Building Startup ecosystems, the solo GP life, and lessons from the dotcom bubble with Kirby Winfield of Ascend.Vc

The road of a solo GP is full of highs and lows, and today’s guest Kirby Winfield has been through all of it. After working in the 90s tech and startup scene in Seattle, Kirby went on to found Ascend VC as a solo GP. We talk about his biggest lessons, the best advice he’s gotten, and dig into some of the stories from the trenches as an emerging manager.

About Kirby Winfield:Kirby Winfield 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).

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In this episode we discuss:

02:45 Kirby’s journey into tech06:08 Lessons from the Dot Com bust12:21 Why founders should get to know public market analysts13:45 Kirby’s early experience as an Angel Investor16:07 Early exits as an investor18:11 Finding his first LPs as an emerging manager21:36 Why he viewed his age as a first time manager as an advantage26:37 Building a better startup ecosystem in the Pacific Northwest31:37 Kirby’s original investment thesis and how is has evolved38:19 Managing as a solo GP45:03 Things to avoid that may be red flags to LPs49:10 Navigating the seed and early stage markets in 202252:50 The best career advice he’s gotten as a GP

Fast Favorites

* 🎙- Favorite Podcast: Chuck D - Narrates the Band the Clash, Invest like the best

* 📰 - Favorite Newsletter/Blog: Chad Sanderson substack - Data Products

* 📲 - Favorite Tech Gadget: Garmin

* 📈 -  Favorite New Trend: Lower valuation caps

* 📚 - Favorite Book: Led Zepplin, The Beatles

* 🤔 - Favorite Life Lesson: Running Everyday Solves Problems

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