If you’ve started a company (or written about them), you know the statistics that venture capitalists typically spew. They consider thousands of deals each year, go deeper into hundreds and invest in only a few. 

But a big curiosity in startup is how a VC gets to those decisions. How does he or she see all those deals, get the knowledge to vet them and ultimately have the confidence to put money to work? 
A visit this week by an investor from Washington, D.C. reminded me just how systematic and yet erratic that process can be.
James Keeratisakdawong (top left) made the trip to Durham on the invitation of American Underground Chief Strategist Adam Klein. Though he hasn’t spent much time here, the Core Capital Partners managing partner is well familiar with the region. His fund is an investor in Raleigh startups Pendo and KnowledgeTree, and partners there like enterprise software companies with the Fortune 500 as customers. We have a lot of those.
Keeratisakdawong is the latest in a string of national venture capitalists to visit independent of the annual CED Tech Venture Conference and speak or meet with companies. Next Monday, on invitation from HQ Raleigh, L.A. (and recent Shark Tank) investor Chris Sacca (top right) will sit for a fireside chat with HQ founder Brooks Bell in front of an audience of entrepreneurs. HQ Charlotte brings Brad Feld to Packard Place June 1.
In a news release, Packard Place co-founder Dan Roselli wrote that the increased density of entrepreneurs and growing clout of startups in North Carolina means “we are a more interesting stop for national speakers.”
To me, the greatest impact of these visits is the insight they give local entrepreneurs into the brains of investors with national and increasingly global lenses. 
Keeratisadawong, for example, shared with me his method of scanning and reading up to 1,000 news articles a day to get a feel for the companies, industries and issues making news. He’s an avid RSS feed subscriber and Twitter miner, selecting stories to save in the Pocket app to browse when he has down-time between meetings with entrepreneurs. 
Staying on top of the news, he says, is his way of thinking through questions to ask entrepreneurs about their businesses.
Building his network is also important. Keeratisadawong has worked and invested in the Washington D.C. area since the mid-2000s. He worked for a small fund run by Dan Moore, an early investor in Discovery Communications, investing in a wide variety of startups, from voice recognition to virtual reality to water innovation. Keeratisakdawong attended business school at Babson College and briefly worked for a startup creating a sort of Airbnb for office space before working for the state of Maryland’s investment group.
After a brief stint last year at a family office, he joined Core Capital Partners in January. While D.C. continues to be a major focus, he plans to make regular visits to the Triangle, Pittsburgh and Columbus, Ohio. Those cities have a combination of talent, early stage activity, big corporates and entrepreneurs who understand venture, he says. 
Klein set up a packed day for Keeratisadawong. It started with breakfast with a group of entrepreneurs that fit his fund’s profile. He toured the AU and sat down with me for a brief interview. Lunch was at Mateo with Lizzy Hazeltine of The Startup Factory and Vickie Gibbs, a serial entrepreneur and mentor in the region. He held open office hours for American Underground companies in the afternoon.
Keeratisadawong told me he had no specific companies in mind when he got to town, nor any particular entrepreneurs he wanted to meet.
“We flex to the market,” he says. “It depends on what the market is building. We are always interested in meeting great entrepreneurs.”
When I probed further about the types of businesses he’s intrigued by, he shared that blockchain/ledger technologies are interesting, the Internet of Things, security and “more complex systems” that typically work behind the scenes and enable technologies.
Some of his favorite Core Capital investments are Olo, which powers mobile and online ordering systems for companies like Which Wich and Five Guys; and FreedomPay, a chip security solution for all the new credit cards with chips.
He’s got some more specific criteria for founders though. They must evolve quickly, from venture backable to scalable as the CEO. They have to understand venture, he says. They should hire extraordinary people. Folks who can rally people is important too, he says. 
Then there’s that combination of luck and market timing too. 

Keeratisadawong’s big takeaway on Durham was “very exciting times for the local market.” He loved the vibe of the American Underground and expects to spend more time in the region.
He had some advice for entrepreneurs too.  In an email follow-up, he passed along the following tips:
  • As you make decisions around financing your opportunities, try to do things that keep as many options on the table.
  • Sometimes you can close investors quickly, but know that VC fundraising is typically a process that takes time.
  • Tell a great story.
  • Celebrate the wins (both big and small) and try not to dwell on the losses too long.