By Jonathan Mendonsa & Brad Barrett


Experiments in Financial Independence


2,135 ratings


115 | Poverty, Divorce and FI by 43 | Bonnie Traux

Bonnie Traux, a blogger and early retiree, shares her story of growing up below the poverty line, scraping her way out of inherited debt, reaching financial independence without knowing what it was, and understanding how to talk about money with your spouse. Bonnie grew up with family income that was technically half of the poverty level, but always debt free. In a town of only 35 people, W2 jobs were hard to come by, so Bonnie worked any odd job that she could find – mowing lawns, decorating cakes, roofing. What did Bonnie do with the income from her side hustles? Bonnie got married shortly after college and inherited significant debt. The first step to getting out of that debt, was learning spreadsheets and prioritizing which debt she would tackle first. Bonnie was managing thousands of dollars of debt and got back to broke, even as her spouse was actively spending and maxing out credit cards. What is Bonnie’s financial advice for people before they get married? Financial literacy isn’t distributed evenly throughout the country – not everyone understands how to manage finances. Not everyone is comfortable talking about money, even with their spouse. If Bonnie could do it again, she would start by talking about fears associated with money. When Bonnie started over she was 30, earning about $25k. Bonnie learned IT with her free time at a reporting job, eventually becoming the manager of an IT team. Before she got remarried, Bonnie and Trin had become very close friends at work and had already talked about finances, so she was confident about their joint approach to money as a couple. Trouble doesn’t have to be a disaster. Getting out of debt on a low income is possible – you shouldn’t have to eat rice and beans your whole life, but if you’re getting out of debt, you might have to them for a while. Bonnie and her husband automated their finances and didn’t give much attention them; they found a comfortable way to live regardless of their increasing incomes. Bonnie didn’t plan to retire, but when work became toxic, their savings gave them the freedom to leave work. Instead of just leaving money in their savings account, Bonnie and her husband began purchasing foreclosed home and renting them out. Without a knowledge of the financial independence community, how did Bonnie determine that she and her husband were financially ready to leave their jobs to retire? Bonnie and Trin are traveling the world for a few years before they decide where to retire abroad. It’s never too late to make tomorrow better. Anything that comes into Bonnie’s blog goes to support a safehouse in Ecuador. Fear of missing out is just an excuse; you are always choosing what you miss out on.   For more information, visit the show notes at 


113 | Swing for the Fences | Grant Sabatier

Creator of Millennial Money and author of Financial Freedom, Grant Sabatier, shares his story of unemployment and entrepreneurship, and his strategies for increasing your income and optimizing your finances. In 2010, with a college degree in philosophy Grant had been laid off twice and found himself living at home as 24-year-old. Grant sent out more than 200 resumes without a single callback before he found the information he needed to start learning Google Ad campaigns. The certification process took about 30 days and he received a job offer almost immediately. The first step to getting out of a rut is being honest enough to admit that you’re stuck. Most people are only 2 or 3 steps away from a life that they’d love. A million dollars could be 10 years away; just take the next step. When Grant looked at all his friends and his parents’ friends, they were stressed about money so he decided to learn how to do it differently. Grant learned how to build Wordpress websites and began selling his services to law firms, quickly securing large contracts at lower prices than large agencies. Grant’s first client became his most valuable client because he served as a credible reference for more than a year. How does Grant recommend getting your first client? What matters is helping your client look good to their boss. Selling is story telling – who you are as a person is more important that what you’re selling. The paradox of the gig economy is that many people are actually less flexible and more stressed about getting their next client than they would be working a 9-5. Whether you’re happy with your current job or not, optimizing your finances through your full-time job is where you need to start. Talking to recruiters in your particular industry will give insight into the direction the industry is moving, what parts of your resume might be lacking, and the market value of your work. How does Grant maintain relationships with recruiters? Face-to-face meetings Taking people out to lunch Form an actual relationship, don’t just try to get something from them. For Grant, forcing someone into a budget that cuts out small things like wine and coffee just reinforces a scarcity mindset. The only way to get from a 5% to a 30% savings rate is to decrease your housing, transportation and food costs. There is a limit to how much someone can cut back, but making money is unlimited. Grant invested 100% of his side hustle income. For more information, visit the show notes at 


