DirtJockey snags $625k from Bay Area investors, but plans to stay in Upstate

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Greenville entrepreneur Josh Lewis landed in San Francisco in January with an empty appointment book, 200 shot-in-the-dark emails and no return ticket.

Four months later, his company DirtJockey closed its first funding round with $625,000 in early-stage investment, or 25 percent more than the goal amount, he said.

“It was definitely a rough thing to fly out there without a permanent plan,” said Lewis, the company’s CEO and one of The Iron Yard’s first graduates. “After having not much luck here, we decided that if we wanted to raise money, we would have to go to San Francisco.”

But being an unknown in Silicon Valley has its challenges as well, said Lewis, who cofounded the company with COO Jonathan Hairgrove and CTO Adam Hodges. The big break, he said, was finding a lead investor who could both introduce and vouch for the team. Fritz Lanman – a well-known investor in Square and Pinterest, among others – was that advocate.

“It was definitely because of our lead investor giving us connections,” Lewis said. “Being from Greenville, not having a track record of doing a successful startup before, a lot of people are looking for a lead investor’s judgment of us.”

Today, DirtJockey helps heavy equipment dealers manage their inventories, which currently exist almost exclusively on pen and paper. One of their first customers, for example, brought two tubs with several hundred legal pads and notebooks containing every contact and inventoried product, he said.

“Technology has largely skipped over it, and the people in the industry itself aren’t very tech-savvy, so you don’t see them solving it themselves,” he said. Used heavy equipment sales are a multi-billion dollar industry, he said, but it’s one technologists and developers rarely see or understand.

“A lot of them use email marketing or Post-it notes,” said Lewis. “Nobody has really tried to solve the problems that dealers have.”

Part of the fundraising challenge for DirtJockey was explaining the market’s problem, but another part – the riskier part – was admitting they wanted to stay in Greenville, said Lewis. Many investors prefer their companies to relocate to their area.

For Greenville’s investment market, the problem is twofold when it comes to fundraising. Investors need to understand and see the potential for technology startups in order to feel comfortable investing, but the Upstate offers very few examples, said Lewis. This means early-stage investment is hard to come by, he said. Startups that can’t find funding in the Upstate then have to follow their investors, perpetuating the vacuum of successful startup examples.

“We want to be that example, and our investors are OK with that,” Lewis said. Many of DirtJockey’s early customers are local to the region. “Once we explained our reasons for staying in Greenville – the low cost of living, for example – they were OK.”

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