SnapTravel: CTO Henry Shi

Tell me about SnapTravel.

SnapTravel is a chatbot that helps customers find the best hotel deals over Facebook messenger. So basically, customers talk to the bot. They tell it where they want to go, how much they want to pay, and other preferences, and the bot will do a search across sites to give our customers the best recommendations at the best prices.

How did you and your co-founder come up with this idea?

We actually stumbled upon this idea. When I initially left Google to run SnapTravel, I had no idea what startup I wanted to do. Like, not a single idea. But we knew that we had a really good team and that we would figure things out.

So for the first quarter, we did some B2B back office processing SaaS-based product. We found some customers, but that project wasn't really scalable, so we decided to shut it down.

In that process, we talked to some people from Hotels.com and Expedia, and we ended up getting into the hotel space with them! We did some brainstorming in the industry and explored ideas around last minute booking.

And in that testing process, we realized people wanted to tell us their travel plans and have us book things for them. And then, since this was early 2016, we saw the trend of chatbots growing. So we decided to get into the chatbot hotel space.

What did you do before SnapTravel?

Before I founded SnapTravel, I worked at Google. And before Google, I ran a social mobile startup in Waterloo called UMentioned. It’s pretty big in the America South, in places like Salt Lake City, Georgia, Alabama, and Mississippi. It got around a couple million hits a day. Originally, I was going to work on that when I graduated, but unfortunately the app turned into more of a gossip hookup app and I wasn't sure why. So instead, I went to Google with the intent of being around smart people, constantly learning, and just being in the Valley. But ultimately, I left to run a startup.

Long story short, Google was a great company. But it's a big company. There was a lot of bureaucracy and I felt like I wasn't learning or being challenged enough.

So I decided to leave after working there for one year. But then during that year, while I was at Google, I met my co-founder Hussein Fazal. And we really clicked! We had common values, beliefs, and goals, and we actually worked together in the background bouncing around ideas for a good six months before I decided to quit and do SnapTravel full time.

During this process, did you ever think it was a big risk to quit Google and create a startup that might not succeed?

Yeah of course. But I mean, the big company is always going to be there. You could always get a nice job if you wanted to. And ultimately for me, I wanted to do what would make me happy.

You know, not to talk negatively about Google, but it just wasn't a good fit for me. It took me eight months before I shipped anything. And before that, I was used to shipping 2-3 times a week. So I felt like I wasn't being challenged enough. And to remain stagnant is to fall behind, so I had to do something about it. And plus — I didn’t actually feel too worried because the market's pretty good for engineers right now.

I guess I was lucky because I had the opportunity to work at both big companies and small companies. So the perspective definitely shows you what is a good fit for you and what you like. If I had never worked at Google, I can't definitively say that I don't like big companies. But now that I have, I can close that chapter of my life. With business as well, you do often see people who do two years in investment banking and then quit to do something else. So it’s good to get different perspectives.

Now that you have your own team, is there anything surprising about running a smaller company?

When you do this long enough, never's really surprising because everyday is a new surprise! Everyday something might be broken, or something else might not work, or something awesome might happen. And it becomes sort of fun.

You might get turned down by ten investors — but then one says yes. So really, you just never know what’s going to happen. And spontaneity is just the nature of being an entrepreneur and being able to take on things as they happen.

Do you think it’s an essential quality of an entrepreneur to be able to “take on” whatever comes at you?

It depends what you mean by take on! I think it’s very important to deal with ambiguity well, because you truly never know what's going to happen next. You don’t know what’s going to happen in a day, month, or year. You don’t know if this path's gonna work out or if this path isn’t. There is a lot of experimentation that goes on, and you never know if it’s going to succeed.

And you that have to be OK with that. You have to be OK with the fact that if you try 5 times, you’ll probably fail 4.5 times. And that’s totally fine!

In talking about failing, what are some of the mistakes that you've made?

Yep, one of my mistakes was that I didn't hire fast enough. Right now [this episode was in Februrary], we only had 5 engineers doing the work of a lot more. So we should have definitely been more aggressive in hiring.

I still haven’t fully finished succession planning either, in terms of getting people to take over if I wasn’t working — like if I was in vacation or something. I also think we can be much more aggressive in how we deploy capital resources to hit bigger growth goals. It is true that currently were doing very well. But we can do even better and be more aggressive.

Do you think those responsibilities fall on you, or should they be delegated to other people?

It really depends on the situation. It's kind of a cultural thing. A lot of the times, I think Canadian entrepreneurs aren't as aggressive as our American counterparts. And so for us, we always try to put on a Silicon Valley mindset. Even now, our company only supports USD. We message on a US number. Our funds are all in the US. So just having that mentality is really important.

