Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Entrepreneur's $10k Tax Lesson

20 Mar 2026 · 0 min

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0:26

In this conversational video, an entrepreneur (Speaker A) recounts a 13‑month relationship with an accountant who repeatedly mishandled tax filings and bookkeeping, despite the entrepreneur’s repeated concerns. The accountant failed to file the 2024 taxes correctly, left the books unbalanced, and shifted blame onto the entrepreneur whenever issues were raised. After switching to a new bookkeeper, the entrepreneur discovered the extent of the errors, learning that correcting the 2024 filings (and similarly for 2025) will cost nearly $10,000. Christian Osgood shares a parallel experience of firing a bookkeeper for the same failures. The discussion culminates in the insight that entrepreneurs often pay a steep price to learn how to identify and partner with competent financial professionals, emphasizing the value of due diligence and the lesson that costly mistakes can serve as phase‑appropriate learning experiences.

This was the accountant that we worked for, for the last 13 months. And there's a lot of little things that went, that felt like it was being mismanaged, but I was constantly being told I was wrong. And it turns out that I was right. This accountant did not file my 2024 taxes correctly. They did not balance my books. They did not do a lot of the things that they said that they were going to do. And every time I raised a concern, it, they put it back on me when I knew that I was right. And when we switched, than you.
I fired a bookkeeper on Monday this week, as of the filming of this, 2 days ago for the same exact problem. It was just like, hey, you didn't deliver the deliverables. And every time it's brought up, oh, well, it's because you didn't give me this one thing that I forgot to ask you for. I absolutely have been there.
So where am I now? My new bookkeeper was the one who revealed it, and I kept on going back to the old one being like, hey, you told me no, but here's the thing. And when push came to shove, it's costing me probably almost $10,000 to redo and refile for 2024. The same with 2025. And so the amount of cleanup that I'm having to do, but here's the reality is I found the right partner, but I had to go through the exercise of going through bad to understand good and appreciate it. So sometimes as an entrepreneur, the taxes we pay is simply to learn the lesson that we needed to know at this phase.