The Do Over

I don’t often have a weekend like I did this past couple of days.

One day filed with friends and errands; and one day filled with quiet and solitude.

Late Saturday afternoon I was shooting hoops with my friend Arin Sarkissian–of Well.io–at a middle school near his house. As we often do, we chat about our startups, yet this time we also seemed to dive into our pasts and the subject came to the selling of my last company as well as my sobriety, which happened around the same time.

“It was weird,” I said, “experiencing something that humbling was the only way I could have a do over.”

(BTW, Eric Clapton’s Cocaine just came on Spotify. For those that don’t believe that Steve Jobs put some secret alien intelligence into OS X, explain that.)

For the past twenty-four hours or so, I have been thinking about the concept of a do over.

Initially, I contained the thought to myself. If I had a real do-over, what would I do differently?

It wasn’t as simple as correcting past mistakes or taking advantage of missed opportunities, it was about enacting real and meaningful change. It wasn’t about a course correction; it was about an entirely new course.

Does that mean I wouldn’t have been an entrepreneur? I doubt it. I love being an entrepreneur, and it’s what I am, more so than just what I do.

But, it would be about making a major life pivot.

Maybe that’s why I get so angry when tech journalists and others with minimal experience actually building and running a business, dismiss the pivot as failure or hyperbole.

For some reason, the emotional journey of building a startup is dismissed and marginalized into explaining it as a ever-changing roller coaster, which is true, but it also so much more as each one of my grey hairs can attest.

While we dismiss ideas as being mundane, there is nothing more special than the moment you come up with an idea that begins to consume you. The question moves from should this idea live to how am I going to do it? You start to think about all the things that Paul Graham writes about in his Startups = Growth post, all the while believing nothing else than you potentially have a fast growing, gigantic idea on your hands.

That feeling is multiplied when you are a first time or young entrepreneur when the feelings of invincibility haven’t been cracked and pitted. You start talking to everyone, maybe even prototype and get early users.

You raise a bit of money, or generate a bit of revenue. Things are going great. Or maybe they aren’t. Either way you are constantly thinking about two things: How do I get this to grow faster, and how big can it get?

And, sometimes, regardless of how things are going, the right thing to do is to raise your hand and say “do over.”

Yes, pivot. Maybe toss everything, or just a few things, but start again down a new path.

Did you lose? Did you fail? No. You saw that regardless of the early success of you (or your competitors) or the lack of success, the business was neither going to grow fast or get big enough to be interesting.

I spend a lot of time with young, first time entrepreneurs who struggle with so many aspects of their business, be it from fast, or lack of, growth. Who either have trouble raising money or find raising so easy that it becomes a burden of expectation. And, for some, they will raise their hands and ask for a “do over.” Many more than once.

Each time I sit in a room, or on the phone, with a founder with tears in their eyes, or a crack in the voice, because of some investor who turned them down, or a board member who doesn’t understand that the lack of traction isn’t because they haven’t implemented the board members favorite feature just yet, asking me if its okay if they pivot, I curse the assholes that have somehow equated pivoting to failing, and caused so many entrepreneurs undue emotional crisis.

I think about myself from six years ago and realize that the emotions and thoughts are not much different. Once its clear things have to change, the decisions are around how and how much, regardless of all the pain and confusion that comes with the decision process.

“It’s your company. Do what you think is best.” I say. “If you think a do over is the right course of action, take it. You might be surprised where the new path leads you. But, mostly know that its the ability to make the decision that sets you apart, not that you have to make it.”

Understanding and undertaking a do over comes from a place from immense strength, and I am proud of myself and all the other entrepreneurs that have successfully executed on a do over. Know this: Nobody gets it right the first time. Nobody. And, for everyone that pivots, It’s fucking hard and it hurts, but we are all better for the humility and lessons it brings. Even me.