Are you paying more tax than you need to? On this episode of the Futureproof Business Podcast, host Daniel Rosenstein sits down with Courtney Epps — tax strategist, entrepreneur and founder of OTB Tax, a full-service accounting firm in Greer, South Carolina that completes more than 2,500 tax returns a year.
Courtney isn’t a typical accountant. She’s a communicator and strategist focused on one thing: freeing up money for business owners and helping them build real wealth.
Note: this article summarizes a podcast conversation and is not tax or financial advice. Talk to a qualified tax professional about your situation.
Why entrepreneurs overpay
Courtney walks through the top reasons entrepreneurs and home-based businesses overpay in taxes — and why most of them come down to a lack of planning rather than a lack of options.
Key takeaways
Your entity structure matters
Choosing the right structure — for example, LLC versus S-Corp — can make a significant difference. Missing an S-Corp election is one of the common mistakes Courtney sees.
DIY tax software can cost you
Courtney explains why relying on consumer tax software can leave money on the table and may even increase audit risk for business owners.
Plan proactively
Tax strategy sessions held before the year ends — not after — are where the real savings come from. Courtney shares client stories, including one entrepreneur who saved $10 million in a single year.
Don’t miss common deductions
From home office expenses to the Augusta Rule, many entrepreneurs overlook deductions they’re entitled to. Courtney also explains why some W-2 employees consider a home-based side business.
Know who does what
Accountants and bookkeepers play different roles. Confusing the two can lead business owners to overpay without realizing it.
Avoid basic mistakes
- Commingling business and personal funds
- Missing or poorly tracked expenses
- Skipping LLC or S-Corp elections
Courtney’s comeback story
Courtney originally wanted to be a doctor, quit her first accounting job in the middle of tax season, and later lost everything in a business sale. She rebuilt — and created a firm that now serves thousands of clients.
Who this episode is for
Small business owners, side hustlers and freelancers who want to keep more of what they earn.
Watch or listen to the full episode
Catch the complete conversation on YouTube or listen on Spotify. Want more conversations like this? Browse all Futureproof Business Podcast episodes and join the newsletter to get new episodes and insights in your inbox.