These entrepreneurs built and sold a tech firm. Now they run VC firm Parkway to fund other startups.

Parkway Venture Capital team from left to right: Analyst Angel Munoz, Chief Operating Officer Brian Hoyt, Partner Robert Bibow, founder/Managing Partner Gregg Hill, Partner Keshia Woods and founder/Managing Partner Jesse Coors-Blankenship

By Alex Soderstrom - OBJ Staff Writer & Orlando Inno Reporter

January 31, 2023, 10:16am EST

More than a decade before they founded Winter Park-based Parkway Venture Capital LLC, Jesse Coors-Blankenship and Gregg Hill met as students at the University of Southern California.

Navigating Los Angeles, the two friends spent a lot of time together in a car. That spawned an adage Coors-Blankenship and Hill still use to decide who they want to work alongside and which entrepreneurs they want to back.

“We try to keep that ethos in our company: Who do you want to spend your time with in the car, so to speak,” Coors-Blankenship told Orlando Inno.

Coors-Blankenship and Hill — founder and CEO of Winter Park-based developer Hill Gray Seven LLC – obviously don’t mind spending time together in a car, office or elsewhere.

Post-graduation, the two joined forces after Coors-Blankenship founded generative design startup Frustum Inc. in 2014. Hill’s H&S Capital invested in Frustum, and the two exited the company when it was bought by Boston-based software firm PTC Inc. (Nasdaq: PTC) for $70 million in 2018.

After that exit, Coors-Blankenship and Hill in 2019 started Parkway, a venture capital firm based in Winter Park and New York City that invests in companies making innovative use of artificial intelligence and simulation technologies. Parkway currently is investing from its $60 million second fund into deals ranging from early-stage seed rounds to larger growth equity rounds.

However, Parkway this year will focus more of its dollars on early-stage investments, Partner Keshia Woods told Orlando Inno. Seed stage startup deals are considered to be more insulated from the public market volatility expected in 2023, according to PitchBook Data Inc.

Here’s more from Coors-Blankenship and Hill — Parkway founders and managing partners — on the company’s approach to startup investing and their thoughts on the local startup community.

How did Parkway Venture Capital get started?

Hill: The Frustum exit was one of the first exits in its space. It was quite historical because 20% of the world’s products are designed with the software, because it’s integrated with PCT and Siemens. We were planning Parkway as the exit was happening. We didn’t wait a single second because the momentum was there. The reason we got portfolio companyTestFit, one of the hottest companies, was because the acquisition announcement came, and TestFit reached out after the exit and told us, "We’re doing something similar to your company but for architects and developers." We met them, and we were the first investors. That’s how we started Parkway, that big win together.

What differentiates Parkway Venture Capital from other venture firms?

Coors-Blankenship: We found companies ourselves. We’ve gone through the whole process of building and selling a company. When we work with companies, Gregg and I and the whole team take that approach. That’s how we compete in a VC market that’s pretty saturated. That thinking allows us to get into deals that even the Sequoias can’t get into. A lot of entrepreneurs are wary of some of the big corporate venture firms.

What does Parkway Venture Capital look for in a potential portfolio company?

Coors-Blankenship: We are looking to have long-term relationships with management teams. We’re looking to have people at portfolio companies we want to work with for a long time. There’s a lot that goes into that: innovation, business management, the grit factor — are they going to get scared when things get tough — friendliness and a collaborative nature.

Has Parkway Venture Capital invested in Central Florida companies?

Coors-Blankenship: We haven’t invested in a local company, but it’s a priority of ours. We’re not really going south that much because the type of thing we’d invest in is in Central Florida. That’s where deep tech will be. We don’t invest in crypto or highly speculative things popular down south. I think the opportunity is there, and we haven’t found the perfect match.

How would you describe the good and the bad of Central Florida’s startup ecosystem?

Hill: There’s a lot of talent in Florida and Central Florida. Two of Frustum’s best, early employees came from Florida. You need more startups and more capital to support these companies.