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 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: https://sidehustlepro.co/class
Social Media
LinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a
Website: https://turbotax.com/business
Side Hustle Pro – @sidehustlepro
#SideHustlePro
Tags:
side hustle taxes, small business taxes, tax mistakes entrepreneurs, solopreneur tips, LLC vs S corp, how to save on taxes, tax deductions small business, self employed taxes, TurboTax experts, QuickBooks tips, entrepreneur finance, business tax tips, IRS deductions, quarterly taxes, money management for entrepreneurs
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