Startups, London, Facebook: Jay Shek on Changing Up the Environment

Read time: 7 minutes

Jay Shek graduated in 2004 from the University of Pennsylvania Jerome Fisher Program in Management & Technology, majoring in computer science and concentrating in finance and management. Right after college, he moved to San Francisco to join the only startup that recruited at Penn, Snapfish. There, he did finance and worked on its acquisition by Hewlett-Packard.

He currently works at Facebook as a product manager, but he previously worked on two startups: Betable, an online gambling startup that led him to live in London, and Locality, a service that allows you to search and compare local businesses. Jay was CEO and co-founder of Locality in New York for five years before moving on to Facebook.

Stories worth noting:

1) How Jay would find his path if he were a student now, and his advice for us.
2) How he recommends everyone to spend some time abroad.
3) The struggles and lessons from running his startup, Locality.
4) How selling — yourself, your idea, your vision — to others is hard but essential.
5) Why he moved from small startup to big tech company, Facebook (Part 2)

What did you do at Penn that that allowed you to explore your interests and passions?

I was part of the M&T program, and I knew before I joined that I was interested in entrepreneurship and technology. I thought it was a great step to get both the engineering and computer science knowledge and some business acumen as well.

Any clubs or work you did during college that you found was really interesting or helped you grow a lot?

I had a senior thesis on information security that had nothing to do with what I do now, but I think it's really just learning to think in different ways. I've always been on the business side of startups, but having the engineering knowledge helps you communicate with engineers and understand the scope and complexity of technical challenges in a project without having to consult other people.

How did having the engineering background teach you to approach problems differently?

I approach everything with a very engineering or systems-based approach. It's useful in tech and a lot of different jobs, but it's not the only thing that you need. Penn prepared me well on the engineering, technical, and business skills. But, there are a lot of soft skills, social skills, like knowing how to sell. Those are skills that a lot of universities shy away from. Nobody wants to be known as a salesperson or someone who cold calls. But those are skills that are very useful in almost anything else you do (more here).

I was a CEO of a start-up, and I sold smart people to try to join me as employees, I sold investors to try to get money, I sold partners to work with us when we were too small to really make a difference to their bottom line. A lot of entrepreneurship is just selling stuff. It's something that you have to learn on your own.

A lot of us don't know where we're going or we feel pressure from our parents or peers. What would you say to someone trying to figure out their path?

I think a good start is to find your strengths. This is something Facebook says, and I totally agree with it:

Our strengths are things that you find joy and energy doing.

It might not necessarily be the things that you are actually best at. You might be really good at cranking Excel, but you may find that it's draining and you don't actually enjoy it. Maybe there are other things, like programming or data analysis, where you're like, “I'm actually in-flow. I don't feel tired because I want to do it.”

Also seek out career counseling. I feel like Wharton only teaches you so much, and doesn't really tell you anything about careers other than 80 percent of people go into financial or consulting.

I wish I knew exactly what I was getting into, what the job would entail, what I’d learn, what the earning potential was. You can really can get this information from talking to anyone 25 or older in these industries.

I joined the one startup that recruited at Penn that year (Snapfish). I could have been more proactive about learning the type of role and the type of company I'm most interested in.

People now are getting relevant business experience significantly earlier than I did.

My first summer in college, I was waiting tables at a Mexican restaurant. The next one I was selling cell phones at AT&T. It didn't even occur to me that I needed to learn about all these industries that early.

What do you think you learned at Snapfish, since that was right after you graduated college?

I think there's a lot of just maturity and polish. I don't want to say it's one specific thing, just like if you take the same smart person when they're 20, 27, 32. The core's the same, the intelligence is there, the attitude is similar, but everything just gets a bit better.

The way that you communicate gets better, your critical thinking gets better, your confidence in your opinions and what you're supposed to do gets better. Being in as many different environments as possible helps that out.

So you worked at a startup in San Francisco and later founded a startup in New York. Could you talk about the differences in the startup culture between those cities?

There are many. After Penn, I went straight to San Francisco to work for a startup called Snapfish. At the time, only a couple of kids my year actually went to SF. Everyone did consulting or finance and moved to New York — it's just what everyone did. So I was very excited to try it.

For early stage tech, NY tech is growing very fast, but it's still a significantly smaller market size than San Francisco. In San Francisco, you just have more access to networks of everything: more smart engineers, angel investors and venture capitalists, experienced people that could be advisors, mentors, or board members. It's a better place to learn and grow.

So if I were to start a company with no other knowledge, I'd probably say San Francisco, but it's balanced against the fact that New York may be a more interesting place to live.

What made you go to London and do you recommend that people get experience abroad?

I moved overseas for an online gambling startup because, legally, an executive of the company had to be based offshore to get an online gambling license outside the US. The startup scene there is much smaller. Before I moved to London, I spent six years in San Francisco, and it was the only place I knew as an adult.

I was really scared of moving out of the country. It ended up being one of the best years of my life. I knew I should have totally done this, that I should have done study abroad. I'm very bullish on it from a personal growth experience.

I was scared that I would miss out on stuff in San Francisco, but the truth is, there's not much you're missing out. Moving to another place stretches you and enables you to make new friends, but it doesn't mean your old friends go away. So I highly encourage it as a personal growth experience.

So after London and after working on that startup, what led you to start Locality?

I finally just decided it was time to do it. Looking back, I would probably have done it sooner. There are certainly things that you learn at companies — not to discount that. But there's just so much more you learn about entrepreneurship through actually doing it. Like, the first time you realize, “I can't make payroll," and I have to tell my employees they're not getting paid. I had multiple situations being a week away from telling our employees that we're running out of money, and you always end up raising money right at the last second.

So I would say don't overvalue prior experience. If you feel like you have a good idea and you're excited to test it out, you don't need ten years of experience to do a startup.

Through your experience of running Locality what was most exciting about it, and what did you gain most from doing the startup?

You get to learn all the different challenges at each stage of the business. It develops your self-confidence by putting you in stressful situations, forcing you to present to people. You have to develop huge confidence without freaking out or over-worrying.

Functionally it just forces you to think very methodically; there's a startup way of thinking that is different from a big company. At a startup, you are under-resourced, so you have to be very selective about what you do. What's the minimal amount of work that you can do, the smallest thing you can build that gives you signal on whether it's the right path or not?

Read on for Jay's advice on convincing, his move to Facebook, and his favorite blog and news sites. (3 min)


Header photo courtesy of The Business of Fashion.

Melinda Hu

Read more posts by this author.

Subscribe to The Sign.al

Get the latest posts delivered right to your inbox.

or subscribe via RSS with Feedly!