A teacher's side blog just earned $16,000 in a single month — but it started as something Bobby never planned to monetize at all. Bobby went from drowning in $40,000 of student loan debt to running Millennial Money Man full-time, yet his biggest regret has nothing to do with debt and everything to do with cash sitting idle for two years. Bobby shares how he paid off student loans in 18 months on a teacher's salary by renting a room from his in-laws and resisting lifestyle inflation. More importa...
Dec 11, 2017•59 min•Ep. 53
Todd Tressiter makes a startling argument: the very simplicity you've been taught to chase in investing might be costing you opportunities. Financial independence isn't just about passively investing in index funds—real estate, business ownership, and strategic complexity might better fit your situation. Tressiter challenges the one-size-fits-all approach, urging listeners to recognize that their unique circumstances demand personalized strategies. Todd Tressiter's Views on Investing [00:03:32] ...
Dec 08, 2017•53 min•Ep. 52
Todd Trusseter drops a truth bomb that might make traditional FIRE enthusiasts uncomfortable: you can reach financial independence and keep your luxuries. In this wide-ranging conversation, financial mentor Todd Trusseter unpacks the current state of the FI community, challenging the assumption that lower expenses automatically equal greater happiness and introducing the concept of "fat fire" — a path to independence that doesn't require sacrificing every comfort. Brad and Jonathan explore how t...
Dec 04, 2017•1 hr 19 min•Ep. 52
Most people who grow up in a trailer park don't end up with a master's degree and a high six-figure net worth — but Lisa isn't most people. A mother scientist and founder of Mad Money Monster, she spent years trapped in a cycle of poor financial decisions and a difficult relationship before discovering the FI community and completely turning her financial life around. Lisa shares her story of defying early limitations, pursuing education despite feeling unworthy, and ultimately building a frugal...
Nov 27, 2017•57 min•Ep. 51
Small decisions—skipping one subscription, optimizing one flight—can quietly stack into 50–75% savings rates while everyone else stays broke. Brad and Jonathan tackle listener questions on how to scale these "marginal gains," why the global FI movement needs local voices (especially in the UK, Australia, and Canada), and how Jonathan used travel rewards to fund his family's South Africa trip almost entirely on points. Key Topics Global Interest in FI The financial independence movement is gainin...
Nov 17, 2017•50 min•Ep. 49
British FI blogger Barney—known online as The Escape Artist—ran the numbers and realized he could walk away from corporate life decades early. But he faced a problem Americans rarely think about: virtually no one in the UK was talking about financial independence. No forums. No playbook. Just a handful of blogs with tiny audiences in a culture that treats steady employment and homeownership as non-negotiable. In this conversation, Barney and fellow UK FI advocate Alan Donegan sit down with Brad ...
Nov 13, 2017•1 hr 27 min•Ep. 49
You're checking your phone 50 times a day, drowning in email subscriptions you never read, and losing hours to small irritations you've accepted as "just how life is." But what if those low-level stressors are quietly draining your progress toward financial independence? After returning from FinCon, Brad and Jonathan unpack lessons from the rapidly growing FI community on building meaningful in-person connections and how those relationships accelerate learning. The conversation then shifts to a ...
Nov 10, 2017•48 min•Ep. 48
Jeff was making $300,000 a year, working his dream job as a physician, and felt utterly miserable. His story isn't unique in medicine — but his solution is. Jeff, a physician who writes at The Happy Philosopher, turned to financial independence blogs after realizing his "perfect" career was draining him dry. But discovering early retirement concepts wasn't enough. He had to learn to be happy now , not just plan for happiness later. He went part-time, cut lifestyle inflation, and built a daily gr...
Nov 06, 2017•1 hr 8 min•Ep. 48
Brad's nine-year-old daughter walked into her parents' room ready to invest her savings—not because she was told to, but because a twenty-minute conversation about compound interest flipped a switch in her mind. That moment kicked off an episode that tears down the myth of homeownership as a guaranteed wealth-builder and shows how geo-arbitrage can fund years of global travel on a middle-class income. Key Topics Teaching Kids About Money Brad shares the moment his daughter grasped compound inter...
Nov 03, 2017•43 min•Ep. 47
Homeownership in Canada's priciest cities will bankrupt you — unless you're willing to walk away from the entire model. Christy and Bryce from Millennial Revolution did exactly that, building a seven-figure portfolio by rejecting the traditional real estate trap and choosing long-term travel instead. Their story challenges the assumption that a mortgage is a non-negotiable step toward adulthood, revealing how ditching property unlocked both wealth and freedom. Chapter Markers Introduction to Chr...
