Joining Speakeasy & Predicting the NBA Finals
In my post last week, I discussed how I made the decision to join a seed stage startup. This week, I wanted to add a bit more color and get into the specifics of why I chose to join Speakeasy, a pre-funding startup.
On coming back to SF
People say that wise men don’t speak in absolutes. Now, I would never claim to be wise, so perhaps it’s not a surprise that when I left SF three years ago to move to London I let it be widely known that I was never coming back. Three years removed from that proclamation, I find myself back in San Francisco eating my words. I don’t bring this up to dunk on SF, but because I want to highlight the extent to which I was excited to join Speakeasy. I was so excited by the opportunity, that I was even happy to be sucked back into the SF tech vortex (albeit part time)
Working at Speakeasy was an offer which I couldn’t refuse, thankfully not in the Godfather sense. Rather, it was a golden opportunity to work with an incredible team on an idea about which I was truly passionate. In my last post, I wanted my experience to be more generally applicable, so I internationally left out specific details about the company I joined. In this post, I want to get as specific as possible, and write about my personal experience deciding to join Speakeasy.
On the Speakeasy Team
As I mentioned in my previous post, team is the most important consideration when joining an early-stage startup, and in fact, that is what originally drew me to Speakeasy. The previous company I worked for (LiveRamp) has a long legacy as a startup factory. Many ex-LiveRampers (the LR-mafia) have had success founding their own companies. Therefore, it was not a huge surprise when my former eng partner, Sagar Batchu, told me he was exploring founding his own company.
As any product manager will tell you, the best tech leads are those who want to get into the customer discovery calls, and spend as much time understanding the ‘why’ behind the roadmap as they do planning out the ‘how’. This describes Sagar to a ‘T’. During the 3.5 years we spent working together, Sagar grew from a strong technical leader into a keen business leader, developing a strong strategy and market understanding. When he told me he was founding, I had no doubt that Sagar would be a great CEO.
As his idea started to take shape, Sagar teamed up with Simon Yu, an experienced operator in the API & Cloud space with the full range of skills which marks a great product manager. Simon has a long track record of not only creating API-based products, but also of successfully shepherding them to profitability. Their partnership was the beginning of a very strong team.
During this time when the idea for the company that became Speakeasy was incubating, I was helping Sagar, as I would any friend. I volunteered info, connections and experience where it could be useful. That said, I hadn’t considered joining them. They were in SF, and I was in the middle of conducting a job search focused on London-based startups. But as I went through several final round interviews, I just couldn’t seem to find the perfect fit. Whether it was team, or product space, nothing really called to me or got me super excited. After about a month of interviewing, I realized that nothing energized me as much as some of the casual conversations I had with Sagar and Simon. I realized that probably meant something and I decided to make the case to them about joining.
No doubt, a huge part of my eagerness was down to the simple fact that the work I had done with Sagar during our time growing LiveRamp’s international business was some of the work I was most proud of. But what also really piqued my interest was the idea which they were noodling on. Their user research had led them to the cross section of developer infrastructure and APIs. They wanted to build an API platform developers would love. This resonated with some of my core beliefs, as well as some of my previous struggles.
On the API Opportunity
When Sagar and Simon told me they were focused on building infrastructure to help the developer community better build & maintain APIs, I was hooked. As I said in my post last week, I don’t think there’s a higher calling than building for builders. And API proliferation in particular, I feel is the most impactful trend in software development (all due respect to the public blockchain). I don’t think that it is hyperbole to say that, thanks to the spread of APIs, it will soon be possible for a single developer to build and run a large, global enterprise on their own. That’s real power in the hands of the world’s best builders. However, there was also a strong personal component. I was very familiar with the pain of trying to build and maintain enterprise-grade APIs.
For 2+ years, I had been the product manager for LiveRamp’s web APIs, and I still remember the nightmares of accidental breaking changes, and tedious version migrations. The daily reality we faced was that our developers lacked a development platform which made it easy for them to iterate and evolve our existing APIs, and there was no bandwidth to develop it internally. At any given point, we had between 5-10 developers dedicated to managing the set of endpoints which were serving 6 billion requests/day. These 5-10 developers not only had to keep the production APIs stable, but also had to build new products to help deliver revenue growth for the company. There were small improvements made around the edges, but an overhaul to the API development platform was out of the question, the business couldn’t afford to allocate headcount from projects that directly generated revenue.
Companies like Twilio and Stipe were great examples of what it was possible for an API to be when it is built on top of a powerful development platform but at LiveRamp, we could only dream. We were just never able to justify the kind of investment that would have been required to get us the platform we needed. I feel sure that there are plenty of other companies that are in the same boat, and millions of developers who can empathize with this experience. Whether it’s a half completed microservices architecture, or a public API endpoint with stale documentation, the lack of an out of the box API development stack is manifested in most developer’s day to day experience. The opportunity to build an API platform that gives all developers access to best-in-class tooling would be a boon to developers building APIs as well as those using them.
On Making the Jump
When I told Sagar and Simon that I wanted to join Speakeasy, they were excited, but wanted me to take a couple days to make sure I was certain. It was, after all, a big decision. As I reflected on it for a couple of days, my conviction in the decision only grew. In addition to excitement about the team, and the idea, there was a tremendous opportunity for personal growth.
A few days later I told them I was sure this was the right move for me and let them know I was ready to come to the Bay as soon as possible to get started (I was eager). They both very kindly told me that I could work remotely from London, but I felt strongly that at this early stage, it was important to be together in-person so we could develop ideas faster. That’s why a few weeks after our conversation, I was on the plane headed back to SF, ready to get to work on building the future of API development.
On the NBA Finals
All that was a couple of months ago now. Since then, we’ve been busy building; working hard to get to the point where we can start to share what we’re building on with the rest of the world. On the list of good decisions I’ve made, my decision to join Speakeasy ranks highly, just below the decision I made to move out of SF 3 years ago :)
But to be honest, being in SF hasn’t been the fire & brimstone I anticipated. While it no doubt has its problems, SF is still a city full of new ideas to ponder and interesting conversations to have. Not to mention, for me, a city full of good friends. It also helps that the remote-first nature of our team means that while I’ve been spending time in SF, I’ve been able to spend time in London as well.
And as I am eating my words, there is yet another proclamation which I need to go back on… When I lived in SF, I may have gone on the record vociferously stating that I would never support the Steph Curry Golden State Warriors. As it happens, my return to SF has corresponded with the Warriors’ return to championship contention. For the most part, I remain an unabashed Warriors hater. However, having drafted and nurtured one of my favorite college players, Jordan Poole, and now going up against another team I have a lot of animosity for in the Boston Celtics (who knocked out my NJ Nets), I find myself in the unlikely position of begrudgingly supporting the Dubs for the Larry O,Brien. So, my prediction: Warriors in six, Jordan Poole finals MVP.