Category Archives: entrepreneurship

To dream the impersonal dream

I’ve been trying to find words to explain what it’s like wanting to make things happen, how it’s not about me but rather about the possibilities I see. One of the books I just picked up from a library has a good quote about it:

Entrepreneurship is nothing about the one who creates a thing and everything about the one who consumes the thing. Entrepreneurs don’t care about the thing they create, in and of itself (as much as they may love what they produce or do). They care about creating it because of the impact it can have on someone else. It’s about that thing as an answer to a question others have long ago stopped asking, or long before they even consider the possibility of it changing for them. (p.50)

And another snippet:

Unless your idea for a business exceeds anything you have ever imagined doing before, is bigger than anything you have believed yourself capable of before this moment, has the potential of transforming a large enough number of people’s lives in the world to make a huge difference in how the world works, and challenges you sufficiently to risk everything you have to make it a reality, don’t do it.

Just don’t do it, dear reader, because it will likely disappoint you in too many ways to mention.  Don’t do it unless you’re ready to rumble.  Don’t do it unless you can put all your fears behind you. Don’t do it unless the pain of not doing it will exceed the probable pain of doing it by a factor of ten.  Don’t to it, because it’s not a game one plays casually.  Don’t do it, because it will confound you, confuse you, threaten to overwhelm you, every single dangerous step of the way. (p.104)

Awakening the Entrepreneur Within: How Ordinary People Can Create Extraordinary Companies
by Michael E. Gerber

Read more about this book…

Here’s what I care about at work:

  • I care about helping new hires, interns, and other fellow Generation Y-ers connect with the rest of the company, and vice versa. I care because I think it would be pretty amazing if all of us newbies were engaged, passionate, and sharing what we’re learning along the way. Ultimately, I want to affect not only the way IBM connects with its new hires and interns, but the way leading enterprises bring these new voices into the conversation.
  • I care about helping interested colleagues learn more about how to use Web 2.0 to improve their personal productivity and collaborate more effectively. I care because I’ve seen how people use these tools to connect and collaborate across the organization for unexpectedly wonderful results. Ultimately, I want to see these tools become part of the culture not only at my company but also in others.
  • I care about helping clients learn from IBM’s experience with social media, and helping IBM learn from them. I care because I believe in what we’ve got inside IBM and I want to help other organizations explore this kind of culture of openness, trust and collaboration. I care because I know we can learn a lot from other companies as well. Ultimately, I want to connect evangelists and champions in different companies so that we can learn from each other’s experiences.

So I guess I’m a bit of an intrapreneur after all. Technology evangelism around Web 2.0 and emerging technologies is officially part of my job, but all of these things are things I do because I have to do them, because I can’t imagine not doing them. =) I’m going to need a lot of help, but there are a lot of people who are glad to help out because these are their visions too. (I like to think that I’m the one helping them!)

Let’s find out how wonderful it can be. =)

What’s your dream?

Entrepreneurship tips from Sarah Prevette (Sprouter) at the Toronto Girl Geek Dinner

Last night’s Toronto Girl Geek Dinner with Sarah Prevette, the founder ofSprouter, was a great braindump of entrepreneurship and networking tips.

Sarah told us stories about her failures and what she’d learned along the way, particularly the importance of talking to potential users and reaching out to the community. Her tips for engaging with the community were:

  • Amazingness. Provide value. Don’t focus exclusively on What’s In It For Me. Be worth talking about. The best way to achieve success is to enable someone else’s.
  • Accessibility. Respond in a timely manner. Don’t ignore reactions, whether positive or negative. The worst thing you can do when people criticize you is to ignore it. Be open. Share the facts.
  • Authenticity. Provide as much information as you can. Be real, be transparent, be honest, and be yourself. Be patient when answering questions. Privacy really is dead, so get used to it.

Here are other tips she shared:

  • Release early, release often. Don’t worry about making things perfect. Worry about making people care. Just push things out. If they hate it, they’ll tell you why they hate it. If they love it, great. It’s indifference that sucks.
  • Be entrenched in the community. Talk to people. Listen. Do your homework. Do the legwork.
  • Twitter is a great backchannel that can add a lot of value to conferences and conversations. If you’re not on Twitter yet, you should at least read it when you go to a conference, and follow what interesting people are saying. Otherwise, you’ll miss out on half the conversation.
  • Twitter helps connect with the community. Twitter accounts for far more of their site visits than either Google or direct traffic.
  • Make sure you activate your network. Collecting business cards is not networking. Adding people to LinkedIn is not networking. Act onyour network. Find ways to reconnect and be relevant. Meaningfully reach out. She mentioned a new habit she’s working on: revitalizing her network by stacking up business cards in front of her, randomly picking five people, and consciously looking for ways to reach out and help that person succeed.
  • Entrepreneurship is stressful but fun. The last year has been the most stressful and the most fun for her.

