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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Most investors have a “bank guy.” And if that bank guy has come through for you a couple times, it’s easy to assume you’ve solved financing.
But commercial lending doesn’t work like residential, and it doesn’t even work like it did two years ago.
And yes… Asher talks fast. Tom and Mark talk fast. Quinn tries to keep everyone on the road.
In this episode, we sit down with Asher Motew and Quinn Keenan from Essex Capital Markets to talk about what’s actually happening behind the scenes in Chicago’s commercial lending world right now — and why serious borrowers are starting to treat debt like something you actively manage, not something you set once and forget.
We get into the real role of a commercial mortgage broker, how they “expose the market” to find lenders you’d never find on your own, how they negotiate spreads, IO, and prepay terms, and why the borrowers who win in this environment are the ones who lock when the deal works instead of trying to time headlines.
And yes… Asher talks fast. Tom and Mark talk fast. Quinn tries to keep everyone on the road.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Mark’s tip is about cost segregation. If you’re buying single-family or multifamily and you have strong W2 income, cost seg can create meaningful year-one tax savings. They mention Kevin’s calculator on the Build Your Team page and encourage investors to run the numbers before they default to “cash flow only” thinking.
Q: What is Essex Capital Markets and how is it different from Essex Realty Group?
A: Essex Capital Markets is the financing division. They help investors and sponsors get commercial debt and equity (not residential mortgages). That means acquisition loans, construction loans, refis, and recapitalizations across investment commercial real estate.
Q: Why would someone use a debt broker if they already have a relationship bank?
A: Because banks get complacent and lender appetite changes constantly. Essex goes out to 5–15 lenders, negotiates on your behalf, and often ends up either (1) getting better terms elsewhere or (2) using the market to keep your relationship bank honest — sometimes sending you back to your bank with improved terms.
Q: What’s the real value a capital markets team provides?
A: Two things: saving time and saving money. They package the deal at an “institutional” level, understand lender appetites in real time, and create competition. Borrowers don’t have the time to track which banks are hot, who’s tightening LTV, who’s offering IO, or who just paused a neighborhood.
Q: How did Asher and Quinn end up running the platform at 24/25?
A: The principal who originally came over to build the platform decided it wasn’t the right lifestyle fit and went back to the bank. The partners looked at Asher and Quinn and basically said: “You two are running this.” They leaned into it, picked up the phones, and treated it like a mission.
Q: What does “middle market” mean to them? Is it deal size?
A: Not necessarily. They define middle market more as people vs. corporations. They’ll do a $600K loan for a newer investor, and they’ll also work on $20M+ and even $60M+ deals — as long as the client is a sponsor/operator who needs real advisory support.
Q: What’s one of their most memorable “wins” so far?
A: A big one was earning the trust of a major Chicago sponsor (Beal) through relentless follow-up. They ended up getting the sponsor better-than-market terms with a bank he hadn’t used before — proving they could add value even to someone with deep long-term relationships.
Q: What are common reasons deals get harder or fall apart?
A: One theme is sponsors trying to “wait out” rates after the deal already works. They’re blunt about it: if the deal works and hits your goal, pull the trigger. The upside of waiting is small. The downside is huge.
They also bring up real friction points like DSCR stress as loans mature (especially 2021-era low-rate debt rolling into today’s higher rates), and the gap between perception (“Chicago is risky”) vs. reality (strong rent growth in many submarkets).
Q: What do they do differently once a deal is in motion?
A: They don’t pass you off. They act like the deal processor/advisor, stay on the lender daily, reduce sponsor noise, and solve problems before the borrower even has to see the mess. They talk about phase two environmental requirements and appraisal issues as examples of how much work happens behind the scenes.
Q: What should investors understand about lender underwriting on expense ratios?
A: Lenders won’t underwrite your NOI exactly as-is — even if you self-manage well. They’ll apply conservative assumptions. Quinn gives practical underwriting guidelines like:
Vacancy haircut (often 5%)
Taxes often modeled as a percent of EGI
Management (5% typical, potentially less if justified)
Reserves per unit
R&M / janitorial per unit ranges
The big point: lender NOI is its own world, and your financing outcome depends on how that NOI gets built.
Q: What’s next for Essex Capital Markets?
A: Build the foundation: more team, more systems, more credibility — then expand. Their bigger vision is becoming a hub for “Chicago financing,” and eventually helping sponsors with both debt and equity, while staying relationship-driven and not turning into a faceless institutional machine.
Show Notes
00:00 Asher and Quinn intro + “tag team” opening
02:52 Tip of the week: cost segregation and Kevin’s calculator
04:46 Why they got into capital markets and how Essex launched the platform
15:08 Essex Capital Markets 2.0: taking over the business in their mid-20s
21:15 Why borrowers with relationship banks still use a broker
23:44 Market exposure: 5–15 lenders and negotiating on the borrower’s behalf
30:50 Big win story: earning trust with a major sponsor and delivering best terms
46:04 Deal hurdles: rate timing, DSCR stress, perception vs reality
51:01 Step-by-step process once a sponsor signs: dealbook → launch → term sheets → closing
55:23 Appraisal fight story: using internal data, comps, and lender pressure
61:41 Underwriting basics: vacancy, taxes, management, reserves, per-unit expense norms
66:37 Vision: building Chicago’s financing hub + scaling into equity advisory
71:40 Chicago fact: how many two-units are in Chicago? (and the Gemini disclaimer)
Takeaways for Chicago Property Managers and Landlords
Commercial lending is negotiable — it’s not “here’s the rate, take it or leave it.”
Relationship banks can still be good partners, but you should test the market to avoid complacency.
If the deal works at today’s terms, don’t gamble on headlines. Lock the win.
The underwriting NOI lenders use is not the same as your operating NOI — plan for conservative assumptions.
A strong capital advisor isn’t just “shopping rates” — they’re controlling process, timelines, and closing risk.
Guest info
Guest Name: Asher Motew and Quinn Keenan
Guest Company: Essex Capital Markets
Guest Link: https://essexcapitalmarkets.com/
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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
