Alexis, Fully Initialized

Today, I’m very excited to return to Initialized Capital as a full-time General Partner alongside my longtime friend and collaborator Garry Tan.

Here’s a little history first. Initialized launched in 2011. Before that, Garry and I were having success as angel investors and founders kept telling us we were providing more value than other much better funded investors.

Before long, we’d raised $7 million for our first Initialized fund, which made seed investments into startups like Instacart and Coinbase. We were on to something.

Since then, we have grown to manage more than $250 million, which is invested in companies that are now worth more than $20 billion (including six unicorns, or startups that are worth over one billion dollars). We’ve recruited a remarkable team of partners, and built a ton of software to scale all of the traditionally high-touch, and less scalable parts of the venture business to better serve our founders.

We want to be the first check and we want to do the work — we aspire to be the kind of investors we wish we’d had when we were founders. And after more than three years of serving back at Reddit, my first “baby” is in a much better place and has a great team in place.

Now I’m back at Initialized with even bigger ambitions than when we started. As a new father of a five-month-old little girl, I want to make sure the world she inherits is as great as possible. This depends on the entrepreneurs of today and tomorrow building companies that truly matter.

Photo credit: Chuck Revell

Taking Care of Your Health While Running A Startup

The first time Zachariah Reitano founded a startup, he went through the Y Combinator program and found himself rushing back and forth between New York City and the Bay Area while struggling to get the company up and running.

“We fell into the stereotype of young founders who felt they needed to stay up all night. We often pulled all-nighters unnecessarily,” he said. “Sleep is not a gas tank. You can’t run it to empty and sleep all day on Saturday.”

He pushed so hard toward exhaustion that he walked into a hospital and literally fell asleep — only to be revived by getting an IV plugged in.

“That was a definite wake-up call.”

This time with his next company Roman, he’s doing things differently. It’s a common experience we see at Initialized Capital — that second-time or serial founders become more disciplined about the way that they manage their health and well-being while running a company.

How charging for our product originally hurt — but ultimately saved — our startup

Five years ago, my co-founder Claire McDonnell and I founded True Link Financial, and did two things that that were totally unorthodox for the time.

First, we didn’t build a startup for teenagers.

We built it for seniors. (We’re a financial services firm that offers debit and Visa cards and investments management for aging Americans.)

Secondly, we charged our customers actual, real money for what we had built.

This was not common practice at the time. Around 2012, we and a whole cohort of other startups — Simple, Plastc, Swyp, Coin, Final, Stratos, Clinkle, and others — were getting card-issuing companies off the ground.¹ We also launched a Visa card — but our goal was to protect older folks from fraud, a $36 billion problem that affects millions of Americans, including my grandmother. Our cards would automatically decline scammy transactions so seniors like my grandmother would be able to still carry a credit card, preserve their independence, and spend their own money — and in order to decline the transactions we had to become the issuer of the card.²

Investing in the future of retail with Standard Cognition: Bringing real time computer vision to all brick-and-mortar stores

Standard Cognition is building the retail experience of the future, where you just walk out to pay for whatever you’re carrying out of a store. It’s seamless, checkout-less shopping for consumers and retailers all over the country.

We’re proud to announce that we just joined Charles River Ventures and Y Combinator in backing the company through an initial $5 million round.

In their first proof of concept, they use cameras to identify who walks in, what goods they’re carrying and what they ultimately purchase. All of these processes are handled on-site at the local store using computer vision techniques Standard Cognition is developing.

The most interesting innovations happen when technology cost curves hit magic levels where they become possible in new packages for the first time. Realtime computer vision with off-the-shelf GPUs has just reached that level now, and we are excited that this team is bringing it to reality today.

The team has not only founded a company together before, it has three PhDs in mathematics and nuclear science and its CEO Jordan Fisher led a team at the Securities and Exchange Commission developing quantitative tools that could make sense of the agency’s data.

For retailers, this will lead to reduced prices, no lines, better stocked shelves and fewer misplaced items. Every year, retailers lose $45 billion to theft, so even before the holy grail of checkout-without-lines, Standard Cognition can make a huge dent in anti-theft in a way existing solutions have only dreamed.

Technology cost curves unlocking new capability is only half of it. To bring amazing tech to market, you also have to have a strong business motivation to do it, and frankly we’re there today. Traditional American retailers face an oncoming crisis as e-commerce continues to take mindshare and revenue directly from brick-and-mortar retail. Standard Cognition is such a powerfully better customer experience that this is the kind of thing that goes from cool to must-have in very short order.

Instacart’s Lead Product Designer on Creating A Design System


Jordan Staniscia tried — and claims he failed — multiple times to create a single, re-usable design system for all of Instacart’s visuals, icons and interactions over many years at the company. 

We at Initialized Capital frequently get asked about how startups should create style guides that define the brand identities of their companies, and so we asked Staniscia to share some lessons with portfolio companies this week. 

So, first off, what is a “design system”? 

Staniscia prefers to use the word “system” because it implies that this is something re-usable; it’s a framework. Design systems are, in Josh Clark of Big Medium’s words, “containers for institutional knowledge.” 

It sits between the design and engineering teams as a common language that helps them stay on the same page. Otherwise, designers will end up in a situation where they have to explain their product vision over and over again and engineers will have a hard time ensuring they’re building an efficient system.