Recap of Startup Mentoring with James Duncan

We held out second Tap in Tuesday Startup Mentoring event with mentor James Duncan co-founder of cloud computing platform Reasonably Smart (recently acquired by Joyent).

The beginning portion of the meetup was a quick recap of James’s background and path through Startup life. What was nice to uncover was the history that lead up to what many in Montreal know as the Startup that exited almost as fast as it got started.

The story of entrepreneurship began for James 3 startups ago as a teenager, and weaved through his years in the UK helping build one of the country’s largest ISP, to his experience at Fantango (photo-sharing website) which was acquired by Canon, the crazy process of getting ready for an IPO with ebookers a (Travel agency in Europe), and then moving back to Montreal and starting Reasonably Smart.

Again one of the key takeaways from the discussion was the format itself. No other medium would come close to sitting “one on one” with someone sharing these experiences. Thanks to James’s openness and candor the meeting was interesting and dynamic. Many topics were discussed but one of the consistent threads that connected each of James’s Startup lessons was the decision to tackle problems that he understood and was passionate about solving. As he openly shared Startup life could be very challenging and offers little financial security. According to James if you choose to take the path make sure you work on a project you can enjoy working on for long hours.

Another clear message was the decision to find great partners and not shy away from diluting your equity share. A lot of new entrepreneurs obsess with keeping as much equity as possible. As James shared “it is much better to own part of a company that is worth something, than 100% of an idea”. Tying into this concept James explained that adding partners increases productivity of a business exponentially; adding a partner (especially one with a complementing skill set) doesn’t just double the chance of success it triples or quadruples it.

Below are some of the questions asked by our entrepreneurs and discussed in length with James:

Sample of Entrepreneur Questions from Q&A portion of meetup

  • How do you deal with feature creep?
  • How do you decide which niche market to customize to if your product is applicable to a few?
  • How much equity do I need to give an advisor?
  • As a technical entrepreneur is finding a business partner more valuable than another tech resource?
  • As a technical entrepreneur I can’t fully gauge how much value a business partner brings, how much equity is their expertise worth?
  • Do you think bootstrapping is better than raising capital?
  • How do you approach maintaining a consistent vision when dealing with partners?
  • Was your first company more difficult to start than any of the others?
  • How do you network?
  • How do you meet important contacts at conferences?
  • What are your feelings on the R&D tax credits?
  • How do you feel about the Startup Community in Montreal?

 2 meetings in, it looks like each of our sessions will offer a unique perspective for our entrepreneur/mentees. Each mentor had their own path and shared their knowledge with their own unique style. Thankfully what remained consistent was the level of openness, the amount of sharing, and detailed Question and Answer portion of the meetup.

The second floor of Café Republic on Peel was a great venue. Creating a laid back environment (sitting around on couches) seems to have made a difference in the “intimacy” of the conversation. Of course it may be that we’ve been lucky so far to have 2 great mentors come through, both very humble and quick to share lessons learned.

At the end of the evening, inspired by the conversation with James, many of the attendees quickly requested to secure a spot for our October meeting with Carl Mercier. Based on Carl’s Startup Camp presentation our next meeting looks to be another great opportunity for Montreal technology entrepreneurs to tap into the experience of our local Startup Community leaders.

To reserve a spot for the October Tap in Tuesday event please use this link:

http://tapintuesday.eventbrite.com/ or email tapintuesday@gmail.com.

Photo: Heri – Montreal Tech Watch

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2 Responses to Recap of Startup Mentoring with James Duncan

  1. From @webmindset – it’d be worth a trip north if I had the time. Interesting post.

  2. It was a great event, really looking forward to next week. Definitely the second best way to learn about starting up, right after actually doing it yourself. Stuff you can’t get in class or at a conference.

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