How to Know Whether or Not to Take Someone's Advice

Here’s something to remember about advice: If you go to a podiatrist and you tell them your back hurts, the foot doctor would probably tell you that the arch of your foot is collapsing and probably pulling on a nerve or something. But if you went to a different kind of doctor, they might think your back pain has to do something with their field. In other words, doctors see what they have been trained to see.

Most people have some sort of bias that informs how they see things. And in many ways, these biases are rooted in how people have been trained to view the world.  

Before I take anyone’s advice about The Hub, I ask myself three things:

  1. Do they have the necessary context? 

  2. Are they free of a really obvious bias? 

  3. Can I stress test the idea with them a little bit?

The third step is really important, although I admit it turns some people off sometimes. But I need to know if I can play devil's advocate, or poke holes in the advice, or ask questions so that the idea can be turned around and held up to the light. That's usually the only way an idea survives enough to get put into action when it comes to The Hub.

When it comes to weighing advice, the usual caveats also apply: Be patient and grateful, and look at the person giving you advice almost as much as the advice itself. There are certain people who have given me many pieces of advice, and maybe 80 or 90 percent of it's good and 10 percent is bad for whatever reason, including a possibility that I disagree with it. I always try to remember not to bite the hand that feeds you, because chances are the person giving advice is someone who's invested, who cares, who wants to give the advice. You want to make sure that you don't turn off people who you trust.

As for how to know if an idea is fundamentally worthy or good, I know that my method tends to turn a lot of people off. But it’s important to challenge every idea and consider every possible outcome. Ask yourself, “What about this? Am I sure? What if this were the case, or what if this happened?” It’s worth letting the person who gave you the advice to really make a case for that advice again and again, in different circumstances. 

That’s why I really like my company’s board, which I set up a few months ago, and I’ve definitely absorbed and digested more advice from them in that time than I have from any one individual in a year. We'll bring something up on a board call, and someone will suggest something. I might respond, and other people with other viewpoints are also able to weigh in. That's a nice way to naturally turn the idea and look for flaws in the light. It's not me going back and forth and back and forth with one human, which can feel like arguing — instead, it’s a group of people who are discussing something. And by the time seven people have spoken on the matter, you've really thought about it pretty carefully. 

It’s also worth remembering that no one knows your company like you, which means their advice will only ever take you so far. I've never spoken about this publicly, but there was a time a few years ago when I was probably the most distracted I’d ever been when it comes to my company. Someone I know and trust, who is an entrepreneur in his own right, had been giving me more and more advice — we were speaking daily and he was quite involved. I started paying them hourly because it felt like I was pulling down too much of his time, and he eventually told me that it was getting to the point where the only way he could help would be to jump in all the way.

He quoted me a price to basically buy him as CEO and I effectively handed him the wheel for three months. It was a vote of confidence in him, especially because he is far more successful than I am. I was still working every day, but he was making all the big decisions. At the time, I thought, if anyone's going to succeed, it's him.

It was a disaster.

The Hub, as a marketplace, is really complicated, and even a hardened entrepreneur would be new to my business. It took a while for our friendship to bounce back, which it has. But I learned something that he had taught me, which is a very lonely thought: The company will live and die with you. No one is coming to save you. I started The Hub, which means I have to finish it and no one's going to rescue me or complete the thought. 

It was a costly lesson to learn, both financially and emotionally. Even in the eyes of my team, it was sort of weird that someone else was calling the shots for a little while, but those three months also caused us to link arms and fix the company together. Sometimes when someone messes things up enough, it makes the problems all the more obvious. It also brought the leader out of me, so we took some steps backwards in some ways, but we've taken more steps forward since. The damage that was caused was replaced by a lot of learning and evolution.

It also reinforced the fact that because it was my decision to put my friend in charge, I was the one that had to fix it. I don't blame him for messing things up. There's a book called Extreme Ownership by a Navy SEAL I like all about how, if you're the leader, everything is your fault. It doesn’t matter if you didn't make the mistake directly, or if it was made by someone that you manage or mentor or hired. That means you didn’t train them or manage them correctly, and it’s worth taking ownership and not blaming anything on anyone else. 

I've been at this long enough to know that, as Marc Andreessen says, there are no silver bullets. There are no out-of-the-park home runs where just everything works one day. Similarly, it's hard to destroy a company in one day too, although that has happened. What you realize is that it's just day after day after day after day of hard work. No mentor is going to save you, nor is any advisor, piece of advice, or meeting. 

You never have that one meeting that just completely changes everything forever. We hear stories like that, but they are so rare. If your company is failing, it's because of a lot of little decisions that were made along the way. Entrepreneurship is all about trying things, and making mistakes and micro-adjustments based on those mistakes. You need to focus on building something for the long haul, and even if you take a little step backwards, you can always take a step or two forwards the next day or next week. It’s easier to bounce back when you realize that anyone’s advice is rarely going to sink you, but you will also sleep more soundly at night if you stress-test that advice to a point where you can live with yourself no matter the outcome.

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