Exclusive Interview with Daniel Debow

A Canadian entrepreneur speaks about his climb to wealth, success, and his newest venture: Rypple

By: Varun Sharma, Staff Writer

Stressed out with the tough job market? Daniel Debow isn’t; a 37-year-old startup entrepreneur in Toronto can’t even think about having a regular job.  He’s very busy working away at Rypple, his latest project that looks to revolutionize the way traditional feedback processes in companies are done.  I had a chance to interview the man himself to explore the life of a successful entrepreneur.

As Debow grew up in Toronto, he took the initiative to do things a little different than most of us.  A big fan of music himself and an avid bass player, he started by organizing rock concerts for students at his high school.  He claims that his choice to continuously remain involved in extra curricular activities, coupled with inspiration from his entrepreneurial grandfather and brother gave him the opportunities and ambition to reach his success.

Debow claims that he isn’t some born-businessman “with a lemonade stand when they’re 14, and a hundred grand walking out of high school.”  Instead he says that he “just fell into it.”

Before beginning his adventures as an entrepreneur, Debow worked as an Investment Banker at Goldman Sachs and as an intern at a very prestigious law firm. But a set path to success and a lot of money isn’t exciting enough for Debow, who claims he enjoys the randomness that comes hand in hand with being an entrepreneur.  Although “there’s tons of risk that can be very stressful and nerve-racking,” says Debow, “it’s very exciting and interesting.”  It seems only natural that this Eric Clapton fan would use business as a forum to express his creativity.

Unlike our most revered entrepreneurs, Debow has a whole lot of formal education under his belt – featuring an LLM in Law, Science & Technology from Stanford to a JD/MBA from University of Toronto. Although Debow admits, “it can be a detriment quite frankly,” he also says that it can be a host of opportunities to develop personal and business relationships coupled with a brand that helps you segue into the business world.  “There’s no way I would have the opportunity to do some of the summer jobs I did or the job that became the first job I took after business school, which was helping to start Workbrain.”

So what is Workbrain?  Well if you’ve ever worked behind the scenes at a Walmart or AMC then you must’ve signed in your shift by swiping your card through a machine that clocks you in and clocks you out.  This fundamentally simple idea helps companies save millions in wages and was sold to Infor for an astounding $227 million dollars. Workbrain’s founder David Ossip happened to be Debow’s old babysitter and asked him to help him write the business plan when he was doing his MBA.  What Daniel thought “would be a great way to keep [him]self occupied” took off into a series of different roles comprising of Director of Operations, VP Marketing and VP Corporate Development, exponentially increasing Debow’s breadth of experience.

Debow believes that it wasn’t his ‘skillset’ that helped him succeed across a range of different roles, but moreover his ability to be a creative problem-solver. Debow says, “I guess I was figuring out stuff and my CEO didn’t have to worry about it, it would just be like alright I’ll make it happen.” Which is why Debow complains, “I don’t need extra people to tell me that we have problems,” what he does need is someone to identify the problem and then go solve it – “the people you want to hire all day long.”

Interestingly enough, one of Debow’s biggest successes at Workbrain was firing people. While we all cringe at the sound of Trump’s “You’re Fired!”, Debow claims that it was one of the most important things for him to learn in his career.

“Its better for the organization, especially startup, to find people in the right spot, sometimes people come in and they’re not the right fit. So I did some of those difficult things early on, which helps out at the core of our business.”

Another notable success for Debow was leading the sale of Workbrain for a very tidy sum. Although negotiating a merger is inherently complicated, the hardest part of it all was balancing “the fact that you’re trying to sell the company while you’re trying to run the company.” This problem ranges beyond the perils of multi-tasking and requires exceptional management in its purest form, as the situation becomes “demoralizing for the people internally and figuring out how to get that right balance in employees is hard”.

The successful sale of Workbrain, marked the beginning of a new venture by the name of Rypple. Co-Founders and CEO’s Debow and friend David Stein saw the market trending towards evolving and simplifying employee feedback and took it head on, afraid of ending up in “regular jobs”.

Do you remember the last time you heard someone complain about the dreaded performance reviews or the lack of feedback at work? Rypple aims to change the way feedback is done by introducing traditional performance review systems to social media. For employees, this combination of social and public feedback is the optimal combination of receiving feedback and increasing reputation to advance in their career. For employers, this results in more informed and thus, happy workers, a transparent process to reward and retain high performance employees and identify the bad apples.

So Rypple came about “to make social goals, social feedback, social coaching… in a very lightweight fun environment.” Rypple is also a dynamically different product with an untraditional team featuring game designers. While keeping in mind that Rypple is just barely 3 years old, it is already hosting customers among the likes of Mozilla and Accenture.  Referring to the significance of securing Mozilla, Debow says, “It’s really important early on to work with visionary customers who embrace your idea and who can help you learn what the market demands.”

After winning HR Executive’s Top 10 products of 2010, what is the next step for Rypple? Three simple words sum Debow’s game plan, “Scale it up”.

Daniel Debow continues to be one of the most successful Canadian entrepreneurs of our time and after the success of Workbrain much is expected from his current project Rypple. Debow started his entrepreneurial career by organizing rock concerts for students in high school and ended up organizing and leading multi-million dollar negotiations. For all of us who aspire to become the next success story – Debow’s advice? Take your work seriously, but don’t take yourself too seriously.

ARB Team
Arbitrage Magazine
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