📶 Ashley Smith (GP @ Vermilion Cliffs Ventures) on operators-turned-investors, the evolution of engineering roles, and how GTM is changing in 2025

"I was supposed to write a short, formulaic fund announcement, but instead, it turned into a 21-page manifesto on how I got here. I couldn’t fake a traditional path—I had to own my story."

"My background is weird. I’ve worked at Twilio, Parse, Facebook, GitLab, and GitHub, all focused on go-to-market for a technical audience. That means I don’t just write checks—I help founders figure out how to get their first five customers and turn early traction into something real."

"I don’t want to be just another check—I want to be the investor founders call first when they need help thinking through a problem."

"Some investors give money. Some investors make intros. I do that, but I also help founders build rounds, refine GTM, and even handle founder therapy sessions when needed."

"I’ve worked with over 100 companies as an advisor. That experience helps me see around corners that first-time founders might miss."

"The best investors don’t try to force their vision onto founders. I wait for them to come to me—I’m not the kind of VC who tells founders what to do."

"One of my first questions is always: Who talks to customers? If a founder isn’t engaging directly with users, that’s a red flag."

"I don’t care where you went to school or if you’ve founded a company before. What matters is curiosity, execution, and belief in what you’re building."

"I want founders who figure things out on their own and don’t expect investors to solve every problem for them."

"AI copilots and automation are making it easier for non-technical people to build. But truly technical founders—people who have been deep in security, infra, or dev tooling for years—are still critical."

"The layoffs we’re seeing in engineering aren’t because AI is replacing engineers—it’s because companies are finally getting disciplined about hiring and efficiency."

"Bootcamps pushed a lot of people into engineering who didn’t actually want to be engineers. We’re just seeing a market correction."

"Paid ads aren’t working like they used to. The new playbook is founders as chief marketers, using social, content, and in-person events to drive awareness."

"LinkedIn is performing better than almost anything else right now, which blows my mind given where social media was a decade ago."

"Go-to-market isn’t one-size-fits-all. The best approach is to test relentlessly, find what works, and double down fast."

"Webinars still work in some markets, but they have to be actually interesting—not just glorified sales pitches."

"A lot of the best people aren’t actively looking for jobs. Keep those relationships warm, because life changes fast."

"I’ve helped founders hire some incredible talent by getting to know unhireable people early, even if they weren’t immediately available."

"If you’re building an open-source company, your best hires might be the biggest contributors to your project—even if they’re happily employed elsewhere."

"Solo GPs spend so much time on back office work—legal, tax, compliance, and all the things you don’t think about when starting a fund."

"Most of the job is saying no—to founders you like, to LPs who won’t back you, and to great companies that just don’t fit your thesis."

"The best founders don’t want to be told what to do. They take advice when they need it, but they’re high-agency people who chart their own path."

Ariel Winton-Jones – "She’s only doing Series A, but she’s brilliant."

Jaren Glover – "Really strong operator-investor hybrid."

Kevin Novak – "Fund size might be too big to be emerging, but he’s doing really interesting work."