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. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: 🚀 Book your free demo call today. Click here or visit: 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 Join TaxElm: 🚀 Visit: 🚀 Check Out TaxElm: 🚀 Join our Free Facebook Group: 🚀 YouTube: 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 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.

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He Put $5M in a C Corp to Avoid Taxes… Was That Smart? (Q&A: Your Tax Questions Answered) is an episode from Small Business Tax Savings Podcast by Mike Jesowshek, CPA.

This episode is 26:44 long.

This episode was published on Feb 18, 2026.

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