Nobody who works for you will tell you you're wrong

Are you making the biggest decisions in your business on your own?

Not the daily ones. The ones that decide the next three years — the hire, the lease, the raise, the price. You run the numbers twice, you think it through at night, and then you decide alone.

It's not that you have nobody around you. You do. They work for you.

Your team will tell you the plan is good. Your accountant will tell you the numbers add up. Your family will tell you they believe in you.

None of them has sat in your chair with their own money on the line.

Almost every founder I meet is carrying at least one decision like this right now.

Borrow someone else's scar tissue

A mentor is someone who has already paid for the lesson you are about to buy — and will tell you the price before you pay it.

That definition is narrower than most people think. It rules out a lot of what gets sold under the name.

• Not a coach. A coach improves how you play. A mentor tells you whether you are playing the right game.
• Not a consultant. A consultant is paid to deliver an answer. A mentor has no invoice riding on what you decide.
• Not a cheerleader. If they only ever agree with you, you have a fan, not a mentor.
• Someone who has done it. Built it, scaled it, and ideally lost money on it. Guidance from someone who has never been wrong with their own capital is theory.

Founders rarely make expensive mistakes because they lack intelligence. They make them because the mistake is invisible from the inside. The person who has made it before can see it from across the table.

In practice it is simple. One person, once a month, one real decision on the table each time. You bring the numbers. They bring the questions you have not asked.

The honest objection is that a mentor's experience can go stale. Someone who built in a different market or a different decade can steer you wrong with complete confidence.

So keep the decision yours. Take the question they ask more seriously than the answer they give.

Your team tells you what you want to hear. A mentor tells you what it will cost.

Google's new CEO said he didn't need one

In late 2001, Eric Schmidt had just become chief executive of Google. He was no beginner. He had already spent years running technology companies.

Board member John Doerr told him to work with Bill Campbell — a former Columbia football coach who had become one of the most trusted mentors in Silicon Valley, and who had sat on Apple's board since Steve Jobs returned in 1997.

Schmidt's first reaction, as he told Forbes in 2016: "I don't really need a coach."

Doerr pushed back. Even the best tennis players in the world have coaches. Schmidt met Campbell, and changed his mind.

Campbell went on to work alongside Google's leadership for the next fifteen years, until his death in 2016. In 2019, Schmidt co-wrote a book about him called Trillion Dollar Coach.

The easy reading is that Schmidt was being arrogant. He wasn't. He was making the most common assumption in business — that mentors are for people who don't know what they're doing yet.

It works the other way round. The higher you climb, the fewer people will tell you you're wrong. That is exactly when you need one.

Why I am recommending it

I have had mentors for most of my career, and I would not have grown without them.

Nobody in my family was an entrepreneur. There was no one at the dinner table who had done it before me, so I went looking for people who had.

As an owner-operator in serviced apartments and hospitality, with full profit and loss responsibility, the decisions that mattered most were the ones I could not test on my own team. Every one of them was easier with someone in the room who had already lived it.

They rarely gave me the answer. They asked the question I had been avoiding.

I have also made the mistakes a good mentor would have warned me about. That is why I mentor founders now. The most useful lessons I ever received came from people who had lost money doing exactly what I was about to do.

Do this before Friday

Write down the one decision you are carrying alone right now.

Under it, write the name of one person who has made that decision before, with their own money — in your industry or not. Ask them for thirty minutes before Friday.

Bring the numbers, and ask one question only: what would worry you if this were yours?