Small Business Tax Savings Podcast He Put $5M in a C Corp to Avoid Taxes… Was That Smart? (Q&A: Your Tax Questions Answered)
Can you deduct free food, rent your house to your business or avoid double taxation with a C Corp?
In this Q&A episode, Mike answers rapid-fire tax questions submitted by business owners across industries. From restaurant deductions to partnership restructuring, foreign contractors, co-mingled expenses, and advanced C Corp investing strategies, this episode walks through what’s legal, what’s smart, and what’s risky. If you want clarity before you file, this is the one to listen to.
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Chapters
(01:00) The Augusta Rule: What’s a Reasonable Rental Rate?
How to properly rent your home to your business, why documentation matters, and whether to use hotel comps or Airbnb rates.
(03:00) Hiring Foreign Contractors: W-8 vs W-9
What forms you need on file when paying international contractors and when 1099s apply.
(04:30) Partnership Owners: Should You Use an S Corp?
How S Corps can reduce self-employment tax, why ownership structure matters, and how to structure it correctly.
(09:00) Business Expenses Paid from a Personal Account
Can you still deduct them? What co-mingling means during an audit, and how to fix it going forward.
(12:00) Do Insurance Companies Need Your Subcontractor’s Tax Return?
Why a signed W-9 is typically all you need and how to protect yourself.
(14:00) Can I Deduct Free Food? Restaurant and Bar Tax Rules
How to deduct employee meals and promotional giveaways correctly. Cost vs retail value explained.
(17:00) FSA vs HRA: Which One Actually Makes Sense?
When high out-of-pocket medical costs justify setting up an HRA and what thresholds to consider.
(19:00) $10 Million in a C Corp: Smart Strategy or Tax Trap?
The personal holding company rules, double taxation, and when retaining earnings in a C Corp actually makes sense.
(22:00) Free Resources for New Business Owners
Where to start if taxes feel overwhelming and how to build a foundation before filing.
Podcast Host:
Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.