This is a pretty individual thing, so the headline is misleading. Ryan does make some great points, but depending on the situation selling a company can indeed make someone happy.
I sold a site/company that I built and operated for 9 years, and while I did miss parts of it, selling it at that point made me quite happy. It wasn't exciting me anymore to work on it, I was interested in other areas, and it was a good thing for all parties involved.
While the money wasn't life changing and was far from making me financially independent, it made me happy to pay off my wife's student loans, put a down payment on a house, save for the future, etc.
The part that really seems hard for entrepreneurs is working for the acquiring company after the fact, or realizing that they loved how their life was when they were running their company. The grass is always greener...right?
Like many things, it's not so black and white. Fred Wilson and Paul Graham are probably both right.
Paul Graham is right that the Facebook IPO being seen as negative (whether that's correct or not) could reduce larger startup valuations which trickles down to early-stage startups as well. The advice in his email is sound regardless of whether the IPO does trigger any type of "downturn" in startup investing.
Fred Wilson also makes great points that Facebook still has an insane multiple while providing a huge win for all its investors and employees, which will bring more money and hope into the startup ecosystem. Not to mention more acquisitions made by Facebook, etc.
Chances are both are partially right and partially wrong, and a number of other factors from macroeconomics to small things in startup world could prove one of them to be "more right" over time.
- At the highest level, whether you "faked it" and dressed up for that investor pitch or job interview doesn't matter. If you have the skills and content the investor or employer is looking for, they will easily look past what you are wearing and whether it's authentic or fake. Mark Zuckerberg didn't dress up for investor pitches, but was able to raise money right? I also tend to think if Zuckerberg had put on some nice clothes, he still would've been able to raise money even if it was obvious it wasn't his normal attire.
- I've hired a lot of people over the years into both startup and larger companies from engineers to sales people, and it was usually obvious if someone was "faking" their appearance. Never have I thought "Boy, this person is being inauthentic and fake, I should not hire them". I've always seen it as a sign of respect that they took the effort. At the same time, I would not think worse of someone who didn't dress up, because I also realize that it's them as people that matter.
- Bottom line: Be yourself, and if being yourself means wearing your normal clothes, that's fine. And if being yourself means you'd like your chances better in some nice clothes, then put those on. Spend more time worry about the content of your presentation or how well you can perform in the interview instead.
I sold a site/company that I built and operated for 9 years, and while I did miss parts of it, selling it at that point made me quite happy. It wasn't exciting me anymore to work on it, I was interested in other areas, and it was a good thing for all parties involved.
While the money wasn't life changing and was far from making me financially independent, it made me happy to pay off my wife's student loans, put a down payment on a house, save for the future, etc.
The part that really seems hard for entrepreneurs is working for the acquiring company after the fact, or realizing that they loved how their life was when they were running their company. The grass is always greener...right?