Certainty and Uncertainty

Uncertainty is an uncomfortable position. But certainty is an absurd one.

Voltaire

We startup founders are strange beasts. We thrive in the manic, hectic life of building a business.

I do at least.

I love the pressure, the tension, the uncertainty of going from zero to one. To build an actual thing that makes money, employs team members, and delivers value to customers.

And I certainly had a lot of that tension and stress in starting Castos.

There were many times that I wasn’t sure how we’d make it, wasn’t sure how to pull the right strings to continue growing, and how/when/where to hire.

Don’t get me wrong, I’ve made nearly every mistake you can make in business, and have the scars to prove it.

But standing here today I’m a much smarter founder, and am making much smarter decisions on how I approach building a business.

In a way I’ve turned from a time of Uncertainty to a time of Certainty.

And I gotta say, it’s not much less stressful.

Stress of Starting Up

You see, I think that we as founders thrive on the shit of going from zero to one.

Once you get to 1: default alive. Let’s call it a $250k ARR, where you can pay yourself, maybe have a team member, have one customer acquisition channel, then you go from not knowing anything to knowing some stuff.

You enter this phase of Certainty.

I think the reason the phase of Certainty isn’t any easier is that in your phase of Uncertainty, when you just don’t know anything, the series of obstacles ahead of you are really clear.

• You have to make payroll
• You have to stabilize the product
• You have to hire those first few people to fill out the team
• You have to continue chasing Product-Market Fit

That’s the playbook for every SaaS business.

But past that is where the water gets muddy.

• What to do to continue to grow past that point?
• How do you make the smartest hires to support growth?
• How do you make the smartest bets possible so that they provide positive ROI for you as a founder, and for the business.

In hindsight this has been a much more complicated stage of the business for me than in the first few years.

Taming Certainty

I’ve gotten a lot of calm in the last few months. And in hindsight I think it comes down to knowing where I’m going.

Even though Castos is a 7-figure, profitable business, there were a lot of unknowns in this middle phase of the business for me.

• How were we going to continue to grow
• Who do we need on the team
• What is my long term strategy
• What market dynamics (i.e. Risks) do I need to be on the lookout for

In retrospect, I started playing defense a bit. I had an asset that I wanted to protect, increasingly as much as I wanted to grow it.

The change in mindset came from acknowledging that settling into a period of calm, of embracing the Certainty that came with the business, was exactly what I needed.

Diverting Energy

I’m getting my mental and emotional energy out in different ways now too. A bit more time at the gym, more quality time with my family, and more time spent ONLY doing the things that I want in the business.

Some of the frustration I was feeling was that I had all of these inputs into the business, and some of them just weren’t paying off. So instead of continuing to run full steam into the proverbial wall, I’m being smarter about every unit of input I have in the business.

This has been the transformative shift for me.

As one of my friends said:

Sometimes the best thing I can do for the business is go play golf.

While I haven’t played a lot of golf lately, I am being much more intentional about every unit of input into the business, and the result is that I’m happier, the business is performing better, and my contribution to the business has arguably never been more meaningful.

Balancing Certainty and Uncertainty

So my question to you is: as you’re navigating from a time of uncertainty to a time of certainty, think about what you are doing that is fueling those two states.

What does the input versus output of your investment in the business mean for your mental state?

Being aware of this balance and finding the right mix for you is what can lead to you being a happy, engaged, and truly successful founder for the long run.