In any city – large or small – commercial buildings are everywhere. They shape skylines, anchor neighborhoods and house the businesses that define local economies. Together, office towers, retail strips, mixed-use developments and industrial sites make up the physical backbone of commerce.
But behind all those buildings is a financing story, and for many owners and developers, that story is far more complicated than it should be.
“Most commercial property owners have relationships with a dozen or more bankers who could finance a deal,” says Jonathan Dickerson, cofounder and CEO of Gumption. “But it’s really hard to know which lenders actually want to do it – and who can offer the most competitive terms at any given time.”
That disconnect – between borrowers who need capital and lenders whose appetite is constantly shifting – is the problem Gumption was built to solve.
Based in Chattanooga and now in its third year, the company is positioning itself as a connective tissue for commercial real estate finance, blending data, software and human relationships to match deals with the right lenders at the right moment.
A market defined by friction
At first glance, commercial real estate might appear to be a mature, highly structured industry. Large firms broker deals, banks finance projects and developers build. But in practice, the lending landscape is fragmented, relationship-driven and often opaque, says Dickerson.
Banks operate within what Dickerson calls “credit boxes” – internal parameters that determine what types of deals they’re willing to finance at any given time. Those parameters can change frequently based on market conditions, portfolio exposure and broader economic signals.
“If we went out to finance a $1.5 million office building, some banks would be very interested,” Dickerson says. “Others would say, ‘We’re not touching office.’”
For borrowers, that creates a moving target. A lender that was eager to finance a certain type of project six months ago might no longer be interested. Another lender across the country might be aggressively seeking that same deal – but there’s no easy way to know.
The result is inefficiency at scale, Dickerson says. Developers and investors spend significant time pitching deals repeatedly to different banks, often with little visibility into who’s likely to say yes, let alone offer competitive terms.
And in an industry where timing matters, that inefficiency carries costs.
Building better matchmaking
Gumption’s core idea is simple: if borrowers could tell their story once and have it intelligently distributed to the right lenders – those whose credit boxes are open and aligned with the deal – financing would become faster, more efficient and more competitive.
“We want to be the engine behind how commercial properties in our cities get financed,” Dickerson says.
The company operates as a hybrid platform and service. On one side, it builds relationships with commercial real estate investors – typically seasoned operators managing portfolios. On the other, it cultivates a network of lenders, including banks and other capital providers.
When a borrower brings a deal to Gumption, the company evaluates it on two primary levels. First is the asset itself: its cash flow, lease structure, location, risk factors and overall viability as an investment. Second is the sponsor – the individuals or entities behind the deal – and their financial strength, experience and track record.
From there, Gumption uses its data and relationships to match that deal with lenders who are most likely to have an appetite for it at that moment. The goal is not to blast deals to every possible lender, but to deliver highly targeted, pre-vetted opportunities.
“Our promise to lenders is simple: we vet the deals and the sponsors,” Dickerson says. “When we send something their way, we’ve done our homework. It’s a strong opportunity.”
For borrowers, that means fewer pitches and faster responses. For lenders, it means less time sifting through low-quality or mismatched opportunities.
Tech builders to problem solvers
Gumption’s founding team did not begin in commercial real estate brokerage. Dickerson and cofounder Tim Coy came from a product and engineering background, having worked together for roughly a decade building software teams and platforms.
The two previously collaborated at Bellhop, a fast-growing moving and logistics company, where they helped scale operations and technology. They later worked on financial infrastructure in the defined contribution space, building systems that powered 401(k) and 403(b) transactions.
“We had billions of dollars running through our pipeline on a regular basis,” Dickerson says.
Despite that experience, the leap into commercial real estate did not come from within their own careers. It came through a third cofounder: Ward Neely.
Neely, a seasoned developer with about 15 years of experience, had built a reputation for urban revitalization projects, particularly in the Birmingham, Alabama market.
At one point, he had no shortage of bank relationships. But during the COVID-19 pandemic, those relationships evaporated.
Neely was in the middle of a $15 million mixed-use project with a significant hospitality component when market conditions shifted dramatically. Banks that had previously courted his business suddenly lost interest.
“He went from having every bank in town calling him to not getting a single call returned,” Dickerson says.
Ultimately, Neely sold the project to a private equity firm, which quickly refinanced it through a lender he’d never heard of – one that was simply outside his network.
The lesson was stark: access to the right lender at the right time could determine whether a developer retained ownership of a project or was forced to give it up.
That realization became the seed for Gumption.
Validating the idea
Before building anything, the founders set out to determine whether Neely’s experience was an outlier or a systemic issue, conducting roughly 75 interviews with commercial property owners, developers and investment groups.
The feedback was consistent.
“We heard versions of the same complaint over and over,” Dickerson says. “It was, ‘Yeah, we know a lot of lenders, but we’re spending way too much time finding competitive debt to fund our real estate projects.’”
