Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Some people wait for opportunity. Others create it. In this episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross talk with Shawn Good, attorney, investor, and founder of the Palatine Real Estate Meetup, about how he turned a single bad condo purchase into a thriving portfolio of off-market deals across Chicagoland.
From flipping hoarder houses and partnering with family to scaling direct mail campaigns that now generate consistent monthly deals, Shawn’s story is a blueprint for combining hustle, strategy, and smart networking. He shares how his background as an attorney gives him an edge in closing complex transactions, how he’s turned lessons from Collective Genius into an entire marketing machine, and how he balances risk while growing both his law firm and real estate portfolio.
Mark and Tom dive deep into Shawn’s evolution from frustrated condo owner to full-time investor and off-market deal creator. Starting in Buffalo Grove with a disastrous HOA experience, Shawn explains how that early setback shaped his long-term approach to buying properties, managing risk, and spotting hidden value.
He discusses his first multifamily purchase at age 27, a distressed 8-unit property financed through persistence and networking, and how mentorship from veteran investors like John Casmon guided his growth. Today, Shawn runs a dual-track career: managing a growing law practice with his father while flipping, wholesaling, and holding properties across Illinois.
Listeners get an inside look at how Shawn spends $7,000 per month on direct mail, targets probate and foreclosure leads, and closes deals in as little as seven days. His story blends calculated risk-taking, relationship-building, and long-term discipline, showing exactly how local investors can thrive in a competitive off-market world.
Questions We Answer in This Episode
Q: How did Shawn get started in real estate?
A: In his early 20s, Shawn followed his dad’s friend, a frugal investor who lived off rental income. Inspired by his lifestyle, Shawn bought his first condo in Palatine in 2013. It quickly turned into a nightmare, the HOA collapsed, the developer went to prison, and he was forced to sell during a deconversion. But the experience planted the seed for his investing career.
Q: What was his first big multifamily deal?
A: An 8-unit building in Prairie View near Buffalo Grove. At 27, with limited cash and no experience, Shawn secured a $700,000 loan from Wintrust through networking at local business events. Despite skepticism, even from his dad, it became his first successful rehab and sale.
Q: How did meetups shape his career?
A: Meetups were everything. After discovering BiggerPockets, Shawn attended the Chicago Multifamily Club, where he connected with John Casmon. That mentorship helped him understand financing, construction draws, and deal analysis, skills that guided his next purchases.
Q: What is his investment strategy today?
A: Shawn focuses on off-market deals through direct mail campaigns targeting probate and foreclosure properties. He combines legal expertise with aggressive marketing to identify distressed owners who need fast, reliable closings.
Q: What are his monthly marketing numbers?
A: He spends around $7,000 monthly, sending roughly 6,000–6,500 high-quality mailers. The goal: one to two off-market deals per month, typically flipped or “wholetaled” (cleaned up and listed on MLS).
Q: How fast can he close deals?
A: His fastest was seven days, start to finish. Being an attorney allows him to manage title, payoff demands, and court paperwork faster than most investors.
Q: What lessons has he learned from the field?
A: Off-market success takes consistency and patience. Sellers often contact him after receiving multiple mailers over time, not just one. Relationships, transparency, and persistence build credibility.
Q: What’s the biggest challenge in this business?
A: Cash flow and risk. Marketing requires heavy upfront spending before returns show up months later. And even profitable deals can lose money due to holding costs, unexpected repairs, or inspection issues.
Q: How does he decide between flipping and holding?
A: Each year, Shawn aims to keep at least one multifamily property for long-term wealth while using flips and wholetales to fund marketing and operations.
Q: What’s next for him?
A: Growth through systems. Shawn plans to expand his off-market team, hire additional legal staff, and acquire 1–2 new multifamily properties each year while scaling consistent direct-mail campaigns.
Show Notes
00:00 Intro – The importance of suburban meetups and networking
01:04 Housing Provider Tip – Don’t forget the lease requirement for “clear to close”
02:39 Guest intro – Attorney and investor Shawn Good joins the show
03:00 Early condo investment disaster and learning experience
04:10 The deconversion process from a seller’s perspective
06:00 Transitioning into law and real estate simultaneously
07:20 First big multifamily: an 8-unit building in Buffalo Grove
08:25 Networking his way to a $700,000 loan
09:25 Learning from BiggerPockets and Chicago Multifamily Club
10:30 How mentorship shaped his confidence and structure
12:10 House hacking a four-flat in Norwood Park and long-term holding
14:00 Expanding into Skokie and Fox Lake with new acquisitions
15:30 How being an attorney helps him close deals faster
17:00 Family partnerships, the pros and pitfalls
18:45 Lessons learned from doing the heavy lifting in partnerships
20:00 Why sewer line inspections are non-negotiable
22:00 Launching his direct-mail marketing operation
23:10 Spending $7,000/month to generate consistent leads
24:30 Handling probate and foreclosure sellers
26:00 Lessons from early mistakes and lost deals
27:20 Managing expectations: off-market isn’t easy money
29:00 Balancing law, real estate, and marketing
32:00 Scaling through teamwork and hiring
33:40 Deciding between flips, wholetales, and holds
35:00 The reality of slim margins in flipping
36:30 Why “luck favors consistency” in off-market investing
38:30 Closing deals in seven days or less
40:00 Five-year plan – sustainable growth, one property at a time
41:30 Lessons from the Collective Genius mastermind
43:30 Wild stories – hoarder houses and extreme cleanouts
45:20 What hoarder homes teach you about hidden value
48:00 Competitive advantages of being a lawyer-investor
49:00 Advice for new Chicago investors
50:20 Recommended book – The Charisma Myth by Olivia Fox-Cabane
51:00 Shoutouts to Dorian from Alpha Adjusting
53:30 Where to find Shawn – monthly Palatine Meetup at Lamplighter’s
Takeaways for Chicago Property Managers and Landlords
Meetups create opportunity. Every connection compounds into new deals.
Consistency wins in off-market marketing. Direct mail works only if you commit long-term.
Legal knowledge is leverage. Understanding title, probate, and foreclosure timelines saves time and stress.
Partnerships require structure. Separate roles, clear agreements, and trust.
Hoarder homes can be gold mines. Beneath the clutter lies significant upside.
Time > Money. Building steady systems beats chasing quick profits.
Risk is real. Not every deal wins, but each one teaches something valuable.
Guest Information
Guest Name: Shawn Good
Guest Company: The Good Law Group
Guest Link: thegoodlawgroup.com
Meetup: First Wednesday of every month – Lamplighter’s, Downtown Palatine
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
