Minimizing “Freak out” execution
People frequently refer to my first entrepreneurial endeavor as a learning experience. They say “well you must have learned a ton,” or ask “what did you learn from that failure that you can apply to this new company?” For the first 4 months after we shut down Untitled Partners, I would try to generate sweeping “lessons learned” and identify mistakes that I made that I will never make again. I wrote a post mortem on the Company very soon after and it was largely in that vein.
It was not, however, until I started working on my second company that I was able to identify the true efficiencies of having gone through my last experience. Caterina Fake wrote an interesting blog post a few months ago, where she described her experience building Hunch relative to her previous experience building Flickr. Reflecting on Flickr, she said:
a lot of what we then considered “working hard” was actually “freaking out”. Freaking out included panicking, working on things just to be working on something, not knowing what we were doing, fearing failure, worrying about things we needn’t have worried about, thinking about fund raising rather than product building, building too many features, getting distracted by competitors, being at the office since just being there seemed productive even if it wasn’t — and other time-consuming activities. This time around we have eliminated a lot of freaking out time.
As I build my new company, JumpPost (we’re hiring), I find myself experiencing a similar level of reduction in “freaking out time.” The best analogy I can draw is to a post-game interview after a lost 6th grade basketball game. The announcer (investors, colleagues, family) asks a 6th grader (first time entrepreneur) on the losing team “what went wrong, what are you going to do differently next game?” The player, responds, “Well, we shouldn’t have played a zone defense in the second half, they were killing us from 3 point land.” I would equate his response to the “sweeping lessons learned” analysis I referenced earlier. While true, this strategic error was not necessarily the biggest lesson of the game. It turns out, during the 3rd quarter of the game, said 6th grader learned how to comfortably dribble with his left hand. 6 months later, the teams meet again, and said 6th grader scores 10 left handed layups without thinking twice. They win, and the announcer asks him “what went differently, how did you guys plan for this game?” The truth is, the team played the exact same zone defense as the first game, but said 6th grader had developed a proficiency and comfort that allowed him to stop thinking about dribbling, and start focusing on the hoop.
This time around, I am not thinking about dribbling. Decisions that I agonized over for a week, I make in 5 seconds, and then move forward. A good example is our name, JumpPost. With Untitled Partners, we spent weeks trying to think of the right name for our Company, because our brand was “extremely important.” We even ended up hiring a “brand consultancy and design firm,” who charged us $25K to come up with a name, logo, and “brand” for our company. We wasted a ton of time and money ($25,000 is a lot of money when you only raised $560,000) at a time when we should have been focusing those resources on more core issues like “what does our customer want?” So the efficiency gained from that lesson, while impossible to zoom in on and identify when asked “what did I learn from the last company,” I was able to realize when naming JumpPost. I needed a name to incorporate, I spent 10 minutes on GoDaddy brainstorming URLs, and then I picked it. If it stinks, or becomes more important down the line, I’ll change it. No need to “freak out” or get distracted. Similarly, I’ll probably use CrowdSpring to develop a logo. Again, 5 minutes replaces thousands of dollars and wasted management bandwidth.
The first time around, everything is unknown, so you don’t know what’s worth digging into, and what is completely irrelevant. Did I really need to spend a day dilligencing my lawyer’s recommendation for a C-Corp vs. an S-Corp? Absolutely not, but I how could I know that the first time around?
This brings me to a more fundamental practice that I implemented well during our first company, but that I am doing even better on now: listening. Right now, I have achieved what would have taken 6 months and a round of capital my first time around, in 3 months with no capital. This efficiency is largely due to a non-“freak out” style of execution. But every entrepreneur’s expertise and play book has gaps. It is why we hire others with complimentary play books and knowledge to streamline the execution toward a goal. But in the absence of financial resources to fill in these gaps, actively seeking out advice from those who have accomplished what you set out to achieve AND being an excellent listener, are critical to pushing the ball forward. Some people think that “running a company” is about being the leader with all the answers. In reality, I am learning that running a company is about being a “student,” recognizing the experience and genius in yourself (where it exists), but more importantly finding it within your team and extended network. Listening to that collective body of knowledge and understanding how to incorporate the learnings into a play book in real time is where it’s at.
Jordan Cooper's Blog: startups, venture capital, etc... 
Hey man – Stumbled onto this from your gchat status message.
This is SO true. I am still on my first company but looking back I get so stressed thinking about how much time and money I wasted because I didn’t know what I was doing. Especially on the technology front – we are now completely re-writing everything.
On the other hand, it’s a sunk cost and I feel much better that we’ve found our feet and are now moving forward at a good pace. But it almost feels like I’ve already had one failure and am on my second company even though it’s still the same one.
Carter Cleveland
November 12, 2009
Great post here, Jordan – I could definitely relate to your experience. It’s critical to aim to fail asap in a company and to always be a “student”, similar to how web projects always go through iterations to improve and change over time.
Looking back at my own experience I realize that every mistake made is always a loss in the short-run and there’s nothing you could ever do about it. But whether that mistake turns out to be a loss or a gain in the long-run is completely dependent on you. Sometimes those failures turn out to be very valuable mistakes that you learn quite a lot from, and as a result, enjoy huge gains from later on. I think it’s a matter of sticking to the path, always taking the tougher road instead of giving up, and constantly learning from short-term mistakes.
Of course, those “freak out” moments and mistakes are tough to stomach. One piece that I find myself coming back to several times over is this “Failure Speech” by Paul Tudor Jones, which I highly recommend – http://bit.ly/YeOcZ.
Sayem Islam
November 13, 2009
Thanks for the link Sayem, very nice read indeed.
Jon McJonJon
November 13, 2009
Jordan, Great post! In my start up career, I’ve experienced more than my fair share of “freaking out” and I see too many of our customers “thinking about dribbling” when they should be taking action. When it comes to creating company names, logos, and other “branding” attributes, I think that few people realize that it’s often an iterative process. Company names, logos and brands develop over time, but most people only become aware of them once they’ve already hit it big. When brands do emerge from nowhere, they are often being developed in a template fashion by someone that has already done something very similar in the past – i.e. the marketing firms that launch sports drinks or the people that create hollywood hits. It reminds me of when advertising people tell small business owners that they should invest in broad based advertising and they use McDonald’s as an example of how it works!
Ben
November 14, 2009