Oct 29, 2017•1 hr 17 min•Ep. 47
Most people chase early retirement to escape work—Tanya from Our Next Life flipped the script and made headlines for it. Her story blew up not because she saved aggressively or optimized her portfolio, but because she asked a question most retirement planners ignore: What am I retiring to? Brad and Jonathan unpack that question in this Friday Roundup, reflecting on Tanya's interview and their excitement heading into FinCon. They discuss why the math of financial independence is the easy part, an...
Oct 27, 2017•50 min•Ep. 46
Walking away from $35,000 in consumer debt changed J.D. Roth's life—and shaped an entire movement. The founder of Get Rich Slowly returns to discuss his evolution from broke blogger to financial independence pioneer, revealing the six stages of financial freedom most people don't know they're progressing through. Key Topics Discussed: Introduction of J.D. Roth [00:00:00] Jonathan Mendonsa and Brad Barrett introduce J.D. Roth, recognizing his significant contributions to the financial independenc...
Oct 15, 2017•1 hr 1 min•Ep. 45
Want proof that entrepreneurship can buy freedom, not just money? Brandon Pierce built a business model that funds his family's globe-trotting lifestyle — proving that the four-hour workweek isn't myth but blueprint. This mashup episode unpacks his journey while tackling listener wins, savings strategies, and the mental shifts required to turn comfort into fulfillment. Brandon's Business Journey [00:01:00] Built a business enabling a four-hour workweek lifestyle Transitioned from traditional nin...
Oct 13, 2017•1 hr 6 min•Ep. 44
Most people's side hustles fund weekend hobbies. Brandon Pearce's bought him eight years of global freedom. After recognizing his call center job offered no real security, Brandon built Music Teacher's Helper — software to manage his piano lessons — and turned it into the ticket for his family to experience life across 36 countries. He joins Brad and Jonathan to unpack the practicalities of running a business from anywhere, rethinking childhood education on the road, and why transformation beats...
Oct 08, 2017•1 hr 7 min•Ep. 44
Most people planning retirement obsess over the accumulation phase—but what happens when you actually reach your number and need to start spending it? Jonathan Mendonsa and Brad Barrett tackle the shift from wealth accumulation to wealth preservation, where having a robust drawdown strategy becomes just as critical as the portfolio you built. Key Topics Covered Community Feedback – Drawdown Strategies [00:06:20] A drawdown strategy outlines how to withdraw funds from investments in retirement wh...
Oct 06, 2017•1 hr 8 min•Ep. 43
Most retirement podcasts obsess over building wealth — but almost nobody talks about the harder part: spending it without running out. Fritz from Retirement Manifesto tackles the decumulation phase that conventional advice ignores, sharing his blueprint for strategically withdrawing from decades of accumulated assets while managing taxes, healthcare costs, and sequence of returns risk. Fritz shares his background and path toward retiring at age 55 after 33 years in corporate America, emphasizing...
Sep 30, 2017•1 hr 16 min•Ep. 43
Most people have never questioned whether they need to live paycheck to paycheck—until they see it challenged on film. Scott Rickins brought his documentary crew to film with the ChooseFI hosts, capturing the anti-consumerism message at the heart of the financial independence movement. Beyond the cameras, the conversation turns to building real-world FI community connections, launching a Slack group for members to share resources, and navigating recent shakeups in the Chase Sapphire rewards prog...
Sep 29, 2017•53 min•Ep. 42
Most people stumble into the FIRE community through personal finance blogs. JW's entry point was a $5 million life insurance pitch right after his first child was born—a moment that launched him from passive saver to active entrepreneur building passive income streams through business acquisitions. JW from thegreenswan.org shares how he and his brothers acquired and revitalized an existing business, creating a family-run income stream while navigating the unique challenges of working with relati...
Sep 24, 2017•57 min•Ep. 42
Living in Los Angeles with negative net worth and below-average income, Paige turned financial disadvantages into a blueprint for reaching FI through shared housing and community resources. Through her story and listener questions, Brad and Jonathan tackle multiple topics: navigating high-cost areas without moving, collecting skills instead of possessions, and cutting through the psychological excuses that keep people from starting their FI journey. Key Topics Library Visits and Nostalgia The ho...
Sep 22, 2017•1 hr 3 min•Ep. 41
Starting later doesn't mean you're behind — it means you skip the years of trial and error. Paige and Sam prove that financial independence works in high-cost areas and on modest incomes, even when conventional wisdom says otherwise. Paige challenged the hosts after they accepted the limiting belief that FI isn't achievable in expensive cities. Living in a high-cost area on $30,000 while earning the same amount, she's on track for FI by 2025 through roommates, maxed retirement accounts, and ruth...