112 | Zero Based Budgeting | How I paid off 1 million in Debt | with Naseema from Financially Intentional

Naseema McElroy, a registered and practicing nurse and blogger at Financially Intentional, explains how to accumulate $1 million in debt, and how she earned her freedom through financial independence. How does someone accumulate $1 million of debt? Naseema is from West Oakland, Ca., where she was taught to either join the military or go to college. She attended the University of Southern California for both her undergraduate and graduate degree, then later completed an accelerated nursing certification program at the University of California in San Francisco. Floor nurses where Naseema works earn above $200,000. How could Naseema have been significantly more efficient with her college education? Many nurses have two jobs: Naseema works part time with benefits (three eight-hour shifts), and a per diem job (two 12-hour shifts) without benefits, at a higher pay rate. Even after finishing her education and working full time, Naseema accumulated more than $1 million in debt, and was living paycheck to paycheck. Most of her debt was student loans and Bay-Area mortgage costs. What inspired Naseema to move from a 5002ft apartment closer to the city into a 40002ft home in the suburbs? Even with the house and the car and the seemingly perfect set up, Naseema did not feel secure, and even owed her family money. Dave Ramsey set Naseema on the course to pay off her debt. What was her first step? Once Naseema began tracking her expenses, she was an early user of Dave Ramsey’s Every Dollar app. A zero-base budget is projecting how much you’ll earn and set aside how much is intended for paying off debt, then adjust the remaining numbers to reflect other obligations and other adjustable expenses. What inspired Naseema to begin blogging at Financially Intentional? Before Naseema sold her suburban house, she had already paid $300k of debt. Naseema chose to leave one of her jobs when it became an unhealthy environment, because living debt-free gave her the room in her budget to do so. Currently, Naseema has moved out of the Bay Area and commutes back into the city 6 days a month for work. Building wealth is a mindset. You have everything it takes to be successful.   Links: Clever Girl Finance The Stock Series For more information, visit the show notes at 


111R | Make the Impossible Possible

Jillian from Montana Money Adventures gives advice for laying out roadmap in your life, right after and Brad and Jonathan review Monday’s episode and highlight activities from several local groups around the globe.   Brad and Jonathan reflect on last week’s episode with Billy Banholzer. A video inspires Brad to learn swimming from his daughter. Your current behavior or mistake doesn’t have to define you for the rest of your life. One of the first steps to Billy’s success was setting goals. What are Brad’s suggestions for developing into a better writer? Billy found ChooseFI while he was looking for a community of people who were pursuing the same things he wanted to pursue. Getting started on the path to financial independence can be really hard at first, but it gets easier as you move further down the path. Brad shares excitement about a local meet up and changes people are making locally. Highlight reel of local group activities: Combined Southern California and San Diego groups have a sold-out meeting where Jillian from Montana Money Adventures will speak. The Nebraska local group is meeting every two months with specific topics. A new group in The Netherlands has more than 20 members. The local group in Portland, Ore., met every week in 2018. A Northern Ireland local group doubled its membership in the past month. Alex, an admin from the Baltimore group, is setting up mastermind groups.   Jillian, from Episode 84, talks about building a life roadmap: Focusing on your values is the first step to building a better life. How did Jillian and her husband create space to talk about their values and what they wanted their life to look like? Be. Have. Do. Jillian uses sticky notes to brainstorm her ideas and organize her thoughts. What is a Quit List? How does Jillian consider seasons of life? Each person’s superpower includes: What you’re passionate about. What you’re naturally good at. What activities you get caught up in and find really fun. Brad talks about listening to where there’s resistance in your life. Could. Should. Want. Writing down your thoughts helps clarify and anchor them. Tickets for Chautauqua 2019 will go on sale soon.   For more information, visit the show notes at 


