Startup Grind Montreal hosts Greg Isenberg - Summary

At 24, Greg Isenberg is both a veteran of the startup world and just getting started.

The native Montrealer started off selling products online while in high school. He then founded a marketing agency that created and implemented strategies for the likes of WordPress, TechCrunch, FedEx, and Microsoft and helped build the popular stock market simulator Wall Street Exchange. 5by, the “video concierge” service that makes recommendations based on your mood and Isenberg’s most recent creation, was acquired by StumbleUpon in September 2013, 11 months after its launch. Currently the CEO of 5by and a Venture Partner at Good People Ventures, he shared the lessons he learned along the way at Montreal’s inaugural Startup Grind event.

In his early days, Isenberg had to make his own job. He admits that “people didn’t trust a lanky 18 year old kid, they wanted someone in a suit.” He decided to build a social media agency if he couldn’t join one. This approach, Isenberg suggests, makes sense when you can research most topics online instead of spending years in class.

While you can learn a lot on your own, Isenberg emphasizes the importance of having the right people around you. He concedes that it is hard work to get an advisor in the area you want. You have to figure out how to be the kind of friend your advisor would want and get into their circle. Isenberg believes finding a co-founder should be taken as seriously as securing mentors: “You’re embarking on a marriage, it’s going to be a tough ride." One simple method for assessing potential co-founders, he says, is to choose only those you would feel comfortable getting a beer with at 3 a.m. The same goes for building a team, where he advocates prioritizing good people over connected people over smart people. If there is a common thread running through everything that Isenberg had to say, it is that people matter: “The people who matter to you have to support what you’re doing,” he says. “If they don’t it’s an added pressure.”

Isenberg doesn’t underestimate how hard the startup world can be. He describes it as “an uphill battle, Everest to the eight power.” You have to be prepared to make fifty cold calls a day and be rejected by almost everyone. You have to be prepared for every idea you suggest to be met with “why won’t Google do that?” or other skeptical reactions. With regards to the Google question, Isenberg suggests responding that Google should do what you are doing but simply has too much going on. In fact, if Google wouldn’t try to enter your space, he suggests that you are probably doing something wrong. When it comes to dealing with more general setbacks, Isenberg stresses the importance of giving yourself regular doses of inspiration to get through the process. Surrounding yourself with smart people, some of whom make you feel small, also helps you stay motivated. Isenberg admits that it may be intimidating to be surrounded by people who are better funded but urges anyone who is shy to realize that they are all basically the same.

When you listen to Greg Isenberg talk about it, pitching sounds like the full-time job that it is. A quarter of the words that come out of your mouth when pitching have to be “great”, he says. Or maybe 30%. He suggests that founders waste all their bad pitches on relatives and other people who won’t impact their businesses. The easiest part, according to Isenberg, is knowing when you have an idea worth pursuing: “If you’re always thinking about it, chances are that’s the idea you want to go with.”

When it comes to the future, Isenberg is both optimistic and cognizant that there are always hurdles ahead. 5by has experienced a rapid rise. It had multiple suitors within four months of its launch (“Once you have one company interested, it’s really easy to get others.”) and was acquired by StumbleUpon in September. Isenberg is now working to keep 5by’s startup culture as it grows. He says the acquisition will allow 5by to access more eyeballs, which, for a service that aspires to be on every sort of screen, is crucial. The future holds potential obstacles but, as Isenberg’s experience reveals, that is the basic reality of running even the most successful of startups.

Startup Grind Montreal would like to thank Greg Isenberg for his participation, Busbud for offering their offices as a venue, Ernst and Young Canada, Uber and The Sparrow for their sponsorship, The Panda Attack and Raquel Pearl for performing at the after party, and the volunteers who made the event possible.