Ep. 229: Understanding the Financial Side of Your Side Hustle with Melissa Whaley

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So it’s about two weeks after tax day here in the US, so by now you’ve probably gone through the tedious process of filing your income taxes.

It’s the unglamourous part of online business that nobody really talks about.

Sure, we all talk about the freedom, flexibility and financial independence that comes with being your own boss and owning your own business – but the flip side of that is that we’re also still responsible for all the boring and sometimes complicated administrative stuff that we also were annoyed by at our day jobs, like filling out expense reports and other tedious stuff like that.

So when it comes to taxes, if you’re a side hustler, you’ve got that extra layer of reporting your side hustle income and expenses on top of your W2 wages, and then making sure you’re paying taxes to all the people you’re required to pay taxes to, like in my case it’s Federal, State and local, and I’m honestly never 100% confident that I’m doing it right.

And I don’t know if you’ve ever had this experience, but the couple of times that I’ve tried to hire a CPA in the past, I left those meetings even more confused than when I walked in, feeling like I needed to learn a whole other language in order to follow the conversation and knowing that this definitely is not the right person for me if they can’t – or won’t – explain things to me in a way that I can understand.

That’s why I’m so excited to bring you today’s guest, Melissa Whaley.

She’s an accountant who works specifically with online business owners like us to help us understand the financial side our businesses without making us feel like total idiots in the process!

I’m so excited to have Melissa on the podcast today, not only for my own selfish reasons because I’ve been doing my books and taxes on my own for so long and have always had this really uneasy feeling about whether or not I’m doing it right, but because Melissa’s just like us.

She started out working at a large tax company, and she wanted the freedom, flexibility and financial independence that comes with running your own business – especially because she’s got four kids! But she saw a gap in the way her clients were being served, and she stepped in to fill it.

Today on the podcast Melissa and I are talking about:

  • Exactly how and why Melissa helps online entrepreneurs and side hustlers like us with our business financials and taxes.
  • How Melissa took a skill she already had and turned it into an online business.
  • The general rule for knowing when you need to start paying quarterly taxes when you’re still side hustling.
  • How to look at your business finances in a way that makes sense as a layperson.
  • What to pay attention to when it comes to your expenses.
  • What to look for when choosing an accountant or CPA.
  • How Melissa manages running her business as a wife and mother of four.
  • Melissa’s best advice for growing your team.
  • The one belief Melissa had to change about herself to get where she is today.

Resources Mentioned in this Episode:

The Legal Roadmap Podcast with Autumn Witt Boyd – Tax Strategies for 7-Figure Businesses

Where to connect with Melissa:

Melissa’s Instagram

My favorite quotes from Melissa:

“When you’re an expert in an area it’s not that you have everything memorized in your head, it’s that you know enough about the subject to be able to research and find the right answer.”

“If you ignore your numbers for too long, that’s a recipe for your business to implode and for you to burn out.”

“When you know the numbers in your business it’s really empowering. It really helps you make that next good decision to move your business in a positive direction.”

“It’s important to be able to step back, evaluate where you’re at and where your business is at and say, ‘Ok I need to make these changes.’”

“We want to have businesses that make us feel good and feel fulfilled and we are enjoying serving other people.”


Melissa is a Virtual Tax Advisor for creative business owners. She helps demystify taxes for people who light up over their work and freak out over their numbers. She is a California native, married to her college sweetheart for 10 years and they have 4 awesome kids together. You can find her chugging iced coffee while geeking out over all things tax.


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Hi, I'm Shannon!

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