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The Essense of Being an Irrepressible Entrepreneur

February 11, 2007 by Ben Yoskovitz

Greg Balanko-Dickson is writing a new book about the irrepressible entrepreneur.

In his brief book overview he asks for people to participate – and one way is for Greg to do an interview with you via phone or email. I asked Greg to send me the questions so I could take a crack at them.

Be careful what you wish for! I suppose I shouldn’t be surprised that Greg asked big, big questions…so here goes.

1) What has been your greatest challenge in business to date, how did you cope with it, and what did you learn?

My biggest single challenge was firing people when I couldn’t afford to pay them. I also consider it my biggest failure. It was a very difficult thing to do, and although it was many years ago, I remember it clearly. I coped by working to separate my feelings of disappointment and frustration and my personal emotions from the business. I was running a business. The business wasn’t doing well (it was during the dot-com bubble burst) and I had no choice. I had two choices: reduce costs (and salaries are always your biggest cost) or fold up shop. I chose to fight another day.

2) When you think of the word entrepreneurship, what does it mean to you?

  • Starting companies from scratch.
  • Passion.
  • Going for it. Trying to hit home runs every single day.
  • Fun.
  • Challenging.
  • Different. You’re an entrepreneur, you’re different. You stand out.
  • A way of life.

3) What has been you greatest success in the last 30 days? Why is it so significant to you?

My greatest success in the last 30 days has been the continued growth of my network with an incredible number of amazing people. I’ve had phone conversations with people I’ve met through the blogosphere. I’ve met new people in-person that rock. I’ve started a Montreal Technology Entrepreneur Breakfast Meetup.

One of my biggest mistakes over the years was not networking enough in my own backyard. That’s changed a great deal in the last 30 days. It’s important because you will succeed in large part due to the power, resourcefulness and extent of your network. And while I can’t say enough about my online network of friends and contacts, there’s nothing that truly replaces meeting face-to-face with someone.

4) When you started your business, what do you wish you had known that you now know? How might things have been different had you known?

Success doesn’t come to you. You have to go out and grab it by the proverbial you-know-whats. That means always looking for opportunities. Turn everything into an opportunity. Find the angle. Make the connection. If you’re selling a blue box and everyone wants red boxes, find a new way of doing it. Either find a new market for your blue boxes, or paint them red, or do something. Success doesn’t just fall in your lap.

But for me, the question is really, “What did you know, but failed to realize was so incredibly important?”

Here are a few:

  1. You can’t carry lousy business partners on your back and succeed in spite of them.
  2. You need to develop a personal brand for yourself. You might not be THE business (it’s helpful if a business can succeed without you) but developing a strong personal brand helps.
  3. You can’t do everything. Find a way to outsource. And related to that, run a lean, mean organization. Stay organized.

5) When you look ahead at the world of entrepreneurship, what do you see, what concerns you, what excites you? And why?

In the technology world there are a few things going on right now that will continue. Namely, it’s getting easier to start new companies, ramp up quickly, launch quickly and do it inexpensively. It’s getting easier because technology is improving and more accessible, not because there’s some magic pill you can take to become a super entrepreneur.

I see more young people getting into entrepreneurship, which is great – although this is something we need to work harder at. They should be teaching entrepreneurship in highschool.

I see more angel investment going into very early stage startups. Examples like TechStars and Y Combinator are great; they show us that you can invest small amounts, bring in lots of expertise and help a couple of guys in a garage make something happen.

My concern with the most recent boom is that we get stupid again. Things are cyclical after all, and there are plenty of younger entrepreneurs that don’t remember the dot-com crash. Heck, there are plenty of people who lived through it that don’t remember it either. Money is being invested more smartly, and less of it is being tossed around, but nevertheless, I’d hate to see another dot-com fiasco with a rat-race of stupid ideas getting millions of dollars to go nowhere.

Filed Under: Entrepreneurship

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Ben Yoskovitz

Founding Partner at Highline Beta, a hybrid venture studio and VC firm that works with large, ambitious companies to identify new areas of opportunity through internal and external innovation.

Previously I was VP Product at VarageSale and GoInstant (acq. $CRM), and Founding Partner at Year One Labs.

Angel investments include: Breather, Spoiler Alert, SendWithUs and others.

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