Episode
508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
- Podcast
- Side Hustle Pro
- Published
- Apr 8, 2026
- Duration seconds
- 2051
- Processing state
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- https://shows.acast.com/side-hustle-pro/episodes/the-tax-mistakes-side-hustlers-make-that-cost-them-thousands
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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 – H…