A Canadian Investing in the U.S. with Glen Sutherland

EP366 How We Almost Lost It All — And Closed Anyway with Ian Drewe


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In this episode, Glen sits down with Ian, founder of Avoca Property, for a candid and action-packed conversation about the real behind-the-scenes journey of closing a multifamily deal.
From early missteps in digital marketing and investor engagement, to legal battles, PE fund bait-and-switches, and $200,000 in legal fees — Ian doesn’t hold back on the tough lessons learned.
They talk about:
The challenges of raising capital without a track record
Navigating flaky commitments from family offices and equity partners
Why retail investors ended up being the key to getting the deal over the line
The unexpected downside of expensive mastermind groups
How Avoca Property is now approaching capital raising before bidding on deals
Why working only with people you trust is the ultimate success metric
Glen and Ian also compare notes on their eerily similar journeys — flipping hundreds of single-family homes, co-GPing larger multifamily deals, and learning (sometimes the hard way) how to structure better partnerships and raises for future projects.
If you’re in the trenches of real estate investing, syndication, or capital raising, this one’s for you. Full of wisdom, war stories, and laughs — don’t miss it.
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A Canadian Investing in the U.S. with Glen SutherlandBy Glen Sutherland

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