"Who hurt you so much that you became a startup founder?"

"Who hurt you so much that you became a founder?"

I laugh knowingly every time a tweet like this pops up—because they're talking about the idealistic ambition, control orientation, and perfectionism that most founders have.?

I've thought deeply about the founder psychosis (because it's my own)—and what founders can do about it (because it's life or death for us).?

Ever wonder why your startup CEO is so anal, cold, or insufferable? If you have—or if you're THAT person—read on.

I've talked to hundreds of founders, and can generally fit the "naturals" into three types:?

1/ The Owner. She cares deeply about controlling her own future.?

Obsesses over dilution in each round, and blows you away with her drive, persistence, and grit. You've never met anyone who works as hard!?

She also might have a weak exec team around her and has trouble letting go of even small tasks.

2/ The Achiever. He appears perfect in every way—how did he find time to work out so much while starting a company? Look at those teeth!?

He went to Harvard, worked at McKinsey, has an adorable goldendoodle. But it's not really clear WHY he started a company except...it's the next gold ring.?

Lots of press, stellar investors, a resume-heavy team—but the substance feels a bit hollow.

3/ The Idealist. His vision is staggering—it would be almost cocky, if not for his sincerity or passion.?

He pours everything into the business.?

He probably has long hair, is poorly shaven, might have gained some weight from the stress. But he's going to make his vision a reality no matter what.?

There's a reason idealists, achievers, and owners become founders. It's because there's no other job that fits.?

As a startup CEO, your strengths around outcaring, outworking, and outpersisting everyone are directly aligned with success—finally!

You can be you, and build something very valuable that delights your users, makes you money, and changes the world!?

AND: the strengths that make founders so uniquely powerful in a startup context often make them terrible coworkers in "regular" work contexts.

It's one of the great ironies (for those of us who have seen it up close) that people who were...

• disliked by their peers and managers
• passed over for promotions
• ignominiously fired from their jobs

... only years later!—can find themselves publicly celebrated as visionaries, leaders, and brilliant businesspeople. BY THOSE SAME PEOPLE.

So: put yourself in a founder's shoes. Despite any early career struggles you may have had, you now find yourself in a position that maximizes your strengths and mitigates your weaknesses.?

A natural response is to put your foot on the gas. Keep being you, but 100x it. To infinity and beyond!?

Here's the problem. It might just be you and your cofounders at first, but when success comes, you're surrounded by a team again.?

Of regular people.?

With lives outside of work.?

Who don't own as much of the company and aren't as incentivized by its growth as you.

And who inherently aren't as suited to the grind, chaos, and ambiguity of a startup.?

(And if they are, the will likely leave soon and go start their own thing).

This is, of course, MY story. (For transparency, I'm an idealist persona to my core).?

And here's a short list, from first-person experience, of management issues that can arise for startup CEOs:?

WORKAHOLISM?

• Requiring people to put in the same hours as you (Owners)?
• Expecting other people can and will work as hard as you. (Achievers)?
• Crafting a strategy that superhuman persistence in the face of crazy long odds. (Idealists)

BURNOUT

Not seeing that your team needs to rest and recharge because:

• You don't need (Owners)?
• Do need to but can keep going (Achievers), or
• Think the cause requires it (Idealists)

PERFECTIONISM?

• Never being satisfied with even good growth, and pushing your team to do more, go harder, and be more creative (Owners)?
• Reacting constantly to the "race" you're in with competitors, trying to differentiate while matching what they're doing, under the pressure of an up-or-out culture (Achievers)?
• Getting frustrated because it's not as great as your vision, "the designs", or customer expectations (Idealists)

For founders, this might be life as usual and, perhaps, even an ideal working environment!

For teammates, this might feel like a creative form of torture.

No wonder wonder startups in general have high churn!?

My experience as a founder has tracked to this.?

And because I care deeply about my team (translation: as an idealist, I want to create the best culture possible) I've thought about what I can do ensure we benefit from my strengths as a CEO while mitigating for my natural weaknesses.

One note here for my founder friends: solving problems around too much work can CREATE MORE WORK.?

... which founders are all too happy to take on as another task to own or problem to solve— sign me up!—and because no one might care as much as you do.?

So, like a roommate who cares enough about your dirty dishes to do them herself, it ends up as more tasks for yours truly.

Be careful here.?

Here's some solutions I've found that work so far:?

1/ Hire people you trust—and make it your first job to give away your job to them.?

Businesses scale in proportion to the number of people who can manage work and drive results. If it's just you, you're going to lose.?

It might feel good at first to "do everything," but you're going to do poor work because you're spread so thin, and then get resentful when people don't thank you profusely.

As businesses scale post-PMF, they have to do a lot more than the purist early days, when the only work WAS already the CEO's job description.?

I think CEOs are need to do 5 things well:

1. Set the mission and vision - why are we here??
2. Craft the strategy - how are we going to win, this quarter/year/decade?
3. Raise money - where do we get the resources to make that possible??
4. Hire the team - who's capabilities and experiences do we need to succeed?
5. Create accountability - how are we tracking against all that, and what happens now??

So, fellow CEOs: if you're post-PMF, scaling, and doing work that's NOT in your JD, like...

...Editing product copy or marketing emails

...Writing PRDs, QAing features, or running standups?

...Revising internal comms or personally planning team bondings?

You need to pivot HARD into finding someone you trust to do that job, or someone to manage the person who does.?

2/ Create goals and hold people accountable.

This doesn't mean you can't help set up the team for success.?

But once they understand the goal and any knowledge you have, STEP THE FUCK OUT OF THEIR WAY.?

Stop yourself by asking "is this in my CEO JD (vision, strategy, fundraising, hiring, accountability)??

I get it: it's hard to watch someone struggle initially. In good cases, they figure it out and grow and succeed. Which is the best.

In bad cases, the trick is to not step in and do their job for them. You have to let them go.

Note: Firing people sucks. It likely means you messed up in hiring or managing somewhere. But it's ultimately about the fit between that person's strengths and what the company needs. And like a breakup, no one ever regrets leaving the relationship too soon.

As soon as you feel that urge to cover for them or micromanage, do the hard thing instead and start thinking about a separation. It's the best thing you can do for them, you, and the business.

3/ Give people time off!?

This is fucking simple: you may be a machine, but your people are not.?

So a good heuristic is that if you're tired, they're exhausted.

Some simple things I've seen work here:?

• After a big launch or milestone, slow down work, reduce expectations, dedicate time to bug sprints, and recognize people's efforts?
• Build in wellness days into your time off policy so people can take "sick days" either for physical or mental health reasons (it's all health)?
• Take time off yourself (even if you don't need to) and encourage your management team too to signal vacation is acceptable, good and overwork is not?

Finally, and most importantly, I'm still figuring this out myself.

At Almanac, we're building a product that:

• Is going up against two 40 year incumbents who happen to trillion-dollar companies?
• Is mind-bogglingly large in surface area and technical complexity?
• Will win based on how our users FEEL when they're in it—meaning that the small details matter as much as the big rocks!
• Will make millions of people's daily workdays meaningfully better. Our mission is my life's work.

So I can make a pretty compelling case to myself to work as hard and long as I can.?

But, BUT: I know I will be kneecapping myself, our mission, and our success if we don't create a sustainable culture that works for our increasingly large team.

I'd love to hear from you: What has worked for you or your companies? What are mistakes I should avoid??