Entrepreneurs on Fire Why Smart Entrepreneurs Never Pay 'Full Price' on Taxes with Adam Williams
Nov 27, 2025
Adam Williams, an attorney and co-founder of Pennywise Tax Strategies, shares invaluable insights for entrepreneurs looking to optimize their tax strategy. He emphasizes the importance of year-round planning rather than seasonal accounting. Williams dives into the Augusta Rule, allowing homeowners to rent out their properties to their businesses tax-free. He also highlights the benefits of utilizing accountable plans for home office reimbursements and the significant savings from choosing the right business entity. Don't miss his advice on the hidden secrets in your tax return!
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Choose The Right Entity And Revisit It
- Review and choose the correct business entity and revisit it annually as your business grows.
- Making an S corporation election often reduces taxes significantly for small business owners and should be evaluated regularly.
The Augusta Rule Applied To Entrepreneurs
- Adam describes the Augusta Rule where renting your home for 14 days or less is tax-free income and how entrepreneurs can apply it.
- He suggests renting your home to your business for meetings, content shoots, or events to convert personal spend into deductible business rent.
Leverage Home Office Reimbursements
- Use a properly documented accountable plan so an S corporation can reimburse business use of your home.
- Reimburse mortgage interest, utilities, repairs and even housekeeping proportionally to reduce taxable income without lifestyle changes.
