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Hey, I’m Jay.
This is where I post my thoughts & Notes on business and other things that I’m thinking about. Enjoy.

Entrepreneurs, We Should Always Have Problems

Entrepreneurs, We Should Always Have Problems

Problems are not the problem.

The way we deal with the problem is likely the problem.

You and I have decided to do something fairly rare and incredibly silly: start our own business. There are obvious benefits to that.

  • We have a greater sense of autonomy.
  • Entrepreneurs tend to be happier at work.
  • True monetary wealth is more likely for us with ownership than for those without.
  • Many other things.

And like all choices, ours comes with downsides.

  • We are less financially stable.
  • Until we are the big company, we are at the risk of being crushed by big companies.
  • We have to learn many things we weren't taught.
  • There are constant fires that are our responsibility to put out.

I've noticed that newer entrepreneurs hold a certain myth about entrepreneurship. They believe that more mature organizations don't have problems, so neither should their startup.

There's this idea that problems will fade as you age.

That's not true, and we should embrace that reality to the fullest.


Your challenges will grow in direct proportion to your own growth.

The larger your organization gets, the larger your challenges will grow.

Some see that as a problem.

It's not.

It's an opportunity.

As the owner, it's our responsibility to handle those problems.

There's good news in all of this.

The same way our challenges grow, our personal ability to handle larger challenges should grow too. So larger challenges may actually become easier to handle because we've gotten better with experience.


While problems don't go away, we should be aiming to build steadier ways to handle them.

I came across a fantastic insight about this from Ray Dalio, the founder of Bridgewater Capital, in his insanely good book Principles.

His fund had been growing at an incredible rate. His company culture was the main reason why. With all the good, he faced the reality that his challenges were growing in proportion to his company.

After about five years of rapid growth toward building Bridgewater as an institution, we had encountered our newest set of problems. This was nothing new. Since I started Bridgewater we always had some problems because we were always doing bold new things, making mistakes, and evolving quickly.
— Ray Dalio, Founder of Bridgewater

New problems are the collateral damage of doing bold new things.

At this stage in his company, he and his team had to decide whether they were going to stay a boutique firm or grow into a true business monster. There were members on his team that didn't want to go down the path of becoming a huge company. They feared for their culture.

But Dalio thought that could have their cake and eat it too.

He believed that they could become huge and maintain culture. But he knew that his growth was going to be very difficult.

It had always been fun being cutting-edge, but we were having a hard time becoming rock-solid. The organization had to renovated in several ways—but it wasn’t going to be easy.
— Ray Dalio, Founder of Bridgewater

He had 738 people working at Bridgewater at the time, and Dalio found himself in a tight spot. Despite all of the people working for him, he realized that the things he was doing couldn't be adequately delegated to others.

When you're the only person who can handle very important tasks, your problems are amplified.

And when you're problems are amplified, it's immeasurably tougher to create rock-solid systems to handle those problems.


Bigger problems, with better systems to solve them.

Let's get straight back to Dalio's thoughts in his book, Principles. His insight and honesty on this is crucial for us to learn from.

To me, the greatest success you can have as the person in charge is to orchestrate others to do things well without you. I could see that despite all of my and Bridgewater’s amazing achievements, I had not achieved this highest level of success.
— Ray Dalio, Founder of Bridgewater

He forged ahead to spread decisions out among certain people in the organization, delegate many important tasks, and open the forum to more ideas.

I've heard of several ways that other leaders have approached this challenge of solving problems better.

Some commonalities that I've seen are the following:

  • Decision-makers come to an agreement on how they'll find solutions. No matter what system they agreed on, they agreed on a system to use.
  • Unilateral decision-making evolved into group decision-making, stopping short of a true democracy. In many situations, power was taken out of one person's hands and put into the hands of a group. But decisions weren't necessarily based on votes. There was still an authority making the final decision.
  • The organization rewards people who raise issues, identifies the people who may have caused the problem, and invites those people to be part of the solution. Unless the culture is incredibly sick or the people causing the problems were horrible people, they were asked to solve their own mistakes in a way that helped their colleagues solve similar problems down the road.


At the end of the day, there will always be fires.

This is a good thing, because this is why people quit.

Few have the ability to face fires day after day and not be discouraged.

Here's the paradox of entrepreneurship: our goal is to control the flames, not put all of them out.

Lean into the problems.

Think about better systems to find solutions.

And don't ever expect them to stop.

You are a problem-solver, which means you need problems to solve.

Here's some great stuff from Ray Dalio.

I've gained an immense amount of insight from Dalio's book, Principles.

My first introduction to Ray Dalio was through this Freakonomics podcast, which is one of my favorite podcasts to listen to on long drives. You might enjoy it too.

And to round it out, here's Dalio's TED Talk from 2017.

The Beauty Of The Right Isolation

The Beauty Of The Right Isolation