“Don’t take advice from anyone you wouldn’t trade places with.”

It’s the best one-line filter for advice out there. Every startup founder gets gobs of unwanted advice from everyone. Most of it isn’t advice; it’s autobiographical anecdotes designed to make the advisor feel or look good. People tell you what worked for them, in their circumstances. That “would I trade places with them?” check works: if you don’t want their life then their path doesn’t matter because their path leads to their life. So don’t take their path. If, however, you want their life, then they’re probably worth listening to, because they know how to get there.

It also stops you from listening to the “gurus”. You know them: the folks who make money teaching other people how to make money. The LinkedIn “thought leader” who rents a luxury car for the photo shoot. If they made that much money, why are they doing this? And I never believe that line about “because my purpose is to help others” if they only help others who can pay them. If they’re not living the life you want, and you wouldn’t trade places with them, then they’re not worth listening to.

The blind spot

But. If you only listen to winners, you’re only hearing maybe a tenth of the story. Nine out of ten startups fail; that’s the established background failure rate. Every “25 habits of wildly successful entrepreneurs” ignores the fact that wildly unsuccessful entrepreneurs also have those habits. The winners wake at 5am. They journal. They meditate. They say no to things. So did the losers. If you just asked 100 founders what they did, and then tried to pick the winners based purely on their habits, you’d get it completely wrong. The difference between the “winner’s habits” and “loser’s habits” lists is fuck all.

Winners can’t tell you which parts mattered or caused their success. Ask a successful founder why they won, you’ll get a varied response from “I’m just that amazing”, “I worked really hard”, “I got lucky”, “I have no idea, but I’m grateful it worked” and others. Ask them for the biggest mistakes they made, and some of them will get very specific, but most will hand-wave. Because they didn’t make many mistakes, by definition. You’re screening out the people who could tell you about what can go wrong.

The potholes

The people who can tell you that, are the people who tried to do what you’re about to do and failed.

Not because their failure predicts yours. No-one, and I mean literally no-one, knows whether you’re going to succeed before you start. But because they know where the potholes are. Which assumptions turned out to be completely wrong. When the money ran out, and why, and what they spent it on that you shouldn’t. What they’d do differently now, with the scars. A good post-mortem is worth more than a hundred victory laps, because failure teaches valuable lessons.

These people are hard to find, and hard to get talking. No-one likes talking about their failures. And no-one likes listening to those stories, because it reminds us that we, too, could just get unlucky and have it all collapse around us. Nobody keynotes a conference on “how I lost my investors’ money and most of my marbles”. I’ve struggled to express the lessons I’ve learned in my many, many, failures. We treat failure as something to move past, not study. Like congenital disease and mental health problems, we fear failure might be communicable. That somehow we are the average of the five people we associate with most (the most fucked-up philosophy I’ve ever heard). And it’s a shame, because the founder who tried your exact thing and got wrecked is the single most underrated source of information available to you.

Don’t take advice from anyone you wouldn’t trade places with. But do take it from someone who tried to walk the path you’re taking and fell. One will show you the road they took, while the other will show you the potholes they fell in. You need both as guides.