Reading “11 Ultra-Successful Entrepreneurs on How to Start Over If You Lose It All,” I was struck -- no, absolutely floored is more like it -- that none of the responses included the one thing you should, without a doubt, do first: assess what went wrong and consider that maybe you risked too much.
Maybe they take that for granted, but still. The only silver lining after losing it all is the opportunity to learn from it at a time when you’re an emotional wreck -- meaning when you’re most receptive to the feedback -- and consider that maybe you shouldn’t have bet it all in the first place.
I don’t care if it’s the love of your life, your job or your life savings: if you’ve ever lost big, then you know what a humbling experience it can be. Sure, it’s terribly painful, but that’s the whole point -- you want to figure out what went wrong to make sure you never have to go through such a gut-wrenching experience again.
I really didn’t get the feeling that any of the entrepreneurs sourced in the piece got that. Maybe that’s why one of them “lost it all three times.” I’m not the least bit surprised that the same thing keeps happening to him over and over. A little soul-searching and humility would go a long way toward ending those boom-and-bust cycles.
Don’t get me wrong. I’m not saying you should dwell on failure, let it get you down or crawl under a rock in despair. But the question wasn’t about a product that failed to take off or losing a few bucks. It was about losing it all. Well, you can’t very well lose it all unless you risk it all. The thing is, repeating that over and over isn’t for everyone.
If losing it all doesn’t cause you to at least consider that maybe you took a bigger risk than you should have, or maybe there are some things you might want to do differently next time, then you’re just asking for trouble. You know the saying, the definition of insanity is doing the same thing over and over and expecting a different result.
Maybe it’s a question of perspective. You see, I grew up with nothing, so I know what that feels like in an intimate way I’d just as soon not repeat. While I have a pretty high tolerance for risk, it’s never made a whole lot of sense to me to risk losing what I spent years working for, especially with a family and responsibilities to consider.
Look, I get it. It’s inspiring to read about gutsy entrepreneurs with nerves of steel and a devil may care attitude. It's good to know that they survived disaster, as will you. But keep in mind, things aren’t always as they seem. At least one or two of those profiled in the piece grew up with money, so their definition of losing it all might not be the same as yours or mine.
I wouldn’t characterize all of them as “ultra-successful,” either. That’s a description I would reserve for a Bill Gates, Warren Buffet or Elon Musk. While they may take big risks, trust me when I tell you, those guys don’t risk it all, not by any stretch.
The notion that you have to bet big to win big is nonsense. Emotionally, perhaps; monetarily, not so much.
Take Barbara Corcoran’s fellow Shark, Mark Cuban, for example. Cuban made a bundle when he sold a company he co-founded, Broadcast.com, to Yahoo for $5.7 billion at the height of the dot-com bubble. But instead of going all in, he hedged against a market crash, so when it did crash, he came out on top. Today he’s an investor, but you’ll never see him bet it all. Not even close.
Then there’s Andy Bechtolsheim, who I spotted eating a bento box lunch yesterday at a popular Japanese restaurant in Palo Alto. Since cofounding Sun Microsystems, Bechtolsheim has written quite a few checks, including the first to Google co-founders Larry Page and Sergey Brin in 1998. But like all smart VCs, he spreads it around.
If you know Bechtolsheim, you know he’s all about the technology. When he meets with young founders, he pays attention. That’s why his most successful venture was a relatively meager $100,000 bet on a search company that hadn’t even incorporated yet. That Google stock is now worth billions.
If you lose big, don’t jump right back on the horse. First take some time to assess whether you’re making the right kinds of bets for your situation. Whether you’re an entrepreneur or not, a little humility and introspection will go a long way.