Pretending to be Superman

Why so many entrepreneurs struggle to make the jump from scrappy founder to scaling CEO

Happy Friday, dear Reader. I’m so glad you’re here.

I’ve been thinking a lot about how fear shapes our decision making as entrepreneurs, often in non-obvious ways.

In talking with hundreds of entrepreneurs I’ve seen a few patterns emerge, and wanted to bring one of them into your awareness.

The featured essay this week involves a fear-based decision that I’ve seen many, many entrepreneurs make:

Why so many entrepreneurs struggle to make the jump from scrappy founder to scaling CEO

I spoke with an entrepreneur the other day who explained that he spared no expense when it came to investing in the growth of his business. He told me about his primo office right in the middle of downtown, which allowed him to attract better talent. He told me about paying for laptops for all his employees, and paying for them to attend conferences for professional development. Better to have well trained people leave, he said, than to have poorly trained people stay. He told me about his unlimited vacation policy.

With pride he explained how all this supported the rapid growth of his business, and then admitted that he himself hadn’t taken a vacation in eight years. He told me about his refurbished desk for his home office, picked up from a garage sale. He told me he was excited to transform his business by implementing EOS, but was going to try to implement it himself rather than spend the money on hiring a trained consultant.

I see this particular inconsistency of thought all the time in entrepreneurs, particularly those navigating the chasm between the resourceful startup founder and the CEO of a growth company (and mostly men, which might say something as well). We make very sane, logical, ROI-driven investments to grow every area of our company…except ourselves.

When it comes to our own professional development, we disregard the investment frameworks that we use (successfully) everywhere else, and underinvest in areas that would make us more effective, or make our job easier, out of a misguided expectation that we should simply be Superman. Rather than addressing our professional development needs as we would any other issue in the business — namely, solving for them — we believe that our shortcomings mean we’re not good enough in some core, primal way, so we can’t justify investing in our own development. Instead we need to simply “be better.” To not need the help in the first place.

Since the point of highest leverage in any company is its leader, this instinct to suck it up and “be better” rather than investing in your own growth as a leader can significantly flatten the trajectory of your company.

To get a company off the ground, an entrepreneur must be uncommonly resourceful. They must double-dip, pinch every penny, and accomplish a lot with very little money. A founder’s ability to succeed at the early stages is a testament to his resourcefulness regardless of circumstance, as much as anything else.

But as a company grows up, that bias to resourcefulness-over-resources that was so helpful in the early stages can blind us to the fact that, just like our employees need development, time, technology and support to perform at their best, we do, too.

The person that started your company is not (yet) the person capable of scaling it. Only by taking intentional action on your own development and support can you change that.

Founder of WHOOP on the future of wearable health, and how our determination can backfire in the long term

Will Ahmed, founder of the Whoop wearable that is everywhere in pro sports and which I wore religiously a couple years ago, appeared on David Perell’s podcast this week, and dropped some useful knowledge:

“If you’re a hard driving person…your feelings can betray you, because your mind can betray you. I mean, this is why you see talented entrepreneurs burn out. It’s why you see great athletes over-training get injured. It’s because their minds are able to push themselves to a place that actually isn’t all that productive.”

Many of the most successful entrepreneurs treat their human bodies as limitations to be conquered. I did for years, hearing and ignoring the warnings, until it caught up to me, too.

Isaac Newton’s third law of motion applies to startups, too: For every action there’s an equal, opposite reaction. It’s easy to convince ourselves that we can work another 100-hour week, pull another all nighter, skip another family event in the name of “hustle.” It’s easy to think just one more won’t hurt. But there’s always a cost.

Mind over matter is only a viable strategy in the short term.

The private sector fueling experiments in Universal Basic Income

It’s easy to be complacent, to wait for the politicians to sort out the world. But waiting for politicians to change the world is a surefire way to grow old with the same world.

Much better to drive the changes you wish to see yourself and then, once you prove that they work, let politicians sort out how to scale them.

Such was the thinking behind My Basic Income, a Berlin startup which is writing a random selection of about 600 people a check for $1,200/month for a year (sourced from millions of donations from random people who believe in UBI and are willing to support it), and documenting the results. Among those results: peace, equanimity, safety, optionality, happiness, and people definitively not quitting their jobs. For only $1,200/mo/person. As the experiment expands, MBI expects that the data behind it will inform policy.

Makes sense to me.

This illustrates the opportunity each of us have to hold ourselves accountable for creating the world we want. One way to change the world is to vote, as 150m+ Americans did last week. A much quicker way to change the world is to do it yourself.


Thank you for reading, entrepreneurs.

May you be happy, may you be healthy, may you be free from suffering.



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