Hey - happy Thursday.
Quick personal one this week. Here's how I actually got to where I am, because the story is messier than people probably assume.
I started in land in 2017, buying cheap rural parcels in Texas, subdividing where I could, and selling them on owner financing. The notes weren't the plan - they were the byproduct. I was using hard money to get into most of these deals, which meant I'd often have to sell the notes I'd just created to pay back the lender and recapitalize. I hated doing it every time. The note was the part I actually wanted to keep, but the model demanded it.
That kept up for a few years. Then in early 2025, I sold a bunch of loans in a couple of large tranches to a handful of investors, planning to keep buying land, keep subdividing, keep recycling, and free up dry powder for a business acquisition I was working on. I had a dumpster rental company in Austin under contract going into the year and wanted to be ready.
The dumpster deal fell apart over funding at their asking price. And the land never came back.
I spent that year mailing. 30,000 letters and about 100 offers on on-market deals, with almost nothing landing. The deals that did come back, I couldn't get comfortable with at the price, and I didn't trust the market. After enough swings, I stopped trying to convince myself I was just one more mailer away.
That's when something clicked. I'd been spending real money on acquisition marketing, doing title work, cleaning up land, finding buyers, and originating loans, all to end up holding paper at the end of it. Why was I doing all that work just to get to the part I wanted? Why not just buy the note? Less return, sure, but way less work. Just jump to the end.
So I bought my first one off Paperstac. A $20,000 note on a parcel in a Texas county I already knew, around a 20% IRR. Easy and clean, and it gave me the itch. The due diligence on buying someone else's note is different from originating your own, but the underwriting instincts were already there. I knew how to read land. I knew how to read a borrower. I just had to learn how to read a tape.
Then Terra Notes fell in my lap. Around February of 2025, a friend in the note space told me the owner was looking to sell. My friend wanted to buy it but didn't want to run it, so he was looking for an operator. I said "why don't I just buy it." I'd been hunting for a business anyway, I was already a customer of the software, and it felt like a fit. Other than the small detail that I had zero software experience. Ha.
That brought me to today. I haven't bought a piece of land since late 2024. Most of my acquisition energy goes into Terra Notes now, growing it, supporting customers, and keeping feelers out for bolt-ons if the right one walks in. I'm not actively marketing for note deals either. Previous sellers bring deals to me, and I just filter for what I want. Less hustle, more signal.
If there's a lesson in any of this, and I'm always skeptical of newsletter lessons, it's that the plan usually isn't the path. I didn't pivot to notes because I had a strategic vision. I pivoted because the land model stopped working and the math on buying paper made more sense. Then a SaaS business showed up at the right moment and shifted the direction again. The through-line was just paying attention to what was working and what wasn't.
That's what this newsletter is going to be about going forward. Not the textbook plays, but the side doors. The actual stories of how deals get done when you stop trying to walk through the front.
Talk soon, Jake
P.S. - More coming on the YouTube content side soon. Stay tuned.