Expert Insights

Angie Moody
Founder & CEO, Ruby Money


Angie represents two of the sexiest shifts in our industry. 

One, top talent is choosing to freelance over the traditional career path, best covered by Ernie Park of Part Time Tech

Two, the freelance economy is becoming it’s own industry, no different than retail, hospitality, cloud computing, etc. 

In Angies case, she represents both trends. Herself, she’s the definition of top talent with experience at Microsoft, Instagram, and Visa to name a top few of her numerous logos. And she is currently building her own fintech, Ruby Money, helping freelancers and solopreneurs with their tax and financial planning. 

A couple themes we will dive into:

  • Why Angie started Ruby Money
  • Corporate headcount game vs hiring the right freelance talent 
  • How to not end up with a 30K tax bill
  • How different labels (freelancer, solopreneur, fractional) can evolve depending on your customer

Our Favorite Quotes

With all your experience and success, you could be doing so many other things and have a much more stable, consistent path. Why choose freelance?

  • In some ways, this was always what I was meant to be doing. And everything I did getting to this point led me to this position of both starting a company and building a company that makes other people successful as entrepreneurs and supports their desire to build companies and to be financially independent. At a very young age, being financially independent was an important goal of mine, I majored in financing, literally, for that reason.”

Angie’s experience with hiring in the past:

  • “But I also remember being at Capital One and Instagram and having to play that headcount game, right? You’re going through the annual process, and you’re like, I need to get five headcount, which a manager gets allocates for but you’re not given the budget. You’re given the numbers, for butts in seats, and what the freelance economy is unlocking is a much better stewardship, it gives leaders a better way to say no, this is the work I want to get done. This is the budget I have to get the work done, let me go find the best talent, and that might not always be full time people.”

Do we need to have different terms to describe Freelancers?

  • “Freelancer, solopreneur, entrepreneur, they all essentially make the same thing. I just put an assortment out there. People can resonate with the word that they enjoy.”
  • “A lot of Ruby Money’s members have multiple income streams, they’re a business coach, they sell courses, they might even sell physical products. So they really do feel like freelance doesn’t quite sum up all that they do. I do think it’s hard to try to pin everyone into into one word.”

How is Ruby Money helping freelancers manage their financials better?

  • “Ruby Money is providing you the education needed throughout the year on what you owe in taxes every time you get paid. So in a way, it’s like replicating that paycheck experience. Sure your client paid you $1000 but I know all these things about you, so I know that your tax rate is going to be about 20% meaning 20% of that $1000 is not your money. We are creating a set it and forget it habit and mentality to save people from ever having that surprise tax moment.
  • “If you are a freelancer, taxes are typically your number one expense. Taxes now become a key part of your business strategy, figuring out how to lower your profits, how to invest in tax deferred retirement plan, how to take advantage of deductions, how to defer certain receivables or payables and really implement a tax strategy that allows you to preserve as much of your profit as possible, as a business owner, because that’s how the IRS is treating you. And so developing the language and the tools to highlight that that knowledge and make smart suggestions. Our sole focus is to eliminate the need to hire a very expensive CPA or bookkeeper and eliminate the possibility of you ever waking up and having a $30,000 bill from the IRS.”

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