Kirby Winfield: Finding Love in the Game [Built in Seattle Ep. #23]
2 min read

Kirby Winfield: Finding Love in the Game [Built in Seattle Ep. #23]

Kirby Winfield, Founding General Partner at Ascend.vc and 3x founder, talks about how he shifted mindset, investing in founders, and loving the game.

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Kirby Winfield is a 3x founder with 3x exits.

But after 20 years of running startups he was unhappy, and unhealthy. Now he's revived his love for the game as a VC.

He doesn't pretend like it's all unicorns and rainbows. He's refreshingly open about his own struggles, mistakes, and lessons and that have shaped how he thinks and works.

Kirby shares his lessons on this episode of The Built in Seattle Podcast.

Episode Highlights

  • How his identity and ego got into an unhealthy state.
  • How he hit reset on his mental and physical health
  • Why founders should be able to ask for help and let their guard down.
  • The power imbalance for founders pitching VCs.
  • What matters after the pre-seed round.
  • How a writing and marketing background has helped Kirby as an investor.
  • The value of being willing to look stupid in public.
  • How he picks companies and teams in the earliest stage.
  • How the challenges & expectations when raising money change between rounds.
  • Why you need vision and selling more widgets is never enough.
  • Why it needs to be "cool" to angel invest in startups to support a hub.
  • The time Kirby got confused with a drug trafficking conspiracy on Twitter.

Kirby Winfield Bio

Kirby Winfield is a seasoned startup operator and investor, and is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B software startups in the Pacific Northwest.

Early in his career, Kirby was a founding team member and operating executive at back-to-back tech IPOs, with Go2Net (GNET) and Marchex (MCHX).

He is also a two-time venture capital-backed CEO, with AdXpose (DFJ, Ignition) acquired by comScore (SCOR), and Dwellable (Maveron, VersionOne) acquired by HomeAway (AWAY).

Kirby has invested in dozens of technology startups, and served as a Board Director of the real estate CRM platform Sharper Agent (sold to LEDR/Z), and the in-store customer experience platform Spectrio (sold to Bertram Capital).

He currently serves as a Board Director at Bean Box, the premier Direct to Consumer gourmet coffee gift and subscription brand, and Keepe, the leading vetted, on-demand contractor network for property managers. Other notable investments include Wrench, Crowd Cow, Dolly, Stackery and Blume.

Kirby has served as Board Chair at Special Olympics of Washington, where he helped bring the 2018 Special Olympics USA Games to Seattle. He is a member of the Board of Trustees of Seattle Preparatory School, Board Member at the University of Washington's Haring Center Capital Campaign, and Board Advisor at the Friendship Circle of Washington. In his free time, Kirby coaches youth sports, and enjoys running, tennis, and traveling with his wife, son and daughter.