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.

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

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.

Amid the IPO gold rush, how should we value fintech startups?

If there has ever been a golden age for fintech, it surely must be now. As of Q1 2021, the number of fintech startups in the U.S. crossed 10,000 for the first time ever — well more than double that if you include EMEA and APAC. There are now three fintech companies worth more than $100 billion (Paypal, Square and Shopify) with another three in the $50 billion-$100 billion club (Stripe, Adyen and Coinbase).

Yet, as fintech companies have begun to go public, there has been a fair amount of uncertainty as to how these companies will be valued on the public markets. This is a result of fintechs being relatively new to the IPO scene compared to their consumer internet or enterprise software counterparts. In addition, fintechs employ a wide variety of business models: Some are transactional, others are recurring or have hybrid business models.

In addition, fintechs now have a multitude of options in terms of how they choose to go public. They can take the traditional IPO route, pursue a direct listing or merge with a SPAC. Given the multitude of variables at play, valuing these companies and then predicting public market performance is anything but straightforward.

It is important to note that fintech is a complex category with many different types of players, and not all fintech is created equal.

The fintech gold rush has arrived

For much of the past two decades, fintech as a category has been very quiet on the public markets. But that began to change considerably by the mid-2010s. Fintech had clearly arrived by 2015, with both Square and Shopify going public that year. Last year was a record one with eight fintech IPOs, and there has been no slowdown in 2021 — the first four months have already produced seven IPOs. By our estimates, there are more than 15 additional fintech companies that could IPO this year. The current record will almost certainly be shattered well before the end of the year.

Fintech IPOs from 2000 to 2021

Image Credits: Oak HC/FT

The era of the European insurtech IPO will soon be upon us

Once the uncool sibling of a flourishing fintech sector, insurtech is now one of the hottest areas of a buoyant venture market. Zego’s $150 million round at unicorn valuation in March, a rumored giant incoming round for WeFox, and a slew of IPOs and SPACs in the U.S. are all testament to this.

It’s not difficult to see why. The insurance market is enormous, but the sector has suffered from notoriously poor customer experience and major incumbents have been slow to adapt. Fintech has set a precedent for the explosive growth that can be achieved with superior customer experience underpinned by modern technology. And the pandemic has cast the spotlight on high-potential categories, including health, mobility and cybersecurity.

Fintech has set a precedent for the explosive growth that can be achieved with superior customer experience underpinned by modern technology.

This has begun to brew a perfect storm of conditions for big European insurtech exits. Here are four trends to look out for as the industry powers toward several European IPOs and a red-hot M&A market in the next few years.

Full-stack insurtech continues to conquer

Several early insurtech success stories started life as managing general agents (MGAs). Unlike brokers, MGAs manage claims and underwriting, but unlike a traditional insurer, pass risk off their balance sheet to third-party insurers or reinsurers. MGAs have provided a great way for new brands to acquire customers and underwrite policies without actually needing a fully fledged balance sheet. But it’s a business model with thin margins, so MGAs increasingly are trying to internalize risk exposure by verticalizing into a “full-stack” insurer in the hope of improving their unit economics.

This structure has been prevalent in the U.S., with some of the bigger recent U.S. insurtech IPO successes (Lemonade and Root), SPACs (Clover and MetroMile), and more upcoming listings (Hippo and Next) pointing to the prizes available to those who can successfully execute this expensive growth strategy.

The IPO market is sending us mixed messages

If you only stayed up to date with the Coinbase direct listing this week, you’re forgiven. It was, after all, one heck of a flotation.

But underneath the cryptocurrency exchange’s public debut, other IPO news that matters did happen this week. And the news adds up to a somewhat muddled picture of the current IPO market.

To cap off the week, let’s run through IPO news from UiPath, Coinbase, Grab, AppLovin and Zenvia. The aggregate dataset should help you form your own perspective about where today’s IPO markets really are in terms of warmth for the often-unprofitable unicorns of the world.

Recall that we’re in the midst of a slightly more turbulent IPO window than we saw during the last quarter. After seemingly watching every company’s IPO price above-range and then charge higher on opening day, several companies pulled their offerings as the second quarter started. It was a surprise.

Since then we’ve seen Compass go public, but not at quite the level of performance it might have anticipated, and, then, this week, much has happened.

What follows is a mini-digest of IPO news from the week, tagged with our best read of just how bullish (or not) the happening really was: