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One of the benefits of getting out of the normal career is that you are no longer being constantly judged on stupid criteria, like what grades you got, how many years of experience you have in blah, etc etc. I once had an interview where they asked me in 5 different ways about my team working experience, does that really give them that much insight?
When I first became an entrepreneur, I thought that would be the end of being judged, from now on I was to make my own destiny, and that has been true to some extent. But you find that here there is a different ladder to climb. Being an entrepreneur is a lot to do with selling yourself, whether it is to investors, clients or potential hires, you have to impress them to succeed. The difference is that the levels are different. Here is the ladder how I perceive it, from the bottom up.
1. Never done any company.
2. No companies but worked for a startup (the more successful the better)
3. Done some small projects
4. Started first company
5, Started a company and have funding.
6.1. Started a company and have well respected investors (first tier VCs being the best).
6.2. Started second company (without the first exiting successfully)
7. Had a successful relatively small exit ($1m plus) or could have took such an exit but are happy making good revenue at that company
8. Had a successful company with a reasonably large exit ($10m plus)
9. IPO!
Obviously those add up and I put two 6s because it would depend on what funding your first company had etc. A lot of gray area but that is roughly how the ladder goes.
Here is something that Kieran said: you can climb ladder by networking and being at all the right events and conferences. But eventually if you go to too many of them you start falling down the ladder because people perceive you don't have anything better to do :).
Another point is that perception matters a lot, some people will value what University you went to and whats jobs you have had. Others will care about how well you are known on the Internet. But you can very much go from zero to the top of the ladder very quickly, which is what makes this exciting. Unlike the career ladder you don't need to have 5 years experience before you are considered for a promotion.
I am aiming for 3 IPOs just so I can be almost unchallenged at the top of my ladder, not for the money at all ;-).