Fred Wilson: 10 Ways to Be Your Own Boss

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

[slideshare id=3690137&doc=tenwaystobeyourownboss-100411080650-phpapp02]

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?


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