Pivoting Too Much
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If your idea is any good, more than likely you're going to have to beat people over the head with it.

I don't know a single founder who immediately hit gold and didn't lose it shortly thereafter. Most successful founders spend years forcing their vision into reality before feeling the pull of product market fit. Often, they succeed right after everyone writes them off.

Lenny's Newsletter asked successful founders how long it took them to feel like they had product market fit. They found it took an average of two years. The shortest felt it in six months and the longest didn't feel it for five years. Five years in the wilderness!

If this is the case, why do some founders pivot so much? I have the distinct honor of having pivoted too much and too little, so I have a few guesses.

It could be that today, being agile or lean is considered the "right" way to build a startup. People mistake this to mean throwing idea darts on a board when a better approach might be to develop an unwavering vision for the future and to be flexible with how you get there, like Airbnb "pivoting" from renting airbeds to renting homes.

Famous founders also tend to forget or downplay how hard the early days were, leading people to assume they found product market fit quickly. Watch the Social Network and it's hard not to think that if you build it they will come.

Pivoting frequently also restricts founders to easier and increasingly saturated idea spaces, which can be ok if you're trying to bootstrap but there simply aren't as many low hanging fruit venture scale opportunities today as when Zuck launched Facebook. Hard markets like biotech, defense, and hardware, where there is less competition, require more time and resources to be successful.

Some founders also fall into the trap of letting investors decide. They test an idea, have a hard time fundraising, and decide to pivot. Contrary to what many investors tweet about themselves, we aren't prescient. Even YC, the best early-stage investor out there, is wrong most of the time.

Startups are hard and one of the hardest parts is knowing when to quit vs when to double down. Sometimes pivoting is the right decision! There's no secret formula. The only advice I can give is to trust your gut. Cliche, I know. But what does trusting your gut mean, exactly?

Don't let anyone else decide. As a founder, you have the most context and the most skin in the game. Of course, talk to users, ask for advice, and gather data, but in the end, it's your job to clear your mind, let your gut crunch the data, and listen to what it tells you to do.

Don't let whatever emotion feels strongest in the moment decide. Lots of people confuse their gut with their emotions. Emotions are often reactive and fleeting whereas your gut, once decided, feels proactive and definitive.

It's human to avoid hard things. If in doubt, give a little extra weight to the choice that's the hardest to carry out.

To be a good founder, by definition, you have to occasionally be willing to do what is right when everyone else thinks you're wrong. If the solution was obvious, the problem you're solving would already be fixed.

Before you pivot, imagine you have a fresh start (no investors, team, expectations, etc.) and ask yourself if you would still start a startup to work on this problem. Don't handicap yourself by picking an idea you only kind of like in order to avoid failure, if you're not obsessed with the idea you likely won't be able to go the distance.

When you're making a hard decision, whether it's pivoting, staying the course, or shutting down, it can help to think of your life like a movie. This is the scene where you listen to your gut, do the hard thing, and it makes your inevitable success that much more satisfying in the end.