Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Entrepreneur's Tax Nightmare

20 Jun 2026 · 1 min

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Christian Osgood set aside $200,000 for taxes after his first big year in business, but an $183,000 IRS bill for excess tax benefits he'd claimed wiped out his reinvestment cash. He learned that tax planning matters as much as profit when you're trying to grow.

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ended up with excess tax benefits that I couldn't use in that tax year and owing $183,000 to the IRS when I was factoring for about $15,000. In your first year of business as an entrepreneur, that sucks. You just— Yeah. You just managed to put aside about— I put aside about $200,000. I'm like, I just set aside more than I made in my active career in previous years. And then getting a letter from the IRS saying, Hello, you owe us all of that. That was a— that was a huge bummer. So it is one of the most important things that you can do when you start making significant money, you have a successful business, putting that money back into your business, especially in the growth phase of a business, is so critical. What I could do with another $180,000 of marketing would have been huge. I agree with you on that.