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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
There’s a lot of noise out there about what it takes to become a real estate investor. People talk big—“I’m going to own a hundred doors,” “I’m going to be financially free in two years,”—and then get stuck before they even make that first move. This episode is for those who are stuck, stalling, or simply need to see that it’s possible.
Because Alex Diaz? He’s doing the damn thing. At 24 years old, he’s house hacked, wholesaled, flipped, and built a marketing engine from scratch—all without the trust fund, silver spoon, or safety net. He’s figured out how to live cheap, market smart, and stay focused. And the best part? He didn’t wait for permission.
In true Mark Ainley style, we dive deep into how Alex built confidence before he had capital, how Craigslist and cold calls still work in 2025, and how to get better every time you talk to a seller. There’s no fluff here—just a kid from Aurora making it happen by taking swings, failing forward, and showing up with the right mindset.
If you’re a property manager or investor looking to scale with intention—or a housing provider trying to figure out how to get that first deal done—this episode is packed with tactical gems you’ll want to implement today.
Learn how to scale your real estate investing business—even without a deep network or big bankroll—by focusing on mindset, volume, and surrounding yourself with other action-takers.
Questions We Answer in This Episode
Q: What advice do you have for property managers or landlords who receive a cold call or direct mail from wholesalers?
A: Don’t dismiss it immediately. Evaluate the numbers, understand the motivation behind the seller, and see if there’s opportunity. Many great deals come from people willing to hustle for them.
Q: How should Chicago landlords vet a wholesaler before buying a deal from them?
A: Ask questions. Who’s actually on the title? Have they walked the property? What’s their relationship with the seller? A good wholesaler knows the details and brings value—not just an assignment fee.
Q: For someone investing in Aurora or Montgomery, what should they know before getting started?
A: Know the pockets. Even within the same ZIP code, values shift dramatically. East Aurora is not the same as DuPage Aurora. Understand schools, turnover, and demand.
Q: What’s the biggest red flag a property manager or investor should look for in a fix-and-flip deal?
A: Over-rehabbed properties in underperforming markets. If the house looks like it belongs in Lincoln Park but it’s in a C-class suburb, the ROI might not follow.
Q: How does being in the same office as other investors improve your game?
A: It normalizes high performance. One flip a year felt like a big goal… until I was surrounded by guys doing 12 or 20. It resets your baseline.
Q: What property management mistakes should investors avoid when scaling with multiple flips or rentals?
A: Don’t manage everything yourself. Once you scale past 2–3 units or deals, hand off leasing, maintenance, or accounting—or you’ll burn out.
Q: What’s your process for estimating rehab budgets as a newer investor?
A: Always walk with your GC. Start with conservative assumptions—budget $30K minimum unless you know it’s lipstick only. And pad the budget.
Q: How are you structuring private money deals for flips?
A: I use hard money for 90% and bring in private lenders for the rest. They get a cut of the profits, and I get to scale faster without tying up cash.
Q: What makes a suburb like Montgomery attractive to investors and managers?
A: Older homes are turning over, low regulatory hurdles, and value-add potential without the red tape of Chicago licensing.
Q: What tools do you use for cold calling, direct mail, and CRM management?
A: Phone numbers route through a CRM, calls are recorded, and I use volume tactics with direct mail and VAs. Follow-up is where deals get done.
Show Notes
00:00 Surrounding yourself with the right people changes everything
01:31 How early exposure to real estate sparked the journey
06:55 Why procrastination—not money—held him back
10:29 The first house hack: finding it on Craigslist and following up for 3 years
14:30 Discovering wholesaling through necessity
16:10 Scaling with direct mail and Egypt-based VAs
21:29 Recording and reviewing calls to improve sales skills
26:38 Partnering with a GC to walk flips and control costs
30:24 Why sharing an office with other flippers leveled him up
34:46 Using hard money and private investors to fund deals
Takeaways for Chicago Property Managers and Landlords
- Wholesalers can be a source of deal flow—just vet them well.
- Younger investors are proving that volume + mindset beats capital.
- Suburbs like Montgomery and Aurora are ripe with opportunity.
- Surrounding yourself with the right people can shift your entire belief system.
- Invest in your systems—record your calls, track your leads, and refine your process.
- You don’t need generational wealth to get started—just hustle and discipline.
- Cold calling and direct mail still work when used with volume and consistency.
- Craigslist and sticky notes may be “old school,” but they still generate leads.
- Taking action trumps waiting for the “perfect deal.”
- Review your own sales calls and learn from your mistakes—it’s free education.
- You’ll scale faster when you stop managing every detail and start delegating.
Guest Name: Alex Diaz
Guest Company:
Guest Link:
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
