Getting Naked with Jon


At the Financial Gym, we call the first meeting you have with a trainer the “financially naked session.” In this meeting, you share everything about yourself financially so the trainer knows where you’re starting and so he or she can make the plan for how you can get where you want to go. Above all other meetings, this one scares clients the most because they are afraid or ashamed of their financial situation.

A few months back on this podcast, I shared my financially naked session and it led to a request for more. Now this is a regular series on this podcast. Getting in the hot-seat today is my first dude! I know that my podcast may seem as though it’s skewed toward women; however, I’ve known for years that guys are listening as well, and Jon is one of those guys. Jon is a longtime listener who volunteered to get financially naked with me and all of you. 

What Are We Drinking?

Jon — Beer

Shannon — Bota Box Malbec

Podcast Notes

  • Jon has been listening to the podcast for three years and he listens to it at work. Jon told a story about how a co-worker saw this podcast on his phone and said he listened to it too. Shannon now has proof that it is not only women who listen.
  • Two podcast listeners were recently hired to be trainers at the Financial Gym.
  • When Shannon was first building the Gym, she only had three clients and used some of her free time to start this podcast.
  • The Gym is growing and this is the first month Shannon had to reassign two clients to other trainers, because she no longer has time to do their quarterly reviews.
  • Jon went to college for criminal justice and always thought he was going to get into law enforcement, but ended up in loss prevention.
  • Loss prevention is a store’s nice way of saying “Don’t take shit from us”.
  • Recently Jon picked up a side hustle as a DJ at weddings and parties in Connecticut, Massachusetts, New York, etc. He lives near Boston right now.
  • The New England money tribe is starting up – sign up if you are in the area!
  • Jon’s office is filled with surveillance screens. While he is watching the screens, he listens to podcasts.
  • When Shannon worked at Best Buy, they had the surveillance screens, and the employee watching them, on the sales floor. When she worked there, CDs were the most common item people stole.
  • Jon works at Sears and says the tool area is a hot area to steal from. He has been doing loss prevention for six years and would now like to transition to something like operations. He is open to new opportunities.
  • Other than this podcast, he listens to Listen Money Matters, Dave Ramsey (previously), Chris Hogan, Clark Howard, Taz and the Moose, The Steve Austin Show, Tony Robbins, Ultimate Health – a little bit of everything.
  • Jon isn’t a Gym client, but he has been thinking about it for the last few months.
  • Shannon has nine new trainers starting within the next couple of weeks.
  • Questions from the financially naked discovery questions:
  • Birthday: June 17, 1991
  • Employer: Sears
  • Salary: $52,000
  • Pay Cycle: Bi-Weekly
  • DJ: Pays per gig; approx $15,000/year
  • Sears Net Pay: $1,350/paycheck; $2,600/month
  • Checking account: $1,100
  • Cash: $600
  • Credit Union Savings/Emergency account: $500
  • Marcus Savings: $100
  • Acorns: $1,430
  • Vanguard Roth IRA: $3,881
  • Work 401(k): $1,700
  • HSA: $3,000
  • Student Loan #1: $17,696.94
  • Student Loan #2: $6,445.34
  • Student Loan #3: $1,174.26
  • Original student loan was about $39,000 – now down about $14,000
  • One student loan interest is 6.8% and the other two are 5%
  • AmEx Credit Card: $87.23 (10% interest)
  • BOA Credit Card: $710 (12.99% interest)
  • Apple/Barclay Credit Card: $800 (0% interest for 24 months)
  • Jon calls his credit card companies every few months to ask for a lower interest rate.
  • Jon pays off his credit cards every month and doesn’t pay interest
  • Credit Score: 737
  • Car Loan: $12,000 (2.9% interest; $241 per month)
  • Rent: $825/month for a studio
  • Renters Insurance: None
  • Car Insurance: $540 every six months
  • Disability Insurance: Yes, through work
  • Life Insurance: 3x annual salary through work
  • Will/Trust: No
  • Children: None
  • Pets: None
  • Average Monthly Expenses: $1,500 – $1,800
  • Goals: Transition to operations or public speaking with a company.
  • Mini-goal: Podcasting or blogging about his experience with little savings ideas and tips
  • Goals 3-5 years: Owning a multi-family home and living in part of it while renting out the rest
  • Goals long-term: marriage and kids
  • What’s important to you (sacred cows): Freedom/travel/flexibility
  • Jon has been in debt repayment mode where he minimizes expenses and pours as much money as he can into his debts.
  • Trainers at the Financial Gym prioritize emergency funds. If you don’t have the cash when an emergency happens, you will end up with debt on your credit card at a high interest. Fund it at three to six months of expenses. For Jon, it would be a minimum of $5,000, ideally $10,000.
  • Shannon recommends that Jon make more money.
  • After your Naked Session at the Gym your Financial Gym trainer will calculate how much you need to reach your goals and tell you how much you need to make.
  • On average, Financial Gym clients make about $5,000 to $20,000 more, within the first year of working with a trainer.
  • Lindsey is the Gym’s salary negotiating expert.

Takeaway:My biggest takeaway is that when your monthly budget doesn’t leave a whole lot for the extras you want in life, set out to make more money. We see our clients at the Gym get $5,000 to $50,000 salary increases just by setting out on the journey to make more. As a side note, Jon literally joined the Gym right after we ended our call. I’m so glad that he’s officially part of the FinGym family, and I can’t wait to see what he accomplishes!

Random Three Questions

  1. Where is somewhere you would like to travel?
  2. What is a show you like to binge-watch?
  3. If you were a wrestler, what would your entrance theme be?

Bonus Question for Shannon: Where would you like to go on vacation for a week?

If you’d like to get financially naked with my team, and drop any fear or shame you have around money, I hope you’ll reach out to us at the Financial Gym. My trainers have literally seen it all, so nothing will surprise us. We don’t care how you got here, we just care about getting you where you want to go. 

As many of you know, we increased our rates in 2019 for new clients, but I have instituted a 15% discount for Martinis and Your Money listeners going forward, so the new rates will not impact you. If you’re ready to manifest your dreams, like Jon, in 2019, head over to, or send friends to, to lock in your low rates today.

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