Screw Your Calendly

Don’t Automate Your Relationship With Your Lifeline; Users

Don’t Automate Your Relationship With Your Lifeline; Users

TL:DR — If you think you are too busy to develop one on one deep relationships with your first users because you are a founder and are “busy” doing founder things, you’re wrong….and you’re most likely going to fail.

What are good qualities of high performing startup? Speed. Being agile. Making the most of little time. Being quick. These are all aspects that come with a startup. Luckily, there are thousands of tools to help us make quicker decisions, automate the things that matter, and execute more efficiently.

There are CRMs, social media management tools, product roadmap tools, user validation tools, tools to figure out if the toilet paper roll should face up or down, etc. As the phrase goes, there’s an app for that. In a world where SaaS dominates (for now), there really is a way to do everything faster. This is the trap that first time founders fall into.

Tools Will Sometimes Kill You

In an effort to be efficient, they oftentimes automate their relationships with potential users. Potentially the first users. You know what’s a hell of a lot more important than staying efficient with your time? Having users. You know what’s a great way to lose users? Make them feel like just a user.

I write this because made this mistake with my first failed startup. I sent out calendar links. I put up a chat on our website. I told people i was too busy when I wasn’t. Why? Because I was a CEO and I had to be busy, because that’s what a CEO is…Busy….Kinda BS right? My job as a founder is to talk to users until we’ve built exactly what they need. That takes time.

Before you are a CEO of your startup, you are a CEO of your product and your boss is all your users. They write your paychecks so you can eat. If you didn’t talk to your boss in your current job, what would happen? If you tried to automate your relationship with your boss, what would happen? You’d get fired. In startup land, your startup dies. What is another important thing about first users?

They are spending their valuable time on your product, when they could be looking at Cat videos, dreaming about traveling, or eating Chik-Fil-A.

YOU HAVE THEIR ATTENTION when there are millions of other things to spend time on. You need to find out why. Find out why before you lose their attention because you won’t have it forever if you don’t engage.

Build something a few people love

Only a small portion of people need to love your product. Even 5–10 people. If you have a product that 10 people come back to every day, you need to learn everything you can about those 10 people. 10 seems minimal but if you find out that those 10 people are the same demographic, then now you know who to sell to. Now you know who needs your product.

When you have a few people that love your product, you gotta reach out and find out why. I’m not talking about surveys. I mean personal emails, phone calls, videochats, coffee sessions, etc. Make them feel like they are a part of the creation of this startup. THAT is how you create loyalty when the product is rocky. You know how to make a user feel like just another user? Getting a Calendly link.

For big time CEO’s I get it. but founders? Your time is not more important than your users, because if it is more important than your users, you’re going to have a lot more time on your hands in a few months or years. Why? Your startup will be dead, that’s why.


Your job as a founder is to find Product Market Fit. That requires building product and talking to users and that’s about it. Efficiency is not your friend here. Going deep is. Understand your users. Know them. Befriend them. Buy them chocolate cake on their birthday. Don’t spend your time on many other things and never be to good for a user, ever.