10 Lessons I Wish I’d Known 23 Years Ago in Real Estate

You want to do well in real estate. So do I. I looked it up last week: I’ve had my real estate license for 23 years. In that time, I’ve had some major blunders (you know my story), and I’ve also had a lot of success. If I could do it over, I would have watched how the wealthy invest. Do they make decisions out of fear? Are they strategic? Where do they put their money?

This isn’t about being greedy or chasing a get-rich-quick plan. It’s about avoiding the pitfalls I’ve seen clients regret later. Here are 10 lessons I wish I’d known then.

Lesson 1: Location, Location, Location

Yes, you’ve heard it. Yes, I’m rolling my eyes too. But many still ignore it. During COVID, some of us were just grateful to get a property—under power lines, next to noise, or in weak school districts. Smart investors are strategic about where they buy.

If you have $650,000 to invest, you choose the best location you can afford—proximity to the ocean, top schools, desirable neighborhoods. A small home in a prime area often outperforms a larger home in a less desirable area, especially when it’s surrounded by higher-end homes that lift its value. Don’t be the nicest house on the block; be the smaller one lifted by the neighborhood.

And for families: living below your means in a better area beats maxing out in a weaker one. You’re working hard to make that mortgage—buy right.

Lesson 2: Buy When Things Are on Sale

In the Great Recession, we panicked, sold everything, and hunkered down. We had equity. We could have stayed. Fear drove our choices. The wealthy expect downturns; they don’t panic—they buy.

In 2008–2009, deals were everywhere. I remember thinking prices would never surpass the 2008 peak—now many markets have doubled or tripled since. You can’t time the market perfectly, but when it feels funky and a great house in a great spot is priced right, it may be time to move.

When COVID hit, I had three listings fall out of escrow overnight. Investors stepped in and bought at a discount. They did very well. Study your market. Act calmly, not frantically.

Lesson 3: Don’t Rush Big Purchases

A lot of pandemic purchases were lemons: wrong location, overspending, deferred maintenance, or hidden road noise no one noticed when streets were empty. Never rush. Investigate thoroughly. The right property will come—if not today, then later.

Lesson 4: Build a Real Network

Successful investors are well-connected. They’re not frantically refreshing Zillow; they have pros bringing them opportunities—especially off-market ones.

Align yourself with top agents who are doing deals. Be (politely) persistent. Show up, follow up, build real relationships. The next great opportunity often goes to the person who has stayed in touch. And yes, we can connect you with vetted agents through our referral network—no obligation.

Lesson 5: Follow the Big Developers

One intimidating (and very successful) investor told me: “I just follow the big guys.” They’ve already spent the money on research and demographics—where schools, jobs, and retail are going. Invest where they invest.

Avoid small, speculative projects chasing quick profit without the fundamentals. Personally, I love Toll Brothers and The New Home Company—strong track records.

This principle even changed my branding. I ditched an unreadable script logo and a problematic orange, and looked to best-in-class brands for timeless color and clarity. Follow what’s proven.

Lesson 6: Don’t Over-Improve

Know what your market supports. Over-upgrading beyond neighborhood norms is a poor return, especially if you chase trends. Tuscan had its moment; farmhouse is fading. Classic and neutral endures and appeals to more buyers down the line.

Think “buy one really good thing” over a pile of trendy, disposable finishes. Quality passes the test of time.

Lesson 7: Think About the Exit

Given a choice between a duplex and a single-family home at similar price, size, and location, most savvy investors choose the single-family. Why? Resale demand. Duplexes sell mostly to investors (who want a discount). Single-family homes attract families willing to pay market value.

Lesson 8: Value Your Time (Use Property Management)

Wealthy investors rarely self-manage. They hire property managers to handle repairs, emergencies, and bookkeeping. If a 6–10% management fee breaks your numbers, you may not be buying the right property.

Lesson 9: Don’t Over-Leverage

Over-leverage creates panic decisions—dropping rent too fast, accepting risky tenants, or selling under pressure. Keep reserves. Give yourself staying power so you can say no to bad deals.

Lesson 10: Foreclosure ≠ Automatic Deal

“Foreclosure” doesn’t guarantee value. Ask why the owner didn’t sell on the open market. Often: bad location or expensive problems (foundation, mold, roof, plumbing). Many flippers lose money by underestimating repairs. Savvy investors look for solid homes in solid areas that appreciate over time—not the bottom of the barrel.

Final Thought

This isn’t about greed. It’s about wisdom. Learn from people doing it right: buy the best location you can, act calmly during downturns, build strong relationships, avoid over-improving and over-leveraging, and always think about your exit.

If this helped, like and drop your questions in the comments—I’ll tackle them in a future video. Thanks for watching.