Here are some notes from the Q&A:

  • What’s your business model? Ad-supported freemium.
  • Aside from the aforementioned stack of business cards, how do you keep track of your contacts? New startups like CloudContacts, NetworkHippo are interesting. (Sacha’s note: Gist is another social aggregator, too. It’s pretty darn awesome.)
  • How do you scale accessibility? Hopes that as usage scales, revenue scales, too.
  • Who built your site? Internally developed. One rockstar doing Ruby, a total team size of three. Shout-out to Jet Cooper team for the design.
  • What tips would you give new entrepreneurs?
    1. Do it. If you have a fabulous idea, do it. Talking about it at dinner parties is not doing it. Researching is not doing it. Do it.
    2. Solicit feedback. Get feedback not only from people who’ll be nice to you, but people who’ll tell it like it is. Talk to your potential users. Push beyond the fluffy responses. Ask for specifics.
    3. Find a way to grow organically, or find the money to do it. Don’t worry too much about equity. Don’t be afraid of investors. Don’t do things in isolation.
  • What key trends are you seeing? Mobile applications, geolocation, better filters. Also general trends like green.
  • What was your biggest obstacle? Not engaging the network enough. Either that, or ego. No, network. You have no idea who’s going to be the key person in your network, so just connect with people.
  • How do you know where to go for funding? Again, network. Ask startups who’ve been funded by investors; they’ll have insights. lists startups.
  • How does the amount of sleep you get compare to when you were a teenager? Used to be a big sleeper as a teenager. Now is usually thrown off by jet lag, etc.

Toronto Girl Geek Dinners is giving away one free pass for people who would like to attend the Mesh Marketing event. Tweet @s_moore with the answer to the question of why it would be awesome for a girl geek to go to the event, and the most creative answer will get a free pass. More details about that and upcoming events at .

Comedy and self-promotion

We headed out for taco salads and soup at the Easy Restaurant on King Street after our last class of improv comedy. My three classmates and the teacher were all deeply into the Toronto improv and sketch comedy scene. I was the lone non-comedian, and I got a fascinating glimpse into that world.

They talked about the awkwardness of telling non-comedians about your interests. When the conversation turns to what people do, they feel that people who are outside the comedy scene just don’t get it, saying: “Oh, you’re a comedian? Tell me a joke.” One of my classmates said that this was probably why practically all her friends are also in the comedy scene. I wonder if they also have problems with the echo chamber effect that we see online, when people end up talking only to people like them.

They talked about the challenges facing the Toronto comedy scene. There are lots of stand-up rooms in Toronto where people can practise their material, but attendance is hit-or-miss. If you liked a specific comedian, it was hard to find out when and where they’d perform next. Shows were better publicized, but individuals were hard to track. I asked them if it was a matter of marketing. To me, it seemed obvious: if you were starting out as a stand-up comedian or an improv comedy performer, why not make it easier for people to find out when you’d be performing next, and share your adventures along the way?

They reacted strongly against the idea of self-promotion. To them, the idea of an amateur having business cards, a website, or a Facebook fanpage smacked of pretentiousness. It was okay if you’d done a number of well-received shows, or had some kind of national profile. If you were just starting out, you needed to know your place.

I found that really interesting because we run into the same social norms against self-promotion in different business cultures, and it can get in the way of connecting.

I think people do want to keep an eye out for teams and people they like. Facebook’s use of “Fan” might turn people off, so they’d need a more neutral space that can keep track of teams, individuals, shows, and locations. It would be a natural fit for Facebook integration, calendar exports, RSS feeds, and mailing lists. You could probably build the whole thing using out-of-the-box Drupal and the Content Creation Kit. Data entry would have to be done manually for a while (listings from Now Toronto and from the major venues?), but it might eventually grow into something that people can update on their own.

I don’t see people paying to use a service like this, but it might be supported by advertising (and perhaps a share of ticket sales, if you have an e-commerce system tied into venues’ ticketing).

In terms of marketing, you’d probably approach venues that don’t have event lists, as well as teams and individuals. Teams and individuals would be your primary channel for marketing. You could also offer a badge for venues, teams, and individuals in order to advertise upcoming shows, and pre-designed flyers (like what Meetup now does), and provide webpages for people who don’t have their personal sites set up yet. Posters near established comedy venues would be good, too, and hand-outs given to people in line. Business cards might be interesting too.

