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Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

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11–20 of 34 posts

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#11
There are more choices than just those two, you could simply build a solid business with respectable turnover and a good profit margin.

If you're not looking for your exit too hard it just might come your way anyway, and building a solid business is one way to work towards that goal.

If you're only focused on your exit and it doesn't happen or the timing is off you are probably in a lot of trouble.

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#12
post #3

I never really understood this debate... as if all companies should go big, or all companies should stay small/medium. Every business is different. Businesses have varying amounts of potential for growth, varying numbers of possible revenue streams, and even varying numbers of directions in which to pivot should things hit a wall. If you're selling people hands-on classes in underwater basket-weaving, it's probably n…

It's not rational, but part of the Silicon Valley mindset is "go big or go home" and oftentimes people don't stop to think whether it's good for their business, they just accept it as fact.

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#14
This is wrong:

"And if you’re lucky enough to get a life-changing acquisition offer like Mike Arrington just did, follow his example. Go for the billion dollars when you start your next company—by then you’ll have more experience and you won’t be risking the kids’ college education."

His mistake is to forget that the two options aren't exclusive. A large percentage of founders in startups successful enough to be on their way to being worth a billion dollars manage to cash out partially en route. So you don't have to choose between trying to make the company a big success and your kids' educations.

How do you decide whether or not to sell? There are two factors to consider: how much you like the work, and how good the offer is. If working on the company is what you want to do with your life, as it seems to be for Mark Zuckerberg for example, then you shouldn't sell unless you need to. Whereas if someone makes you an offer so good you'd be crazy to refuse it, then you might want to take it, even if you hadn't planned to sell.

(Strictly speaking, if you have shareholders, you have a fiduciary duty to do whatever's right for them. But since the founders' level of motivation is usually the dominant factor in the future value of early stage startups, in practice that usually reduces to doing what you prefer.)

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#15
post #14

This is wrong: "And if you’re lucky enough to get a life-changing acquisition offer like Mike Arrington just did, follow his example. Go for the billion dollars when you start your next company—by then you’ll have more experience and you won’t be risking the kids’ college education." His mistake is to forget that the two options aren't exclusive. A large percentage of founders in startups successful enough to be on t…

He's local to me (at least when he's at Duke) and was a guest speaker at one of my systems engineering classes at NCSU (a class on knowledge dynamics and learning organizations). The professor had sent us two of his previous posts on Techcrunch (http://techcrunch.com/2010/02/27/can-entrepreneurs-be-made/ and http://techcrunch.com/2010/03/06/replicators-innovators-and-...).

I had sent some critical comments back but it seemed the rest of the class, which didn't have any real-world experience whatsoever, took all of Wadhwa's essays as gospel.

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#16
post #10
post #8

Earlier quoted context omitted.

Well, a billion dollar company might enable you to make a 'bigger' difference. You help make your employees wealthy (Google's millionaire emplyees), you help shape whatever sector you're in (hopefully for the better). You create value for you shareholders. Everyone's a winner, theoretically.

Your argument is only true for people who have only one business idea. If you have a wealth of ideas, you can execute one and sell at a point that gets security for your self and your family, then execute another and aim bigger, but with your downside risk eliminated.

Is that common, though? When I think of companies that shaped the tech industry in a huge way, very few are companies founded by people who had already had a big exit and were on to their second or third company after already becoming millionaires. Impact on the scale of Apple, Google, Microsoft, Sun, nVidia, Oracle, etc., seems to involve founders who stay with their companies and guide them over a period of decades. Jobs did try the second-company route via NeXT, which had some impact, but he eventually had to return to Apple to get the kind of impact he wanted, which he wasn't able to do via NeXT (though he brought a good part of it back with him).

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#17
post #3

I never really understood this debate... as if all companies should go big, or all companies should stay small/medium. Every business is different. Businesses have varying amounts of potential for growth, varying numbers of possible revenue streams, and even varying numbers of directions in which to pivot should things hit a wall. If you're selling people hands-on classes in underwater basket-weaving, it's probably n…

The debate is for people/companies who have a choice-- obviously you're right about the fact that there's no debate where there is no choice. Mint sold for $150m, but perhaps could've aimed bigger. Blogger sold pretty early-- perhaps they could've been/beaten WordPress. Google famously tried to sell for $1m to Excite. LOTS of companies who sell early have an opportunity to aim bigger. I think partial cash-out Series…

The problem with the Mint example is that the acquisition price was really quite high. Patzer's personal stake was $40 million(!). That's in the same ballpark as he might make in an IPO 5 years later, after being diluted to hell. It's FU money 4-6 times over.

I think cashing out a couple million only works when a) the founders are obsessed with the company's mission above all else b) the acquisition offer is small enough that VCs can give the founders ~20% of their would-be cash now.

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#18
post #5

I don't even understand the debate: Your lifespan, healthspan, lifetime happiness and ability to run a company will only go up once you cash out for 4-10 million or more. You've literally solved the money problem at that point. Why would you risk that on a vanity billion dollar exit?

Some people would rather be famous, be the toast of the town, be adored by who they perceive as their peer group, leave who they perceive as their peer group, be on the front cover of Newsweek, get a movie written about them, etc... than have life, or health, money, or a successful business.

It is basically the Achilles question, right? Durable since the classics: would you like to live long or die gloriously?

(Like most dichotomies, there are almost certainly options in the solution set not mentioned.)

Re: Should Entrepreneurs Bet It All On The Billion Dollar Exit, Or Cash Out Small?

#19
post #10

Earlier quoted context omitted.

Your argument is only true for people who have only one business idea. If you have a wealth of ideas, you can execute one and sell at a point that gets security for your self and your family, then execute another and aim bigger, but with your downside risk eliminated.

Is that common, though? When I think of companies that shaped the tech industry in a huge way, very few are companies founded by people who had already had a big exit and were on to their second or third company after already becoming millionaires. Impact on the scale of Apple, Google, Microsoft, Sun, nVidia, Oracle, etc., seems to involve founders who stay with their companies and guide them over a period of decades…

Jobs also had Pixar, which had an undeniable impact in it's field.

Here's a question to test if you really believe the argument you seem to be making:

You have the idea of your lifetime. It's a billion dollar idea. You are looking for a co-founder, and find two amazing prospects.

They are equal in every way (education, drive, interests, etc) except one: Jim spent the past five years working at a startup that he just sold for $20m. Tim spent the past five years working in an office job.

You can only pick one of them. Do you prefer Tim or Jim?

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