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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
For our milestone 400th episode, we sat down with a Chicago heavy-hitter whose career spans lending, development, and commercial brokerage. Kevin Rocio doesn’t do small talk — he does numbers, systems, and results. From building union-focused mortgage programs in the ’90s to exiting lending before the 2008 crash, to training brokers on how to properly price two- to four-flats with GRM (not cap rate), Kevin lays out a blueprint every Chicago landlord and investor can use right now.
Chicago is a block-by-block city with unique risk, reward, and regulation. Kevin explains why owner-occupied and investor math diverge on two- to four-units (insurance, exemptions, operating costs), how to price to bring “all the kids to the yard,” and why specialization and follow-up beat being a generalist. We also cover post-COVID deal flow (virtual tours, digital OMs, remote closings), mentorship that actually helps, and the mindset to walk away from bad deals — even when a commission is on the line.
In this episode of the Straight Up Chicago Investor Podcast, you’ll hear how Kevin turned a lending empire into a multifamily practice that serves Chicago landlords, brokers, and investors — and why the right valuation method can mean the difference between 300 days on market…or 90 buyers through the door in two days.
From union pipelines, to GRM vs. cap rate for two-to-four-units, to COVID-era efficiencies that stuck, this one is loaded with takeaways for anyone operating rentals in Chicago.
Whether you’re buying your first three-flat or running a portfolio across neighborhoods, Kevin’s playbook will help you price better, screen smarter, and scale faster.
Questions We Answer in This Episode
Q: How did Kevin build a lending business that served Chicago landlords and union workers?
A: By designing union-specific mortgage programs and becoming a trusted advisor to blue-collar borrowers, which created a durable pipeline of Chicago investors and future landlords.
Q: Why did Kevin walk away from mortgage lending before the 2008 Chicago housing crash?
A: He read the cycle, saw risk piling up, and protected his reputation and clients by exiting — a lesson for landlords about discipline over deal-chasing.
Q: Why are so many Chicago two- to four-unit buildings priced wrong?
A: Most listings rely on CMAs or cap rates. Kevin shows why Gross Rent Multiplier (GRM) is the correct pricing tool for Chicago two-flats, three-flats, and four-flats to attract both investors and owner-occupants.
Q: What’s the real difference between owner-occupied and investor math in Chicago?
A: Taxes (homeowner/senior exemptions), insurance per door, and operating assumptions change valuation. Price off investor-realistic numbers or you’ll repel your target buyers.
Q: How does “price to pull the market in” work for Chicago small multis?
A: List at the GRM that matches area comps to invite maximum demand, then let qualified buyers bid the price up — instead of starting high and chasing the market down.
Q: What should Chicago landlords know about DIY repairs in older housing stock?
A: Small mistakes become big capex. Kevin’s $50 wax-ring “fix” became a $1,500 ceiling repair — a reminder to hire pros for plumbing, masonry, parapets, and life-safety items.
Q: How did COVID permanently streamline multifamily transactions in Chicago?
A: Video tours, virtual OMs, and remote closings stuck. Many investors (even locals) now buy without in-person tours, accelerating underwriting and decision cycles.
Q: What does effective “mentorship” look like for new Chicago investors?
A: Education first (structured courses), then mentors as sounding boards for underwriting, neighborhoods, and deal structure — not generic motivation.
Q: What qualities does a successful Chicago commercial broker/landlord need?
A: Financial literacy, the discipline to say no, specialization (not generalism), and rigorous follow-up — especially on two- to four-unit underwriting.
Q: What’s Kevin’s competitive advantage that Chicago landlords can copy?
A: He doesn’t push deals; he aligns deals. Prioritize fundamentals and fit over forcing a closing — long-run portfolio returns beat short-term wins.
Q: What’s Kevin’s #1 tip for first-time Chicago buyers?
A: Study neighborhoods deeply. Chicago is block-by-block. Know tenant bases, ward politics, and building history. New construction is fine if you’ll live there; investors should favor proven rent rolls.
Show Notes
00:00 Episode 400 milestone, five years of weekly consistency and listener wins
01:24 Why impact matters more than any single deal
02:30 Housing Provider Tip: Update your insurance broker after big capex (roofs, electric, HVAC)
04:18 Introducing Kevin Rocio — lending, development, brokerage, education
05:32 Lending in 1991: rate sheets, unions, and relationship building
07:18 Building union-specific mortgage programs and trusted pipelines
08:07 Exiting lending in early 2008 — reading the cycle and protecting reputation
09:50 Pivot to commercial: Marcus & Millichap (2009) → @properties (2011)
12:58 Alternative credit (pre-subprime), two-step path back to conventional
17:24 Why Kevin avoids small talk and focuses on numbers and service
20:07 2009 playbook: help residential agents add an investment pillar
25:12 Why 2–4 unit listings expire: using CMAs/cap rates instead of GRM
27:21 GRM vs. cap rate for Chicago small multis; matching comps apples-to-apples
33:18 COVID efficiencies that stuck: virtual tours, digital OMs, remote closings
35:06 Scale and referrals: 20–30 deals/yr, millions in residential referrals back out
36:58 Ownership perspective: family portfolio ~2,000 doors (outside IL) informs advice
38:26 First deal in 1984: early “house hack” and compounding over time
41:03 Mentorship that helps: education, then targeted guidance and accountability
49:48 Who shouldn’t be in commercial: if you won’t do the math, don’t do the deal
53:26 What’s next: more of the same — numbers, service, results
53:37 Competitive advantage: don’t chase closings; align the right deals
54:13 First-time Chicago buyer advice: block-by-block nuance, avoid paying “owner” pricing as an investor
55:27 Reading habit stack: Crain’s, Real Deal, Illinois Business Journal
57:01 Chicago resources Kevin recommends (brokers and specialists)
58:02 How to connect with Kevin (Rock Advisory Group IG, LinkedIn)
Takeaways for Chicago Property Managers and Landlords
- Use GRM (not cap rate) to price two- to four-unit buildings; match comps precisely (mechanicals, unit mix, parking).
- Separate owner-occupied from investor underwriting: taxes, exemptions, and insurance per door materially change value.
- Price to invite the whole market, then let demand bid you up — don’t start high and chase the market.
- Post-COVID tools (video tours, remote closings) reduce friction and speed decisions — keep using them.
- DIY on vintage assets is risky; hire pros for plumbing, parapets, lintels, and life-safety.
- Specialize and follow up; being a generalist costs you listings, buyers, and referrals.
- Mentorship works best after you learn the basics; use mentors for underwriting and neighborhood nuance.
- Discipline > deal hunger: walk from bad numbers; reputation compounds faster than commissions.
Guest Name: Kevin Rocio
Guest Company: Rock Advisory Group
Because finding good tenants and property management shouldn’t feel like online dating.
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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
