Getting Financially Naked with Dylan

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Getting Financially Naked with Dylan

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 so that 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 year ago 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 Financial Gym client Dylan. This is a super special naked session, because Dylan is actually the reason why I started recording and sharing these naked sessions, and thankfully she’s agreed to finally do one herself.

What Are We Drinking?

Dylan — Decaf Pumpkin Tea

Shannon —  Black Cherry Schweppes

Podcast Notes

  • Dylan is the reason for financially naked podcasts, because she requested more of these after Shannon did hers last year.

  • Dylan leads the Atlanta money tribe and they just had their second anniversary. There are now money tribes across the U.S.

  • It has been a learning experience for Dylan and she enjoys meeting others interested in personal finance.

  • Next week, Caitlin is heading down to Atlanta to look at locations for The Gym. The plan is to open a Gym location there by the end of 2020. The D.C. Gym location is opening first.

  • At the same time, Shannon is going to Austin to look for Gym locations. There is a concentrated group of clients in that area.

  • Shannon will be in Chicago this week looking at locations, and Bridget will be in San Francisco looking at locations. Hoboken, New Jersey will be the fifth location.

  • It is so important to have goals and shoot big, because they eventually happen if you stick with them.

  • Dylan found The Gym through this podcast. When she moved to Atlanta from Nebraska, she started listening to NPR and podcasts. She moved without a TV so she had to find other ways to entertain herself. She also has a dog, so she takes a lot of walks and has time to listen to podcasts.

  • She bought a new car for her move and her money was depleted, so Dylan joined The Gym in November 2017. Joy has been her trainer. Dylan was a little nervous for her Naked Session, but she was starting from nowhere so she could only go up from there.

  • She was excited to share her finances and have someone else give her the next step.

  • In her time with The Gym, she has visited all 50 state. Dylan completed that by September 2019. When she turned 25, she had a quarter life crisis and decided to travel more.

  • Dylan wanted to visit all 50 states in five years. She visited 46 states in five years and the other four she visited between ages 18 and 25.

  • It is hard to answer what her favorite state is, because visiting a city doesn’t represent the whole state and because it depended who she was traveling with.

  • Arkansas surprised her, because it was so beautiful and she thinks Wyoming is underrated. The mid-western states have some gems if you try and if you have an open mind.

  • As she went along, she learned how to travel hack with credit cards and by visiting people in those states, so travel became a little cheaper.

  • The Gym officially has clients in all 50 states and they have clients on three islands in Hawaii. The Raleigh/Durham area and the twin cities have a good cluster of clients on their heat map.

  • Questions from the financially naked discovery questionnaire:

    • Birthday: January 23, 1990

    • Job: Disability Insurance Industry

    • Pay: $81,000 (was $55,000 when she started at The Gym); $2,000 every other week

    • Checking #1: $1,000 (used for bills)

    • Checking #2: $2,000

    • Barclays Savings: $10,090 (new since starting at The Gym)

    • Betterment: $21,700 (new since starting at The Gym)

    • 401(k): $59,855

    • TD Ameritrade IRA: $4,390

    • Real Estate: $13,000 (Rental house in Nebraska; amount was saved since starting at The Gym)

    • HSA: $1,900

    • Student Loan Debt: None

    • Credit Card: Paid off every month

    • Car: Paid Off

    • Credit Score: 760

    • Rent: $1,700

    • Average Monthly Expenses: $3,500 (increased in 2019, due to Christmas shopping and moving to an area with more restaurants and bars)

    • Will: Not yet

    • Goals 1-3 years: Get a job potentially working for The Financial Gym, move, buy an income property by herself, travel to all continents within three to five years

    • Goals long term: Marriage, kids, giving more to charity

    • What’s important to you (sacred cows): Travel, experiences, and her dog

TAKEAWAY: My biggest takeaway is that people feel afraid of judgment no matter what their financial health looks like. Let’s stop judging the financial digits in our life and embrace what we look like at every step of the journey. They’re just numbers after all. We shouldn’t let them define us.

Random Three Questions

  1. What is the first continent you want to visit?

  2. What is a show you like to binge watch?

  3. If this was your last night on earth what would be your last meal?


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. 

The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. If you’re ready to manifest your dreams, like Dylan, in 2020, head over to, or send friends to, financialgym.com to get set up today.

Shannon McLayComment