Back in 2015, I was new to both Chicago and real estate, but I had big plans. My ambition? To become a real estate developer—not just any developer, but one tackling large-scale projects.
At the time, I was still an outsider to the industry, though I had years of business experience in another field. I also had spent three years deep in study, learning everything from syndication to development and determined to bridge the gap between knowledge and action. I was actively piecing together my strategy, meeting with lenders, architects, and developers, preparing to dive into real estate development.
I had a list of developer idols—the kind of people who weren’t just building homes but shaping skylines with billions in developments.
The Cold Call That Changed Everything!
I started reaching out to the top real estate developers in Chicago, asking for mentorship. Many didn't respond, but then—one call changed everything
Giovanna took my call warmly. She asked me to send an email, promising to personally print it and show it to her boss the next day.
And sure enough—she did
The next day, I received an email that her boss was willing to meet with me the following month! That person was no one but Chicago's iconic developer, Dan McCaffery of McCaffery Inc!
I was stunned. How could someone at his level take time for someone at my stage?
The Meeting That Shifted My Course:
On September 22, 2015, I stepped into Mr. McCaffery's office.
He shook my hand warmly and asked me to call him Dan! and that 30-minute conversation completely redefined my career path for the next 10 years!
My takeaway from that meeting?
Instead of jumping straight into development at the scale I envisioned, I needed to:
✔ Get my real estate license.
✔ Immerse myself in income properties.
✔ Master multifamily and commercial real estate.
✔ Learn property management. AND
✔ BUILD RELATIONSHIPS—EVERYWHERE.
The Long Game:
That meeting led me on a full-circle journey—from getting licensed, to diving into property management, to eventually owning my own real estate firm and then to real estate development
Had I ignored that advice, I might have taken on too much, too soon and faced major setbacks
Lessons for Anyone Starting Fresh:
Don’t be afraid to reach out to people you admire. You’d be surprised who’s willing to help
Follow up relentlessly. High-level people are busy. Persistence isn’t annoying—it’s a sign of tenacity
Be ready to prove yourself. Sometimes, the wait or the multiple follow-ups are a test of your commitment
Show gratitude—and ask how you can give back. Many mentors don’t expect financial returns, but they take pride in seeing you succeed.
Use these meetings as fuel. Let them motivate you internally and expand your network externally
Have you ever had a meeting that changed your career trajectory? Who gave you that pivotal piece of advice?
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