A business idea for someone who’s really interested in the comedy scene, perhaps! =)

Visual notes – Gary Vaynerchuk and Democamp Toronto 24

Funny aside: When Jay Goldman handed Gary Vaynerchuk a bottle of water, Gary offered it for sale. Little things like that reinforce story.

Key take-aways: Passion and patience are everything. Hustle. Out-care others. Offer good stuff. Pay attention to everything. How do you scale? By trying.


Notes from the demos and the pub, before I broke my fountain pen:


Explanations for scribbles upon request, or when I can make time for it! =)

From the book bag

I love reading. Love love love love.


Here are a few more books:

image Fight For Your Money: How to Stop Getting Ripped Off and Save a Fortune
David Bach, 2009

Decent reference, useful form letters. Nothing too surprising in terms of advice. I like this more than his other books, which tend to hammer in the Latte Factor a bit much. Good to give to people who are just starting out in Canada.

The Illusions of Entrepreneurship: The Costly Myths That Entrepreneurs, Investors, and Policy Makers Live By
Scott A. Shane, 2008

Surprising data-driven insights into entrepreneurship. Depressing in some places (such as when he’s looking at the statistics for women and entrepreneurship), and encouraging in others (such as when it comes to capitalizing new businesses). Something to read in a library.

How are these Friday book reviews working out for you? How can I make them better?

Tips for entrepreneurs

SCHEDULED: 2010-09-17 Fri 08:00

One of my role models is leaving IBM to explore the world of entrepreneurship. Jamie Alexander has a lot of development experience. He built a number of sites, including PassItAlong, an internal social learning system we use at IBM. He’d be the first to admit he needs help with the business side, though, and he’s looking forward to learning more about marketing and adoption. He’s applying to the Digital Media Zone incubator at Ryerson University, and will check out the local technology events.

What advice could help a new tech/web entrepreneur get started? Here are a few tips I picked up by osmosis from the Toronto technology scene. What do I know about it? I haven’t started a company yet. But this is what I’ve heard from lots of conversations and books, and it might be useful. I’m hoping people will pitch in with other ideas.

Learn from companies that have done it. There are a number of interesting local companies that you can learn from, like Idee, Freshbooks and LearnHub. How did they do it? How did they identify and go after their market? How did they bootstrap? Did they need investment, or did they self-fund their growth? What challenges did they encounter and how did they deal with them? There are lots of events that feature companies in different stages of evolution. Go to them and ask questions. Read blogs and news articles online, too. But don’t get too focused on how people have done things before – the world is always changing, and there’s no sure-fire recipe for success.

Connect with mentors and the community. There are a number of tech events for startups. Go. Meet people. Learn from others. Connect with potential mentors, investors, and partners. There are plenty of online networks, too. Don’t get stuck in the new media echo chamber – you’ll still need to actually make a product or service, and you still need to go out there and build or discover your audience – but connect with people who can share what they’ve learned. I just did a quick search for Toronto startup events and found (Sept 24-26, 2010 at Ryerson). There’s always something going on.

Make it easy to keep in touch. “Do I have to use Twitter?” Jamie asked. If you’re starting a Toronto web startup, yes. It makes it easier for people to talk about you and your sites. Create a Twitter account and a blog, and use that to make it easy for people to find out more about you, interact with you, and refer to you. Reach out and connect with people. Share what you’re learning. Make it part of the way you work. You need that network. Why limit it to just the people you can regularly e-mail or have coffee with?

Collaborate. You don’t have to do everything yourself. Find people with complementary skills and who believe in your vision.

This is easier said than done. Where can you find business people if you’re a tech person? Startup events are one way to do it – you’ll find people of varying experience. Look for people who have succeeded before. Ask your mentors for referrals. Look for people who have failed before but know what they’re going to do differently next time. If you’re partnering with someone who’s also new to this, factor that into your planning, then hustle as much as you can. Don’t let an artificial tech/business division isolate you. You need to know your customers. You need to know the business side as well as the tech side.

Here’s a tip from entrepreneurs who have learned the hard way: get things in writing. You might be great friends now, but get your partnership on paper, and make sure you can live with the exit clauses. Sure, you probably won’t waste your time suing people, but it’s good to be clear about expectations and contingency plans.

Ship. Make something. Sell it to somebody. Seth Godin has lots of great insights on the value of shipping on his blog and in his recent book, “Linchpin.” Make something happen.

What else can help a new Toronto tech entrepreneur?

See also: