From 1st time founder to 2nd

Hi, 

Recently, I have been thinking a lot about what it means to be a “second-time” founder. What does that mean, and why has the meme become so ubiquitous around entrepreneurship circles. 

If you don’t know the reference, here is a version of the format: 

There are hundreds of directions that people take it, but as I leave my first founder experience, the questions of what I would do differently have been spiraling around my head.

I have crystallized it down to one thing, that has ramifications for everything… not just entrepreneurship. 

When you are special you don’t have a different path, you get more benefit from the traditional path. 

The story of this lesson starts way before I started The Hero’s Journal. I was working at a running store in Redmond, WA called Super Jock n Jill. One of the cool things about working here was it was right at the base of the hill Microsoft’s main offices were located on. 

Every once and while some of the executives from Microsoft would come into the store looking for shoes, and the way we sold shoes was basically an hour long conversation. 

One day, the head of marketing for xBox came in looking for shoes, and I was basically able to interview him for an hour, and he said something I will never forget, “I just followed my easy A” he would continue to say, “I had a marketing course for my major and all of my friends were struggling to bet Bs and I really didn’t try very hard and I got an A.” 

On that day, following the easy A became a heuristic, but I misinterpreted the meaning for the first 10 years trying to utilize its power. 

You see, what I thought it meant was to find your special skill and then you would get ahead because it's hard for everyone else and not for you. 

In simpler terms, if you are special you play by different rules. 

This idea is a trap. This idea is synonymous with the first time founder trap.

When we were starting The Hero’s Journal, there was immense pride in the fact that there was nothing like it. Explaining it was hard because we didn’t have any frame of reference, and traditional talking points didn’t work for us because we were special. 

The special-ness bled into our marketing procedures, shipping process, and so on. 

We thought we built a product so special that we had to operate by different rules. The issue with this belief is that even when you are special you start to deal with common problems. How do you solve common problems? Common procedures… the same ones that we were too special for. 

It bleeds into the nature of the business and starts to muddy up all of the decision making. 

So, what is the “second-time” founder perspective? 

Being special doesn’t give you a new path, it makes the traditional path more effective. 

When you have an easy A level talent you aren’t held to a different regiment, you get more out of the traditional regiment. 

Feeling special is an addictive feeling. I am very millennial in the belief that I think there is something uniquely special about everyone, and if you are lucky enough to find yours, that is not the end of your worries, but the beginning. 

Being good at your thing is only one piece of the puzzle, you cannot delude yourself into believing that you play by different rules. 

Bye, 

Kyle