103 | The Trades Path to FI – Captain DIY

Tinian Crawford, blogger at DIY2FI and licensed electrician, talks about his path to licensure, the advantages of trade jobs and his transition to pursuing financial independence.     What jobs are represented in the FI community? Base salary for an electrician is $70 minimum. Many people go to trade school in high school or immediately after, so there’s very little financial education in the trade-work community. Tinian’s father built his childhood house, and Tinian was enlisted to help with construction projects on their property. Does Tinian find value in the graphic design education he received in community college? Tinian’s first job was building signs – many of which were lighted signs – which piqued his interest learning about electrical work.   What education do you need to start electrician licensure training? Tinian’s one-year program cost $25k. To be fully licensed, an electrician has to do a 5-year apprenticeship. Making $70 an hour comes when you work for yourself. Do most electricians jump right into owning their own business? Tinian’s recommendation: stick with a contractor you can learn from for your day job, and start taking jobs on the side. Additional trade jobs that would be great for FI: Garden landscaping and design Plumbing Tinian’s wife suggested that they save $20k by the time their first child was born. In order to avoid high childcare costs, Tinian and his wife split their schedules as much as possible. Tinian hopes to leave his day job at some point, but still needs to learn more about managing benefits and figuring out exactly how much he needs to support his family. In order to prepare for leaving a day job, it’s important to identify how much life will cost after the change. Beginning their investing with a local financial advisor and a socially conscious portfolio was a mistake for Tinian.     Links: DYI 2 FI DIYCaptain - Twitter Burrito Bowl Diaries “Eliminating the Excuse” – Saving Sherpa


102R | The Triple Tax Savings of Health Savings Account

Brad and Jonathan explain the long-term tax benefits of using a Health Savings Account to pay for medical expenses, discuss the benefits of new index fund investing options, review Monday’s episode with Timika Downes.   Brad and Jonathan are getting back to traditional health insurance, and excited about the Health Savings Account (HSA). Most companies offer health insurance options, typically including: Low monthly premium + high deductible High(er) monthly premium + low(er) deductible. The IRS defines a high deductible plan as anything higher than $1,350 for an individual, or $2,700 for a family. Employees with high deductible plans have access to an HSA (eligible accounts). An FSA (Flex Savings Account) is a reloadable account, that is primarily use-it or lose-it Putting money in an HSA is tax free, and rolls over to future years, and drawing it out for medical purposes is tax free. 2018 HSA contribution limits: $3,450 for individuals $6,900 for families After 65, if you have unused money in your HSA, you can draw it out like a traditional IRA and just pay your normal tax. Brad intends to save his receipts and wait to be reimbursed until later, as HSAs will earn interest the same as any investment account. ChooseFI community members recommend Lively or Fidelity. Review of Monday’s episode with Timika – similar concepts and action points as the recommendations from Alan in the Side Hustle Coaching Series. You don’t need permission: just take action. Dan writes in to report that he’s reached FI! ChooseFI has listeners across the globe – although not all the tax and investment information are relevant to international listeners, the lifestyle conversations are. Brad and Jonathan highly recommend Vanguard because they have low fees, which means investors keep more of their returns. In last few months, Fidelity began offering zero-fee funds and Vanguard has lowered its minimum investment from $10k to $3k for several funds. Investments abroad can have very high fees. Zero fees are not the only thing to consider when picking accounts: tax efficiency is very important as well.   Links: Vanguard Ratchets Up Index-Fund Price Battle


