Cultivating an entrepreneurial culture is done at the ecosystem level, and it just happens to be Cliff Holekamp’s passion.
Holekamp is co-founder and general partner of venture capital firm Cultivation Capital, founded in the Midwest a little more than a decade ago. If the company name gives off a nurturing vibe, it’s intended.
The name “came from us wanting to tend to startups with the same care and attention a farmer would give to their crops,” he said. “It’s a nurturing perspective on investing.”
Cultivation is focused on early-stage life sciences and health tech, agricultural tech and geospatial tech, along with software and IT. In other words, helping startups get access to the money and resources they need to succeed.
“Big corporations think in terms of leveraging assets and resources, but startups have none of those things,” said Holekamp, an entrepreneur himself. “So, by default, your network is fundamental to growth. You have to be able to bring external assets and resources to bear.”
Uprooting to Greenville
It’s why Holekamp says he chose to shift his home base from St. Louis, Missouri, where Cultivation is headquartered, to Greenville.
“I hate to be a cliché, but in 2020 during COVID, the office went remote,” he said. “I later found that as a managing director, the digital transformation made it possible for us to work anywhere. My wife and I asked ourselves if we could go anywhere, where would it be?”
Anywhere they chose had to make sense for their two school-age girls, for their own business needs, and for quality of life.
“At the end of the process, we chose Greenville,” he said. “Plus, I had responsibilities for growing our Southeast presence, which was challenging from St. Louis.”

World-class schools, business acumen, community support
A big factor was Greenville’s selection of schools, specifically Christ Church Episcopal School.
“We didn’t proceed with buying a house and making a move until our kids were accepted to Christ Church,” Holekamp said. “For families with the ability to go wherever they want, having a world-class, independent educational opportunity is an important part of the formula. We wouldn’t have chosen Greenville without it.”
Since then, he’s discovered a network of entrepreneurs who have been supportive and a community that has been welcoming.
“The startup community here is in its nascent stage, but it’s strong,” he said. “It’s filled with good people. They’re well-connected and on a good trajectory.”
Even before the Holekamps arrived, he said many Greenville business leaders connected with him.
“Greenville is serious about business, serious about economic growth,” he said. “It’s a rising-tide community.”
It is also sandwiched between two major economic centers — Atlanta and Charlotte, North Carolina.
“Greenville has the second-best geography in the country after Southern California (in terms of) its proximity to larger business markets,” he said. “That was a factor.”