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Bootstrapped Giants

CEOs, Stop Doing Work.

Published about 2 months ago • 5 min read


Like many people reading this, I used to CEO all wrong.

What I used to do: tell people to email me things, or send me “to-dos” like reviewing a contract, writing a product spec, or preparing a sales deck and I'd get them done.

And here's what my schedule was like: I'd have meetings all day to look at progress, make decisions, host interviews, and more. All the while, I'd barely be present.

Since I had so many things to get done, I'd always be multi-tasking. After work, I'd head home to put my kids to sleep. Then have a pile of work to get done and spend all night working on it.

And still, I'd miss deadlines and be a bottleneck. And people would be frustrated.

I did this for YEARS.

Then in a short span, I read three articles around the same time and decided to embrace what I read.

Fred Wilson on "What a CEO Does"

Jack Dorsey on
"Being Editor in Chief"

And Sam Corcos on
"His Calendar"

Read/watch those when you get time but here is the TLDR for any CEO:

By the time you are at 5-10 people, YOU should NOT be "doing any work." What I mean by that is you shouldn't be the responsible person for "individual contributor" work.

Whether it's building a financial model, making a deck, writing a product spec, or even a sales follow-up. STOP being responsible for individual work items.

And, in the rare case, you are, ensure you have scheduled time on your calendar to get it done.

This took me a long time to embrace. Why? Because of my inertia combined with guilt.

I am a badass worker. I can sell, I can follow up, and I know ALL the Excel keyboard shortcuts.

And sometimes, it's just easier to get it done myself. Then, combine that with the guilt of all these people cranking around me.

If they're working, how can I be so removed that I just float between meetings and make suggestions?! It felt wrong.

Nonetheless, I embraced it and never looked back. Not only was I happier, my TEAM was more productive and more fulfilled.

Here are some of my KEY learnings:

Most entrepreneurs are high achievers. So we are used to looking at our ability to get shit done. And my ability, probably like yours, is extraordinary.

But every entrepreneur eventually hits a ceiling where their to-do list grows faster than their ability to get things done.

Andy Grove, the founder of Intel, wrote in his famous book "High Output Management," that the manager's job is to look at and optimize TEAM output.

So if you do nothing, but the company's revenues and profits grow and deadlines are met, then declare victory.

Stop measuring your productivity and start looking at what the team gets done.

I personally rarely make "to-do" lists for myself. I don't have anything to do!!

Instead, I write company/team priorities and work to ensure those are met.

Here's the thing: most CEOs know they are supposed to do this.

When GrowthAssistant was first scaling, I'd watch Adriane, its CEO, try to set company priorities hastily off the side of her desk while diving deep into a new client contract.

That is likely the reality for you, too.

But to set great priorities, you have to make TIME. Time to get information, time to understand the market, and time to just think about what matters and why.

One of my favorite analogies for startup CEOs: you're actually an investor.

Your people and where they spend their time are your stocks. If you put the right people on the right things, you get great returns.

If not, you lose money. Make the time to allocate people's time and energy to the highest leverage areas.

To do that well, you can't simultaneously own individual responsibilities.

Beyond the priorities, you also have to figure out the sequence and urgency of things.

What matters when and why? That puzzle needs critical thinking and attention. Make time for it!

Your job is your people. EVERYONE on your team needs feedback, guidance, and alignment to ensure what they are doing is going to meet the needs of customers/the market.

Imagine an NFL coach getting on the field and taking a snap. Or a maestro jumping in to play the tuba.

It would be… RIDICULOUS. Yet, every day Founder/CEOs do just that!

Not only are they clearly NOT right for that role, but what will happen to all the other players/musicians?!

They all are looking for guidance and feedback.

Part of your job is to regularly give feedback on both work products AND people's individual development. They want to work on things that matter and know that they matter.

That part of your job is non-negotiable in creating strong team output.

Another goodie from Grove's "High Output Management": think about some of the best feedback you've ever gotten in your life and the manager who gave it.

It took that person a few minutes to say it to you and it's likely something that's made you better for YEARS.

That is some serious leverage.

Another habit to end: stop "filling the gaps" your team is missing with yourself.

Your job instead is to always be recruiting and bringing the right resources at the right time.

If you ask any of our Gateway X CEOs, they will tell you that's one of my biggest value adds.

When they need a person, an expert, or an agency, I can get it to them, usually on the same day!

Imagine how much your team will love it if you're always bringing great people in the door.

And imagine how much more productive EVERYONE gets. Again, your job is to recruit the best-position player, not jump out on the field to play mediocre football (or tuba).

And last...

I know, I'm a broken record here. I won't re-explain this.

Instead, I'll give you a HOW: surround yourself with people who compliment you/fill your gaps. If you do this, it lets you focus on your Zone of Genius (X Factor) areas, since you know you have reliability at important things, but not where you will thrive.

For example: I like to focus on Sales & Marketing. More specifically, selling to big clients or thinking of creative marketing hooks. I also like strategy and math.

What I don't love: Ops. Say, for example, setting up Hubspot.

Enter Nak, COO of GX. He's the ying to my yang. Anything I pull him into within weeks will operate smoother.

He thrives on figuring out what's wrong and fixing it. He can take Hubspot and set it up so well that things will be on track and nothing will get dropped. He'll accelerate the hell out of the pipeline.

It works.

Lastly, a word of caution: sometimes people read this and do the "other" CEO thing, which is to completely abdicate the CEO role.

They'll hand the reins and start flying around, attending conferences with brief office check-ins or flyby ideas.

I AM NOT advocating that. The opposite.

The best CEOs are SUPER dialed in. They know the numbers better than everyone. They know when things will be done and have a master plan. They are overseeing daily.

And to be the best, they have stopped doing work.

Try it.

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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