"He compares those assembly-line-esque entrepreneurs who say they are just “the startup guy” to a 40-year-old man who still hangs out at a disco trying to pick up young girls."

The money quote. Really. I really have no respect for the 20-something "entrepreneur" flipping companies left and right (most of which don't have long term value). Replace "startup" with "business" and "founder" with "owner" and a lot of these companies look quite shaky.

Nice to see there are some people who still but weight in real, long term value.

I think this is an incredibly unfair assessment, to the point of being downright silly.

Taking $20 million for a company that's been around for a few years or in this man's case $750 million (!) is not immature or unwise by any stretch of the imagination. Saying no to $750 million, in many instances, leaves the realm of "risky entrepreneur" and enters that of compulsive gambler. He made $750 million before the crash: genius, not stupid.

Perhaps the reason Bezos and Jobs, etc. stuck around to make their companies successful is because there wasn't a Google around back then with infinite amounts of money ready to throw at them. In fact, the story of many of these "early" Silicon Valley companies is about big companies missing the opportunity to buy them or crush them (IBM with Microsoft, Yahoo almost owning a stake in Google, etc). Let's also not forget that in the first bubble the path to riches was IPO, not sellout, thus it makes sense that people would stick with their companies longer, because that was the way to get rich.

To me this is all just a function of the market. Today IPO's are much more rare, and the market pushes towards buyouts.

I don't think his issue is with the amount of money these founders make, but the pyramid scheme nature of many startups. For a company to be actually worth 750 million it's got to be producing ~75 million or more each year in profit at some time in the near future, or have a lot of assets.

Facebook may be slightly profitable, but if they are not pulling in around 100 million in profit each year within ten years they are worth less than one billion today.

"He compares those assembly-line-esque entrepreneurs who say they are just “the startup guy” to a 40-year-old man who still hangs out at a disco trying to pick up young girls."

Amusing, considering that he seems to have sold 3 companies himself and is now building a fourth. Sounds like "assembly line entrepreneurship" to me. Maybe he thinks 40 year old men hanging out at discos trying to pick up young girls are rolemodels? ;-)

To be fair he does say "“I think that’s a character flaw, and I have it. I have sold all my companies, and I wish I hadn’t sold a single one" but I'd rather listen to people who actually follow their own advice vs "wishing" they had the discipline to do it. At best this is like a philanderer advising celibacy to others.

"Flipping" makes sense if you want to buy a castle in South America and hold asados and you have people willing to pay the big bucks for your company.

"Value" is very much in the eye of someone who pays for it.

Recognizing and monetizing value isn't something that I'd snub my nose at. The basic idea is that there are often other suitors who can build a company better than you - why should there be any shame in this?

I suppose the question of long term value can be pretty subjective, but in a world where the average age of a Fortune 500 company is less the work life of an average worker, and the immensely greater access to markets with ever smaller amounts of capital, it's also fairly easy to see why many of these companies deserve the valuations they get. As someone who likes to drink the "koolaid" I tend to think that those who build companies to flip have a much greater likelihood of failure - and it's those who aim to build sustainable and great companies who are often the same ones that create the luck to be bought out at a significant premium. Besides those who do the entrepreneurial thing quickly learn that business is a marathon not a sprint.

As for the original quote, I'd disagree. I think it's incredibly important to understand your weaknesses and let's face it, not all entrepreneurs are great managers. Heck, there's practically an entire field of academic research that considers the differences between leaders and managers. Creating an organization and having the ability to come up with the initial ideas does not generally use the same skill sets as building, running and maintaining an organization.