Why This Entrepreneur Sold Everything for Bitcoin—and What Happened Next

What we talked about.

Ben, a Canadian real estate broker who built a 29-property student rental portfolio over 17 years, sat down with Sunny Ray to explain why he sold the last of his real estate holdings to go all in on Bitcoin. He traces his journey from discovering Rich Dad Poor Dad at age 14 to falling down the Bitcoin rabbit hole with his father five years ago, a shared obsession that turned into daily calls about sound money. Ben unpacks what real estate taught him about low time preference, patience, and pricing hard assets, and why he believes Bitcoin will become the ultimate unit of account while real estate trends toward zero against it. He discusses his own timing, selling out and buying Bitcoin right before a major drawdown, and why he remains unfazed. The conversation also covers his take on Michael Saylor's strategy, self custody, and node running, plus his current focus, building Industry Day for the Canadian Bitcoin Conference 2026 happening this October.

A real estate mogul explains why he liquidated 29 properties to go all in on Bitcoin.

The questions, and the answers.

Where did you grow up, and what was the version of you before Bitcoin that nobody in this space would recognize?

I grew up in Fredericton, New Brunswick. At 14 I came across Rich Dad Poor Dad and got obsessed with investing and real estate, even learning about fiat money from it. I bought student rental properties in university with a business partner on a handshake, eventually growing to 29 properties and a full construction company. I spent 17 years as a real estate agent before Bitcoin.

What did selling and financing real estate teach you about money, value, and risk that no classroom could?

Real estate taught me low time preference. It's not a get rich quick scheme, cash flow services debt while equity is the real goal. It also taught me to stick to a thesis instead of chasing every new strategy. Refinancing to pull out equity without triggering taxable income taught me how to responsibly recycle capital long term.

Do you think real estate is about to get demonetized by Bitcoin?

I believe Bitcoin will be the new denominator and everything measured against it trends downward over time. High value, productive real estate in prime locations will always have demand, but the speculative Airbnb and flipping model is under serious threat. Overall I see real estate trending toward zero against Bitcoin because Bitcoin has fixed supply and no physical decay risk.

If Michael Saylor were watching right now, what would you tell him given the bear market sentiment against his strategy?

Keep doing what you're doing. Builders build. I look at the balance sheet and don't see him unable to weather this storm. My advice would be to rebuild the USD reserve rather than draw it down for dividends, because right now the market values having a strong cushion more than the pure math justifies. Focus more on sentiment right now.

When did Bitcoin first truly land for you, the moment it actually clicked?

It was setting up a node and doing my first real transaction. I merged some UTXOs and moved value on a weekend outside banking hours, and it settled in ten minutes. Watching it clear the mempool into a confirmed block was a huge aha moment. Doing that with family members, like my uncle who's a banker, still gets me excited every time.

Walk me through how you actually got to the decision to sell your last real estate and go all in on Bitcoin.

It was a slow five year process of comparing the two assets side by side. Bitcoin is globally liquid, verified by every node, and has zero physical decay, though full custody responsibility. I decided at Strategy World 2024 that I wanted to be a global citizen rather than tied down by property. I sold my real estate October 7th and bought Bitcoin October 8th.

What did you get wrong early on, any belief about Bitcoin or money you had to unlearn?

I think there's more I don't know about Bitcoin than I do know. I got into Bitcoin in November 2021, bought near the top, and rode it all the way down through the FTX, Celsius, and Luna crashes. Real estate had already taught me low time preference, so even that drawdown never had me worried.