What's The Approved and Accepted Way to Make Money?

There's been a lot of talk about money lately here in the Valley, it seems.

Whether it's a product of the exceptional $19 billion acquisition of WhatsApp by Facebook, Google's $3.2 billion Nest buy, the IPOs of Twitter and Facebook, sky-high valuations of private companies, or a real and growing gap between the 1% and the rest, discussion of venture funding rounds and money often appears to be as big a conversation point as the products and innovation that's made this place unique.

As my colleague +Scott Knaster often notes in his blog "Witless to History", he and I are good examples of the typical longtime Silicon Valley employee - people who have been close to the action, but never quite in the center of it. No acquisitions to our name. No multi-million IPOs. But it's not necessarily a lack of effort on our part.

As I wrote nearly five years ago in "Good People, Bad Companies", one typically needs both skill and luck to deliver a dramatic change in life status. Great employees work for mediocre companies, and mediocre employees are sometimes rewarded handsomely for being in the right place at the right time.

So I posited the question, if we celebrate our financially successful entrepreneurs, what about those who've toiled away with similar effort for similar amounts of time, but never got that financial windfall? And in the reverse, what about people who have made quite a bit of cash, but didn't go the textbook route?

What if a person who had put in an honest day's work for an honest day's pay, got lucky by striking it rich on the Lottery and, instead of making $20 million via some acquihire, they made $20 million by picking the right six numbers? Is that someone who should be held in the same level of esteem?

What if they took a two week vacation and played their cards right, making millions at a World Poker Tour event? You may not like watching poker on TV, but you'll find some of the best players come from the Ivy League schools with top degrees, but they prefer pocket Jacks to JavaScript - so they're smart folks practicing their craft.

What if their "Poor Aunt Hortense" passed on and left them some money, or  what if they correctly saw that marijuana related stocks were going to go nuts on the NASDAQ this January, and they made ten times their money? Would they be congratulated?

Silly questions, maybe - but not any more silly than writing posts about how Box CEO Aaron Levie has a "small" position of around 4 to 5% of his white hot company. If we are at the point now where having single digit percentages of stock of a company worth billions of dollars is to be mocked, I too look forward to being mocked in the same way.

It seems to me that while we recognize the true value of an individual extends well beyond their bank account, the entire plot of which companies are raising funds, which funds are raising rounds, which companies are valued at what, and which people made cash is outstripping the story behind why some of them are making money.

The technology that many of these newly rich people have invented or impacted is changing people's lives for the better - be it in connecting people around the world, saving energy, or keeping memories safe forever. They're taking risks and solving problems that are hard - and that dedication is being rewarded. And that should be okay - as should the rare soul with the mathematical chops to make it big in the professional poker world (it's super duper hard), or the guts to pick stocks worth less than a penny, and see potential. If you do it right, consistently, why not reap in the rewards?

What I think we risk by acting as commentators on what people make as much as we are commentators and users as what people actually create, is that we start to reinforce a false mantra that those with greater wealth are those with greater worth. People who do exceptional things have been compensated at exceptional levels for a long time, be it in business, sports or entertainment. And there are no guarantees. As I wrote back in August, it can take an equity event (or two) for an entrepreneur to even afford to stay in the Valley, so you're seeing people play Frogger on LinkedIn, moving from hot company to hot company, hoping to stay on the right one that helps them leapfrog tax brackets.

The 20th hire at a multi-billion dollar acquisition will always make more money than the co-founders of a non-profit, no matter how hard either of them works. That they ensured the financial well being of their family, possibly for generations, is to be lauded. But it doesn't make them better human beings. It's important for us to not lose sight of those for whom there are other goals, or for whom luck has not always been there. It's very hard to win the Lotto.

Disclosures (per usual): Google owns Nest. I own Nest products. I'm not great at poker, but wish I were. I do play the stock market, sometimes even those penny stocks - because, why not.