How Steve Khoshabe Built Speedwagon Capital Partners on Unseen Opportunities

Real estate, in Steve Khoshabe’s view, is about the discipline of observation. As the CEO and founder of Speedwagon Capital Partners, Khoshabe has spent nearly two decades affirming the belief that the most valuable opportunities often appear disguised as complications, overlooked sites, distressed situations, or assets that others may dismiss too quickly.

Khoshabe traces the origin of the firm back to the 2008 financial crisis, where uncertainty and inaction were prevalent. “My partner and I had sold a mortgage business, and we were trying to figure out what’s next,” he says. “At the time, the real estate sector was collapsing, but to us, it presented itself as a viable opportunity to start buying.”

Navigating an unfamiliar territory, he acknowledges not being aware of the terminologies necessary to sustain in the industry. “We were told that we needed to start a fund to purchase real estate, but 18 years ago, we didn’t even know what starting a fund truly meant,” he says.

Between 2008 and 2011, Khoshabe notes that Speedwagon was incredibly active, allowing them to acquire high-profile properties at a time when real estate investing was sparse. One of those investments, 400 North LaSalle, now houses their Chicago office. These purchases helped them establish credibility. “Not only did these investments prove to be lucrative, but we also got a lot of attention in the market. So that was memorable,” he says.

From the outset, the firm chose unconventional sourcing methods. “Of all the real estate deals we’ve completed over the years, nearly all of them were sourced off-market,” he says. In his view, purchasing from the market is similar to walking into a store and paying the price on a tag. “Anyone can do that, there’s no art in that,” he adds.

The art, for Speedwagon, lies in asking questions that may often be overlooked. The firm reviews a plethora of real estate opportunities each month, examines only a small fraction closely, and may close on just one. The firm champions this selectivity and exclusivity as integral requirements. “You have to be incredibly patient. It really is all about maintaining your discipline,” Khoshabe explains.

That patience is reinforced by the fact that Speedwagon invests significant personal capital into every transaction. “If we’re writing a check ourselves, we have to really love the deal,” he says. Each underwriting process begins with a critical question: What would have to happen for this to lose money? He focuses on identifying and eliminating the ways a deal can fail, operating on the belief that if the downside is controlled, the upside will take care of itself.

Some recent notable examples Khoshabe highlights are the purchase of an abandoned steel mill in northwest Indiana and the conversion of a landfill to a truck parking facility. Rather than seeing an obsolete site, Speedwagon saw an answer to a growing national infrastructure problem: the truck parking shortage.

Across the United States, freight movement has outpaced the infrastructure designed to support it. Over 2.2 million parking events, including 300,000 long-duration stops, occur annually on the US highway ramps. This is further exacerbated by the fact that for every 11 trucks on the road, there’s only one available parking space. Khoshabe further observes that zoning constraints and land scarcity near highways can make new development difficult, forcing drivers into unsafe parking situations.

Speedwagon converted the landfill into a useful space for truck drivers, with fuel services and amenities. Additional locations are in development. “At first, it was just an acquisition, but later, our mission became to solve this logistics bottleneck,” he says.

According to the company, Speedwagon has provided liquidity to other operators during challenging periods over the years, transactions made possible by a network built through constant communication. Khoshabe likens the process to farming. “We spread seeds every day by talking to people. We don’t know when the harvest comes, but we know it will.”

The company’s portfolio validates that belief, spanning all areas of the US. Every out-of-market opportunity shares a common trait. “Something would often appear wrong at first glance,” he shares. “Distressed ownership structures, family disputes over assets, zoning complications, or properties that required imagination to understand. And when it comes to that, people often get scared off. We just dig in a little deeper.”

Real estate today is more competitive than ever, he observes. Capital is abundant, information is widespread, and hindsight makes past decisions seem obvious. What remains rare, Khoshabe emphasizes, is the willingness to do the homework and tolerate long stretches without action.

After 18 years in the industry, Speedwagon Capital Partners continues to grow by searching for the next problem worth solving. For the company, the origin of that next opportunity is intentionally unpredictable. The method, however, remains consistent: patience, discipline, conversation, and the conviction to see value where others hesitate.