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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Real estate investing rarely follows a straight line.
For many Chicago investors, the first step is not buying a perfectly stabilized multifamily building. Sometimes it starts with handwritten bandit signs, cold calls, awkward seller conversations, small wins, bad deals, hard lessons, and figuring things out one step at a time.
In this episode, Tom Shallcross and Mark Ainley sit down with Mark Skowron to talk about his progression from wholesaling to fix and flips, multifamily ownership, out-of-state investing, and long-term asset management.
Mark started investing around 2010, when there was far less real estate education available online. He built his early business by taking action, testing marketing channels, building buyer relationships, partnering with nonprofits, using virtual assistants, and eventually shifting from wholesaling deals to holding assets.
His story is a strong reminder that momentum matters, but so does staying in your lane, protecting your downside, building the right relationships, and knowing when to simplify your portfolio.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Hardwood floors do not need to be perfect every time you turn a rental. Mark explains that older oak floors in Chicago and the suburbs can still rent well even with some imperfections, and refinishing them every single turnover is often unnecessary.
Q: Who is Mark Skowron?
A: Mark is a Chicago-area real estate investor who started in wholesaling around 2010, later moved into fix and flips, multifamily investing, out-of-state deals, and asset management.
Q: How did Mark first get into real estate?
A: Mark studied finance at DePaul, worked in insurance and financial advising, then reached a point where he wanted more freedom. That led him to start learning about real estate and wholesaling.
Q: What was Mark’s first marketing strategy?
A: His first strategy was bandit signs. He bought 1,000 signs, wrote them by hand, and put them around suburbs like Roselle, Schaumburg, Streamwood, Des Plaines, and Carpentersville.
Q: What happened with Mark’s first deal?
A: His first deal came from a bandit sign in Des Plaines. He met with a seller who needed help, got the property under contract, found a buyer, and worked through the closing even though both sides were new to the process.
Q: How did Mark build confidence as a wholesaler?
A: He shifted from only focusing on sellers to also focusing heavily on buyers. Once he understood what buyers would actually pay, he became more confident making offers to sellers.
Q: What was Mark’s approach to finding buyers?
A: He interviewed buyers and asked about their last two deals. That helped him learn what they really bought, what markets they liked, and how serious they were.
Q: How did Mark scale beyond one marketing channel?
A: He tested multiple lead sources, including bandit signs, relationships with other wholesalers, online lead sources, direct mail, text campaigns, ringless voicemail, and nonprofit relationships.
Q: What mistake did Mark make when he went outside his lane?
A: Mark bought a car wash in South Carolina while living in Illinois and moving to Texas. He thought the numbers made it look like a bargain, but he later realized he was outside his circle of competency and lost time, money, and energy.
Q: What does Mark focus on today?
A: Mark has shifted more toward asset management. After building a portfolio of around 180 units, he has been simplifying down to the assets he wants to keep long term, especially properties that cash flow, turn quickly, and do not demand too much management time.
Show Notes
02:09 Housing provider tip: hardwood floors do not need to be refinished every turnover
03:08 Mark Skowron joins the podcast and shares his DePaul and finance background
05:06 Finding the itch for freedom and getting started in real estate around 2010
07:03 Handwriting 1,000 bandit signs and learning early marketing the hard way
08:56 Mark’s first wholesale deal in Des Plaines from a bandit sign
13:19 Building new lead channels through We Buy Houses websites and joint ventures
15:00 Why Mark shifted his focus from sellers to buyers
18:02 Hiring his first virtual assistant and learning how to delegate
23:42 Building relationships with nonprofits and buying distressed single-family packages
45:28 The South Carolina car wash mistake and the lesson of staying in your lane
Takeaways for Chicago Property Managers and Landlords
Hardwood floors can have vintage charm without being perfect.
Every turnover does not need to become a full renovation.
Early investors should focus on taking action, not waiting for perfect information.
Wholesaling requires seller empathy, buyer relationships, and follow-through.
Knowing your buyers helps you make better offers to sellers.
The best buyer question is simple: “Tell me about your last two deals.”
Multiple marketing channels protect you from relying on one source of leads.
Virtual assistants can help, but only when instructions and expectations are clear.
Out-of-state investing works better when you have trusted people on the ground.
Stay inside your circle of competency unless you have the team, knowledge, and systems to support the risk.
Guest info
Guest Name: Mark Skowron
Guest Company: Festival Properties
Guest Link: https://www.chicagowebuyhouses.com/
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
