{"id":188586,"date":"2026-07-14T08:01:00","date_gmt":"2026-07-14T14:01:00","guid":{"rendered":"https:\/\/www.biggerpockets.com\/blog\/?p=188586"},"modified":"2026-07-14T08:01:03","modified_gmt":"2026-07-14T14:01:03","slug":"deal-diary-andy-gil","status":"publish","type":"post","link":"https:\/\/www.biggerpockets.com\/blog\/deal-diary-andy-gil","title":{"rendered":"Deal Diary: How Andy Gill Turned a Mailer Into 30 Units"},"content":{"rendered":"\n\n\n\n\n\n\n\n\n\n
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Category<\/b><\/p>\n<\/th>\n

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Details<\/b><\/p>\n<\/th>\n<\/tr>\n<\/thead>\n

Name<\/span><\/td>\nAndy Gill<\/span><\/td>\n<\/tr>\n
Location<\/span><\/td>\nConnecticut<\/span><\/td>\n<\/tr>\n
Occupation<\/span><\/td>\nGeneral contractor and real estate investor<\/span><\/td>\n<\/tr>\n
Assets<\/span><\/td>\n58 rental units across multiple properties, plus a 30-unit portfolio in phased acquisition<\/span><\/td>\n<\/tr>\n
Investment strategy<\/span><\/td>\nValue-add multifamily, phased management-to-ownership acquisition, private financing<\/span><\/td>\n<\/tr>\n
Financing<\/span><\/td>\nCommercial loans (five-year ARM), seller-held notes, private lending<\/span><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Andy Gill lost his business in the Great Recession and spent years relearning how money actually works. He raised two kids in an 850-square-foot house, drove used cars, and refused to take on debt he didn’t understand, all so he could eventually buy something that would never disappear on him the way his business had.<\/span><\/em> He didn’t buy his first rental until he was 44.\u00a0<\/span><\/em><\/p>\n

Four years later, he owns 58 units and is in the middle of acquiring a 30-unit portfolio using a structure he came up with himself: managing properties he doesn’t yet own until the sellers are ready to hand over the keys.<\/span><\/em>\u00a0<\/span><\/p>\n

Here’s how he built it.<\/span><\/em><\/p>\n

You didn’t start investing until you were 44. What finally clicked?<\/span><\/h2>\n

I had a <\/span>bad<\/span> business experience that <\/span>taught me<\/span> I <\/span>didn’t understand<\/span> finance <\/span>or a<\/span> P&L. I <\/span>had to get smart, and then I<\/span> found a mentor who taught me that if you can’t measure something, you can’t manage it.<\/span> Once I had those skills, I realized owning the asset, not just improving it for someone else, was the actual goal.\u00a0<\/span><\/p>\n

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

You came up with an unusual way to source your most recent deal, a 30-unit portfolio. Walk us through it.<\/span><\/h2>\n

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.\u00a0<\/span><\/p>\n

I designed mailers with a cartoon version of myself in a flannel with a tool belt and a dog, saying something like, \u201cBeing a landlord sucks; you should sell to me.\u201d I sent out about 600 of them and got 100 calls back.\u00a0<\/span><\/p>\n

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.<\/span><\/p>\n

How did you actually structure the deal once he was ready to sell?<\/span><\/h2>\n

We did two contracts. The first was a management agreement so I could take over the properties immediately, <\/span>see<\/span> under the hood, and get comfortable with them before committing real capital. The second was the <\/span>purchase and sale<\/span> agreement.\u00a0<\/span><\/p>\n

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 <\/span>capital gains<\/span><\/a> and <\/span>depreciation<\/span><\/a> recapture on a property he’d owned for a long time.\u00a0<\/span><\/p>\n

We’re about halfway through the transfer now, with the rest planned over the next 12 months.<\/span><\/p>\n

What made this structure work for both sides <\/span>instead of<\/span> a standard sale?<\/span><\/h2>\n

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 <\/span>moving<\/span> 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.\u00a0<\/span><\/p>\n

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.<\/span><\/p>\n

What financing do you rely on now, and what do you look for in a deal before you buy?<\/span><\/h2>\n

Our first deal was a commercial loan with a five-year ARM, and we created a lot of <\/span>equity<\/span><\/a> just by stabilizing the property early on. Once you prove you can execute, people become willing to lend to you privately, and most of our financing now is private.\u00a0<\/span><\/p>\n

On the property side, I want <\/span>cash-on-cash<\/span> return<\/span><\/a> so I get my money back quickly, and I look for markets with around 3% <\/span>organic<\/span> historical <\/span>appreciation<\/span><\/a> so I’m not just parking money somewhere flat.<\/span> I also stay away from anything with knob-and-tube wiring, a bad roof, structural issues, or old sewer laterals, since those are the expensive surprises that show up later if you don’t catch them in inspection.<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"

Category Details Name Andy Gill Location Connecticut Occupation General contractor and real estate investor Assets 58 rental units across multiple properties, plus a 30-unit portfolio in phased acquisition Investment strategy […]<\/p>\n","protected":false},"author":613755,"featured_media":181544,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[4252],"tags":[],"class_list":["post-188586","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-deal-analysis"],"acf":[],"comment_count":0,"_links":{"self":[{"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/posts\/188586","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/users\/613755"}],"replies":[{"embeddable":true,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/comments?post=188586"}],"version-history":[{"count":0,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/posts\/188586\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/media\/181544"}],"wp:attachment":[{"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/media?parent=188586"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/categories?post=188586"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.biggerpockets.com\/blog\/wp-json\/wp\/v2\/tags?post=188586"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}