Usually we focus on short-term rental investing, tax strategy, and how high-income professionals can offset W2 income through STRs. Today's different. Michael sits down with his college friend Eli Cohen, who's acquired $600 million in multifamily real estate over 15 years, to talk about something every investor needs to understand: knowing when to walk away.

In 2022, Eli stopped buying. Not because he ran out of capital. Because the returns didn't justify the risk anymore. This conversation is about market timing, discipline, and deal selection principles that apply whether you're buying your first Airbnb or your tenth apartment building.

We break down:

Why Eli stopped buying. The Fed said "we no longer have your back." Eli listened and shut down acquisitions. Groups that kept buying are now facing capital calls and wipeouts.
The controversial REIT take. Public REITs are cheaper than private multifamily deals right now. You get diversification, liquidity, no promote fees, and better debt costs. "Why would anyone pay more for an illiquid private deal?"
When Eli DID buy in 2024. San Francisco off a major REIT, well below pre-COVID pricing. Denver dramatically below seller's cost basis. Both below replacement cost with strong fundamentals.
Michael's deal selection story. "I looked at dozens of STR deals. One came up with crappy iPhone photos. We knew it was different. Made an offer the next day. Strong cashflow and appreciation followed. You need the reps to develop conviction."
The fast food arbitrage. Operating businesses and real estate trade at different multiples. If you own both, you can shift value between them. Eli's developing chicken restaurants across Texas using this strategy.
The power of showing up. Michael drove up with his daughter in a stroller. The sellers were grandparents. They gave her a teddy bear. "That teddy bear is worth a million dollars now."

Whether you're buying short-term rentals, multifamily, or restaurants, the principles are the same. Do the reps so you recognize the right deal. Know when the market doesn't justify the risk. Walk away when it doesn't make sense. Move fast with conviction when you see the right one.

This isn't your typical STR episode, but the lessons on market timing and deal selection apply to any real estate investor.

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