Don’t Be a Dick… And 10 Other Things I Learned the Hard Way About Leadership

They fired me. They fired me as CEO. Then they fired me as a board member. Then they took away my shares. And now none of them ever talk to me.

I started the company, I had the initial idea, I raised $30 million for it from A+ investors (i.e. “rich people”), I bought two companies for it, I hired the first 50 employees, and then I was shown the door.

The reason? I was a bad leader.

Here are some things I didn’t know about my own company:

  • I didn’t know what our product did.
  • I didn’t know any of the clients.
  • I didn’t know how much money we made.
  • I didn’t know how much we lost.
  • I didn’t know the employees.

I just didn’t do anything… for… anyone.

I never wanted to talk. I would lock myself in my office and people would knock and I would pretend not to be there.

Being a leader doesn’t mean you are the guy who runs things.

Being a leader doesn’t mean you created something or you did something great in the past or some other person has given you any kind of authority.

I’m going to make a list. Forgive me. Feel free to add to the list or add your own experiences in the comments.

In fact, I would really appreciate if you can add to this list.

After running 20 or so companies (most of them failures), after investing in 30 companies (most of them successes), after advising or being on the board of a dozen companies (most of them successes), I have a sense of what I think a leader is.

I may be wrong but this is my list.


Most important by far: you care about the success of others more than you care about your own success. Everyone around you needs to ultimately become better than you.

If all the people around you achieve more than you, then life will be good. You don’t have to believe me. I’ve seen this happen repeatedly.

In my first job I worked very hard. But I always gave my boss all of the credit. He kept getting promotions.

After every promotion, people would come to my tiny cubicle and congratulate ME.

You don’t need to be the top of the pyramid to be the leader.

If you just focus on this one principle in all of your actions, then you are a leader.

Exercise: Figure out how the people around you can have a successful day.


I wrote a book called “The Power of No.”

But now I’m about to tell you to say yes.

If someone presents an idea to me, the key is to say, “Yes, and…”

Help them explore their idea. Help them be creative around their idea.

“Yes, and…” is the first rule of good improv for a reason. It allows others to create something new.


a. “Yes, and…”

b. List what’s good

c. How you would improve

d. What is the core vision of their idea?

e. Connect the “why” of what they are suggesting to the initial vision. Does it work better than the initial idea?

f. Be open to the fact that you might be wrong. ALWAYS ALWAYS you might be wrong.



I always imagine a good leader is surrounded by people who call their mothers at the end of the day and tell them, “Mom, you can’t believe what I did today. Let me tell you about it.”

Not that every day is fun. Because some work isn’t.

But make sure every day your employees can call their parents with one new thing they are grateful for.

Maybe they learned a new skill.

Maybe they met a new client and created value for that client. Maybe a client they hated was fired. You can’t let your employees get the disease that bad clients are all too happy to spread.


An organization of less than 30 people is a tribe.

There’s evidence that 70,000 years ago, if a tribe got bigger than 30 people, it would split into two tribes.

At 30 people, a leader spends time with each person in the tribe and knows how to listen to their issues.

From 30–150, people you might not know everyone. But you know OF everyone. You know you can trust Jill because Jack tells you you can trust Jill and you trust Jack. (This is the invention of “gossip.”)

Above 150 people, you can’t keep track of everyone. It’s impossible. (Look up “The Dunning Number”). This is where humans split off from every other species.

We united with each other by telling stories.

We told stories of nationalism, religion, sports, money, products, better, great, BEST!

[Note: Read Yuval Harari’s book “Sapiens” or listen to one of my two podcasts with him.]

If two people believe in the same story, they might be thousands of miles apart and total strangers, but they still have a sense they can trust each other.


We are delivering the best service because…. We are helping people in unique ways because…. We have the best designs because…. We treat people better because….

A good story is a CALL TO ACTION to the people around you: Go from the ordinary world into the extraordinary world!

First you listened to people, then you took care of people, but now you unite people under a vision they believe in and trust and bond with.

