What I’d Tell My Younger Self: What I’d Do Differently

Yesterday morning, I was scrolling through reader questions and one from Paul caught my eye: 

“If you started all over again, Saul, what would you do differently?”

I sat with that for a minute, made another cup of tea, and thought about how every decision I made seemed right at the time. It’s only now, with distance, that I can see where I stayed too long or moved too slow.

Jeff Bezos has a quote that nails it:

“We are stubborn on vision. We are flexible on details.”

That’s the game. The vision (building value in real estate) never changed. But the details? The strategy, the asset class, the tactics? I should’ve shifted those faster when the market moved.

So here’s what I’d do differently, broken into four moves.

Jump To Commercial Sooner

I spent a decade in housing and brokerage, selling 2,000 homes and renovating hundreds of them. It taught me everything: how to see problems, how to fix them, how to move fast.

But commercial real estate has leverage that housing doesn’t. More complexity, sure, and more moving parts, but way more upside per deal.

Looking back, I could’ve made the move ten years earlier. Would I be further ahead today? Probably.

But here’s the thing: you can’t see it while you’re in it. You only see it looking back.

Pivot Strategies Faster

Between 2009 and 2012, I was selling REOs (bank-owned properties). The model was printing money during the financial collapse cleanup.

But I got stuck. When the market started improving around 2012, I should’ve seen it coming and shifted faster. Instead, I kept riding the REO wave until it dried up.

Wayne Gretzky said it best: “skate to where the puck is going, not where it is.”

I should’ve been more flexible, anticipating the next move instead of optimizing the current one. No business model is permanent. Even Apple and Tesla constantly evolve. The fundamentals stay the same (improve quality, reduce cost), but the execution changes with the market.

Focus on Quality

Early on, I chased quantity: more deals, more transactions, more activity.

But here’s what I learned too late: quality assets require less of your time and attention, and they appreciate more over time.

Don’t get me wrong: value-add deals are still the bread and butter. They deliver fast wins and taught me how to operate. But quality assets compound differently. Even without the quick value-add pop, they grow steadily and demand less mental bandwidth.

Learn Ground-Up Development

This one stings the most.

I spent years fixing problems on existing buildings through value-add and repositioning. It works, but it also gets saturated fast.

Ground-up development is a moat. Once you learn how to build from dirt (efficiently, affordably, and with quality) no one can take that skill from you.

The barrier to entry is high, the competition is thin, and the market doesn’t saturate nearly as fast as value-add does. It’s like an art form. You’re not just fixing, you’re creating.

That’s a competitive advantage that sticks with you forever.

Looking Back

Here’s the honest part: I don’t have an ounce of regret.

Everything happened exactly as it needed to. Every skill I built in housing made me better in commercial, and every pivot taught me something new.

And if you asked me this question ten years from now, my answer would probably be completely different. Every year, you gain new wisdom, and the goalposts keep moving.

Fifteen years ago, I would’ve said, “I wish I built a massive house-flipping operation across the country.” Today, that answer sounds insane. There’s nothing left to fit and flip, because such a big portion of homes already got renovated in the last ten years.

The real lesson isn’t about what I should’ve done. It’s about staying flexible while keeping your vision clear.