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This year marks my 25th anniversary in real estate, and it’s given me a chance to reflect on what’s worked, what I’d change, and what advice I’d give to newer agents looking to accelerate their success.

How It All Started

Back in the summer of 2000, I was a full-time teacher running a small deck-cleaning and staining business called Deck ReShine. It was a side hustle that helped me make a little extra money over the summer.

One day, I was power washing a deck for a gentleman who happened to own a real estate company. As we chatted, he looked at me and said,

“Mike, have you ever thought about getting into real estate?”

At the time, I hadn’t — but his words stuck with me.

A few weeks later, I enrolled in a licensing class. By October 2000, I had my real estate license, and shortly after that, I landed my first listing — an $80,000 condo in Glen Ellyn’s Raintree subdivision.

I’ll never forget that first listing. It was small, but it meant everything.


From Decks to Luxury Listings

Fast forward 25 years, and I’ve been fortunate to achieve record-breaking sales in markets like Wheaton, Winfield, Wayne, Naperville, Oak Brook, Barrington Hills, Bloomingdale — and even the highest sale price ever in LaSalle County.

But it didn’t happen overnight.

Success came through trial, error, and a lot of lessons learned the hard way. If I could go back and start over, here’s what I’d do differently — and what you can do right now to shorten your learning curve.


5 Key Lessons from 25 Years in Real Estate

1. Don’t wait to step up your price point.

I waited almost 10 years before pursuing the upper price points — and that was far too long.
If you want to grow faster, start positioning yourself for higher-end clients now. Don’t wait for permission.


2. Invest in your CRM early.

Your database is your business.
Don’t just buy software — use it. Tag your contacts, segment them into A, B, and C groups, and stay consistent with your follow-up.

  • A-list: Top clients and referral partners — touch base often.

  • B-list: Warm leads and connections — nurture them regularly.

  • C-list: Everyone else — stay visible through consistent content.


3. Think like a marketer, not just a REALTORⓇ.

The best marketer will always outperform the best agent.
I live by this philosophy:

“It’s not the market. It’s the marketing.”

Every home is unique — and your marketing should be, too. Learn to tell stories, create visuals, and differentiate yourself from the competition.


4. Invest in yourself.

Early in my career, I worked with coaches like Joe Stumpf and Dean Jackson — and those investments paid off in massive ways.
Conferences, courses, and coaching aren’t expenses — they’re accelerators.

If you want to stay relevant in a rapidly changing market (especially with AI and new tools emerging daily), commit to lifelong learning.


5. Every transaction is different — focus on people, not deals.

After thousands of transactions, one truth stands out: no two are the same.

Behind every sale are people dealing with major life transitions — marriage, divorce, relocation, financial stress, or new beginnings.

When you focus on helping people, not closing deals, real estate becomes a purpose, not just a profession.


Real Estate Fact:

Agents who specialize in listings just 20% above their current average sale price often see their income increase by 35–50% in their first year.


Your Next Step: Step Up Your Price Point

If you’re ready to elevate your business, I’d love to help you.

Join me for my next in-person LUXE Designation Training on November 19th in Schaumburg, Illinois — a full-day event designed to help REALTORSⓇ step into luxury with confidence.

You’ll learn how to:

  • Attract high-end listings

  • Position yourself as the trusted luxury expert in your market

  • Implement proven marketing systems that work in any market

👉 Learn more and register here: LuxuryDesignation.com/Chicago


Here’s to the next 25 years — and to helping more agents step up their price point, dominate their market, and build the business they deserve.

Talk soon — and remember: Prove Them Wrong.
– Michael LaFido

Michael LaFido
Founder & CEO | Luxury Listing Specialist Designation (LUXE)
Michael@MarketingLuxuryGroup.com
LuxuryListingSpecialist.com
LuxurySpecialistGear.com

Click HERE to see where Michael is speaking next or where his next LUXE class will be.