One of the Big Challenges of Later Stage Entrepreneurship

“Everything you had to do to get this thing where it is is totally different from everything you have to do to get it to the next level.”

Another company founder told me that. It’s something I’ve started to find more and more true.

To start a company requires bullheadedness bordering on delusion. Ignorance is an asset. The less you know about your odds of success and all the challenges to come, the better. You need a ton of confidence in your vision, and a stubborn refusal to listen to all the common sense approaches.

If you listened to the market, it would tell you, “We’re fine thanks, your company isn’t needed. If it was, someone would’ve done it already.” So you don’t. You follow the future you can imagine, and only work with those few who see it too. Taking advice is very dangerous, and erring on the side of rash and brash is an advantage.

That’s how you go from nothing to something. That’s how something truly new enters the world. It’s willpower and belief followed by dogged execution in the face of doubt and defeat.

But when you’ve got something and you want to turn it into something bigger, the necessary attributes for success shift. You still need some of that fire, but you also need a more open mind. Early on, you can’t afford to ask questions like, “Will this really work? What proof do I have?”, but later you can’t afford not to.

Early on you can’t be objective about your company. It’s your baby. You only see it as the dream vision despite the world telling you otherwise. You have to. Later, you’ve got to be objective about your company. You’ve got to assess what’s stupid and fix it. You can’t fear any question. You can’t fear any information. You need to take the horse blinders off. They were necessary to get started – without them the world would overwhelm your attempts to forge ahead. But now you need to expand the context within which you operate.

This is hard for an entrepreneur. It’s easy to get wrong. It doesn’t mean you turn into a focus-group junkie. It doesn’t mean you give up on the idea that, “Consumers don’t know what they want until we show them”. It doesn’t mean you mold yourself after the competition.

But it does mean you stop the extreme practice of willful blindness needed at the outset.

It’s similar to growth in other areas. The first time you pick up a basketball, you can’t afford to know all the things you’re doing technically wrong. Too much info from experts would reveal how bad you are and you’d never get started. You need to be dumb enough to think you’re good, or at least have a chance to be good. That’s how you get good.

But after you develop some skill you can’t be ignorant of your shortcomings anymore. It no longer helps. Now you need to look closely at your technique and find where it lacks. Now you need to learn from people who have mastered the game better than you. You don’t need to lose your unique approach, but you do need to objectively assess your performance and adjust your game.

This is a hard phase for me. I like the thought of holding nothing too precious to assess and improve. But I also hate advice seeking and analysis paralysis. I’d rather fail being different than succeed being the same. Half of that is a good instinct I shouldn’t discard, half of it is laziness or pride. Hard to tell which is which sometimes.