The next big thing

Sunday, June 17, 2007 by Dave Winer.

Re the current thread about entrepreneurship and aging... 

1. I think Fred Wilson's intentions are good.  

2. I think it's great that VCs have blogs now, so they can post ideas like the one he did, so we can respond to them, and hopefully figure out how to bridge the gap between our understanding of the world and theirs. 

3. I am not the entrepreneur I was in my 20s, and that's where I'd like to begin today's story. 

When I was young, I had an incredible drive to prove myself and that caused me to invent something new, want to use it to change the world, and made it possible for me to go through some horrible stuff to make it work. Really horrible stuff.  

Once, I remember having a thought, at work very late at night, the ony person in the office (I had been the first in the office that morning too) wondering what my last day at Living Videotext would be like. I couldn't visualize it. I was so dug in, so committed, and the situation was so hopeless, I just couldn't see a positive outcome. But in my 20s, I didn't give up. I kept going. 

Later, when my board of directors, most of whom were a generation older than me, told me to shut the company down, I told them to fuck off. I knew I had a hit product in the pipe, we just had to get through a couple of months of hell and then the sun would shine. (BTW, thanks to Guy Kawasaki, a VC who blogs, for believing in me, and helping us dig out of that hole.) 

Today's Dave would never do any of that. I would give up long before I made my investors their 20x return. Fred's theory is correct, when applied to me. I am a cashed out 50-something ex-entrepreneur. But the problem with Fred's theory is that it flushes away the biggest opportunities in front of him, the ones that could make him an investor in the next Apple, Nikon, CNN or Sony -- at their startup. All it takes is a little flexibility. In other words, our pair of posts present an opportunity to close a big gap, and create a new kind of entrepreneurship that takes advantage of the power of youth, and also takes advantage of the rarest of things, a 50-something person who has spent a life studying creativity, and knows how to keep the wheels moving, even if experience has taught him some very hard lessons about what to try and what not to try (in other words Clay Shirky's thesis is correct too, even though it's only a sliver of the whole picture). 

Here's a challenging question. If age is such a killer, why is today's Steve Jobs doing so incredibly well, where the young Steve Jobs shipped a loser (Lisa), then an almost loser (Mac) which was saved over his objections (he had some very wrong ideas about users and stubbornly held to them) and then was either fired or quit in a rage (depending on whose story you believe). Today, people seriously consider the possibility that Jobs's vision of the future may prevail over Gates's. I only use Macs these days. Did I think that would be possible, even five years ago? Never. So did we underestimate Jobs? Absolutely! The 50-something Steve Jobs disproves Wilson's hypothesis. 

Me, I'm discovering not only new ideas that are world-shakers, at an incredible pace, but I'm also learning how to make them work in the real world in ways I never could have before. In the 80s, with all my focus and intensity and will to succeed, I only managed to make a modest success, and when we flipped the company, the products died shortly after I left. I suspect that will be true of many of today's flips as well.  

But in my 40s, I learned how to make three things work, all non-commercial, but all huge, and all will eventually create commercial opportunities and wealth for people like Fred Wilson. And in the last year, I have openly proposed four more ideas that I believe are all world shakers, each of which could turn into an Apple-sized company, and while I would never volunteer to be the CEO of the company (I'd leave that to a younger person) I would like to play a key role, akin to that of a producer or a director of a movie or HBO series, in the creative side of the work. That's where a guy like me shines. And if there had been a better talent system when I was younger, I would have been cast in that role then too. 

So maybe that's the point. Maybe this is the beginning of a conversation that can last a few years (long blocks of time are something older people understand much better than younger people). I've sure had my complaints about venture capitalists. Now we're hearing their complaints about us. Does Fred have an open enough mind to consider Hypercamp, Checkbox News, Podcast Player or Social Camera as possibile businesses? Does he know enough young possible CEO types who could contribute their talents to such ventures? Does he have the vision to help create a system that can take advantage of all our talents? 

BTW, I could never have written a post like this when I was in my 20s. While in my heart I knew the answer was "working together" I didn't know how to actually do it.