A while back, one of my tenants came to me with a personal ask.
He was running a bodega out of a small retail space I owned. Convenience store, hot and cold sandwiches, busy with Uber Eats and DoorDash. Located just off a major thoroughfare with tons of morning traffic.
At the time, he had been my tenant for just over three years.
Never once late with the rent. In fact, he would call a day or two before the first of the month and ask if he could send it early.
I had seen him hustle over the years. I watched the business grow, bit by bit. First it was just a small store with regulars. Then came earlier hours. He started opening at 5 a.m. instead of 8, just to catch the rush of commuters grabbing breakfast, coffee, cigarettes, and sandwiches.
He got approved for food stamps. Installed a lottery machine. Delivery orders picked up. He was always working, always improving. The store was clean, the shelves were full, and the energy was good.
We talked from time to time. He mentioned that he was thinking about buying out his partner. Nothing formal at first, just letting me know what was on his mind.
Then one day he came to me with a clear ask.
He wanted to borrow $25,000 to take full control of the business.
I had never done a deal like that before. But I had always been interested in investing in real small businesses. And more importantly, I believed in him.
He even offered to let me borrow his Porsche for a weekend just as a thank you for being easy to work with. That wasn't part of the deal, but I took it as a sign of trust and respect.
We sat down. He showed me his numbers. Food stamp receipts. Lotto sales. Credit card volume from the past few months. It all looked solid.
But I didn't want to become a business partner who had to track sales and profits. I didn't want to be in the business. I just wanted a fair return.
So we structured it a different way.
We drafted a new lease. His base rent went from $2,500 to $4,000 per month. That extra $1,500 baked in both the loan repayment and a profit component.
On paper, it's all treated as rent. Clean. Simple.
We also signed a promissory note on the side. No collateral. No liens. Just an agreement between two people who trust each other.
To him, I think it felt like a favor.
To me, it was an investment in someone who had already proven himself.
That was over 18 months ago. And since then, the rent has been paid on time every single month. No issues. No reminders. Just like before.
I didn't need a syndication. I didn't need a pro forma. I didn't need a cap rate.
I just needed to pay attention.
Sometimes the best investments don't show up in your inbox. They're already paying rent on time. They're showing up early. They're growing without making noise.
And sometimes, they just need a little help to level up.
Have you ever backed someone just because you believed in them?