How Buying a Former Jail Changed the Way I See Business Opportunities

August 5, 2026

Published in:

Global Perspectives

When an entrepreneur purchased an abandoned county jail from a government auction without ever seeing it in person, the project’s success depended not on construction, but on uncovering its history and marketing its potential. This EO Toronto elumni's journey reveals how research, storytelling, and trusted relationships can create extraordinary hidden value.

Asad Jail Cell Interior.jpg — Asad Halai inspects the jail he bought sight unseen. Photo courtesy Asad Halai

I was sitting in Toronto when I bought a jail.

Not visited. Not toured. Bought — sight unseen, off GovDeals.com, a government surplus auction site most people have never heard of because most people are not shopping for a former county jail in Eatonton, Georgia.

It was listed at $110,000 USD. No bids. I called my cousin, Hussain, late one night with a proposition: a partnership, built on nothing but a clear vision to convert the building into a boutique hotel or Airbnb. He said yes immediately. We closed at $115,000 USD— a price that reflected the building's current use, which was none, rather than what it could become.

Buying Blind, Then Doing the Work

Only after the deal closed did I actually go to Eatonton and see what we had bought. The building had two levels: sheriff's quarters and processing on the ground floor, cells above. Bars, masonry, the particular quiet of a building constructed to hold people against their will.

Buying sight unseen from a government auction site is usually a fast way to lose money. It worked here because the real risk wasn't the building's physical condition — county surplus listings tend to be honest about what they are. The risk was whether we could turn a building nobody wanted into a story somebody would pay for.

That work only starts after you own it.

Photo of an historic architectural plan. — Finding the jail's historic architectural plan was key to the project's success. Photo courtesy Asad Halai

Turning History into a Marketing Document

The value we created was almost entirely intellectual. I engaged Denise, my trusted designer, to do the historical research — meticulously tracking down the building's original architectural plans and reconstructing its layout and character. Separately, through LinkedIn of all places, I found Kevin Tomson-Hooper, a local history enthusiast who connected the project to the town's heritage and managed to get us an actual copy of the original jail plans. Those plans were a goldmine: Proof of the building's story, not just its dimensions.

From there we assembled a global team to turn research into a sellable package. My engineer, based in the Philippines, prepared the bill of quantities. My assistant designer, in Ecuador, produced the renderings that let a buyer see the building as what it could become. None of us were ever in the same room. All of us were working off the same set of decades-old blueprints and a shared conviction that this building deserved better than sitting vacant.

We didn't list a former jail. We marketed a "Turn-Key Boutique Hotel Conversion Opportunity — Historic Plans Included." That framing is what attracted a genuinely sophisticated buyer pool instead of the tire-kickers who circle any distressed government property.

Asad Zara Patty Burns.jpg — Asad Halai visits the historic jail with his daughter and business intern, Zara, and Patty Burns, who helped find its eventual buyer. Photo courtesy Asad Halai

The Exit

Patty Burns, whom I had come to trust in the Eatonton area, helped place the property with its eventual buyers: a husband-and-wife company that specialize in boutique hotel conversions in Georgia. The sale closed in 2025 for $315,000 USD— a gross profit of roughly $200,000 USD on a building that had sat with zero bids at $110,000 USD a few years earlier.

Nobody poured a foundation. Nobody hung a door. The profit came entirely from research, narrative, and knowing which buyer would pay for what this building actually was.

How EO Helped Me Think Bigger

I joined EO Toronto in 2018 and stayed until 2023, when my family made the decision to world-school our kids and start traveling. The jail purchase happened in the middle of that membership. I don't think I would have made several of the calls I made — buying a government-auction building sight unseen, trusting a stranger from LinkedIn with the town's original blueprints, assembling a deal team across three continents I'd never met in person — without the confidence my EO Forum gave me.

My Forum, the WolfPack, was critical during this period. Not because anyone in that room had ever bought a jail. Because the habit Forum builds — telling the real version of what happened, not the flattering one — is what empowered me to think clearly about a deal this strange while it was still unfolding, instead of only making sense of it afterward.

That habit followed me into the book. We Bought a Jail is out now on Amazon, and it is built the same way a good Forum share is built: The win sitting right next to what could have gone wrong, not one without the other.

The Lesson

The niche-asset lesson is the one I share most often when people ask about this deal: The buyer for a former jail is never browsing listings for a three-bedroom house. You don't find that buyer with a listing. You find them by doing the research nobody else was willing to do, and by trusting the handful of people — a historian, a stranger on LinkedIn, a broker, a cousin willing to say yes at midnight — who make that research usable.

None of that happens without a network built on more than transactions. EO gave me that first, years before real estate did. EO Forum doesn't teach you how to underwrite a former county jail. It teaches you that the version of the story worth telling is the one with the mess left in — and that the people who will say yes at midnight are worth more than any amount of capital you could raise on your own.

Contributed to EO by Asad Halai, founder of The Property Junkie. Asad was an EO Toronto member from 2018 to 2023 who left to world-school his children through travel. He remains a proud elumni of that chapter.