Dave Sinkinson on the startup mindset—is it in you?

For this week’s MVP, we’re chatting with Dave Sinkinson.

Lots of us have a great business idea, but how many of us could actually run a business? More than you might think actually, says Dave Sinkinson, younger sibling to Chris and one half of the brother duo behind Startup Different. The business-book-plus-podcast is their current project. The serial entrepreneurs are dedicated to bootstrapping others’ startups to be as successful as theirs: the Sinkinsons’ on-campus safety app, AppArmor, which Dave started as an MBA student and sold for $40 million in 2022. 

We chatted with the young Toronto-based business-starter about where he got his gusto, why he walked away and what’s next. Hint: It’s the last thing you’d expect and perfect if you stink after the gym.

You did an MBA at Queen’s University. Did you always want to become an entrepreneur? 

My dad had a photocopier business and my brother Chris, who’s 10 years older than me, had been doing his own startups for years. I watched them and very much wanted to do my own business, but I realized that I lacked the technical capabilities to actually build the thing. I went to Chris and asked, “How can we work together?” Chris and I probably had like five or six different products on the go—until one took off.

Would that be AppArmor? Tell me about it and where the idea came from. 

While at Queen’s, I saw that the school, like basically all colleges and universities in North America, had these blue light emergency poles to call campus police. They cost about $10,000 a pole and were notorious for breaking down. At Queen’s, we did an audit and found a bunch of them weren’t working so I pitched the school an idea of a mobile app that could call security instead. It was super basic, but it evolved so your location could be sent to security in real time. We added mass notifications, so if there was an emergency on campus, people could receive alerts. 

By the end of my time, the app had 50-odd features. But it wasn’t a single app; it was hundreds of custom-branded apps for various institutions. At NYU, it was SafeNYU; At Queens, it was Secure; at York, it was YorkU Safety, and so on. 

Sounds like you could have rode that out forever. Why did you jump ship? 

We had a bit of what’s called a “WFIO” moment—that’s “we’re f—ked, it’s over.” The idea comes from Ben Horowitz’s book, The Hard Thing About Hard Things. Our WFIO was COVID-19, because our business was about people congregating. Luckily, we had longer-term contracts and a development team, so we ended up building a new module that tracked whether people had been in contact with somebody who had the virus. When vaccines started coming out, we had shot verification tools. 

It was a difficult time, and we’d been figuratively sprinting for a while. I started to burn out. The options became: scaling up to try and go to the next level or selling and cashing in my chips. It was a hard decision, but I’m really happy with what we chose.

In entrepreneurship, you don’t get that many opportunities to just lock in a win, so we took it. 

And now you’re back to the drawing board. What’s next? 

I’ve launched a new product. It’s very silly, but super fun. It’s a physical product called Manshowr, a $3-dollar single-use body-sized wipe in a sachet. You throw it in your gym bag or with your camping stuff or in your car, so when you don’t have access to water or you don’t have time to have a shower, you can have a Manshowr. 

I’m definitely starting over by literally walking into gyms here in Toronto to say, “Hey, can I leave this here? Can I sell these wipes? I’ll be back in a couple of weeks and you let me know how it goes.” 

I wanted to do something totally different, so it’s fun. I am a little bit worried though, because I know it’s going to take up a lot of my time and focus and energy.

Is work-life balance a challenge for you? 

Absolutely. I have two young kids right now and I want to make sure I’m physically and mentally present when I’m around them. But I need to be doing something. 

Not that I was doing nothing after the exit, but I was doing much less than before, and I felt unhappy. I really struggled with questions like, “Who am I? What am I doing?” 

I’ve learned I need to be busy to feel a sense of purpose; this is just who I am. I’m balancing this OK right now. Sometimes my wife or other people would say, “You seem insanely stressed.” And I had no idea. That’s when I know I better rein it in a bit and take my foot off the gas pedal for a minute.

What advice would you give to someone who is considering launching a business? Does everybody have it in them? 

No, I don’t think everybody has it in them. Not because I think entrepreneurs are exceptional, I just think it’s a combination of different personality types and different obligations in your life. 

Some people are more motivated to climb the corporate ladder than to solve a problem. But I do think you can definitely become an entrepreneur if you’re so inclined by learning the skills and strategies. It’s just very challenging for some, whereas for others, it comes very naturally. 

As for a tip, I’d say one way to tell if you’ve got entrepreneurism in you or not is by asking, “Are you willing to try? To put yourself out there and maybe feel really stupid?” I know I’m gonna walk into those gyms and feel pretty dumb. I know I’m going to get shut down sometimes. I’m cool with that and I’m still willing to try. You have to be willing to put yourself out there.