102 | From 90K of Debt to 6-figure Side Hustle | Timika

Blogger and podcaster Tamika Downes reveals how she went from $94K of debt to owning a six-figure income-earning side hustle while continuing her job as a school nurse and raising three children. Timika’s early financial experiences came through immigrant parents, from Barbados, hustling and saving. Having a side hustle was common place in Timika’s family. Despite her family’s habit of saving, Timika finished her education with $94K of debt. After her undergraduate Timika had $24K in debt. Student loans for her master’s cost $35K A second, nursing degree, cost another $30K Choosing to pursue something that you’re not quite ready for can often lead someone to pay more than necessary. Nursing degrees don’t have to cost $30K; immediately after high school students can become qualified Certified Nursing Assistants (CNAs) working in hospitals or nursing homes while starting at a community college and finishing through a bridge program at a 4-year school. Nursing is a trade; find the most efficient way to get qualified. Many universities offer tuition assistant to the children of faculty/staff, often including tuition at other universities. What options did Timika consider in order to decrease her student loan debt? Timika’s mindset changed when she started to own her life circumstances; taking responsibility for her finances was a natural result. Instead of buying a $20K car, Timika bought a $20K business – a lice clinic. Timika spoke with out-of-state clinic owners and did her homework before deciding to invest in the set up for her clinic. Since opening the business, Timika has increased her talentstack to include: Securing a business lease Blogging Website management Business finance management Timika went to coding bootcamp, for 75% discount as a female minority. The lice clinic is now almost passive income: Timika only devotes three hours a week and has hired employees who manage the rest.   Links: House of FI Reluctant Frugalist Saving Sherpa The Road to Retirement: (Re)Learning to Love Work For more information, visit the show notes at


101R | Side Hustle Coaching Series Part 4

Brad and Jonathan talk about their experiences with W2 jobs and building side hustles, Jose shares his own side hustle tip, and Alan and Tallis wrap up the 4-part Side Hustle Coaching Series.   Brad and Jonathan are jumping into planned spontaneity. Do your actions align with your values? Brad recounts how the accounting firm he worked for right after college, one of the biggest in the U.S. at the time, folded and within 9 months no longer existed. W2 jobs aren’t all that risk-free after all. Having a side hustle is about diversification. Jonathan talks about how Dani is building an audiobook side hustle, using some of the techniques and strategies that Nick Loper talked about in Monday’s episode. Willingness to pivot your side hustle idea gives you a better chance at building a side hustle that actually works. Voicemail from Jose with a side hustle tip from Task Rabbit – sign up to help others with random tasks, and add a little extra cash to your pocket. Brad’s opting to rent a car through Turo, through which customers rent someone’s personal car, similar to AirBnB.   Side Hustle Coaching Call Episodes to review: Episode 30, Episode 56 (Part 1), Episode 77R (Part 2), Episode 85R (Part 3) Tallis reviews how her initial cold calls, starting from further away geographically and becoming increasingly local as she refined her sales pitch. Tallis has 4 dance classes she’ll be teaching soon! Tracking results and feedback from the start of your business is important. Measuring results, and using valid tools respected within the medical community will be important to Tallis’ business. Where does Tallis want her business to go in the next 2 years? Keep pressing forward – it’s impossible to know how the business might grow, but Tallis is building entrepreneurial skills and opening options for her future.   Links: 10 Big Chain Stores That Will Secretly Match Amazon's Low Prices


101 | Finding your Side Hustle Idea | Nick Loper

Nick Loper, founder of Side Hustle Nation, talks about the benefits of developing a side hustle, and methods to actually develop a good side hustle idea.   You can only cut so much from your expenses; a side hustle helps you expand your earning potential. Nick thinks working just a 9-5 job is risky – what happens if you get fired? Nick advocates several methods for developing side hustle ideas. Method 1: Intersection Method Write out three columns with lists that include what you can do, what you like to do, and the people in your network. Nick used the Fiverr website to test out his first side hustle idea. How important is it to pivot, instead of being discouraged by failure? Some of the best ideas are developed once a business is already in motion. Method 2: What sucks? Find simple sticking points in life and solve the problems. Some people find things on Amazon that suck, and find a way to make them better. There are manufacturing companies in China and the U.S. that work with small orders and require minimal up-front investment. You don’t need a brand-new idea, you just need a different market. Recommended episodes from Side Hustle Nation: Episode 173: How to Turn Your Ideas Into Recurring Revenue, with Stephen Key Episode 263: The Top 3 Amazon FBA Private Label Product Research Strategies for 2018 and Beyond Method 3: Rip, Pivot and Jam Find a business model that’s working, pivot it to a new market, product, etc., and then do the work. Are there side hustles that Nick no longer recommends? Sometimes the opportunity cost for a side hustle may not be worth the cash. One of the best side hustle ideas Nick has heard: Flea Market Flipper. How difficult is it to develop a passive-income side-hustle? Think Maids: found a category of businesses on Yelp that had really poor reviews, and found a way to provide better customer service.   Links: Smart Passive Income GoCurryCracker


