Saturday, January 9, 2010

Harley Finkelstein, Serial Entrepreneur Interview

A couple of weeks ago I met a 26 year-old serial entrepreneur with the attributes that I believe exemplify what it takes for the new generation, and the rest of us, to succeed in this new economy and new world. He recently completed a law degree and MBA at the University of Ottawa, and has a ‘day job’ practicing law with a leading corporate law firm in Toronto.

Marty: Welcome to Startup Professionals interviews. Tell us about your entrepreneurial activities.

Harley: In 2002, as a first year undergrad at McGill University, I launched my first start-up, Finkinc, which today is considered to be a leader in the collegiate apparel & promotional products market. With the success of my first business I began investing in other startups when I entered law school, and we built a model whereby we provide micro funding (equity-side) and strong mentorship to startups, with a primary focus on student entrepreneurs. Our latest startup is, an online t-shirt shop that sells exclusive licensed t-shirts such as the Rolling Stones, Batman, the Transformers and David Bowie.

Marty: When did you know that you were destined to be an entrepreneur?

Harley: When I was about 11 years old I recall building an office in my family’s garage where I could take (mock) phone calls, meet (fake) clients, and sell my proverbial widgets. I guess that’s when I realized that I liked the idea of being in ‘business’ (albeit at the time I don’t think I had any idea what that really meant). However, I think I realized my passion for entrepreneurship when I launched Finkinc in 2002. The catalyst for starting the company was simple: I needed to support myself and afford rent, tuition, and all of my other necessary living expenses.

My passion was further substantiated when things didn’t initially go very well with our venture, and bills were starting to pile up. It was rather eye-opening that despite losing money I loved what I was doing with our businesses, and this passion for the ‘journey’ rather than for the ‘destination’ was all I needed to get hooked on entrepreneurship. For the first eighteen months I played the role of CEO, bookkeeper, receptionist, production manager and janitor, and despite my lack of interest in having to calculate sales tax or ‘schlepping’ boxes to the post office, I woke up every day engaged, impassioned and in love.

Marty: What’s the most challenging aspect of being an entrepreneur these days from your perspective?

Harley: For me, the most challenging aspect of being an entrepreneur these days is the diminution of barriers to entry (ironically, this is also something I find to be really exciting).
With the emergence of e-Commerce, entrepreneurs can now open an online retailer in a matter of minutes and have a third party handle shipping, inventory and even billing.

While it may be true that most unqualified sites will likely fail soon after launch, the ability to even compete with established E-tailers (even if it’s only for a matter of days) is something that was impossible ten years ago. The flip side of this challenge is that this innovation-evolution has allowed one of our newest startups,, to make some real waves in the Canadian t-shirt industry, and we’re now competing head to head with some of the most established brick and mortar retailers in the country.

Marty: What is a key personal attribute you see in the new generation of entrepreneurs?

Harley: I think it’s our generation’s technological curiosity and our natural (or second nature) understanding of IT. The days of saying ‘I don’t have to ever learn that’ or ‘I have an IT guy for that’ are long over. Having grown up concurrently with the materialization of the internet, today most young entrepreneurs understand far more about the nuts and bolts of their business’ technology than past vintages of entrepreneurs (generally).

The second key attribute is little more complicated. There has also been a (positive) shift away from the ‘Gordon Gekko’ paradigm and model of success, and I think that young entrepreneurs today have a strong understanding that business is not just about dollars and cents, but about building value for themselves, their investors, their community, and even their society. I believe that today’s young entrepreneurs understand that it’s less about ‘kill or be killed’, and more about innovation and making the lives of their customers better…sorry Gordo.

Marty: Any advice you would like to give to someone contemplating a startup?

  • Go out there and just do it.
  • Find strong mentors to emulate, and build yourself an advisory board (even an informal one) to help vet new ideas and plan your strategy.
  • Talk to everyone and never be afraid to ask questions.
  • Set clear goals and deadlines for yourself, and while perseverance is crucial, know when to cut your losses and move on.
  • Finally, the more sh*t you throw on the wall, the more that has the potential to stick… even if that means getting a little dirty, so shoot the puck!
Marty: Harley, thank you very much for your insights and your role-model leadership for all of us! You can find out more about Harley’s entrepreneurial activities or contact him directly through his business site SuperAngel.

Marty Zwilling



  1. What keeps entrepreneur going when everything going down?

  2. Thanks for the post....can someone elaborate me the terms "licesnced t-shirt" ....

  3. Thanks for the comments - Licensed shirts have logos that we print with the authorized permission and guidance of the owner of the intellectual property.

    have a look at our site @

  4. Many scientists with promising inventions dream of launching “the next Microsoft” and reaping huge financial benefits.

  5. Build a business is an easy part. The hardest is to make your business profit and open a job opportunity. That is what entrrpreuners do.

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