Why Most Bosses Suck

You’ll never do your best work under someone who hasn’t done theirs.

Most bosses suck.

And the ones who (seriously) refer to themselves as “the boss”… they definitely suck.

It’s not always their fault. But it’s almost always your problem.

Because here’s the truth:
You’ll never do your best work under someone who hasn’t done theirs.

So why do so many suck?

It usually comes down to one of a few things.

1. They say they could never work for anyone else.

Which sounds bold, but it’s actually just hypocrisy. They expect you to do what they say they could never do themselves. And that mindset makes it almost impossible for them to become great leaders, because their ego is turned up so fucking loud they can’t hear anyone else.

2. They love being the boss more than doing the boss work.

Being a leader is a lot of freaking work.

The accolades are 2% of the job. The infinite responsibility is 98%.

Real leadership is not about shouting orders or sending Slack zingers. It’s about managing the work, not just managing people.

Meaning: Respect doesn’t come from your position in the org chart.

Meh.

It comes from watching someone lead by example, solve problems, and roll up their sleeves when things get messy. There is absolutely nothing more admirable than watching your leader do the work… because it makes you want to work harder.

3. They want the credit, even if they won’t admit it.

The dodos crave the credit. It feeds their status. They want to be recognized on the zooms calls, called out in press releases, and given the accolades and shoutouts from stage.

There is nothing wrong with that, until you learn that there is more to life than feeling better about yourself.

The best leaders I’ve seen are deeply insecure about taking credit. Because they know no one builds anything great alone. They stutter to use the word “I” and default to using the word “we”, because they know that WE > ME.

It’s not false humility. Come on. They know better. It’s really just earned perspective.

Think about it, Big Man Yoda didn’t need any credit.

4. Their title is on everything that doesn’t matter.

I get it, on social media, your title might matter. But if you're putting “CEO” in every Slack message, calendar invite, and Google Doc, you’re not reinforcing your status… you’re just reminding yourself who you wish you were. Chill with the title like its an academic degree. It’s almost as dumb as putting MBA after your name.

For the record, I have an MBA too.

Nobody cares.

5. They’ve never worked for a great leader.

This one makes me sad.
You can’t lead well if you’ve never seen it done well. I learned what leadership really looks like from the Navy SEALs I trained with, from a partner at Goldman Sachs, from Peter Loewy, who I built five companies with.

I am sorry, you can’t learn leadership from a book. It’s a good first step, but there are more steps. You have to feel what it’s like to be led by someone you’d follow into battle.

6. They don’t respond, but expect you to.

Good leadership is also grounded in day-to-day mechanics.

• They ask for reports but never acknowledge them.

• They ghost Slack threads.

• They show up once a month and say shit like, “We just need to lock in.”

We all know that’s not good leadership, but we let it slide because that’s what the org chart gave us.

For the record:
Leadership is fucking hard.

I am sorry to tell you that if your team is underperforming, it’s probably because you’re modeling it (probably without your knowledge).

7. They think you work for them.

But everything changes when they realize they work for you.
The job of a leader is to unlock your people.
To help them be the best they can be.
To push them to find their zones of genius.
To help them do their best work.
To help them win.
Anything less is just plain unhelpful.

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What I Had to Learn (the hard way)

After years of therapy, here’s what I know about myself:

1. I am an OK employee.

2. But I am a good partner.

I don’t care about politics, reporting structures, or chain of command. This isn’t the Navy and I’m not a SEAL.

When I was younger:

• I used to chase the title.

• I thought being CEO was the point.

• I thought leadership meant being at the top.

• Getting all the credit was the game.

• Being the one everybody looked up to was the ultimate flex.

But I was wrong.

So wrong.

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What I Actually Wanted

After five exits, helping build two billion-dollar companies, investing in 100+ businesses, rebuilding my health, and doing it all while trying not to compromise my family too much, I’ve realized something really important:

I never wanted the “top job.”
I just wanted the biggest version of the work I loved.

I really hope you read that again.

And I had to figure that out by starting with what I hated:

• I hate being around people who play status games

• I hate red tape and internal politics

• I hate when someone chooses my focus for me

• I hate being told what to do by someone less capable

• I hate when people don’t take responsibility

• I hate crappy work ethic

• I hate scorekeeping and transactional relationships

• I hate being around people who aren’t kind

• And I really hate being around people who don’t hate to lose

At a minimum, I wanted the opposite of all that.

And that meant I had to stop chasing the job I thought I was supposed to want.

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What I Want Now

I don’t have a problem reporting to someone.

But I’m at a point in life where I don’t need a job.

So there are only two reasons I’d ever “work for” someone again:

1. I have immense respect for who they are, and I want to learn from them.

2. I care about them so much that I want to make them successful.

If I get both like I do now with with my partners Alex and Leila… that’s the dream.

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If You’re Still Reading This

Thank you.
Maybe you’ve had to deal with some of these frustrations too.
Maybe you’re trying to become a better leader yourself.

Here’s what I know:

• If you lead, you can always lead better.
  There is no bigger multiplier in your business than a team operating in their zone of genius.

• If you’re on a team, pick your environment carefully.
  The right leader will unlock a better version of you than you’ve ever seen.

And one last thing…

You will never work for me.
And I will never work for you.

But if you want a partner,
If you want a collaborator,
If you want a work bestie building something insane…

Come join us.
We’re building something epic at Acquisition.com.

Big bonus if you love the Anaheim Ducks.

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