How to break into Silicon Valley as an outsider

Domm Holland, co-founder and CEO of e-commerce startup Fast, appears to be living a founder’s dream.

His big idea came from a small moment in his real life. Holland watched as his wife’s grandmother tried to order groceries, but she had forgotten her password and wasn’t able to complete the transaction.

“I just remember thinking it was preposterous,” Holland said. “It defied belief that some arbitrary string of text was a blocker to commerce.”

So he built a prototype of a passwordless authentication system where users would fill out their information once and would never need to do so again. Within 24 hours, tens of thousands of people had used it.

Shoppers weren’t the only ones on board with this idea. In less than two years, Holland has raised $124 million in three rounds of fundraising, bringing on partners like Index Ventures and Stripe.

Although the success of Fast’s one-click checkout product has been speedy, it hasn’t been effortless.

For one thing, Holland is Australian, which means he started out as a Silicon Valley outsider. When he arrived in the U.S. in the summer of 2019, he had exactly one Bay Area contact in his phone. He built his network from the ground up, a strategic process he credits to one thing: hard work.

On an episode of the “How I Raised It” podcast, Holland talks about how he built his network, why it’s important — not just for fundraising but for building the entire business — and how to avoid the mistakes he sees new founders make.

Reach out with relevance

Holland’s primary strategy in building networks sounds like an obvious one — reach out to relevant people.

“When I first got to the States, I wanted to build networks,” Holland said, “but I didn’t really know anyone here in the Bay Area. So I spent a lot of time reaching out to relevant people — people working in payments, people working in technology, people working in identity authentication — just really relevant people in the space working in Big Tech who were building large-scale networks.”

One of the people Holland connected with was Allison Barr Allen, then the head of global product operations at Uber. Barr Allen managed her own angel investment fund, but Holland wasn’t actually looking for money when he reached out to her. He was much more interested in her perspective as the leader of an enormous financial services operation.

Barr Allen took an immediate interest in Fast based on her experience in the space, and she offered to introduce Holland to some VCs. The first investor she introduced him to — Jan Hammer of Index Ventures — made a pre-seed offer after just one conversation, and Holland asked Barr Allen to join him as co-founder and COO at Fast.

“Raising money isn’t the only thing,” Holland said. “You’ve got to hire people, you’ve got to build a team, you’ve got to build customers and suppliers, and you’ve got to build entire ecosystems. So anybody who would be interesting in that area, anyone I could learn from, anyone that would be helpful to me, I spent the time to meet with.”

Keep it short and strategic

When he was building a network in the Bay Area, Holland said he would schedule 10 to 20 meetings a day — and that he often still does.

He lays out a reliable system for connecting with new people:

1. Do the research to identify the people you need to be talking to. Holland said he receives dozens of emails a day from founders asking to pick his brain or refer them to investors. But it becomes clear that many of these folks have adopted a “spray and pray” approach without first doing the groundwork — their outreach includes no background information, or they’re operating in an industry where Holland has no expertise or interest. “You’re putting yourself in a bucket with everyone else that has done the same thing,” he said. “They need to spend more time researching and on bespoke communication.”
2. Write up a short outreach email. People in the startup world are busy, so providing contacts a condensed piece of information they can quickly read and understand is key. Early on, Holland hit on an effective template: “I would say, ‘Hey, I’m an Aussie founder, I just arrived here in San Francisco, I’m building X, would love to tell you about it.’” In just a few sentences, he conveyed what he was doing — which he already knew would be relevant based on his research — and also intrigued them with his Australian background.
3. Go in planning to have an interesting conversation — no ask required. Holland noted that not every outreach effort included an ask for funding, or for anything at all beyond a 15-minute conversation. “The more relevant you are to the person, the less you need to give them an ask,” he said. Talk about your common interests and see where the conversation leads. “With some people, you’ll form great connections, and with some, you won’t. That’s just part of the process.”
   

   No shortcuts (it’s all about relationships)

   Even though Holland seems to be on the fast track to startup success, he emphasizes that there’s no easy path. There’s no database that will connect founders with a thousand eager investors, and there’s no presentation deck bright or shiny enough to close a deal for you.

   “Nothing beats building human networks,” he said. “That’s the way that you’re going to get this done in terms of fundraising.”

   Plus, he added, doing the hard work of reaching out and taking meetings shows people across your industry that you have what it takes.

   “Showing that you can do that is also showing that you can build the business because that’s what you’ve got to do to build a client base, to build a team,” he said. “These are important traits that you need to show that you can successfully execute on.”