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Summary:

Fred Wilson will be giving a talk at the 99% conference later this week entitled “10 Ways To Be Your Own Boss.” Prior to the talk, Wilson has provided a preview of his presentation, which gives his views on the various categories of entrepreneur.

Union Square Ventures’ Fred Wilson will be giving a talk at the 99% conference later this week entitled “10 Ways To Be Your Own Boss.” Prior to the talk, Wilson has provided a preview of his presentation, which gives his perspective on the various categories of entrepreneur:

  1. The Sole Proprietor: Matt Drudge
  2. The Partnership: Openshop Studios
  3. The Husband & Wife Team: Daily Lit
  4. The Boutique: Union Square Ventures
  5. The Federation: Allen & Co
  6. The Project: Avatar
  7. The Tour Bus: The Hype Machine
  8. The Startup:Red Stamp
  9. The Breakout: Foursquare
  10. The Company: Twitter

Wilson is probably the most prominent technology investor in the world today. Though he’s led investments in some of the web’s greatest successes stories — including Boxee, Delicious, Feedburner, Foursquare, Meetup, Tumblr and Twitter — he’s perhaps more widely known for his blog, A VC, and the insights he shares on running technology startups.

He only hints at what he’s planning to talk about at the conference, but his slides reveal a useful perspective from an authoritative voice: the notion that web businesses can be successful and influential without using the venture-backed startup model.

The examples cited sit on a continuum, ranging from small, loosely bound collaborators to larger, more traditional business structures. For web workers seeking to fulfill their entrepreneurial ambition, this illustrates that there are many paths to success. Perhaps choosing the structure most appropriate is more important than the product or service being produced.

I’d be interested to hear from you whether these categories are suitable descriptions of your own circumstance. What kind of entrepreneur are you?

  1. “Though he’s led investments in some of the web’s greatest successes stories — including Boxee, Delicious, Feedburner, Foursquare, Meetup, Tumblr and Twitter ”
    how are these some of the web’s greatest success stories? By what metric?

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    1. Delicious was bought by Yahoo, Feedburner was bought by Google, Foursquare is run by the same people that did Dodgeball (also bought by Google), and Twitter is pretty much THE social media/networking hotspot on the web. I’m not sure on the status of Boxee, Meetup, or Tumblr other than that they are fairly successful in that they have a decent number of users.

      I’d say the statement is justified.

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    2. Vijay, each of those services enjoys a userbase of millions and an extended larger audience too; services like Twitter and Foursquare have also had significant cultural impact

      As Michael points out below, many have been successfully sold, providing a return to their investor…and by the measure of an investor, that’s all they need to do.

      If usage and ROI aren’t indicators of success, then I’m not sure what is :)

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  2. [...] of Union Square Ventures is slated to speak at the 99% conference in New York City this week, and WebWorkerDaily has snagged a preview of his presentation. The slideshow gives a look at ten popular companies and [...]

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  3. [...] of Union Square Ventures is slated to speak at the 99% conference in New York City this week, and WebWorkerDaily has snagged a preview of his presentation. The slideshow gives a look at ten popular companies and [...]

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  4. [...] of Union Square Ventures is slated to speak at the 99% conference in New York City this week, and WebWorkerDaily has snagged a preview of his presentation. The slideshow gives a look at ten popular companies and [...]

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  5. [...] Fred Wilson: 10 Ways to Be Your Own Boss (webworkerdaily.com) [...]

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