The Insurance Real Estate Investors Forget Until Something Burns

By Mike DeHaan, Dan Austin, Dylan Koch · September 28, 2026

Nothing makes an investor read their own insurance declarations page like watching another investor's house burn. After Mike DeHaan's fire, Dan Austin and Dylan Koch both pulled their policies out and went line by line. In this episode they walk through what they actually carry, where they found gaps, and why they've gotten suspicious of anyone selling insurance on commission. Then they close with a blunt take on how much of the 2021 real estate guru boom was skill versus timing.

What coverage did the hosts add after the fire?

Dylan says the fire pushed him to actually do the work: he reviewed every policy, bought term life insurance on himself, increased the coverage on his home, and added a scheduled jewelry policy for his wife's pieces. The one thing still on his list is an umbrella policy.

Dan did the same review and came away feeling generally well insured but under insured in a few specific spots. His point was that most operators never look until an event forces them to.

On umbrella coverage, Dan remembers paying roughly $500 to $600 a year for around $5 million when he first bought it. Mike says his $5 million policy now runs about $1,100 a year, or roughly $90 a month. Mike's argument for it is simple: it sits on top of your other policies and protects you up to that limit if something goes wrong and you get sued, including situations that have nothing to do with your rentals, like a car accident.

• Umbrella liability coverage on top of existing policies
• Term life insurance
• Scheduled riders for high-value personal property like jewelry
• Key-person policies between business partners

Why do business partners need insurance on each other?

Mike and Dan took out policies on each other. Dylan shared a story that explains why. A local investor in his market was an equal partner with another investor, and the two had no insurance on each other. The partner died in 2020 from what Dylan described as a COVID complication, and to pay out the widow's share, the surviving investor had to sell the entire portfolio to capture that equity. Dylan says it was millions of dollars and a long ordeal. With a policy in place, he says, the sale never would have been necessary.

Mike's reaction: it undoes everything the two of them built over years. Dan framed the premium as a small operating cost relative to the alternative, and asked the practical question nobody wants to answer out loud — do you actually want to be business partners with your partner's spouse?

Dan also made a point about the paperwork side. Between term life, umbrella, multiple LLCs and trusts for estate planning, everything is intertwined, and your spouse needs to know how it works. Mike's view is that estate planning should be set up with a professional who can oversee how the pieces connect, but Dan pushed back that a professional isn't a substitute for your spouse understanding the plan.

Should you trust a commission-based insurance rep?

Both Dylan and Dan complained about the upsell cycle. Dylan filled out one website for term life and says his Instagram and Facebook feeds have been nonstop life insurance ads ever since. Dan says after he and Mike bought policies, the rep immediately wanted a full review of their financial picture, and when Dan asked to combine two logins, the request turned into another pitch.

Mike says he had a whole life policy for about four and a half years and left partly on principle — he got excellent service while he was being sold, and later his questions went into the void with replies coming weeks later from an assistant. His read is that some firms compensate reps heavily on first-year product sales, which incentivizes selling even if you don't stay.

Dan brought up his father-in-law, who is up against required minimum distributions from his tax-advantaged retirement accounts and is trying to figure out the most efficient way to take the money. Dan says the two people he consulted were both insurance salespeople, and both suggested rolling that retirement money into a prepaid whole life policy that would distribute back to him and pass to his family. A financial planning practice owner Dan and Mike had lunch with told them flatly not to do that. Dylan compared the pitch to the "infinite banking" marketing he saw years ago — a lot of hoops for an outcome he thinks you could get more simply elsewhere.

Mike's rule covers more than insurance: with any commission-based rep, some will shoot you straight, but understand they only get paid when the deal closes. As Dan put it, follow the incentives. Dylan added a separate operational note — he used to spread policies across agents chasing the best price, and now consolidates with one person even at slightly higher cost because he can text one guy and get an answer.

Was 2021 guru success skill or timing?

Mike brought the conversation back to real estate with an uncomfortable point: he thinks nearly every real estate guru you know, himself and Dan included, made a significant portion of their money because they happened to already be buying before and during 2021. Nobody saw it coming and timed the entry. They were already in motion when the boom hit, and it was leveraged returns on top of that. Dylan noted his first property was April 2022, which makes him the exception, though he credits his own portfolio's performance partly to being in a Midwest market that hasn't taken a big correction.

Mike says the tell is that many of those same people now act like they knew, and that a number of them have since lost ground and can't figure out how to make a dollar. Dan's addition: those are the ones who believed they were the reason for their success. Dylan says if you dropped the same influencers into a different market, some would still have done well, just far less spectacularly.

The hosts don't treat luck as an excuse to sit out. Dan's framing is that people with meteoric rises were prepared and had what was needed when the timing arrived. Dylan brought up Malcolm Gladwell's Outliers and the argument that Bill Gates had access most kids didn't. Mike calls it educated luck — you can improve your odds without knowing the outcome. And Dylan's counterpoint to the waiting crowd: imagine sitting in 2008 through 2010 being right about the market and still buying nothing.

The episode is part insurance audit, part macro tangent, and part reality check on the 2021 cohort. Listen to EP 508 for the full conversation, including the hosts' back-and-forth on Treasuries, the yen and liquidity.

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Educational content from the Collecting Keys podcast. Not financial, legal or tax advice.