May 17, 2022


Skillful Business Crafters

How becoming a venture capitalist helped this Seattle startup vet turn his life around

Kirby Winfield and his daughter, Kate. (Photo courtesy of Winfield)

When it comes to startups, Kirby Winfield has seen the highs, and he’s seen the lows.

The longtime Seattleite spent nearly 20 years in various leadership positions at four companies — two that went public (Go2Net, Marchex), and two that were acquired (AdXpose, Dwellable).

The exits were worth celebrating. But going through the startup ringer took a toll on Winfield’s life. He was overweight and had prediabetes. He never saw his family.

“The whole thing was an absolute mess,” Winfield said.

His antidote? Jumping into the venture capital world.

Winfield is the founding general partner of, a Seattle-based firm that invests in Pacific Northwest tech startups at their earliest stage. Ascend has quietly made more than 40 investments over the past two years.

Winfield’s path to venture capital started after vacation rental startup Dwellable sold to HomeAway for $18 million in 2015. He knew something had to change with his lifestyle.

So he got healthy. And he realized that taking another startup plunge as a founder or early employee wasn’t in the cards.

“I had to take a hard look at myself and really think about what I liked and what I was good at,” he said. “It turned out, what I was pretty good at was picking the right teams and times and markets to bet on.”

The Dwellable leadership team: Nathan Kriege, Adam Doppelt and Kirby Winfield.

That thesis proved itself as Winfield tried his hand at angel investing. Then he made a bigger bet: that there was room for another venture capital firm focused on early-stage startups across the Pacific Northwest.

In 2019 Winfield raised $15 million for Ascend’s first fund. The limited partners include tech execs such as DocuSign founder Court Lorenzini; OfferUp CEO Todd Dunlap; RealSelf founder Tom Seery; AI2 CEO Oren Etzioni; and many others.

Ascend has backed a number of Seattle startups including meat marketplace Crowd Cow, e-commerce software provider Fabric, and real estate marketplace Keepe. It focuses on companies in four sectors: e-commerce, marketplace, software-as-a-service, and AI/ML.

Winfield’s pitch to founders: experience and empathy.

“I made every mistake in the book as a leader that you could make,” Winfield told GeekWire. “When I looked at that body of work, the best use of it was going to be to help founders try to be successful.”

Founders say they appreciate having someone who’s been in their shoes.

“Kirby’s empathy for us as founders results in timely advice on all fronts, and when an introduction is needed Kirby is often the very first person who we turn to,” said Spiral CEO Elena Zhizhimontova.

Bryce Bennett, co-founder and CEO of gig economy startup Solo, called Winfield a “true partner in the ambiguous journey that is founding a venture-backed startup.”

Winfield has used his platform to provide resources for founders, like the “Seattle Startup Toolkit.” He wants Ascend to be a “connective tissue.”

“I saw a lot of founders really struggling to connect with investors,” Winfield said. “That’s not an issue in Silicon Valley.”

Seattle still pales in comparison to the Bay Area and New York City when it comes to local VC dollars available to startups. But there are a number of new early-stage firms such as Ascend, Flying Fish, FUSE, Pioneer Square Labs, Graham & Walker, and others trying to capitalize on a growing ecosystem that has been sizzling as of late with record funding, several new unicorns, and more job openings.

There are also longstanding Seattle-area firms such as Madrona Venture Group, Voyager Capital, and Founders’ Co-op that have raised funds over the past few years.

Still, Winfield appears to have carved out his own niche in the Emerald City.

“We are still in the second inning as an ecosystem,” he said. “If you can start to deploy capital and build a brand in this ecosystem at this stage of its development, you’re going to build a legacy and you’re going to return a lot of money for your limited partners.”

Ascend is currently participating in the latest cohort at Oper8r, a new accelerator program for emerging fund managers.