Lessons From Doing it All Yourself – And Then Not



In this episode of The Hidden Upside, Chris Shebib interviews Andrew Hines about his journey through real estate investing and entrepreneurship. Andrew talks about some of the forcing factors around scaling and shares information about his current focus on three main businesses: townhouse development, a glamping campground, and media and podcasting.

Andrew talks about his journey from teaching entrepreneurship at Ivey Business School to becoming a mortgage broker and real estate investor. He shares how he got into renovating student rentals and how it was lucrative for him. He then talks about how he pivoted into running his own construction company and developing townhouses and single-family homes.

In his first real estate investment endeavour, Andrew learned the importance of not trusting people blindly and of having systems in place to prevent small mistakes from snowballing into larger problems. He also learned the value of keeping an eye on his investments, whether they be local or remote.

In the interview, Andrew discusses his experience working as a contractor. He talks about how most of his work was simply making calls to the next person on the list. He also talks about how, when someone didn’t work out, he would just call the next person. He notes that he made some great contacts on his first project that have followed him through to today.

Andrew’s present investing focus is specific to Florida new construction homes as well as hospitality stays in Ontario Canada. Andrew has international investing experience dating back to 2012.

An advocate of the BRRRR model of investing, Andrew owns his own construction company and has built dozens of new construction units and houses. He also regularly speaks on topics of economics, development, student rental investing, private lending/borrowing and financing strategies.

Instagram @theandrewhines
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Other episodes you’ll enjoy:
Pivoting for the Times and Getting Creative

Having the Courage to Leave It Behind

Down on the Farm: Rural Investing and Diversifying

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