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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Jake Clopton isn’t just another lender. He’s a Chicago-based real estate financing expert who built a commercial loan empire starting with cold calls during the 2008 financial crisis. In this episode, Jake breaks down how he scaled his business, the outlook on interest rates, and why property management thrives during downturns. From Fed policy to commercial lending networks, he offers real-world insights that every Chicago property manager, investor, and landlord should hear right now.

From cold calling from his apartment to running a nationwide commercial lending and insurance platform, Jake shares what it takes to succeed in today's market. Learn how to build lender relationships, analyze financing in an era of stagflation, and avoid the risks of over-leveraged syndications.

Jake emphasizes the long game. Early in his career, he wasn’t landing million-dollar deals—he was just trying to get one banker to return a phone call. That hustle, consistency, and willingness to build his business one cold call at a time laid the foundation for what would become Clopton Capital. His story is a reminder that every successful business starts with persistent action and a willingness to fail forward.

As the conversation continues, Jake explains how access to capital can swing wildly depending on timing and relationships. A deal that gets rejected in January might get approved in March—not because the terms change, but because a bank’s internal liquidity or lending priorities shift. This dynamic reinforces the importance of working with someone who has deep connections in the lending industry and knows how to find opportunities others miss.

Jake also touches on how personal discipline in business reflects in outcomes. He still cold calls because he believes it keeps his instincts razor sharp. He’s not just the owner delegating tasks—he stays close to the ground, understanding trends in real time, and maintaining the grit that was the foundation that built his business. That principle resonates with real estate operators, especially in uncertain markets like 2024, and currently in 2025.

Questions We Answer in This Episode

Q: Why is property management a counter-cyclical business?
A: Jake and Mark discuss how a down economy benefits property management. When investors are hesitant to sell, they often hold onto properties and hire professionals to manage them, especially when the market is uncertain.

Q: What’s the number one skill Jake attributes to his success?
A: Cold calling. Jake built his business on relentless outreach, making hundreds of calls a day. Even now, he keeps that muscle sharp. For new investors or brokers, he believes nothing beats the power of direct communication.

Q: How does Jake differentiate himself from traditional lenders?
A: While most investors only speak to two or three bankers, Jake speaks to hundreds. His team gets multiple opinions from different people within the same bank, allowing them to uncover deals others miss.

Q: Why do deals get stuck even when properties are performing well?
A: Rising taxes, increased insurance premiums, and interest rate volatility. Many deals were underwritten too aggressively and didn’t leave room for changing conditions.

Q: How can investors take advantage of energy efficiency programs in Chicago?
A: Jake shares how Elevate Energy provided $300K worth of free upgrades to one of his buildings. Understanding local incentives is a hidden advantage in the Chicago market.

Q: What are the biggest lending risks in 2024-2025?
A: Overleveraged multifamily deals with variable-rate loans are struggling, especially when operators lack capital reserves and rent growth slows.

Q: How should new landlords treat their real estate investments?
A: Like a business. Jake emphasizes that real estate isn't passive—it requires systems, communication, and long-term planning.

Q: What is stagflation, and why does it matter?
A: Stagflation is slow growth paired with high inflation. It creates a dilemma for the Fed and uncertainty in interest rate movements—directly affecting deal structures.

Show Notes

00:00 – Fed policy and why rates aren’t easy to predict
02:46 – Housing provider tip: Don’t rush emergency repairs at night
04:22 – Jake’s story: from trading LIBOR to financing real estate
08:09 – Why brokers outperform banks in today’s lending environment
13:00 – The power of cold calling and networking
16:44 – Scaling with partnerships and affiliate networks
22:26 – Understanding short vs. long-term interest rates
29:13 – Construction costs, tariffs, and the impact of uncertainty
34:06 – Syndication risks and the danger of overleverage
40:48 – Insurance markets and national reinsurance effects
44:10 – Chicago's advantages: incentives, neighborhoods, and infrastructure
46:11 – If Jake ran the Fed: his interest rate outlook
47:45 – Competitive advantage: large lender network and experience
48:21 – Advice for new landlords: run your property like a business
49:04 – Book recommendation: Never Split the Difference by Chris Voss
50:06 – Chicago resource: Elevate Energy and utility rebates

Takeaways for Chicago Property Managers and Landlords

Property management tends to grow in slow markets as owners pause selling
Cold calling is still a powerful skill that separates pros from the rest
Lender relationships can be the key to getting a deal across the finish line
Local energy efficiency programs can dramatically cut expenses
Run your real estate like a business—don't expect passive income
Syndications with high leverage are risky in today’s interest rate environment
Insurance premiums are rising across the board—shop every year
Inflation, tariffs, and construction delays should factor into underwriting
Relationships matter more than ever—banks change based on timing
Learn to navigate both traditional and alternative lending sources
Embrace market chaos—opportunity often hides in disruption
Understanding long-term interest rate trends is key to long-term success
Develop repeatable systems—leverage your time and team to scale

Guest Info Name: Jake Clopton
Website: cloptoncapital.com
LinkedIn: Jake Clopton

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,