100R | Know the Rules

Brad and Jonathan explain how simply knowing the rules can save you thousands on taxes and college financing, Brad talks through the IRA Conversion Ladder and Capital Gains Harvesting, and a few updates from the community. The financial independence movement is growing, and seeing a lot more press coverage. Messaging matters: The Wall Street Journal published one article with two different headlines. Pursuing financial independence isn’t about buying brown bananas, despite what some media would suggest. Brad reached financial independence with intentionality about his priorities in his life. Brad and Jonathan don’t aim to tell people what decisions to make in their life, just give options and information. What did Brad’s family do to reach financial independence? Housing: chose to move to a less-expensive cost of living area Cars: Brad & his wife drive 15-year-old cars Food: don’t go to restaurants often Set up a life that doesn’t cost that much. Pursuing financial independence actually allows people to pursue jobs that they love. If life costs a lot and someone is in debt, it’s very hard to walk away without taking major risks. Knowing tax rules is a huge component of pursuing financial independence. Knowing the rules in regards to paying for college makes a huge difference in how much financial aid your student might be eligible to receive. A message from Matt about researching the actual requirements necessary for a job in nursing – the cost of nursing school can range from a few thousand dollars to more than $100k. Studying nursing in a less expensive area still gives you qualifications to practice anywhere in the U.S., with a potentially huge payoff. Roth Conversion Ladder & Capital Gains Harvesting – the goal is to pay little or no tax. Roth IRA Conversion Ladder: Starts with traditional IRA/401k. If you want to retire before 59.5, taking money out is taxable income. If you’re not collecting significant income, taking money from an IRA is unlikely to push you into a high tax bracket. Capital Gains Harvesting If you’re income is low, your tax bracket can be incredibly low. Email from Dan explaining how he and his wife paid off many of their debts, found a way for his wife to be a stay-at-home mom, and started a small side hustle. Brad shares a frugal win of the week at the optometrist. For more information, visit the show notes at 


100 | Welcome to the FI community

Brad and Jonathan look back at the ChooseFI’s growth during the past 100 episodes and hit the highlights of financial independence for new community members and recap their own financial independence journeys.   Jonathan considers himself a reluctant frugalist, but the idea of not having to work won him over. Brad and his wife were natural savers, but chose to move from Long Island, NY, so that they could save more and work toward financial independence. If you want to take back your years and have the option to stop working before your 60s, you’re going to have to live differently and make different choices. The key to long term freedom is saving money. The benefits of pursuing financial independence are felt long before reaching FI. Jonathan put himself in a position to leave his pharmacy job when it stopped working for him and his family. A huge quantity of life’s stresses can go away if you’ve got some money in the bank. What you earn minus what you spend = the gap. The goal of the ChooseFI community is to help you grow the gap, and pursue what you’re most interested in. ChooseFI isn’t about the money, it’s a life optimization strategy. Small sacrifices add up in the long term. What is a talent stack, and how did it change Brad’s life? Starting with current income is the wrong place to start calculating the number you need for retirement. FI number = 25 x annual expenses (4% rule of thumb) If you’re only saving 1%, it’ll take you 100 years to replace on year of expenses. Getting as close to possible to a 50% savings rate is when things really start to move quickly. Being rich isn’t watches and cars – it’s money saved and pursuing what’s more important to you in life. What major decisions put Brad on the path to FI?   Links: Mr. Money Mustache


