Taxes can be one of the most stressful parts of running your own business. The rules are complicated, the deadlines are firm, and one wrong move can cost thousands.
But when you finally get a system down, it’s an oddly satisfying feeling. For Miami dancer Caitlin, that sense of order came from treating her work like the business it is.
But when she posted her approach online, a tax strategist stepped in to point out a way she could be saving even more.
Expert Reviews Miami Dancer’s Business Setup
TikTok creator Dwight Dye (@dwightdye), a tax strategist, recently stitched a video from Caitlin (@caitlinsometimescherry) in which she broke down her 2024 taxes. The clip got more than 476,000 views.
“My total income for 2024 was $710,635,” she says, explaining that $413,249 came from her club’s 1099 NEC form, while $297,385 was self-reported cash.
At her club, card payments automatically get reported to the IRS, while cash tips are up to the dancer to report—something she says she does because she invests heavily and needs to prove her income.
She also shared that her tax write-offs totaled $148,767, leaving $561,868 in taxable income. After switching her LLC to an S corporation in 2024, she began paying herself a $200,000 “reasonable salary,” with $80,380 withheld for taxes. Even with those withholdings, her CPA determined she still owed $64,363.
“She was doing so good until she said her CPA told her she owed another $64,000 in taxes,” Dye says in his reaction.
He noted that while she’s on the right track, her salary might be set too high, leading to extra payroll taxes—and that she could benefit from more advanced strategies, like equipment leasing.
How Equipment Leasing Could Work
According to small business lender Lendio, equipment leasing is a long-term rental agreement where a lender buys equipment and rents it to a business for a set period.
Monthly payments remain consistent, and at the end of the term, the business can buy, return, or renew the lease.
Dye claimed that if Caitlin had invested about $70,000 into equipment, she could have wiped out the rest of her taxable income through depreciation losses, eliminating her tax bill and getting her federal withholdings refunded.
While this can work in some cases, it typically depends on the type of business and whether the equipment is considered necessary and ordinary for operations.
In Caitlin’s case, she’d need to ensure any leased items genuinely qualified under IRS rules—otherwise, the deduction could be challenged.
Commenters Share Their Thoughts
In the comments, some ignored the tax strategy entirely, focusing more on Caitlin’s line of work in Miami.
“All I can think is all of the lustfull men that gave her $700k, is sad,” one person wrote.
Others, however, talked about their experiences with tax strategists.
“We worked with a cpa firm that we assumed was good. We switched and HOLY COW does having a tax strategist make a difference!” one user shared. “Many people get caught up in bragging about how much taxes they pay. It is NEVER something to brag about. It’s a sign you have a bad tax guy.”
“She needs more elections for 401k, SEP Ira, etc. no way can $70k in deductions wipe out $70k in taxes owed. Prove it,” another said.
Dwight responded to the last comment: “With the equipment leasing strategy, she could have bought $600k of equipment. The losses from the depreciation would have offset all of her income.”
BroBible has reached out to Dwight via email and Caitlin via TikTok messages for comment.
@dwightdye I’m impressed with how she structured her business, she’s thinking like an entrepreneur 👏 BUT… she’s still leaving money on the table. She could’ve saved so much more money! @caitlinsometimescherry With the right tax strategist in your corner, you could take it even further and legally save way more on taxes!