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After 60 angel investments and a stint at Oracle, these former tech execs have plans to revamp the venture capital industry

  • Kyle York was sitting pretty after Oracle bought his employer, Dyn, for a reported $600 million-plus in 2016.
  • He turned that financial success into an active hobby as an angel investor, backing about 60 companies, some of which were acquired for big bucks or went public.
  • Oracle shuttered Dyn this summer, not long after York left.
  • York and his Dyn friends looked at their angel investments and decided their next adventure together should be a new kind of venture capital firm with no limited partners, no management fees, and lots of data to make better decisions. 
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Kyle York made a killing when Oracle bought his New Hampshire startup, called Dyn, for a reported $600 million-plus back in 2016. He wasn't a founder at Dyn, but had spent 10 years there as its vice president of sales and marketing, growing it from a tiny startup. After Oracle took over, he stayed on and became a key exec. 

But in the summer of 2019, Dyn was shuttered, amid a period when Oracle went through major restructuring and layoffs.

York had resigned a few months before Oracle closed Dyn, after shepherding his teams through a layoff and restructuring in March. He had enjoyed working at Oracle until the stress of these changes took their toll, he told Business Insider. But it felt time to move on. He wondered what to do next in his life.

The answer was right in front of him. Dyn had become a beacon of success in New Hampshire's tech scene long before it came to Oracle's notice, and its founders and early employees had done well — becoming big angel investors, particularly in and around their hometown. 

York discovered he loved angel investing. Not only did he pour funds into 60 very-early stage companies, but he put his brainpower were his money was and advised them, too. Some of them went on to be wildly successful: Fastly, for example, which just went public. Another baker's dozen of York's portfolio companies were acquired, including the 2018 purchase of Sapho by Citrix for a reported $200 million. 

Read: After selling his company for $6.5 billion and doing 40 angel investments, Ross Mason is joining an unusual quant-like VC firm

His success was rewarding, and not just financially but emotionally, too, he said. 

"While I was building Dyn, I was building this portfolio on the back of a general thesis: the folks building SaaS or cloud computing startups tend to be engineers who can code," he tells us. "But a big gap [for founders] is, how do I bring to it market, build a salesforce, fundraise strategically and thoughtfully?" 

As a marketing and operations guy, he had that expertise. And he offered it to founders at the earliest stages, rather than after they have a product built and then had to figure out who would buy it and how to sell it.

So when York stepped out of Oracle he decided to hang his shingle as, a VC firm, with cofounders Joe Raczka and Adam Coughlin, who were his friends since childhood through the Dyn and Oracle days. 

Not a traditional VC

But he doesn't want to be a traditional VC.  York and company are neither raising a fund nor taking management fees.

York loved running a company and selling products, so his venture firm will do so as well. He's creating a market research analysis platform to provide founders with data, market intelligence, go-to-market insights, research and analysis tools.

And he's spearheading a syndicate of angel investors, to help angels and startups find each other.

"We have the largest SaaS-only syndicate on AngelList, with about 1,000 angels who back every deal we do," he says. This allows founders to skip a family-and-friend round and raise their first $250,000 to $500,000 from experienced angels.

And York has put his own skin in his game. "I'm 100% funding the operating business that's running the syndicates and building the products," he said.

York has become one of a growing number of venture investors that want to upend the traditional way of supporting entrepreneurs by supplying them with data —not just with capital, advice and introductions.

Another is SignalFire, which recently hired MuleSoft founder Ross Mason as a partner after Mason sold his company to Salesforce for $6.5 billion.