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Home.forex news reportHere's Why I Just Sold All My Shares Before the End of...

Here’s Why I Just Sold All My Shares Before the End of 2025

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  • Boston Omaha Corporation was my largest investment five years ago.

  • At the time, the stock was flying high and there was a lot to be excited about.

  • Since then, there have been some major red flags, and the business hasn’t performed nearly as well as I hoped.

  • 10 stocks we like better than Boston Omaha ›

Let’s rewind the clock five years, to the end of 2020. The COVID-19 pandemic was still a disruptive force in everyday life, and the stock market was rising rapidly after major economic stimulus and optimism that life would return to normal.

My portfolio also looked very different than it does today. In fact, my largest investment at the time was a company called Boston Omaha Corporation (NYSE: BOC), an emerging conglomerate that drew comparisons to an early stage Berkshire Hathaway (NYSE: BRK.A)(NYSE: BRK.B).

Fast-forward to the present time, and let’s just say that things didn’t go as well as I would have liked. In fact, after paring down my position a few times over the past couple of years, I finally sold the rest of my position in Boston Omaha a couple of weeks ago. Here’s why.

Man in suit looking at stock chart going down.
Image source: Getty Images.

To be clear, I never intended for Boston Omaha to become my largest investment. I started buying shares in 2017, when it was a recently public company. I added a bit when the initial wave of the pandemic sent the stock plunging, and I had an average cost basis of about $17 per share.

Well, in early 2021, when the meme stock craze was going on, Boston Omaha spiked to nearly $50 — and suddenly, what had been a midsize position became my largest investment.

I bought Boston Omaha because there was a lot to like about the business. Management focused on three main businesses (billboards, broadband, and insurance) that had solid economics and were making some minority investments that looked promising.

Things were going well for a while. Just to name a few things, the company’s minority investment in Dream Finders Homes (NYSE: DFH) became a 10-bagger when that company went public. The billboard business was growing rapidly, the fiber assets were being built out fast, and Boston Omaha announced an asset management business that would raise third-party capital to invest and collect fee income from.

To put it mildly, the thesis didn’t play out as I’d hoped. Business results have been unimpressive. In the most recent quarter, billboard revenue grew by just 2.5% year over year. Broadband assets aren’t delivering the cash flow that was expected. And the asset management business is in the process of being wound down after failing to get any traction with its capital raising efforts.



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