099R | Market Fluctuations | Stick to Your Plan

Brad and Jonathan review Monday’s episode about generous giving and resource stewardship, then catch up on voicemails and updates from the community about dental school, fall activity ideas, and the recent dip in the stock market.     Jonathan recaps his recent family vacation and travel to FI Chautauqua Greece. Chautauqua was most importantly about community. Jonathan saved nearly $1,200 on a bill for his son’s broken leg just by asking for an adjusted cash-pay price. The Playing with FIRE Kickstarter event far surpassed expectations. More than 1,000 supports More than $100k Review from Monday’s episode with Michael Peterson. Michael continues to work because he wants to be able to give. Geoarbitrage might not always be what we think; moving to ‘less expensive’ countries also usually involves a big lifestyle change. Considering oneself to be a steward of resources, not just an accumulator of money, puts members of the FI community in a unique position to be generous and consider their impact on world. Voicemail from Brian Feroldi from Motley Fool: stock market is down about 10%, but no need to panic, as drops in the market are normal and bound to recover in the long term. Buying stock when it’s down is like buying stock that’s on sale. Voicemail from Chris who tries to support 2nd and 3rd generation FI by supporting childhood entrepreneurship. Hansi asks the community for help brainstorming 31 free/inexpensive things for couples to do in the fall. Drive to look at fall foliage Toast pumpkin seeds Backyard fire pit Josh, a dentist in Oregon, opted to go to dental school in Oklahoma for half the cost of a school in Boston, and then chose to work in a rural group practice to significantly increase his income. Using money he put into his 401k, he purchased a practice in Bend, OR and improved his lifestyle. Expects to pay more than $1.2 million of loans in the next 5 years. In the medical industry, working in more remote locations tends to increase income. Voicemail from Matthew who is a military dentist – military pays for the cost of dental school, plus a stipend, in exchange for a few years of service to the military, and a guaranteed job.   Links mentioned in this episode: FI Chautauqua   For more information, visit the show notes at


095 | A Military Path to FI | Military Dollar

The author of the Military Dollar joins Brad and Jonathan to discuss the various ways that service members can optimize their finances and choose financial independence, including retirement plans, financial planning, health care benefits and the GI Bill.   Working in the military can set someone up to retire after 20 years with a pension and the ability to pursue whatever interests them. Why do many young members of the military actually have financial problems? Has Military Dollar ever seen any specific education for new servicemen? How could a young person change his/her mindset to make more frugal choices and pursue FI? Why did Military Dollar decide to pursue financial independence? How did she get started? What was MD’s savings rate early on? How has MD set herself up to potentially retire by 41? What was the moment that changed MD’s mindset and approach toward finances? How do most military members approach debt? What does the optimized path to FI look like in 2018. What’s the difference between the old Legacy Retirement and new Blended Retirement System? What advantages does the Blended Retirement System have for people who don’t stay in the military for 20 years or more? What is the biggest difference between the enlisted and the officer’s route to FI? How can people plan for and understand relatively predictable promotions and pay raises? If someone starts young and doesn’t increase their lifestyle spending, getting to a 50% savings rate is very possible. Within the military retirement system, what investment options are available? Active duty health care = free for you and your family. How does the GI Bill work, and how does that help with college expenses? The GI Bill can be passed onto family members, but does include a service commitment. If the GI Bill is used by a service member’s children, or after separating from the military, there is a housing allowance available. GI Bill will cover all tuition and fees as an in-state student for public universities. GI Bill will cover approximately $22k for private universities. What is the Yellow Ribbon program, and how does it help cover the difference? What is the minimum time of service to qualify for the GI Bill? What’s next for the MD whenever she retires from the military? How does MD balance her commitment to the military with her interest in serving her community? How will MD know when it’s time to retire? For more information, visit the show notes at