Sep 18, 2017•1 hr 10 min•Ep. 41
Most people think you need decades of saving before taking a year off work—Noah and Becky did it in five. This episode explores how they and others are reframing financial independence not as a distant "retire early" goal, but as "retire often"—building in career breaks while still accumulating wealth. Brad and Jonathan unpack the gap year mindset alongside stories from community members who've used high savings rates to create lifestyle flexibility long before hitting traditional FI numbers. Th...
Sep 15, 2017•1 hr 4 min•Ep. 40
A couple in their twenties grew their savings rate from 6% to 58% in just a few years — then decided to quit their jobs and travel for a year. Noah and Becky share how they went from conventional financial practices to leveraging scholarships, travel rewards, and FI strategies to fund their gap year adventure. Noah, a moderator in the ChooseFI Facebook group and creator of Money Metagame, initially struggled to convince Becky that financial independence was achievable. But once she saw the numbe...
Sep 10, 2017•1 hr•Ep. 40
A single millennial could retire at 30 by making a handful of smart money moves in their 20s — that's the math Brad and Jonathan break down in this week's roundup. But the conversation goes deeper: how do you pass those lessons to the next generation before they rack up debt? This episode explores listener stories of strategic early financial decisions that create outsized long-term wealth. Key topics include the "cruise control path" to FI, where minimal early investment sets you up for freedom...
Sep 08, 2017•55 min•Ep. 39
Gwen graduated college with $10,000 saved—not borrowed, saved—while her peers were drowning in five-figure debt. She did this without wealthy parents, inheritance, or a trust fund. Her secret? She refused to accept the default path everyone else was sleepwalking through. In this episode, Gwen from Fiery Millennials walks through her unconventional approach to college and early career. She used dual enrollment to knock out college credits before graduation, joined the Air Force to avoid student l...
Sep 03, 2017•59 min•Ep. 39
Most people spend decades chasing a bigger house, a nicer car, and a promotion that demands even more hours — only to realize too late they've been running in place. Brad and Jonathan break down why the conventional path to "success" is fundamentally broken and how financial independence flips the script. Instead of trading time for money to buy things you don't need, FI lets you reclaim your time to pursue what actually matters. Key Topics Discussed Introduction to the Why of FI [00:00:42] Crea...
Aug 28, 2017•35 min•Ep. 38
Brad's wife Laura pulled off 16 nights of free lodging across a 17-day family vacation—no hostels, no camping, just strategic coordination and a stack of credit card points. This mashup episode covers how they made it work, why rushing to see everything kills the travel experience, and tackles listener questions on achieving FI in expensive cities, navigating lifestyle creep, and making the most of networking opportunities. Travel Rewards and Planning [00:03:40] Brad's trip cost zero for 16 nigh...
Aug 25, 2017•1 hr 4 min•Ep. 37
Scott Rickins didn't stumble into financial independence because he was broke—he found it while earning six figures, living in a California beach town, and working with brands like Facebook and Microsoft. His problem wasn't a lack of income; it was that more money kept leading to more spending without any additional happiness. Scott Rickins, founder of 99Bravo Productions, shares his journey toward financial independence after discovering the FI community and deciding to document it through Play...
Aug 20, 2017•1 hr 4 min•Ep. 37
Most early retirees obsess over how much they need to retire—but the real danger isn't your portfolio size, it's when the market tanks. Brad Barrett and Jonathan Mendonsa break down sequence of return risk, the often-overlooked factor that can make or break your retirement in the first five years. Building on their conversation with Big Earn, they explore why market downturns can be a saver's best friend but an early retiree's worst nightmare, and what you can do about it. This episode covers li...
Aug 10, 2017•1 hr 1 min•Ep. 35
The 4% rule might fail you—but not for the reason you think. Average market returns matter far less than when those returns happen, especially in your first decade of retirement. Brad and Jonathan sit down with Big Earn from Early Retirement Now to unpack sequence of return risk: the hidden danger that can derail even a well-funded retirement if you're unlucky with market timing. Big Earn breaks down why withdrawing during a downturn compounds losses in ways the accumulation phase never prepares...
Aug 06, 2017•1 hr 12 min•Ep. 35
Most investors panic when the market drops 20%. Brad and Jonathan argue you should celebrate. This episode tackles the counterintuitive truth that market crashes can supercharge your path to financial independence — if you're young and still accumulating. Brad and Jonathan unpack the psychology of investing through market volatility, exploring why downturns are opportunities rather than disasters for accumulation-phase investors. They break down how buying shares at lower prices during crashes c...
Aug 04, 2017•1 hr 12 min•Ep. 34
