Rachel (00:00)
Welcome to Simple Chats by Simple Ventures, the place where we explore insightful ideas and startup journeys with members of the Canadian tech and business community. Today, we're chatting with Mike Stern, former co-founder and leader of Connected, a leading product innovation and software delivery firm that was acquired for nine figures by ThoughtWorks in 2022. Thanks so much for joining us, Mike. Thrilled to have you.

Mike Stern (00:23)
Thank you for having me.

Rachel (00:25)
So maybe we can kick off to just learn about you. Tell us about your backstory.

Mike Stern (00:30)
Okay, where do I begin? I am from Toronto, born and raised. I have a mixed family background. So my mom came to Canada when she was 19 from Venezuela. My dad's family is from Russia and Poland. They came to Winnipeg first and then to Toronto. And so we've got a mixed bag in my family in terms of nationalities, religions, languages…

What better place than Toronto to experience that kind of childhood? But really I was always in an intersection. I felt a little bit like a misfit without feeling like a sort of permanent and singular home. But I think that informed a lot in terms of what I did later on. And it gave me just this sort of permission to be interested in all sorts of different things — whether that was business, curiosities, sports, arts, etc.

Rachel (01:21)
And let's double-click there on permission to be interested in all sorts of things. What's something interesting that most people wouldn't know you've dove into?

Mike Stern (01:30)
When I was in grade two, the first business that I started was performing magic shows for my friends at their birthdays. And the compensation came in the form of extra loot bags that were put over afterwards.

Rachel (01:47)
So the key question is, are you still taking clients for anyone listening?

Mike Stern (01:52)
Yeah, my wife just asked me that question this morning for our daughter's upcoming birthday next week.

Rachel (01:58)
That's fantastic. So from grade two magic shows to poli-sci — you were a poli-sci major at school. Can you tell us about that? What was that choice and then how did you progress from there into your career?

Mike Stern (02:09)
Yeah, so at McGill, I majored in poli sci, minored in econ. I took all sorts of other interesting courses at McGill. I ran a sort of glorified party promotion business, which was probably business number three for me and probably learned just as much doing that than what I learned in school. And that McGill story is really just a continuation of what I experienced when I was young — being exposed to different cultures, different interests.

McGill and Montreal was just this amazing platform. And while poli sci wasn't something that I wanted to really pursue into a career, it was an amazing foundation of history and philosophy and let me create a bit of a bedrock of different ways of thinking that I think were helpful for later on.

Rachel (03:00)
So how did you go from school into your career? What was that transition? How did you start and eventually land in founding your company Connected?

Mike Stern (03:08)
Definitely a circuitous path and in hindsight, probably still doesn't even make that much sense. It certainly didn't feel like it made sense during. But right after school, I joined a company called Blyth Education. Sam Blyth hired me on to help him disrupt K–12 education, starting with the OAC credit. We sent thousands of kids abroad to do OAC credits, but in a much more novel way than in a typical classroom.

We'd send students to Oxford, England to learn English or the Galapagos Islands to learn biology. We also built local schools in Toronto, more at a mid-market price for struggling students who couldn't afford to go to private schools but still wanted to have their best shot at great universities.

From there, I went to BlackBerry’s venture fund. It was a lot of fun — I got to download and test all the new apps and recommend the ones we loved, then support those developer teams. After that, I joined Xtreme Labs — amazing little company at the time, I think I was the 10th employee. Led by Farhan Thawar, Amar Varma and Sunny Madra. We were really at the very beginning of the mobile app wave.

You name it — we helped build some of the most recognizable and ubiquitous mobile apps: Uber, Twitter, helped with Facebook going mobile. We had lots of fun scaling that business. A key takeaway was learning how to scale world-class engineering teams in Toronto, concentrating talent downtown when everyone else was in the suburbs. That was novel.

After Xtreme was acquired by Pivotal, I wanted to build kind of the 2.0 of Xtreme. That became Connected. Mobile apps were becoming more important — but also more complicated. We were going from a single app connected to the cloud to an entire ecosystem — multiple clouds, hardware, edge devices, etc. Connected was born to help large, ambitious tech organizations deliver new connected products.

Our most famous projects were helping Peloton bring their first and second generation bikes to market. We also helped conceive and deliver the Facebook Portal product. Probably three or four dozen other major consumer products. We got really lucky with the right people and clients at the right time — all bootstrapped.

I remember getting the email from our first client — a team building a connected lacrosse stick — and in that instant we were off: booked our trip to San Francisco, started doing user interviews and hardware research. From nothing to something — true zero to one — in a few weeks, without outside capital.

Rachel (08:17)
That urgency and fighting for survival is something I’ve seen in a lot of great founders. Sounds like your “two to three week” zero to one period could take others six months. When you evaluate founders now, what traits do you look for?

Mike Stern (08:45)
The biggest one is urgency. Speed. Founders need to move incredibly fast. Yes, intelligence and experience are great, but what separates the best is urgency — grit, determination, moving quickly despite rejections. It’s the single most important quality I’ve seen in the best founding teams, including our own.

Rachel (09:55)
That really resonates. But is urgency just for the zero to one phase? Or does it remain important as the business grows?

Mike Stern (10:15)
Good question. I’d say it’s unfair to treat urgency as the only thing that matters. As we grew Connected over 8+ years, we had to combine that urgency with thoughtfulness. There were many moments where we reevaluated our core assumptions. So yes — urgency matters throughout, but you also need strategic thinking and deliberate decision-making.

Rachel (11:06)
You built a huge business and rooted it in Canada. Why stay here? What made Canada fertile ground for what you were building?

Mike Stern (11:25)
It wasn’t always easy or obvious. Most of our clients were in the U.S. — the most ambitious clients. But Canada, and Toronto in particular, was the best place to build our team. Talent density is amazing. There’s an “ambition problem” here, but it’s solvable. I learned at Xtreme Labs that you can build big ambition into young Canadian talent — and that becomes a strategic advantage.

Toronto also gave us a diverse, cosmopolitan testing ground for global consumer products. Not easy, but we couldn’t have built Connected anywhere else. I wouldn’t have done it differently.

Rachel (13:09)
That idea of building a Canadian team but serving global clients is powerful. As you know, Simple is relentlessly focused on building great Canadian HQ’d businesses with global impact. We’re lucky to have you involved. What made you want to support our mission?

Mike Stern (13:43)
I’m grateful to be an LP and help however I can. Three reasons: First, the Simple Ventures model is unlike anything I’ve seen before. It’s truly novel in Canada. Second, the team — you, Mike, and everyone involved — is world-class. Inspiring and ambitious. Third, the rigor with which you validate ideas, kill bad ones, promote good ones… I haven’t seen that product mindset since our early Connected days. I love it. Founders coming to Simple benefit enormously from that engine in the background.

Rachel (15:03)
Thank you for all of that reflection. Super appreciated — and energizing to have you involved.

Mike Stern (15:10)
Thank you. Thanks for having me.