094R | Transitioning to Entrepreneurship | A Case Study in Estimated Taxes

The logistics of estimating and paying taxes as an entrepreneur, Brad’s frugal win of the week, and emails from the ChooseFI community. Brad and Jonathan are at FinCon in Orlando, Fl. Brad describes his family’s frugal win of the week at Old Navy. Review of the tax implications of winning a non-cash prize. How do some entrepreneurs put themselves in a position to fail because of taxes? Case study: how to make estimated tax payments as a new entrepreneur. Brad wants to pay the least amount of money in taxes, but ensure that he definitely pays the minimum amount to avoid incurring penalties. Knowing due dates and technicalities is important. It’s key to have money set aside in case you do owe more at the end of the year. What is the safe harbor provision? If you have blended W2 and non-W2 incomes, you do have to estimate based on previous pay stubs. Why would someone owe payroll tax? Brad uses a different bank account to reserve money he thinks he’ll need for taxes, and uses an account to submit his taxes. It’s important to know that you’ll owe a lot of money on April 15 every year. Email from Ally reporting two life wins: Keeping an inventory for what’s in her freezer by writing on the front like a white board. Using checkboxes to keep track of the three things she accomplishes every day. Is FI getting to the UK? Playing with FIRE documentary has been submitted the film to Sundance. Scott, writes an email, to explain how pursuing financial independence and information from ChooseFI has changed his life.   Links: “How to retire in your FORTIES without earning a fortune” – Daily Mail


094 | Solo 401K vs SEP with Waffles on Wednesday

Mr. and Mrs. Waffles on Wednesday (WoW) talk about winning on a TV game show, starting their own business, learning the tax code to maximize 401K contributions, and volunteering internationally. How did Ray win on the Price is Right, and what did he win? What were the tax implications of his winning? How was Ray’s experience at the IRS building in Los Angeles? Why did Jonathan receive a tax penalty last year, and how did he respond? How did Mr. and Mrs. Waffles on Wednesday decide to start a blog, and how did they decide on a name? Why do we have to just live for weekends? How did Ray win-over Mrs. WoW to financial independence? What decisions did Mr. & Mrs. WoW make after they chose to pursue financial independence? How did the pursuit of FI change their careers? What type of business did Mrs. WoW open, and how did she keep her overhead costs down and ultimately increase her income? What is a Solo 401K and why did Mr. WoW choose that option? What is the advantage of a Solo 401K for owner and spouse, and how does the math work? How important is it to control your tax rate? What happened to the Mr. & Mrs. WoW’s retirement accounts when they opted to bring on an employee? What is a Mega Backdoor ROTH?   How did Mr. WoW find a plan administrator who could help him set up his accounts? Does Mr. WoW manage his own taxes, or use an accountant? What adjustments has Mrs. WoW made in the past four years that made a positive difference in her life? How does someone volunteer for international aid organizations? Do Mr. & Mrs. WoW add some site seeing or vacation to the volunteering they do? How do they plan for these trips?   For more information, visit the show notes at


