After Failure, What Comes Next?

Once I wrote a post titled After Your First Big Success, What’s Next? The comment thread was powerful and fascinating, as was the direct email feedback I got, including the following note:

Having failed at a lot of things, I’m completely comfortable tackling this. But let me establish my bonafides first.

My first company, Martingale Software, failed. (We returned $7,000 of the $10,000 we raised.) My second company, DataVision Technologies, failed. I didn’t have success until my third company, Feld Technologies. While my first angel investment was a success, I resigned as the chairman after the VCs came in and left the board after the CEO was replaced. In the late 1990s, what looked like my biggest success at the time went public, peaked at an almost $3 billion market cap, and then went bankrupt three years after the IPO. And the second VC fund I was part of, which raised $660 million in 1999, was a complete disaster.

As the cliche goes, I learned a lot from these failures.

I’ve had many more. I remember firing my first employee, which I viewed as a failure on my part, not hers. I remember the first CEO I fired and staying up all night prior to doing it because I was so nervous and miserable about the decision I’d made to back him. I remember the first company I funded as a VC that failed and struggling to figure out how to shut it down after everyone else fled from the scene. I remember the first time someone threatened to sue me for doing a bad job for them. (They didn’t.) I remember the first time I was sued for something I didn’t do. (I eventually won.) I can keep going, but you get the idea.

There is no right answer or magic salve for getting past failure. If you are going to be an entrepreneur, you are going to experience it a lot. It’s just part of the gig. Tweet This Quote

What’s next is simple. It’s whatever you do next. In some cases this will be easy–you’ll already be on to the next thing before the previous thing you were working on failed. In many cases it won’t be easy–you’ll be wallowing in the quicksand of the failure well after the other bodies have been sucked below the surface.

How you deal with your own emotions, and perspectives, is an entirely different matter.

I love the approach of Jeremy Bloom, the CEO of Integrate (we are investors) whom I have immense respect and adoration for. In 2006, at the Winter Olympics, he was the best freestyle mogul skier in the world. On his last run, he was expected to take gold. Halfway down, he missed a turn and placed sixth. As Jeremy told me, he gave himself 24 hours to be angry, depressed, upset, furious, frustrated, confused, and despondent. I imagine him in his room in the Olympic Village systematically destroying all the furniture. One minute after 24 hours, he was on to the next thing, with the failure solidly in his rear view mirror.

Now, 24 hours is a short amount of time. I’ve often carried my failures around for longer, but never much longer than a couple of days. I separate how I feel from failure from how I feel about life and what I’m doing. Interestingly, for me, failure isn’t the thing that gets me depressed, it’s boredom combined with exhaustion. But that took me a long time to figure out.

Talking to people about your failures is helpful, rather than holding them inside. I talk to Amy (my beloved) about them. I talk to my partners about them. I talk to my close friends about them. I don’t ignore the failure or try to bottle it up somewhere. Rather, I set it free, as quickly as I can.

Talking to people about your failures is helpful, rather than holding them inside. Tweet This Quote

In our book Do More Faster, we have a chapter on the wonderful story of the failure of EventVue. After it failed, some of Rob and Josh’s friends from the Boulder Startup Community had a wake for EventVue. We celebrated its life, buried it, and moved on. I loved this idea and have done it a few other times for failed companies. It’s important to remember that even in death you can celebrate the wonderful things that happened during life.

But ultimately, you have to know yourself. There is no right answer or magic salve for getting past failure. If you are going to be an entrepreneur, you are going to experience it a lot. It’s just part of the gig. Start by understanding that, and bye asking yourself what you are really afraid of. And, after you fail at something, let yourself experience whatever you want to experience, remembering that it’s just another small part of the journey through life. And then go on to whatever is next, in whatever time you are ready for it.

This article published in 2014. It has been reposted to inspire further conversation.