102R | 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. Th...
Nov 23, 2018•50 min•Ep. 102
102 | 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....
Nov 19, 2018•48 min•Ep. 102
101R | 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 al...
Nov 16, 2018•52 min•Ep. 101
101 | 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, wh...
Nov 12, 2018•55 min•Ep. 101
100R | 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...
Nov 09, 2018•44 min•Ep. 100
100 | 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 a...
Nov 05, 2018•49 min•Ep. 100
099R | 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 K...
Nov 02, 2018•1 hr 5 min•Ep. 99
099 | Michael Peterson, owner of a bacon-themed concession stand in California, talks about downsizing his family expenses, spending 8 months of the year managing a non-profit in El Salvador, and why generous giving is important to him. For more information, visit the show notes at https://ChooseFI.com/099 ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page t...
Oct 29, 2018•57 min•Ep. 99
098R | An exciting conversation with Jared about his path to FI as a traveling physical therapist and his current 5-month trip abroad, as well as a voicemail about healthcare planning and a review of Monday’s episode. For more information, visit the show notes at https://ChooseFI.com/098R
Oct 26, 2018•58 min•Ep. 98
098 | Samantha Keith, author of The Debtist blog, explains what it means to have more than half a million dollars of student debt, and how she plans to pay it off in less than 10 years. For more information, visit the show notes at https://ChooseFI.com/098
Oct 22, 2018•55 min•Ep. 98
097R | A conversation with Larry Hagner from The Good Dad Project updating Brad on the recent financial changes he’s made in pursuit of more financial independence and his family’s budgeting strategies, as well as highlight’s from Monday’s episode from The White Coat Investor. For more information, visit the show notes at https://ChooseFI.com/097R
Oct 19, 2018•1 hr 5 min•Ep. 97
097 | Dr. James Dahle, founder of The White Coat Investor, talks about getting his start as a doctor and a blogger, setting up inheritance funds for his children, thinking through his investing strategies, and the motivation that keeps him working on the White Coat Investor. For more information, visit the show notes at https://choosefi.com/097
Oct 15, 2018•1 hr 6 min•Ep. 97
096R | An in-depth conversation with JL Collins about a recent controversial interview given by Suze Orman, and clarification of what concepts are truly at the heart of the financial independence movement. Frugal wins of the week from Brad & Jonathan: garbage pickup and cell phone batteries. What questions did Dominick Q, from Monday’s episode, ask that were most impactful for Jonathan? Jonathan explains how he uses a planner at night to set himself up for success the next day. What three things...
Oct 12, 2018•58 min•Ep. 96
096 | Dominick Quartuccio defines life ‘drift’, advises Brad & Jonathan on how to take inventory of their habits, and evaluates the role technology plays in helping or hindering progress toward our goals. For more information, visit the show notes at https://choosefi.com/096
Oct 08, 2018•1 hr 16 min•Ep. 96
095R | Brad and Jonathan get an update about the “Playing with FIRE” documentary, they recap FinCon 2018, and review feedback from the community about Monday’s episode with the Military Dollar. For more information on this episode, visit the show notes at choosefi.com/095r ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards ...
Oct 05, 2018•46 min•Ep. 95
095 | 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 see...
Oct 01, 2018•1 hr 1 min•Ep. 95
094R | 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...
Sep 28, 2018•54 min•Ep. 94
094 | 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...
Sep 24, 2018•1 hr 15 min•Ep. 94
093R | 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-...
Sep 21, 2018•1 hr 9 min•Ep. 93
093 | Harry Campbell, The Rideshare Guy, talks about what it takes to be a successful Lyft and Uber driver, the strategies he used to start his blog, and how he transitioned from aerospace engineering to full-time blogging. For more information, visit the show notes at https://ChooseFI.com/093 ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for...
Sep 17, 2018•1 hr 11 min•Ep. 93
092R | Plans for ChooseFI to support education, the value of a life resume, travel rewards tips for active duty military, and hurricane preparation. For more information, visit the show notes at https://ChooseFI.com/092R
Sep 14, 2018•53 min•Ep. 92
092 | 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 2 nd generation FI. What did his journey look like? How did Will present and convince his family tha...
Sep 10, 2018•1 hr 14 min•Ep. 92
091R | An overview of how to own a house with an IRA, Jonathan attempts to optimize his recipes and shopping list, a list of the top 5 ChooseFI episodes and a travel rewards win. ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards Note: We may receive a commission if you are approved for cards on this page 3) Most importantl...
Sep 07, 2018•1 hr•Ep. 91
091 | Rich Carey, officer in the U.S. Air Force, talks about learning to live frugally, buying his first townhouse, and building his real estate empire from one to 20 houses in Montgomery, AL. ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards Note: We may receive a commission if you are approved for cards on this page 3) M...
Sep 03, 2018•1 hr 19 min•Ep. 91
090R | 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 ...
Aug 31, 2018•52 min•Ep. 90
090 | James and Steven pull back the curtain on veganism, talking about the health, lifestyle and financial benefits of veganism, alongside the practical details of how to actually make it work. ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards Note: We may receive a commission if you are approved for cards on this page 3)...
Aug 27, 2018•1 hr 13 min•Ep. 90
089R | An introduction to the Family Bank and what ChooseFI’s accountant-on-call thinks about it, as well as how to navigate rental car insurance, and what soft skills are crucial to a career in retail? ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards Note: We may receive a commission if you are approved for cards on this...
Aug 24, 2018•1 hr 3 min•Ep. 89
089 | Robert, from The College Investor, talks about his lucrative job as a Target store manager, building his blog into a highly profitable side hustle, his relationship with frugality, and the keys to success in a retail interview. For more information, visit the show notes at https://ChooseFI.com/089
Aug 20, 2018•1 hr 1 min•Ep. 89
088R | Cities that are the best for pursuing financial independence, how to hack your career, ideas for building a side hustle and how to assess the return on your college investment. For more information, including resources, visit the show notes at https://ChooseFI.com/088R ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit car...
Aug 17, 2018•56 min•Ep. 88
088 | Millennial Boss and FIRE Drill podcaster, J talks about becoming a creator, career hacking, and salary negotiation, alongside of pursuing FI, side hustles, and a growing podcast. ——————- Thank you for being a part of the ChooseFI community! 🙂 If you want to support us, here are some easy ways: 1) Leave an iTunes review: http://www.choosefi.com/itunes 2) Use our page to sign up for travel credit cards Note: We may receive a commission if you are approved for cards on this page 3) Most impo...
Aug 13, 2018•1 hr 11 min•Ep. 88
