Hire Fast, Fire Faster: Why 10 Hires Get You 1 Rockstar
Most small real estate operators treat a bad hire as a failure. Mike DeHaan and Dan Austin treat it as tuition. In this episode they break down why you may cycle through ten people to find one rockstar, why the first person in a new role teaches you what the role actually is, and how to tell whether a mistake is the employee's fault or your system's. Mike also shares what rebuilding after a wildfire taught him about insurance policies and public adjusters.
Why does it take ten hires to find one rockstar?
Dan's answer to "how do you find great people" is blunt: you go find them, and along the way you hire some bad ones. He and Mike have had multiple employees let go or quit because they didn't fit. His rough math is that if you're intentional about interviewing and filtering, bringing in ten people and getting one rockstar is probably a realistic ratio.
The cost isn't mainly money, Dan says, it's the time you spend building up someone who was never going to work out. That's where "fire faster" comes in. You can only interview a person so much. Dan's view is that your gut tells you inside the first two weeks whether someone is going to be great, and anything after that is you convincing yourself you can train them to a level they won't naturally reach.
Mike adds a distinction worth keeping. Not everyone who isn't an instant A-player should be cut. Dan says some of the people they kept weren't obvious standouts on day one but were good people they could grow into a role over time, just probably not into the top sales seat or a COO role.
- Hire fast, fire faster, but expect most hires won't be the rockstar
- Judge fit early instead of spending months training personality
- Separate "not an A-player in this seat" from "not a good employee"
What can a bad hire teach you about the role?
Mike pushes back on the idea that failed hires are wasted time. He compares it to the driving range: if you can't hit the ball well, going and getting reps isn't a waste, it's the only way you improve. Hiring and training work the same way, and you will do both poorly at first.
He says that in their lending business, almost every role is on its second or third iteration. With each one, the first hire showed them what they didn't want so they could hire the person they actually needed. That matters most when the role is new to the company, because you don't yet know what good looks like. The resume reads well, the interview goes well, and a week in your gut says something's off.
Dan's take is that standard job titles are only a starting point. In lending there are boxes labeled processor, underwriter and loan officer, but you still have to build the role around how your company actually operates and the experience you want borrowers to have.
Is it the employee's fault or the system's?
Both hosts land in the same place: when a mistake creates real exposure, it's almost always a process gap, not a staffing problem. Mike says the only issues that were a genuine threat to the business came from something in the system that wasn't totally clear. Dan's line is that you can't be upset at an employee when the process was never vetted out.
Dan is candid that handing off high-consequence work is uncomfortable. In lending, the employee has no stake in a buyback; the owners have their net worth on the line. But the ceiling is simple math. Only so many files can pass through two people, and if you won't go above that, that's the size of your business. The alternative is letting the team run the system you built and hoping you built it well enough to catch errors.
They also push back on micromanaging remote staff. Mike describes owners who screen-track a virtual assistant, see fewer hours than they expected, and panic, without asking whether they even had a full week of work to hand over. Dan's framing: you budgeted for the role, so if the person finishes faster, add work as their performance earns it. He also warns new remote hires they'll be bored at first while you train them. Mike notes the talent pool has changed since they started hiring overseas around 2020, when applicants often had scattered freelance work; now he sees candidates from the Philippines applying on LinkedIn with years of experience at a single company.
What did the wildfire teach Mike about insurance policies?
Mike says losing his house changed how he reads policies. His coverage was set at 125% of the home's value, and his personal property coverage paid replacement cost at current market value rather than depreciating older items down to nothing. He estimates that structure is worth close to $500,000 more in potential payout than some policies he's seen, at a difference of less than $200 a month. His conclusion: if you make real money, pay the extra.
He also worked with a public adjuster named David. Mike notes public adjusters are compensated based on what they recover, so their incentive points toward a larger claim, while the insurance company's job is to pay as little as possible. Dan says that isn't villainy, it's just the business. Mike says David knew which code requirements applied and how mitigation crews needed to pack, clean and demo, and that he wouldn't have known to ask for items like landscaping coverage, which he learned could be worth as much as $60,000.
Speed mattered too. The first mitigation company ghosted him, so Mike told every other company he was completely flexible and could meet on short notice. Eight of them came to the house over two days.
- Know whether your personal property coverage is replacement cost or depreciated value
- Ask what's covered beyond the structure; Mike says they won't offer what you don't request
- Local relationships help: Mike's bank manager sorted out depositing $3,000 in smoke-damaged cash that survived the fire
The full episode has more on Mike's rebuild timeline, what survived the fire, and how Dan onboards remote staff. Listen to EP 505 of Collecting Keys.
Frequently asked questions
How quickly do Mike and Dan decide a new hire isn't working?
Dan says your gut tells you within the first two weeks whether someone is going to be great. Anything after that is usually you talking yourself into training them up.
Are failed hires a waste of money?
Mike argues they're reps. He says almost every role in their lending business is on its second or third iteration, and the first hire taught them what the role actually needed.
Why did Mike hire a public adjuster after the wildfire?
He says the adjuster knew the code requirements and how mitigation work needed to be scoped. He also flagged coverage Mike didn't know to ask for.
Scaling a Real Estate BusinessTaxes, Legal & Insurance
Educational content from the Collecting Keys podcast. Not financial, legal or tax advice.