Which Generation Is Your Brokerage?
Joe De Sena, the founder of Spartan Race, has a two-word warning I can’t shake: complacency kills.
He starts with a line made famous by novelist G. Michael Hopf: “Hard times make strong people.” The rest of the cycle goes like this. Strong people create good times. Good times create soft people. And soft people bring the hard times right back around.
Most of us treat that like a bumper sticker. Joe’s point is that it’s one of the oldest patterns in history.
The Four-Generation Rule
In the 1300s, the historian Ibn Khaldun observed that a family’s greatness rarely lasts more than four generations. The first builds it. The second watches it being built. The third copies the habits without understanding them. The fourth assumes it was always theirs, and loses it.
The muscle that built the thing doesn’t get passed down with the thing.
Now read that again with your brokerage in mind.
The Four Generations of a Brokerage
- The First Generation: The founder. Every agent was recruited by hand. A phone call, a coffee, a follow-up, then another follow-up.
- The Second Generation: The leaders who watched it get built. They still make the calls, mostly, because they remember what happens when you don’t.
- The Third Generation: They run the recruiting script and the onboarding checklist, but they don’t know why either one matters. So the first time it gets inconvenient, it gets skipped.
- The Fourth Generation: They assume agents will keep showing up. The roster feels full, so the recruiting calendar goes quiet. Then a competitor makes an offer, three top producers walk, and there’s nobody on the bench.
Here’s the uncomfortable part. You don’t need four generations to get there. The 2020–2022 market created a lot of fourth-generation brokerages in just a couple of years. Plenty of agents licensed in that market never learned to prospect. Plenty of leaders hit numbers they’d never seen and stopped recruiting.
Good times make soft systems.
Choose to Be the First Generation
Joe’s challenge is personal. He argues we can’t escape the cycle as a society, but each of us decides which generation we are. The same is true for a brokerage.
- Recruit When You Don’t Need To: The best time to build your bench is when the roster is full. If recruiting only happens in a crisis, you’re already behind.
- Have the Hard Conversation: Coach the agent who’s coasting. Challenge the manager who stopped recruiting. Comfortable silence is how retention problems start.
- Teach the Why: Don’t just hand your managers the script. Tell them the story of why every call matters. Pass down the muscle, not just the system. Habit stacking without the why is how the third generation is born.
- Put Obstacles in Front of Your Team on Purpose: A stretch goal. A 90-day recruiting sprint. A new market segment. Joe’s view is that a life without obstacles produces a person who can’t handle one. A brokerage works the same way.
Your agent count, your brand, and your reputation in the market were all built by someone who fought for them. Your job is to remember how it was built and keep building it that way.
Complacency kills. Choose the hill.
Win the day!
A System Will Produce What A System Will Produce, Nothing Less and Nothing More!

Want help applying this in your brokerage? Book a 30-minute conversation with Mark at calendly.com/mjsession.

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