Deal Diary: How Andy Gill Turned a Mailer Into 30 Units

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You didn’t start investing until you were 44. What finally clicked?

I had a bad business experience that taught me I didn’t understand finance or a P&L. I had to get smart, and then I found a mentor who taught me that if you can’t measure something, you can’t manage it. Once I had those skills, I realized owning the asset, not just improving it for someone else, was the actual goal.

Our first purchase was 12 condos in Connecticut. I brought in a partner to go 50-50, and because they were identical units, I could understand the whole deal at once: how rent would move, what improvements were needed, and how to handle tenants. That gave me the confidence to keep going.

You came up with an unusual way to source your most recent deal, a 30-unit portfolio. Walk us through it.

I had an idea that if I could take over management of properties I didn’t yet own from older landlords who were frustrated, I’d already be in the first position to buy when they were ready to sell.

I designed mailers with a cartoon version of myself in a flannel with a tool belt and a dog, saying something like, “Being a landlord sucks; you should sell to me.” I sent out about 600 of them and got 100 calls back.

One came from a longtime friend I didn’t even know owned apartments. His wife wanted him to travel more. A year later, he was ready to talk.

How did you actually structure the deal once he was ready to sell?

We did two contracts. The first was a management agreement so I could take over the properties immediately, see under the hood, and get comfortable with them before committing real capital. The second was the purchase and sale agreement.

For the first property we transferred, we used a formal appraisal. After that, we agreed on a flat per-unit price instead of paying for eight more appraisals, since some units were bigger or in better areas, and it evened out over the whole portfolio. He held a note on the remainder, which also helped him manage capital gains and depreciation recapture on a property he’d owned for a long time.

We’re about halfway through the transfer now, with the rest planned over the next 12 months.

What made this structure work for both sides instead of a standard sale?

For me, by the time I actually buy each property, I already control it completely. I know the tenants; I know the problems. I’m already collecting the rent, so it’s essentially just moving the deposit from his account to mine. For him, it meant he could stop dealing with tenants and maintenance immediately without giving up the tax position he wanted from an outright sale.

He’s actually so happy with the arrangement that we’re now talking about partnering on new development deals together using an affordable housing designation that lets us bypass some zoning restrictions and increase density.