose the latter, transforming her...
Nov 02, 2020•53 min•Ep. 266
Most people think financial independence means doing less work—but what if it's actually about doing more of what energizes you? Brad and Jonathan challenge that assumption by exploring how aligning your career with your passions creates both fulfillment and financial momentum. The episode centers on talent stacking: combining above-average skills to become exceptionally valuable in the job market. Rather than pursuing mastery in a single area, stacking complementary abilities—say, writing, basi...
Oct 30, 2020•51 min•Ep. 265
You might think money problems stem from poor decisions — but Lisa Peterson's research points to a different culprit: what happened to you as a child. Lisa Peterson, author of The Mindful Millionaire , reveals how the CDC Kaiser ACEs study connected adverse childhood experiences to adult financial struggles in ways most people never consider. Introduction to Financial Trauma [00:00:00] Awareness and Healing [00:04:28] Self-awareness reduces vulnerability to repeating financial mistakes. Understa...
Oct 24, 2020•39 min•Ep. 264
Most people who lose weight gain it back within months—yet Jonathan has kept 25 pounds off for half a year. The difference wasn't a diet plan or workout program. It was accountability. Jonathan explains how regular check-ins with friends and family created a framework that sustained his progress long after initial motivation faded. He and Brad connect this to Annie Duke's work on decision quality, showing how the same principles apply whether you're managing your health or your finances. By aimi...
Oct 23, 2020•47 min•Ep. 263
Most people judge their decisions by how they turn out — but what if that's exactly backwards? World champion poker player Annie Duke argues that focusing on outcomes instead of process is one of our biggest decision-making mistakes. When outcomes cloud our judgment, we miss the chance to learn from what actually mattered: the quality of our thinking at the time we chose. Duke's new book How to Decide offers frameworks to break this pattern. Through strategies like pre-mortems (imagining why a d...
Oct 19, 2020•1 hr 7 min•Ep. 262
You just spent three weeks trying to convince yourself not to sell the car your daughter was terrified would break down. Sound familiar? Financial independence isn't just a target number in a spreadsheet—it's knowing when holding onto something "frugal" has crossed into actively hurting your family. Brad and Jonathan tackle a listener mashup covering the emotional weight of car ownership, when to let go of a reliable old vehicle, and how home equity lines of credit (HELOCs) can provide financial...
Oct 16, 2020•49 min•Ep. 261
Most immigrants retire early — they just don't do it through index funds. Julie Alma Tavares, a Dominican immigrant who once buried herself in consumer debt working in fashion, discovered this firsthand. After a health crisis involving her father forced her to rethink everything, she ditched the shopaholic lifestyle, adopted a survival-based budgeting approach, and paid off her debt while building wealth through unconventional strategies like master leasing. Her mission now: normalize financial ...
Oct 12, 2020•44 min•Ep. 260
Most people earning six figures still feel trapped paycheck to paycheck—here's the mathematical escape route they're missing. Anyone serious about leaving the 9-to-5 grind needs a concrete target, not vague retirement dreams. The hosts break down the process of calculating your financial independence number using actual expenses—not hypothetical budgets or aspirational spending. The core formula is straightforward: multiply your annual expenses by 25. This gives you the asset base needed to supp...
Oct 05, 2020•40 min•Ep. 258
Your spouse maxes out their HSA for years, the funds compound tax-free, and then you need cash for actual medical bills — what could go wrong? Turns out, plenty. This episode explores practical strategies for navigating Health Savings Accounts effectively, from eligibility rules to strategic withdrawals. MK shares her personal experience managing an HSA with her spouse and the unexpected complexities of actually withdrawing funds when medical expenses arise. The discussion covers the importance ...
Oct 02, 2020•53 min•Ep. 257
Robin and Melissa Steffensen turned a $200 flea market find into a $2,800 sale in under two weeks — and they've built a six-figure business doing it. The Flea Market Flippers have mastered the art of spotting undervalued items at flea markets and reselling them online for substantial profits, primarily through eBay. In this conversation with Brad and Jonathan, they break down their arbitrage-based business model, from researching items and negotiating prices to managing shipping logistics and sc...
Sep 28, 2020•38 min•Ep. 256
Most entrepreneurs fixate on funding, growth targets, and exit strategies — but what if the real goal is designing a life that doesn't need an exit? Corbett Farr learned this the hard way after his venture-backed startup collapsed in 2008, forcing him to question everything about how he'd defined success. Since then, he's built multiple online businesses — not by chasing investors or scale, but by understanding his minimum viable income and building audiences first. As an indie entrepreneur and ...
Sep 21, 2020•43 min•Ep. 254
Most people think financial independence is just a number in a spreadsheet. Brad and Jonathan show why that mindset keeps people trapped on the hamster wheel—and what to focus on instead. This episode strips away the noise around FI to reveal what actually moves the needle: community support, strategic decisions on housing and transportation, and reframing independence as freedom rather than a dollar amount. Brad and Jonathan reconnect with listener questions and share crowdsourced wisdom from t...