Companies live and die on this. One company I advise built itself up by buying 200 regional offices; now it’s unifying them under one brand.

The key to this company’s success is how powerful the story will be that it tells of that brand. Why are they delivering the greatest value? People need to believe in the story.

By the way, this is how humans killed everyone else.

Because we could plan and coordinate in much larger groups than any other species even though we were far weaker.

That’s why there are no other sapiens left on the world. No Neanderthals.

Proof: Within 3,000 years of humans first landing in Australia, no species was left that could put up a fight with us. We killed them all.

Yay humans!


Everyone has pain they don’t want to feel.

I used to be afraid to look at the stock market because I was afraid I was losing money.

Or I would be afraid to ask a woman out because she might say no.

Only by struggling through pain do we learn and get better. The moth has to break open the cocoon in order to fly.

If we open the cocoon for that moth, it will die.


The other day someone cancelled an appearance on my podcast at the last minute.

I had rescheduled other meetings and even changed the time I would see one of my daughter’s plays so I could interview this person—a very, very successful entrepreneur.

She wanted to reschedule but I said no, even to the detriment of my podcast and all the people who work with me on the podcast who were looking forward to the interview.

I wasn’t angry with the person. She’s running a business and was probably very busy. And people reschedule all the time.

I just didn’t like that it was last minute. I had studio time booked and no space to fill it.

I have a vision for my podcast.

Everyone who comes on is someone who has transformed their life and created the life they wanted to. I want my listeners to be helped by the transformative stories of my guests.

The world is changing very fast and it’s scary. I want to help people be less scared and I know I am less scared when I hear the stories of my guests and learn from them.

If I don’t treat my own projects with respect, then how can I expect others to?

If I don’t treat myself with dignity, then how can I expect the people around me to treat me, or even each other, with dignity?


One time an employee asked to meet me outside the office. She was crying. I asked her what was wrong. She was afraid she was doing a bad job with a client.

And she was. But it turned out the real problem was she heard one of my business partners talking poorly about her behind her back and this was affecting her every day at work.

This was the real problem that had to be fixed. And it was. And then everything, employee, client, partner, etc. went well.

In 100% of cases, there is a good reason and a real reason.


If my daughter says, “I want to study in the library,” then she has a good reason.

But there might be boys in the library. The real reason.

A leader listens to the good reason.

But then listens even more closely to try to figure out what the real reason is. There is ALWAYS a real reason. Listen for that and see if you can help.

A good solution solves one problem. A real solution solves 100 problems.


A sick leader is not a great leader.

A leader who is spending time with people who are not good for them is not a good leader.

A leader who doesn’t constantly practice creativity is not a good leader.

A leader who is not grateful for the abundance already in his or her life will never lead his vision into abundance. He won’t know how.

There’s no such thing as instant health. There’s only such thing as practice and progress.

All you have to do is check the box on progress. Progress compounds every day into enormous abundance.


Warren Buffett says he skips to work and that he would do the work he does for free. Maybe it’s easy for him to say that because he has $50 billion.

But I’ve gone through and read his letters from the 1950s when he was first starting out. These letters are not publicly available. I had to really try hard to find them when I wrote the book on them in 2004.

He loved what he did when he was just starting out, with no money, working in his living room.

He took glee in finding companies that nobody else knew about. GLEE!

Don’t do something just for the money.

Money is a side effect of persistence. You persist in things you are interested in. Explore your interests. Then persist. Then love.

Then… side effects.


Before I can lead anyone I have to lead myself.

I have to read. I have to try and improve 1% a week. I have to spend time with good people.

I can’t make excuses. I have to take extreme ownership. [See Jocko Willink’s book “Extreme Ownership” or my podcasts with him].

I have to be creative every day.

I have to learn 1% more a day.

I have to challenge myself to do the things I am afraid to do.

The definition of success for me is: “Was today successful?”

The best way to have a successful tomorrow is to have a successful today.

Share This Post

Other posts you might be interested in: