A Real Cool Hand

I'm Craig Sturgis and this is a web site.

Swing and a Miss

If you’ve been paying attention to some of my recent writing you may have noted a more downbeat and reflective tone. The open secret behind a lot of this reflection is that the business I co-founded has stopped operating and is shutting down.

Naturally, this was a really big disappointment for all of us. Rationally, I know I will almost certainly have worse days in my life, but the way I felt the day we had to break the news to our team that we were out of money is not something I want to experience ever again. It felt like I’d let everyone down, from our investors and service providers, to our homeowners who spent their time and money with us, right on down to the dogs who wouldn’t get to spend days at our office anymore.

After a little bit of time, I don’t feel ashamed of the failure or have a desire to whitewash our story. We have no need for flowery “sunset” euphemisms. We took a big swing, and we didn’t connect.1 The disappointment lingers, but I have a big sense of pride in what we built, our culture of communication, speed, and continuous improvement, as well as the hard problems we were able to attack and make a dent in before we ran out of fuel.

I think calling attention to lessons learned when things don’t go as planned and the practice of writing post mortems is just as valuable as hearing the success stories that inspire us to take those big swings. Jim’s version of ours is here:

This is the End – Haven Post Mortem

It’s a really succinct summary of the many factors that led to us not being able to make the business work. The biggest lesson not spelled out in that post that I’ve internalized is one that’s really painful as a “product guy.” It was a line I’ve heard many times but didn’t really and truly understand until recently- the market is way more important than the product.

I can link the famous Mark Andreessen post but hopefully most have read it already. I did way back when, and didn’t learn the lesson, but it’s so blindingly obvious in retrospect. Even the best product in a market that isn’t good enough or isn’t ready will still fail to generate a sustainable business.

The iPhone is arguably the most successful single product in history not purely because Apple states that its mission is to make great products, it’s mostly because the smartphone market is maybe tied with railroads as the greatest market in human history.2

I still believe in creating great products — it’s the main thing that motivates creators. But, I have a new passion for minimizing wasted effort starting with laser targeting the right market first, then building the best possible product that fits that market, and making the iteration cycles take as little calendar time as possible.

I do still have a perfectionist instinct to indulge by making the things that I’m proud to share with others, but in the future I will make sure it’s a labor of love first and any business that comes out of it is a bonus.

In the end, my Haven stock is not going to make me wealthy and I do not have an “exit” on my resume. But, compared to the opportunity costs of a more comfortable job or a bigger salary, I believe the last few years with Haven and what is now SmarterHQ before that have given me an education I couldn’t have gotten any other way. I’m excited to leverage that hard fought knowledge and learn even more in what I do next.

One of our Haven lunch and learn speakers3 said something that really stuck with me. I don’t remember the exact quote so I’ll paraphrase:

This is not a line of work that has a high probability of success, but nobody here is going to starve. If you stay in it long enough and learn enough, you’re probably going to be successful.

It may take me a year or five or ten, but if I’m fortunate enough to stay on this Earth, I see myself taking another ride on the founder rollercoaster. There’s always more to learn, and there’s no better way to learn than by doing.


  1. Maybe I can use this metaphor to get my twitter circle to start arguing about hitting a home run vs. a major league pitcher vs. hitting a hole in one from the tips on a PGA tournament par 3 again.

  2. Almost all of this particular point is I’m sure cribbed from / better articulated by the brilliant Ben Thompson of Stratechery whom you should be reading and subscribing to if you are interested in the business of tech.

  3. Another thing I think we did way better than any other version I’ve been a part of in the past