The Achilles Heel of Advice

The achilles heel of startup advice is that you only get the person’s specific experience in life but it is wrapped up in the form of generalised insight.

The listener is as much to blame as the speaker, failing to take the time to understand who the person is giving it and why they might say that.

There are many ways to win in poker. You can raise it up with a high pocket pair and keep betting consistently after the flop when you think there is no danger. You can slip in with small suited connectors and then move all in when your straight or flush appears. Or you can bet with nothing but your belief the other players are not strong.

Most advice feels like “you need to be aggressive and raise it up before the flop all the time” but misses the context of the cards your holding (problem/product), your personality (founder/team/company) and the personalities around the table (market/competitors).

What’s more, great advice can only tell you what worked in the past. What worked before for the truly great companies only can rhyme with what will work for the next truly great companies.

The great companies of the future always look uniquely weird and strange. They build their path in life but not doing what was done before and thinking from first principles. Don’t be Steve Jobs or Mark Zuckerberg, be yourself.

Finally, startup advice is also subject to the same market distortions with supply and demand. The more people are telling startups to do a certain thing, the less likely that certain thing will work.

Jason Lemkin and Aaron Ross telling you to hire SDRs, cold email and create an inside sales machine was transformative five years ago but now follows the law of shitty clickthroughs.

You have to be in Silicon Valley to succeed and so you need to raise a $2m seed round to hire 4–5 engineers who live in poverty getting paid $120k/year and were also told they need to be in Silicon Valley. And so on. Everything breaks the more times it is followed.

Your only chance in life is not to be popular. But don’t take my advice.