The Andrew Hines Real Estate Investing Podcast · Andrew M. Hines

The Ultimate Expert Tips for Young Real Estate Investors with Jack Bernstein

·1 hr 4 min·4 clips

Jack Bernstein says the market has optimism now, but “there’s still pain for the next 6 to 12 to 18 months.”

Andrew Heinz opens by welcoming Jack Bernstein back after a few years away from the show. He frames Bernstein as a driven entrepreneur with a story worth hearing. The conversation looks back at Bernstein's earlier history, including his attempt to become a professional snowboarder. Heinz describes him as someone who has taken a few hits and kept going. That personal arc becomes part of the wider investing discussion. They spend time on the current market and what it means for investors. Heinz says people are starting to think about doing deals again. He also reminds listeners that his cash flow spreadsheet is available on andrew-heinz.com for anyone who wants to run the numbers. Bernstein talks through what he looks for in opportunities. Private lending comes up as a major theme. He explains that there is still juice in real estate, especially for people who can access off-market deals. He compares lending returns with ownership returns. He also talks about lending to other businesses beyond real estate. Restaurants, laundromats, and similar operating businesses all come up. Some of those lending relationships have turned into equity partnerships. He says the conversion terms were attractive enough to make that move worthwhile. Bernstein notes that borrowers are often distressed when they are not going to a bank. That makes lending a way to hedge risk while still leaving room for upside. Heinz asks whether he has always been a one-man operation. Bernstein says he now has a full-time assistant. The assistant handles enough work to make a real difference. Bernstein says that growth has made the business more manageable. Heinz circles back to the idea that there are still deals available in Ontario. Heinz says that belief is part of why he became a multifamily realtor there. The closing stretch focuses on steady growth, active businesses, and staying focused on day-to-day execution. Bernstein says his main attention is on his coaching and realtor businesses. Heinz ends on a friendly note and suggests they should not wait years before recording again. The episode keeps returning to the same practical question: where is the real opportunity now, and how do you protect yourself while you chase it?

As heard by us

A grounded look at market conditions, private lending, and how real deals evolve.

Jack Bernstein's return to Andrew Heinz on episode 283 is a grounded look at market conditions, entrepreneurship, and private lending. The conversation circles through Bernstein's early aim to become a professional snowboarder, then settles into how he evaluates deals, secures…

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Want Jack Bernstein's real estate money talk, moving from private lending to where deals still show up?

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