Sep 18, 2020•56 min•Ep. 253
Divorce didn't ruin Julia Harder's finances — it saved them. After years of watching her natural saver instincts clash with a spouse's reckless spending, Julia found herself starting over. What followed wasn't just financial recovery; it was a complete rebuild of how she thought about money, community, and trusting her gut. Julia's story begins as a natural saver whose traditional financial approach collided with a partner's irresponsible habits. After her divorce, she turned to Dave Ramsey's Fi...
Sep 14, 2020•54 min•Ep. 252
Most people worry about being the first in their family to achieve financial independence — Anne Zanka's grandparents built it during the Great Depression and passed down something more valuable than money. Anne shares how her grandparents, who survived the Depression with "two nickels to rub together," instilled lessons about saving and investing in stocks that enabled her to graduate college debt-free and now guide her own children toward financial independence. Chapters Introduction to Genera...
Sep 07, 2020•41 min•Ep. 250
Most people pursuing financial independence fixate on one type of capital — the financial kind — while seven other forms sit untapped and undervalued. Laura Aldani from Rich and Resilient Living joins Brad and Jonathan to flip that script, explaining how permaculture principles apply to personal finance and why building social, intellectual, experiential, spiritual, living, cultural, material, and financial capital creates a more resilient life than a fat investment account alone. Key Topics &am...
Aug 31, 2020•48 min•Ep. 248
You're not paranoid if someone really is controlling your money. That gut feeling you've been ignoring? It might be your most reliable data point. Financial abuse doesn't announce itself with a dramatic confrontation—it creeps in slowly, decision by decision, until you wake up one day realizing you can't access your own bank account or explain where the money goes. Rachael Partleton learned this the hard way, and what she discovered about the systems supposedly designed to help victims is even m...
Aug 24, 2020•50 min•Ep. 246
A traditional four-year degree might cost you $100,000 and four years of your life—but Google just announced they'll treat their new six-month online certificates as equivalent to a college degree for hiring purposes. The career landscape is shifting beneath our feet, and the old gatekeepers who controlled access to opportunity are losing their power. Future-proofing your career means understanding that skills now outweigh traditional credentials. With online certification programs from major co...
Jul 31, 2020•46 min•Ep. 239
Most students spend four years and $40,000+ on their first two years of college. Jerry Born spent 59 days and $30. This deep-dive unpacks exactly how he did it — and how you can replicate parts of his strategy. Jerry walks through the mechanics of earning college credits through platforms like Sophia Learning and CLEP exams, navigating credit transfer policies at traditional universities, and front-loading college credits while still in high school. The conversation reveals a blueprint for cutti...
Jul 27, 2020•59 min•Ep. 238
Most people think they need to be world-class at one thing to succeed. But here's what actually creates opportunity: combining skills you're merely good at in ways no one else has. This approach to personal growth—called talent stacking—turns ordinary abilities into extraordinary advantages. Key Topics Introduction to Talent Stacking [00:00:00] Definition and importance of a talent stack in enhancing personal and professional opportunities. Personal Updates [00:01:01] Brad shares news about his ...
Jul 24, 2020•45 min•Ep. 237
The skills that build wealth are the same skills that build health. Both require replacing unconscious bad habits with intentional good ones, both reward long-term thinking over quick fixes, and both demand you recognize the triggers that derail you. Brad and Jonathan share how their financial independence journeys reshaped their approach to fitness—and why momentum in one area creates momentum in the other. Key Topics Discussed Introduction to Fitness and Financial Independence [00:00:00] How f...
Jul 22, 2020•50 min•Ep. 236
The Barrett kids turned their Lego hobby into an eBay business—and discovered market inefficiency before they could spell it. When buyers overpay for certain figurines while undervaluing others, that's not just a kid's pricing mistake; it's the marketplace at work. Their parents seized the moment to teach supply and demand, negotiation, and yes, handling failure when listings don't sell. The Barrett family's Lego business venture teaches practical lessons about money management and market analys...
Jul 17, 2020•56 min•Ep. 234
Most people treat networking like a last-minute scramble — reaching out only when they need something. Jordan Harbinger, who spent a decade building one of the world's largest podcasts, argues that's exactly backward. Networking isn't about collecting contacts; it's about giving without keeping score, staying connected long before you need help, and treating relationships as your most valuable asset. In this conversation, Brad and Jonathan unpack Jordan's system for reconnecting with dormant con...
Jul 15, 2020•1 hr 10 min•Ep. 233
Most parents spend years teaching kids to clean their room but never explain how money actually works. Doug and Carol Nordman discovered a better approach through trial, error, and honest conversation — and the insights from raising a financially independent adult might surprise you. Doug and his daughter Carol share practical lessons from their new book on teaching financial independence to the next generation. Through methods like the Kid 401k, profit-sharing for education, and age-appropriate...
Jul 13, 2020•1 hr 6 min•Ep. 232
Most people think casseroles are just a way to disguise food you're trying to get rid of. Brad and Jonathan flip that assumption, showing how a simple framework—protein, starch, vegetable, binder—turns random leftovers into intentional meals that cut grocery bills and food waste. They cover the leftover casserole challenge, adapting 529 plans when college isn't a given, teaching kids networking skills early, and why acquiring marketable skills matters more than chasing degrees. Key Topics Leftov...
Jul 10, 2020•50 min•Ep. 231
