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

If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan

Save your seat here.

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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508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)