508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
Side Hustle Pro
Nicaila Matthews Okome | Side Hustle Pro Media
4.7 • 1.8K Ratings
🗓️ 8 April 2026
⏱️ 34 minutes
🧾️ Download transcript
Summary
If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know.
In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits.
This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it.
Main Takeaways
- Lack of consistent tracking is the biggest mistake that leads to overpaying taxes
- Many solopreneurs miss deductions simply because they are unaware of what qualifies
- Staying organized year-round is the key to reducing stress and maximizing savings
Highlights Include
- 00:00 – Introduction to tax season for solopreneurs
- 02:00 – Lisa’s journey into tax expertise and entrepreneurship
- 05:20 – LLC vs S corp: what you actually need to know
- 08:20 – When taxes start to feel complicated
- 09:30 – Why tracking income and expenses is critical
- 11:40 – Common deductions people miss
- 13:00 – Home office deduction explained
- 14:20 – Section 179 and equipment write-offs
- 15:10 – What you can’t deduct (clothes, hair, makeup)
- 16:40 – Business credit card interest deduction
- 17:20 – Employing your kids as a tax strategy
- 18:00 – SEP IRA and retirement savings for entrepreneurs
- 19:00 – Qualified Business Income deduction
- 20:10 – Key tax law updates and 1099-K changes
- 23:20 – How to stay organized with QuickBooks
- 25:40 – How TurboTax experts support business owners
- 27:10 – Lisa’s personal system for staying organized
Links Mentioned in This Episode
- TurboTax: https://turbotax.com/business
- QuickBooks: https://quickbooks.intuit.com
Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
- Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
- Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
- YouTube: https://www.youtube.com/sidehustlepro
Announcements
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Social Media
LinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a
Website: https://turbotax.com/business
Side Hustle Pro – @sidehustlepro
#SideHustlePro
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Transcript
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| 0:00.0 | something that I get confused about in the lane of content creation. It's the things that go into |
| 0:05.4 | content creation, right? Like sometimes you get your makeup done. Sometimes you need to get your hair |
| 0:09.7 | done. Sometimes you need to get clothes, right? And so that's a real dicey area where every time I look, |
| 0:14.9 | they're like, no. They're like, Michaela, no. That is a great area. I wish clothes, but no. |
| 0:20.5 | Yeah. What are they going to update that tax law? |
| 0:23.1 | Yes. |
| 0:23.9 | You're listening to Side Hustle Pro, the podcast that teaches you to build and grow your side hustle from passion project to profitable business. |
| 0:32.6 | And I'm your host, Nikaela Matthews Okome. |
| 0:35.4 | So let's get started. |
| 0:40.2 | Hey, friends. Hey, welcome, welcome back to the show. It's Nikaela here. And today we're |
| 0:44.4 | talking about something every entrepreneur and side hustler faces tax season. It's a topic that |
| 0:50.3 | can feel overwhelming, which is why I'm so excited that today's episode is brought to you in |
| 0:54.3 | partnership with TurboTax experts for business. Whether you're just starting your side hustle or |
| 0:59.1 | growing a full-time business, filing as a sole proprietor or LLC comes with its own set of rules. |
| 1:04.8 | Joining me today to help us navigate it all is Lisa Green-Lewis, a CPA and TurboTax expert with over 20 years of experience in tax |
| 1:12.5 | preparation. She's worked as a public auditor, controller, and operations manager, and has also |
| 1:18.1 | been self-employed so she understands firsthand what it looks like to run a business and stay on top |
| 1:23.5 | of your taxes. In this episode, we're breaking down what solopreneurs need to know, the common |
| 1:28.8 | mistakes that cost you money, and how to stay organized without the overwhelm. Let's get right |
| 1:34.3 | into it. Lisa, welcome, welcome to the guest chair officially. I want to thank you for being here. |
| 1:42.5 | Thank you for having me. Yes, of course, because this is something |
| 1:46.0 | that I've been meaning to talk about for a long time and it's something that I am getting together |
... |
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