At that point, the founders saw a clear opportunity. If they could gather data on lender behavior and credit appetite, and combine it with a curated network of relationships, they could streamline the process for both sides of the market.
Part of what makes the problem so persistent is the sheer scale and fragmentation of the lending ecosystem.
“About 4,800 banks operate in the United States,” Dickerson says. “That figure grows significantly when credit unions, private debt funds, insurance companies and other lenders are included.”
In total, the number of potential capital sources approaches 10,000.
Large commercial real estate firms – such as those that handle institutional deals – already provide capital markets services, connecting borrowers with lenders. But those firms tend to focus on large transactions and major clients.
“With those firms, the focus tends to move upstream, toward larger and larger loan transactions,” Dickerson says.
Gumption is targeting a different segment: what Dickerson describes as “Main Street commercial real estate,” typically involving loans in the $2 million to $40 million range.
This segment is more fragmented, less efficiently served and more dependent on local and regional banking relationships – making it a natural fit for a data-driven approach.
A hybrid model
While Gumption emphasizes its platform, Dickerson is quick to note that technology alone is not enough in commercial real estate finance.
“We call it a platform because it’s built on relationships with both lenders and borrowers,” he says. “When transactions involve millions of dollars, you want to speak with someone.”
That balance – leveraging technology to improve efficiency without removing the human element – is central to Gumption’s model.
Gumption’s revenue model reflects its focus on outcomes rather than access.
The company does not charge lenders transaction fees. Instead, it operates as an extension of the borrower, earning revenue only when it successfully facilitates financing.
“They only pay us if we deliver a lender with competitive terms on time,” Dickerson says. “If we’re not delivering, we don’t deserve to be paid.”
Early traction and growth
Now entering its third full year, Gumption is still a relatively small company, with a team of about 10 people, including its three cofounders. But the company has begun to demonstrate traction.
One of the most telling indicators, according to Dickerson, is repeat business. Commercial real estate investors who initially approach Gumption with a single financing request are returning with multiple deals.
“We’ve had some groups come back and submit eight financing requests,” he says. “Once we prove we can deliver competitive terms quickly, we become part of how they get deals done.”
Geographically, Gumption’s activity has been concentrated in the Southeast, including Alabama, Georgia, Tennessee, Florida and Texas, with growing activity in other regions.
The company has also worked on projects that are locally recognizable, including financing for the Park Tower redevelopment in downtown Chattanooga – a historic building that has been renovated into a mix of residential, hospitality and commercial uses.
Timing the market
Gumption launched during what Dickerson describes as one of the most challenging periods for commercial real estate in recent memory: the post-COVID environment.
Since then, the market has remained volatile, with shifting interest rates, changing demand patterns and evolving risk perceptions among lenders.
However, there are signs of recovery. One of the indicators Gumption tracks is the volume of loan requests for new development projects, which Dickerson says are up significantly from last year.
Increased development activity is often viewed as a signal of confidence in the broader economy.
“There’s an old adage: you can gauge a city’s health by how many cranes are in the sky,” Dickerson says.
For Gumption, improving market conditions could amplify demand for its services, as more projects move forward and competition among lenders evolves.
Chattanooga-based story
Although Gumption operates nationally, its roots are firmly planted in Chattanooga, where it’s part of a growing ecosystem of startups and investors.
Brickyard, a venture capital firm and accelerator focused on early-stage companies, is the company’s lead investor. Dickerson says being embedded at its East 16th Street headquarters has been a significant advantage.
“Being surrounded by other companies in the trenches – it’s an accelerant,” he says. “You’re around other founders, especially those working with emerging technologies like AI, and that creates opportunities to learn from each other and refine ideas quickly.”
Gumption’s investor base also includes strategic partners from the commercial real estate industry – firms that not only provide capital but also use the platform themselves.
That combination of venture backing and industry alignment has helped the company refine its approach as it grows, Dickerson says.
Looking ahead
For now, Gumption’s expansion strategy is closely tied to its clients.
“We follow our clients’ deal flow,” Dickerson says. “If they’re buying assets in new markets, we go with them. That’s how we build the network.”
As investors pursue opportunities across different regions, the company extends its network of lenders accordingly. While the Southeast remains its strongest base, Gumption is gradually expanding into new markets as deal flow demands it.
Still, the company’s ambitions are broader than geographic growth.
“We’re trying to modernize how capital flows into commercial real estate,” Dickerson says. “This has always been a relationship-driven, manual process. It can be faster, more efficient and a lot more transparent.”
If successful, that shift could reduce friction in a system long defined by personal networks and limited visibility.
“We want to make the whole process faster and more efficient,” he says. “Every building comes down to a financing decision – and we want to make sure it’s made with better information and better alignment.”