What are some of these cultural differences between Canadian and American entrepreneurs?

A big part about Canadian entrepreneurs, and this is not our fault, is that we must be focussed on revenue and profitability. Because the funding opportunities aren’t as big. If your startup doesn’t make money, then you'll probably just run out of money and be out of business.

Whereas in America, you can still lose money (ie Snap, Uber, Amazon), and your company can still run for years.

Another difference of it is just the level of ambition. I’ve been fortunate enough to have worked with really great startups. I used to intern at LendUp when they were 10 people — now they’re over 150 people, and they’ve raised 200 million. Just seeing that growth and the passionate way the CEO speaks, it really drives home the vision and level of ambition that they have.

Obviously, it’s really hard to quantify, but ultimately, for Americans, the world is your oyster. But for Canadians, it sometimes feels like only Canada is your oyster.

Going back to your education, how did Waterloo impact your life?

I think Waterloo is an amazing school, and I definitely don’t regret it at all. They offer an amazing education, amazing co-op program, amazing entrepreneurial programs (ie Velocity), and a lot of my good friends are from there.

Some of the smartest entrepreneurs I've met are from Waterloo, and it's a great ecosystem. And also, look like their tuition. It's dirt cheap compared to Stanford or MIT. And you know I've worked with interns from Stanford and intends from Waterloo, and there is no difference. It's just an all-around amazing school.

Plus, the quality of the training is really high. I wouldn't say the education is useless in terms of curriculum, but a lot of that Waterloo comes down to the training, the work ethic, and the environment of people you meet — those were more impactful than my courses.

Why did you choose to double major in both economics and computer science?

I mean, I was still interested in learning how to run the business side of things. I looked at the courses available, and I realized, hey if I use all my electives to take courses in economics, I can get a major in that. So I was like, okay, why don't we just do that.

So I did that and it was okay. Econ has always been interesting, and I liked the way they teach you to think about things on the margins, like opportunity cost, and how people make decisions, and I found that really cool.

So for students choosing between business and tech, do you recommend that go to business school or that they study computer science instead?

In general, I think people should do what they like. It's really cliche but it's true, and I’m just lucky that what I do at work is also what I really enjoy.

And what I enjoyed just so happened to be software programming and building things.

But for a lot of people, that may not be the case. So I think that's the most important thing — whether it's computer science, UX design, product management, business, or whatever it is, the only way you can do something really well is to like it.

For tech, I think right now tech is a very hot space. But tech in 2017 is like investment banking in 2007. Things come and go.

And for most people, they have to really figure out why they’re truly doing a decision. So you start from there — asking yourself if you really like that industry, or if you’re just there because it’s a trend.

But in terms of the practical, yeah, it never hurts to have a computer science or STEM background. Obviously, it helps. But I definitely wouldn't do it just for the sake of doing it.

Again, only do it if you truly enjoy it. And if you don't, then there are other ways of being in tech. I have friends who have no computer science background, but they'll do product management or design or venture capital — you get the picture. There's no one way to get to your final destination. But I think it's more important to first figure out where you want to go and why you want to go there.

What is your favourite thing about being an entrepreneur?

For me, it’s just the freedom. You’re more or less the master of your own destiny, and that’s an amazing feeling. Whatever I do, directly impacts my life’s outcome. That's super exciting for me.

On top of that, every day is different! There are so many changes and different challenges that you never get bored of work.

If you had the chance to re-do your career, would you do anything differently?

I would’ve tried to have a more long-term perspective. A lot of times when you're young, especially if you have Asian parents, you can be myopic about what the future holds. Like oh, if I don't get into Harvard, my career is over.

Which is not true, because your career is a long time, and you need patience and persistence. For me, not going to Harvard was the best decision, because by going to Waterloo, I ended up not having students loans, making money from my co-op experiences, getting those internships through the Waterloo community, and generally having a great time. All at the fraction of the cost of Harvard. So having a long-term perspective is really important.

Any last comments?

At the end of the day, it’s most important that people do what they're truly passionate about. For me, I'm really fortunate that what I studied in college was what I liked, and it also happened to pay well.

So I was really fortunate. But that's not the case for everybody, and that's OK, because it's more important to find what you're passionate about, and follow that path, rather than falsely pursuing today’s hottest career field. Sure, it might be software today, but in the future it might be accounting, and then the next big thing might be medicine. So I really think it’s better to be chasing your own dreams than to chase what other people think your dreams should be. That's what I would take away from my experiences trying different startups and different companies.