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

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

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.