Greg Isenberg is not a typical 25 year old.
While most 25 year olds stare at both a mountain of student debt and an uncertain future ahead, Greg Isenberg can already lay claim to having built and sold three successful companies. His most recent venture, the video concierge 5by, was recently picked up by StumbleUpon for an undisclosed amount. We spoke to Greg about taking gambles to pursue your dreams, what it’s like for Canadians in the Valley, and why he isn’t just sitting around drinking mojitos on a beach.
Can you talk about the first trip you took down to the Valley?
I always knew the Valley was a special place after hearing about all the companies that are based here. So when I was 18 or 19, I decided to visit for a couple weeks. I had no agenda besides learning a bit about how things go down here and meeting people.
Time in the Valley is on a different metric than time in Montreal or Toronto. People are made or broken so quickly here, and the excitement that creates is what drew me here.
Can you talk specifically about 5By and the sale of 5By.
The goal with 5by was to solve the “what to watch” question. Entertainment is meant to be effortless, it’s meant to be laid-back, and it’s meant to be easy. I found that I wanted to press one button and watch funny videos, or another button and watch the best entrepreneur videos, or press yet another button and watch the best design videos. There wasn’t a place where you could do that in a simple and beautiful way.
And so that’s the essence of 5by.
It started off as a project between myself and some friends, and then, when online video started exploding, we quickly realized the potential the platform had. People don’t have the time to go through and sort all their videos. We started in Montreal, and within 11 months of starting the company we sold it to StumbleUpon.
Do you still think Montreal is the best city to build a minimum viable product?
Yeah, but when I say Montreal I mean any city that’s not New York, San Francisco or London. It’s the same with Toronto. Relatively speaking, in Toronto you can build a startup for a lot less. A million dollars of seed funding lasts two, three or four times longer in Toronto than it does in the Valley. That allows you to make more mistakes. You can also try a bunch of different things, be more aggressive, and then once you have gotten a key insight around a particular product, you can decide to branch out and get a U.S. office. That’s the reason Canada is so well positioned to be creating way more startups.
We’re like the farm team, basically.
Yeah, that’s exactly what it is. It’s the farm team of startups. I think the government is really starting to get that with what they’re doing with the tax benefits, the SR&ED credits and all that jazz.
I’m bullish, but I think what Canada needs is to do is build a bridge between the Valley and the rest of the country. I feel like sometimes they have these one off events in Canada where they’ll bring in a bunch of people, but they feel forced and ineffective for me. More people in the Valley need to have an invested interest in Canada.
How do you think the government can get that going?
I have some ideas. For instance, why not get a private jet and then every month put a bunch of the most prolific American entrepreneurs on a plane and fly them to Waterloo for a great dinner with a celebrity chef? You can start with Waterloo and then show them Calgary and Vancouver. They need to see our ecosystem first hand to really get a feel for it.
As Canadians, we often have trouble because we’re too humble. We’re too nice. I think we’ve got to be a bit more aggressive and decide how we want to position this country from a technology standpoint.
What big opportunities do you see for Canadian entrepreneurs in the near future?
I think we need to be really, really aggressive when it comes to product development. A lot of people build products that are one notch better than their competition and the company that built that product becomes a billion dollar one. What Canadians can do, maybe even better than people in the Valley, is reimagine what something can look like.
For someone debating a move down to the Valley, what’s one thing they’ve probably never thought of that you think they should know?
First of all, although you can penetrate the cool kids scene, there are still a lot of cliques. I was talking to a guy today and he said that he thought coming to the Valley meant he wouldn’t find an old boys club here, but he quickly realized that there are there are tight knit groups here and it’s hard to break into them.
At the end of the day, if you’re not trying to speak to those people, then there’s no reason to be here. If you’re spending 3k a month on a one bedroom apartment, you might as well go back to Toronto. My advice to those people is, first of all, getting into those groups is not going to happen overnight. It’s something that you have to invest in. Don’t look at a move here as a two month thing. Look at it like a two year thing, or a ten year thing. You really have to put in the effort. You’re not going to become best friends with people overnight, it just doesn’t happen.
You’ve already accomplished a tonne at a young age, what motivates you to keep going?
What I love about this place is that the guy living next door to me has sold his company for a couple hundred million dollars, and another one of my neighbours is about to take his company public. The bar is so high that I don’t feel like I’m killing it.
I think we still have a lot to figure out with 5by. I mean, we want to make it the de facto way for people find the best videos on the Internet. Until then, there’s still a lot of work to be done. I don’t know if I’ll ever really be satisfied, to be honest.
But I love the journey and the process.
What are your favourite productivity tools?
I’m obsessed with productivity and so I’ve gone back to something very simple: pen and paper. Literally writing, “What are the three things I want to do today?” and not leaving work until I scratch the last one off the list. Also, instead of bringing a laptop or iPad to meetings—because find I get distracted by them—I bring a pen and paper.
Are you currently reading anything or have you read anything recently that you really enjoyed?
I just picked up The Hard Thing About Hard Things by Ben Horowitz. I don’t really enjoy—the last business book I read was probably Lean Analytics—but I am looking forward to getting into this one.
What do you think you’d be doing if you weren’t doing what you were doing now?
I’m so consumed with this that I can’t even think about anything else to be honest. Once we’ve achieved success here, whatever that looks like, then who knows? We’ll see.
This interview has been edited and condensed.
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Christian Borys is a contributor to Toronto Standard. Follow him on Twitter.
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