Q&A: Daniel Debow, the tech innovator who hit the jackpot—twice

Rypple purports to bring the performance review into the social media age. Employees can receive recognition on a Facebook-style wall and ask for feedback via private messages. What was wrong with the traditional, pen-and-paper performance review?
What was right with it? It’s slow, inefficient and way too formal. Rypple makes feedback fun and social, and it reaches an employee right away, rather than six months after the fact. It uses real lang­uage, too. No one says, “You exhibited the com­petencies of leadership and decisiveness.” They say, “You were a rock star. You kicked ass on that deal.”

Rypple users can give each other badges that say “You’re #1!” and “Thumbs up,” which seems goofy. Do people really crave that kind of hyper-positivity at work?
Yes! People aren’t robots. Recognition means a lot. People care a lot about money, of course, but once they reach a certain compensation level, salary ceases to be a significant motivator. Coaching, recognition and relationships with management matter more.

In 2007, you were part of the team behind Workbrain, a workforce management company started by David Ossip and David Stein, and you just sold Rypple, which you started with Stein, for $65 million. What do you know that the rest of us don’t?
Nothing. I’m just willing to take some crazy risks and fail a lot along the way.

Rotman dean Roger Martin, philanth­ropist Seymour Schulich, PayPal foun­der Peter Thiel and others kicked in $13 mill­ion in seed money for Rypple. What’s your secret to getting people to part with their cash?
Courting investors is like dating. You’d never ask someone to marry you on the first date. My business partners and I didn’t show up and say, “Here’s our pitch. Give us a million dollars.” Instead, we developed relationships with smart, thoughtful people. When the time came, we knew people who’d be able to help us.

How did you celebrate the sale of Rypple?
I bought an Audi S4. I crashed my Mini, and the Audi has a little more crumple zone. I just hope it’s not a jerkmobile.

Does it have racing stripes or a spoiler?
No, none of that.

Then you’re okay. You completed a law degree and an MBA at the University of Toronto simultaneously—graduating first in your class—and then did another law degree at Stanford just for kicks.
Do you ever slack off?
Oh, totally. I’m completely lazy, messy and absent-minded. I regularly get in trouble with my wife for forgetting to pay bills and parking tickets, and I’ve had my credit card cancelled more times than a responsible person should.

Your credentials as a trend spotter are pretty solid. What’s the next big thing?
Talking to your computer. When you consider the advances in voice recognition and artificial intelligence, and you see what Siri—the assistant that’s built into the iPhone—can do today, imagine what Siri will be able to do in four generations.

Isn’t that how Terminator 3: Rise of the Machines starts?
I’m not saying machines are going to start thinking for themselves. But I am thinking about the way Scotty talks to the computer on Star Trek. That’s not as far off as people think.

Salesforce, the San Francisco–based tech company that bought Rypple, hired you as a vice-president. Why did you choose to stay in Toronto?
It’s home. It’s got great restaurants, theatre and music. My friends are here. That said, I love California. Everyone there is drunk on the future and always trying to reinvent it. We could do with more of that optimistic spirit here.