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

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

April 8, 2026 · 34 min

About this episode

This episode discusses common tax mistakes made by side hustlers and how to avoid them with insights from CPA Lisa Greene-Lewis.

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…

People in this episode

Host: Nicaila Matthews Okome

Guest: Lisa Greene-Lewis

Topics covered

Keywords

Mentioned in this episode

Organizations: TurboTax, CPA

More episodes of Side Hustle Pro

Explore listener stats, chart rankings, contacts and more on the Side Hustle Pro podcast page.