Lesson: Designing Your Experience with Jeff Veen

Step: #10 Career Lessons: What are career lessons for startup employees?

We woke up one morning and the mechanism that we used to push fonts out to people's websites was way behind. We were totally stacked up and it turned out we were getting twice or three times the traffic on a Friday morning than we normally ever would. It turned out that one of our partners and our lead investor, at the same time, had rolled out some new features on their product and we are getting a lot of press for it and they had an unexpected amount of traffic, so we got an unexpected amount of traffic. All of a sudden nothing was working. It was terrifying and it's Friday and it's like right before Christmas and all these things were conspiring to make it a really bad weekend.

So two things happened. One was that it really showed the reason why people come to work at a startup is that they are willing to take on the risk and they are willing to put in the effort because they have the ability to make so much impact, so much more impact.

That's what happened. We had a small team of our developers stay through the weekend, and essentially rewrote an entire chunk of this service that they were planning on developing a new architecture for and were going to spend eight weeks on it and they did it in three days instead. Talk about minimum, viable, just crank-through all of that to get it out, to be able to support it, to fix the problem and to feel a tremendous pride in the work, in the team, and in the product.

But it also helped us start to figure out this methodology of, "Okay, what's wrong? How do we solve a problem like this? How do we get out of the way, so that the people who can solve the problem will solve the problem?"

I think those things are inevitable in the life of a company that can come from all different directions. It can be a big technical problem, it can be a big competitor out of nowhere, and it can be a lawsuit that you never expected. Those will happen in the life of every company. Those things essentially are the character building things that cement a team together, if they don't kill them.

I started my career in journalism, actually, which was a little before the web because I've been doing this for 20 years. As long as you can do the web, basically. As a freelance writer, I got a job at Wired magazine and that's where we started. I worked on the editorial team for three days, then they were like, "You know HTML? We're building a website." I thought that was great because I'd always been very into technology as a hobby and publishing and storytelling as a profession. That was a perfect mix of it and that's how I got started on the web.

What I learned at Wired magazine was the value of mentorship. One of the creative directors of Wired was responsible for the new website that we were building and she wasn't very familiar with the technology. She worked in QuarkXPress, was amazing on the print side and I knew the technology very well, but wasn't that familiar with design, really. I was a writer. This is Barbara Kuhr who is one of the two creative directors here. She literally had me push my desk into her office and we sat there and built this thing. She would design and I would type HTML as fast as I could and use Photoshop probably 1.0 or something to cut up the images; all of that stuff.

I learned way more than I could have going to art school or anything like that seeing her process for how she would do design, seeing the compromises that we had to make in the technology, and how she would respond to that. That just totally informed so much of what I did.

I wanted to do much more of that outside of just publishing when eventually Wired went through acquisition and things like that. So I left after a number of years and started a company Adaptive Path doing consulting to get that broader range, which I really liked. That was fantastic. I got to work on things like the NPR website, but also Flickr and Blogger and just a whole array. WeightWatchers.com, just all kinds of stuff. Very diverse. That was fun.

The client management part of a service company like that I found a little less fun. So eventually, I asked the partners at Adaptive Path, my friends and colleagues, if we could do a product inside the consulting company like what 37Signals was doing at the time and stuff like that. So we made Measure Map which we sold to Google after about a year, so that was awesome. But then, I had to leave Adaptive Path and go to Google and it was at Google where I learned about scale and how if you're thinking about doing something a billion times a minute, you're not thinking big enough. That kind of unbelievable scale.

Take the design background that I got from Wired and Adaptive Path and combine it with the crash course in massive systems and computer science that we got at Google is where came Typekit came from. I wanted to make design tools, which I loved, with designers as an audience. But we realized the best way to do that was by hosting the world's fonts and put those things together. That's how we had both the understanding of what to provide for the web design community with the confidence that we could actually pull it off.

So we did that for about three years and then sold that to Adobe where we're doing an even bigger scale now. Not just for fonts, but for all the creative tools entirely. So it's been an amazing ride.