Kirby Winfield judges GeekWire’s Elevator Pitch competition. (GeekWire Photo / Kevin Lisota)

Ascend is ready to help more startups fly.

The Seattle-based pre-seed venture capital firm led by startup veteran Kirby Winfield on Tuesday announced a $25 million second fund.

After two decades in leadership at four startups, Winfield jumped into venture capital in 2019, raising $15 million for Ascend’s initial fund. To date, he’s backed more than 70 startups across the Pacific Northwest.

With the new fund, Ascend is placing a bigger bet on artificial intelligence, joining other venture capital firms pouring cash into the growing sector boosted by recent generative AI advancements.

“AI is having a platform-shift moment. It would be irresponsible not to double down,” said Winfield, who is an investor in residence at the Allen Institute for AI.

Winfield raised a majority of the new fund at the beginning of 2022, just before startup funding dried up amid the tech downturn.

U.S. angel and seed deal value last year still managed to eclipse 2021 levels, though deal activity hit a 10-quarter low in the first quarter of 2023, PitchBook reported.

Winfield predicts that startup fundraising will “get worse before it gets better.”

“I would imagine there’s probably another downward correction in valuations in the next year,” he said.

Startups at their earliest stage are typically more insulated from broader market volatility given their nascency. Many investors like to say that the best companies form during downturns.

More than 1,300 microfunds, or funding vehicles that are $50 million or less, have been raised over the past three years, according to PitchBook. And some multi-stage VCs are investing out of new seed-specific funds.

“We have become even more convicted around investing at pre-seed,” Winfield said. “This is where we want to play. We want to take more ownership at that stage.”

Winfield, a Seattle native and Ascend’s sole general partner, is well known for his eclectic sneaker collection. But it’s his mentorship and empathy that founders routinely praise, along with an active social media presence that’s carved a unique niche in the region’s startup ecosystem. Winfield built that reputation on the back of his startup experience, helping to take Go2Net and Marchex public and selling AdXpose and Dwellable.

Six companies in Ascend’s portfolio have exited: LegUp, Syncfloor, Makara, Dolly, Worksphere, and Battlesnake. Others including Groundlight, Why Labs, Xembly, and Fabric raised subsequent rounds.

“We’ve really found some conviction around our thesis,” Winfield said.

Last year, the firm added startup vet Jen Haller to run operations. “She’s an absolute force multiplier and leverage point for our founders,” Winfield said.

Ascend’s limited partners include current and former tech execs from the Seattle region and beyond.

Winfield expects to invest in around 40 companies from the new fund, which will also target startups building e-commerce infrastructure and B2B software.

Ascend joins a number of other Seattle-area venture firms that have raised new funds in the past few years, including Madrona, Fuse, PSL Ventures, Trilogy Equity Partners, Flying Fish, Founders’ Co-op, Unlock Venture Partners, and Graham & Walker.

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