Courtesy of Will Chockley

PCH Driven: 75 and Sunny’s Wil Chockley on How to Pitch Your Startup

Jaime Williams
­Jamie Williams is the host of the “PCH Driven” podcast, a show about Southern California entrepreneurs, innovators and its driven leaders on their road to success. The series celebrates and reveals the wonders of the human spirit and explores the motivations behind what drives us.

On this episode of the PCH Driven podcast, 75 and Sunny venture firm partner Wil Chockley shares his thoughts on skills early-stage founders need and advice on how to give the best pitch possible.

The pandemic quickly changed how the tech world worked, creating an exodus of people from the Bay Area to L.A., Chockley said, as jobs went remote and lockdowns forced people to decide where they wanted to be stuck, at least for the short term.


"I think that influx of new tech blood has really helped the tech scene. But prior to all of that, L.A. was already sort of a robust hub for innovation and the core areas geographically for a few industries like aerospace… And then entertainment," said Chockley.

Chockley is a partner at 75 and Sunny, a venture firm founded by Zillow co-founder Spencer Rascoff, who also co-founded dot.LA. Chockley assesses potential investments; about a third of his time, he said, is spent looking at prospects in proptech, but he's also interested in what he calls “HR tech” or the future of work.

On the fundraising side, Chockley has learned what skills to look out for in founders. The single most important ability, he said, is storytelling. Being able to translate a company’s data while also painting a vision for its future takes craft.

"You are first selling your idea to investors; you're selling your idea then to potential employees when you're looking to hire them. And then you're looking to sell your product or your idea to potential customers. So being able to sell well is being able to tell a story well," said Chockley.

The pandemic, he added, has opened more funding avenues for founders in every city. Zoom video calls have become the norm for the venture capital industry, allowing startups to get funding from investors outside of Silicon Valley and far from their headquarters.

"I feel like everything has merged, so everyone is interacting with everybody. And so, what's happening here in L.A. is really what's happening all over the country," said Chockley.

While making those pitches to investors, Chockley said some things to keep in mind is to be enthusiastic and be receptive to feedback. But also when you introduce the problem, your product is the solution.

Click the playhead above to hear the full conversation, and subscribe to PCH Driven on Apple, Stitcher, Spotify, iHeart, Google or wherever you get your podcasts.

dot.LA Engagement Intern Joshua Letona contributed to this post.

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