This transcript was generated from the episode audio and may contain minor errors.
[Music]
Crypto tax whisperer takes on the IRS. Welcome to Side Hustle School, my friends. In this week's first $1,000 segment, we'll discover how an unassuming accountant turned a chaotic batch of crypto trades into a full-scale practice complete with custom software and national training programs. And of course, this is part of the feature we call your first $1,000. It's all about how somebody gets going with a new project, a new side hustle, small business, whatever the case may be, and actually makes money.
Not just, hey man, I have a business idea, but hey, I'm actually gonna start this business and it's going to be a money-making business. Not a hobby, not just something I do for fun, but something that enriches my life in a financial way. Not to say you can't enrich your life in other ways, of course, but our focus here on Side Hustle School is income-generating projects. So this feature comes to us today from Jackie. We're gonna hear her comments.
We're gonna hear a little bit of a story. I always encourage our storytellers to focus on some specific lessons, maybe a couple of anecdotes and such, but often a takeaway or at least something that a listener can then use as encouragement for their own ideas. Like you might not be an accountant, you might not want to work in crypto, that's okay. The whole point is to take the skills you already have and find a way to adapt those skills in a new way that can lead to something fun and exciting for you, okay? We're all about fun and exciting here for more than 3,000 episodes.
Let's hear today's story from Jackie. [Music]
My name is Jackie McCain. I'm an accountant who immersed myself in the chaotic world of cryptocurrency taxes. Just a few years ago, I was doing what I call normal accountant things, balancing spreadsheets, chasing down receipts, and mostly dealing with straightforward returns. Then, a friend asked for help with his crypto trades.
He had hundreds of transactions across multiple exchanges and none of his forms aligned. He was panicking about an audit, and honestly, I was intrigued. Seeing the disarray, I realized a huge need existed for specialized guidance in crypto taxation. That first job took me hours of manual sorting and reconciling. After tallying up his capital gains and losses, I charged him $2,800.
Higher than my normal rate for a standard return. He was happy to pay. Clearly, I crossed the first $1,000 threshold with my first complicated return. As I dug in further and got to know other people in the crypto world, I saw a pattern. Crypto traders rarely keep clean records and tax rules aren't always straightforward.
After several similar gigs, I standardized my approach, creating a step-by-step system for sorting exchange transactions, performing cost basis calculations and reconciling mismatch info. I realized I could pivot this into a real niche practice. As crypto soared in popularity, my client list ballooned. I knew I couldn't keep doing everything manually, so I spent my evenings and weekends tinkering with some basic software tools to automate the transaction imports and cost basis calculations. It was rough around the edges, but it saved me at least several hours for each client.
My new crypto tax engine soon became a selling point. I branded myself as the crypto tax whisperer, an accountant who not only understood the IRS guidelines, but also had a proprietary system to handle complex transaction histories. Clients loved it. Within a year, I made over $100,000 in fees from crypto traders alone. As I gained traction, other CPAs started asking me questions.
They wanted to learn how to handle their clients' crypto portfolios. At first, I offered free advice on LinkedIn, but demand grew quickly. That's when I realized I had a second revenue stream on my hands. I started a three-part training program for CPAs, covering everything from the basics of blockchain transactions to advanced cost basis challenges. My next step is to formalize the program, bundling the training with a subscription to my ever-improving crypto tax software.
Each CPA pays a few hundred dollars a month for access, which adds up fast. By the end of my second year, I was on track to clear $250,000 annually, a far cry from my early beginnings chasing W-2 forms. There's something satisfying about translating a tangled web of transactions into a tidy spreadsheet the IRS can't dispute. Not to mention, I found my sweet spot as the crypto tax whisperer, quietly making sense of the madness. - Big thanks to Jackie for telling us about her first $1,000.
I hope you found it encouraging, listeners. If you have a question or a comment, you know where to go, sidehustleschool.com. We've got notes pages for every episode. We've got a free email series you can join. I'll show you a weekly newsletter that goes out, guess what, every week.
And of course, you'll be the first to hear about new things as well. Podcast comes out every day. Always completely free. Subscribe or follow wherever you prefer to listen. My name's Chris Guillebeau.
This is "Side Hustle School." [Music]
From the Onward Project.
