Startup log: first impressions

LogoAs you may know, I recently left TripAdvisor to live the ups and downs of startup life. Now, one of the things that happens when you’re in a place for a long time is that you start to accrete responsibilities. You take ownership of cleaning up a particular error report. Or you set up automated jobs to monitor your area of the code. Or you’re the go-to person for a particular technology. Or you’re the person who knows why something was done a particular way. Or you’re the organizer of one or more important meetings, and are frequently invited to others.

This is normal, and each informal responsibility represents a way that you’re stepping up and looking after your corner of the business. At the same time, each adds a measurable frictional cost to your productivity, until finally it feels as though there’s nothing left but meetings and a flood of email. It becomes the norm, and it’s hard to imagine a reality in which you didn’t filter 90% of your email and manually delete 90% of the rest. Or spend most of your time in meetings. Or suffer from constant interruptions.

So the most astonishing thing in my recent transition was, perhaps, the most banal. In an instant, my email volume was cut to almost nothing. Moreover, everything I do receive – without exception – is personally relevant. The change was so shocking that for a while I found myself automatically checking for messages to delete, a well-trained monkey going through its routines.

The next thing was the technology. TripAdvisor has a fairly conservative stack – Java servlets, N-tier service-oriented architecture, postgres database…  Scratch, on the other hand, has a much more modern, Javascript-based application. There’s almost no technical debt, because the code base hasn’t been around long enough to develop any. In one stroke I’ve gone from being highly knowledgeable about the architecture to a complete newbie – and have had to scramble to learn my way through the code base.

Time also expands. It reminds me of an educational tour I took to Cuba a dozen years ago – every day was so packed with different activities that we’d be discussing something that happened “a couple days ago”, only to realize that it had actually been that morning. In the same way, when all the habitual interruptions (email curation, meetings, etc.) disappeared, I started packing a lot more stuff into each day, each of which suddenly seemed to contain way more time than before.

But perhaps the biggest change was a transition that Ben Horowitz described in Peacetime CEO/Wartime CEO. It took a couple days for this to sink in, but there’s a huge difference between working for a highly profitable market leader… and a tiny startup with a beta product and an unproven model. It isn’t just that you have fewer resources, or that there aren’t people to do specialized tasks, or that “you’ve got to be scrappy” – it’s that the way you think fundamentally has to change.

There’s only one team, one product, one focus. Risk management isn’t about project success, it’s about company survival. You need to proactively go out and define the problems, not work through an existing backlog. There’s no long-term context to work within, or to change – everything is up for grabs. There are a thousand things like this – some little, some big – and it can be daunting at times… But this is how it works.


You knew this was coming, right? I’m looking for software engineers who are going to bring something new and wonderful to the team. People who have the skills, play well with others, and are excited about working in a no bureaucracy, collaborative, high personal impact zone. We’re working on an exciting, useful product, and to succeed we’re going to need to peel the technical onion – starting with execution on web and mobile, then into increasingly deep problems of analytics, machine learning, and… well… figuring that out’s going to be part of the fun. :) As for location, we’re moving into an awesome space next to South Station, so lots of great stuff around.

If you’re interested, please send an email to


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