The Jack Dorsey Guide to Entrepreneur Success (in 140 Characters or Less)

Jack Dorsey had his first visit to Toronto last week as the guest speaker for C100’s accelerateTO.

Held at the new Mattamy Athletic Centre formally the Maple Leaf Gardens, the event couldn’t have had a more Canadian backdrop. Dorsey was there for an interactive interview with Chris Albinson, Co-Founder of the C100 and Tweets from the crowd and those watching the live stream.

Dorsey, of course, requires no introduction—he is the man behind two of the most successful tech startups from Silicon Valley. A little communication tool you made have heard of called Twitter (now said to be valued at $16 billion as it heads into IPO) and a mobile payment company called Square which is doing $15 billion in transactions annually and is set to open its first Canadian office in Kitchener-Waterloo in 2014.

Dorsey took the stage with a calm confidence carrying a mug of hot water (he’s not a huge fan of coffee). He sat down and told the sold-out 750-person crowd the story behind his success and how he never intentionally sought to be an entrepreneur.

Yet you could say that entrepreneurship is in Dorsey’s blood. His father and mother were both in the business for themselves. His father’s first business was a pizza shop. His mother took ownership of a failing café and brought it back to life. Jack’s time working at his mother’s café as a barista would come in handy years later with Square, a mobile payment system aimed to make payment processing easier for small to mid-size businesses.

Jack explained that both Twitter and Square were created because he knew what he wanted to see in the world and when it didn’t exist he went out and built it. His authentic passion for creating a business out of a need to create rather than a need to simply start a business was quite evident as he walked us through his life and how Twitter and Square came to be.

The interview with Jack was filled with tons of lessons for anyone starting their own business. We’ve jotted down 10 of these golden nuggets in true Twitter style: 140 characters or less.

1. An entrepreneur is not a person who starts a business—it’s someone who takes significant risks in building something for the world

2. Entrepreneurs build something they want 2 see in the world &makes bets w/ the world that everyone wants the same thing…sometimes u win

3. You have to be passionate about what u are building & build it 4 urself otherwise it won’t be fun & will cause a lot of contention in the long run

4. A great team can do great things. If you design and engineer a great team it will reflect in the product

5. Build a product like the Golden Gate Bridge – reliable & won’t fall down but is inspirational and delightful and will want to be shared

6. Your product should Show not Tell – it should show why its meaningful and if it resonates with people it’s doing the right thing

7. Building a product is important but so is building ur Board b careful who u put on ur board – u need ppl who can coach, teach & support u

8. When hiring a VC ask yourself is this someone that will push us in meaningful ways that add value to the company & not react 2 the market

9. Be prepared to show VCs 140 reasons why startup may fail & 10 reasons why it’ll succeed and ask do you trust us? If not we’ll find those that do

10. Some say you can’t have your foot on one dock and another in the canoe. I say why not? Move the dock

BONUS: Some fun facts to leave you with from the C100 session: Other names for Twitter that were considered according to Dorsey were Twitch and Jitter. And Square was originally branded Squirrel until Jack ran across the Canadian POS system of the same name and had to go back to the drawing board.

Photo: Fast Company