Alex Medick

August 1, 2022

Sometimes you have to do hard things.

Sometimes in startup land, you have to do hard things. 

A lot of folks out there think startups are on some linear growth path where you have an idea, you build it, and you stay the course.


In startups, you have to get used to the culture of experimentation. Sometimes what you start out building is thrown to the wayside while you find a more profitable opportunity hiding in the nooks and crannies of your current build. 

Don’t believe me? Here are some examples:

Slack founder Stewart Butterfield and his team set out to create something new and original for the massively multiplayer online role-playing game (MMORPG) market. 

was founded in 2011 as a spin-off company that branched off from its predecessor, was founded in 2007 by Justin Kan and was just a livestream of Justin’s day to day life.

Twitter was once a side project created by the podcasting platform Odeo during a company hackathon. It was nothing but an outlet for a few employees, and although CEO Ev Williams supported it, investors and the press couldn't care less. Just look at this decade-old TechCrunch review:

"What is this company doing to make their core offering compelling? How do their shareholders feel about side projects like Twttr when their primary product line is, besides the excellent design, a total snoozer?"

Like I said, not everything is linear.

With a non-linear path to growth and profitability, you have to be agile and pivot accordingly. 

With that, not everyone on the team can grow with the company or make the adjustments you need. I know that’s harsh, but it’s a cold truth that a lot of folks don’t seem to talk about.

The people you hire for Path A, might not be great for Path B. Or I’ve even had people absolutely reject the new path altogether and give the middle finger to change. They even fight it.

Both scenarios are hard, but happen. It’s hard. But as a startup founder / CEO / executive / whatever, sometimes, you have to roll with the hard and do the hard things.

Making calls on what’s best for the company, even when it means letting folks on your team, you have to do it. You trying to hold onto them in a failing path is not helpful for you, them, or the company.

In fact, you might think you’re helping, but in the end, it’s actually just delaying the inevitable.

The best thing to do in these scenarios is be swift, be kind, and help the person you’re letting go get started on the right foot for their next journey.

Sure, they might be pissed at you for a little, but in the end, they’ll thank you for taking them out of the situation - one you both know they should’ve been done with a while ago.

Startups are hard. They’re crazy. They’re fast. They’re controlled chaos.

Not everyone can be at all parts of the journey.

Everyone has their moment in time.

It’s happened to me before, and I’m sure if you’re reading this, it will happen to you.

It’s not the end of the world.

Every phase in life is just another part of the journey to reaching the destination you are meant for.

Is pivoting missions and people hard? Sure. But sometimes, you have to do the hard things. 

And you know what? Startups are fucking awesome. And if you can handle the hard things, then this life might be for you.


About Alex Medick

Dad, Entrepreneur // Building INSIDE