Getting Financially Naked with Will Pay

MAYM Podcast Episode_Will.png

Getting Financially Naked with Will Paybarah

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 Will. If you pay attention to podcast art, Will is actually the designer of Martinis and Your Money’s new podcast art, as well as the art for our new Financial Gym focused podcast called Financially Naked. Will joins me today to share his digits, his side hustling, and his journey with The Financial Gym.

What Are We Drinking?

Will — Black Coffee

Shannon —  Black Cherry Schweppes

Podcast Notes

  • Will is a freelancer and he paints murals and does design work, podcast art, t-shirts, logos, photography, and videography.

  • Will used to graffiti walls and he was tired of getting in trouble, so he started doing lettering and typography. He went to art school and studied packaging design. 

  • Will has a full-time job as a creative director for GIR (Get It Right). They create some of the best kitchen tools on the market. 

  • His five to nine is his freelance work and he spends a lot of time at The Gym.

  • The Financial Gym likes to support its clients, and the new Martinis and Your Money look was created by Will. He is working on artwork for the other Gym podcast, and he also created a mural at The Gym, based on Cardi B’s line, “I make money moves”. 

  • Several Gym clients side hustle by doing warm up calls. 

  • Will never knows when that next freelance job is coming, so he doesn’t plan to make a transition to full-time freelance work. He is able to work remotely for his job, and he has a good balance with his full-time job and his freelance work.

  • One freelance job he had was teaching an online class on lettering, for Skillshare. They paid him based on royalties and every now and then he gets money in his inbox. 

  • Will says no to jobs if the job is above his skill level, the timeline is too short, or the client is right for him. He doesn’t like saying no, so he says yes to everything. How he says no is N+0. N equals the number you would normally charge plus another 0. Some clients say yes and others say no. If you don’t want to do it, raise your rates until they say no.

  • As a new freelancer, pricing your work is difficult until you get established. He did work for next to nothing for his dream client, but he charged more for a large client. It is a sliding scale.

  • You should know your worth and be paid your worth, but sometimes it is about the opportunity. It may pay dividends down the road, if a client refers you. It can grow.

  • Say yes to everything, especially when you are early on, because you don’t know what direction it will take you.

  • Will originally wanted to focus on typography and lettering, but he started taking on photography when it was slow. Don’t pigeonhole yourself.

  • Will has been a client of The Gym for almost a year. He has gotten a lot better at stabilizing his finances. Some months he makes $0 in his freelance, other times he makes more than his full-time job. 

  • Since he started at The Gym, saving has been steady and he is able to project what he will save in 2020.

  • Everyone benefits from talking openly about finances.

  • Questions from the financially naked discovery questionnaire:

    • Birthday: June 1

    • Job: Creative Director at GIR

    • Pay:$100,000 annually; $2,700 net pay, twice a month

    • Freelance: $775 average per month; $8,000 to $9,000 per year

    • IRA: $100 a month 

    • Checking #1: $2,000 for rent

    • Checking #2: $1,000 for everyday expenses

    • Savings #1: $2,500

    • Savings #2: $11,000

    • Travel: $600

    • Moving Fund: $2,300

    • Roth IRA: $12,500

    • Traditional IRA: $18,000

    • Taxable Investment Account: $16,000

    • HSA: $1,500

    • Credit Card: $0; paid off every month

    • Credit Score: 805

    • Rent/Utilities: $2,400 (was $2,800); splits in half with his partner

    • Renter’s Insurance: Yes

    • Health Insurance: Through his employer

    • Will: Not Yet

    • Children: No

    • Average Monthly Expenses: $3,500 - $4,500, not including rent

    • Goals 1-3 years: Get his assets to match his salary, move out of New York to more nature (west coast, Colorado, Maine, or Vermont), save/purchase real estate

    • What’s important to you (sacred cows): Food, traveling, snow boarding, and experiences. Goal for 2020: travel every month to a different place to photograph the Milky Way.

TAKEAWAY: My biggest takeaway is that sometimes a side hustle can be just that. Too frequently, people think about a side hustle becoming a main hustle, but it’s okay to just keep it on the side and let it enhance your full-time earnings. 

Random Three Questions

  1. What is a place you haven’t been to yet that is on your bucket list?

  2. What is a food you hated as a child and do you still hate it as an adult?

  3. If you weren’t working where you are, what else would you be doing?

Connect with Will

Website: willtypeforpay.com 

Instagram: @willpay


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 Will, in 2020, head over to, or send friends to, financialgym.com to get set up today.

Caitlin LyttleComment