093R | Other Mountains to Climb | With Joe Saul-Sehy from Stacking Benjamins

Brad, Jonathan and Joe Saul-Sehy, from Stacking Benjamins, talk about what is rewarding to your soul, give feedback to a ChooseFI community member who’s considering selling his business, and recap Harry, the Ride Share Guy’s strategies for become the center of a niche.   Hurricane Florence’s path didn’t go near Brad and Jonathan, but there were tornadoes. FU money is better than FI money. Meet up in Florida during the week of FinCon 2018. How did Harry (from Monday’s episode) become the go-to guy for ride-share drivers? What strategies would help someone become the go-to person in a particular niche? How can you solve a problem that you, and other people, have? Find people who like and trust you. How is retail changing in 2018? How did Harry pursue unusual opportunities to make extra money? Could the “destination filter” as an Uber or Lyft driver and the potential to deduct you commute drop someone into a lower tax bracket? How did Joe from Stacking Benjamins become a financial advisor? What did the phrase “other mountains to climb” mean to Joe and how did it impact his career? What did Joe value about going back to school to be a teacher, but not actually becoming a teacher? What does it mean for something to be “rewarding for your soul”? How did Joe need to adjust his business in order to sell it? Where does financial independence stand within the personal finance world? Is financial independence about playing defense or offense? Voicemail from Jon, looking for advice about whether he should sell his business to become FI, or continue working with a few side hustles. Could Jon restructure his business to reduce stress and create a more positive working environment? What’s wrong with a life well worked? Is there value in purchasing a business that is inextricably tied to a single person? Coming up soon, Stacking Benjamins is doing live shows in Orlando, Kansas City and Ferndale, Mich.   For more information, visit the show notes at   ——————-   Thank you for being a part of the ChooseFI community! 


092 | Will Boland | CarLotz and Entrepreneur Case Study

CarLotz co-founder Will Boland talks about making the leap from investment banking to entrepreneurship, the challenges and benefits of leading a growing company, and what it means to build a life resume. How did Will become an entrepreneur? What was the inspiration for CarLotz? What experience during his work in investment banking gave Will the motivation to become an owner/manager? Will is 2nd generation FI. What did his journey look like? How did Will present and convince his family that it was a good idea to pursue entrepreneurship instead of continuing with his well-paying job? Did Will accumulate significant student loans while completing his undergraduate degree and master’s? What is a life resume, and does Will keep track of his? What role have mentors played in Will’s career? Will has been very open and honest with mentors and co-workers about his specific goals. How does he create an environment at CarLotz to encourage the same from his employees? Why didn’t Will’s mentor want to see his business plan? What was the thought process when Will and his co-founders could only secure small startup investments?   What is the advantage of selling a car on consignment? What hiccups did CarLotz overcome in their early days of business? “If you aren’t embarrassed by the first iteration, you’re launching too late.” How does Will encourage employees to share good ideas? Why do pursuing FI and starting a business complement each other well? How did Will and his co-founders create space to share work-place challenges within their partnership? Has Will caught up, financially, to where he’d be if he had continued his job in investment banking? Is he happy with where he’s at? Does CarLotz need to be a financial success in order to keep Will on track to reach financial independence? Why is running Will’s favorite life hack?   For more information, visit the show notes at


090R | Longest Vacation Ever

Brad gets back from vacation, Jonathan talks about bringing vegetarianism into his diet, and voicemails from the community highlighting CLEP tests and a 401k win. Brad is back from a month-long vacation in the U.K. Is this Brad’s first experience with “slow travel”? Where will Brad’s family go next? If you can optimize small things, they add up. Brad joined a ChooseFI meet up in London, with Barney from The Escape Artist and Ken from The Humble Penny. Is there a more efficient way to be active than slaving away on the treadmill? Are your health and exercise habits actually adding value to your life? Brad thinks maybe he’ll try a vegan diet for a short time, as was recommended on Monday’s episode. How has Jonathan incorporated additional spices into his family’s meals? “Eat food, not too much, mostly plants” – Michael Pollan How much money could Jonathan save if his family went vegetarian? What is intermittent fasting? Email from Alex, confirming the advantage and benefits of veganism. Does veganism have a PR issue? What tools will Jonathan use to increase his vegetable diet during the next few weeks. Voicemail from Ben, about using CLEP tests, which are free for members of the military, to decrease the time it takes to complete a university degree. Voicemail from Michael: strategically moving money from taxable investment accounts into non-taxable accounts will move him into a 0% tax bracket.   Link to Jonathan's InstaPot: Instant Pot

ChooseFI Podcast


115 | Poverty, Divorce and ...


Bonnie Traux, a blogger and early retiree, shares her story of growing up below the poverty line, scraping her way out of inherited debt, reaching financial independence without knowing what it was, and understanding how to talk about money with ...