Three Years In: My Take on the Coterie Journey

Coterie birthday

By David McFarland, Coterie Insurance Co-founder & CEO

It’s been three years since we started this journey to transform small business insurance. While that’s not much time, Coterie Insurance has grown significantly and we’ve learned innumerable lessons along the way.  On our birthday, I’m taking a look back at our progress to truly appreciate how far we’ve come, sharing some lessons I’ve learned, and looking forward to the future. 

Creating your own momentum is difficult

When you join a company you’re metaphorically jumping into a moving river. Emails are coming in, meetings are happening, product is being sold, and there is a lot of exciting stuff happening. That’s the reason that people are hired onto the team.

When you start something new, nothing is happening. Literally, nothing. 

Try it out. You can start anything you want right now. There isn’t much special about it. Just stand up and say “I’m going to start X!” and you’ll be in the same position as most founders on the first day of starting their company.

No difference. 

So, when there is nothing going on, you need to make something out of nothing. This is hard. 

This isn’t something that you can figure out like a math problem. It’s almost something you have to just will into existence. 

Honestly, it feels like pounding your head against a wall. You don’t really see any cracks forming, the wall is standing strong, but your head is throbbing, everyone thinks you’re an idiot, and it’s probably not super healthy to your body and mental state. Even so, you persist in keeping it up because you believe that this wall will come down. 

Sometimes it does. 

Sometimes it doesn’t. 

Regardless, all that slamming your head into a wall is hard but you’re the one starting this thing so you better be prepared to look a little stupid and take some pain. 

This is probably one of the hardest parts of starting a business. But, if you hang in there, work hard, and are fortunate enough to get some great people on your team and market tailwinds, then it’s super rewarding. 

Coterie Insurance is now made up of nearly 100 team members spread across four time zones. It’s an incredible honor to lead this team of passionate and hard-working people committed to transforming small business insurance.

First-order negative, second-order positive wins aka do the hard things

At Coterie, we talk a lot about making decisions that are first-order negative, second-order positive. This means that we advocate things that are initially difficult but have a beneficial return in the long term. This is akin to saving money for retirement, studying for a test, or exercising. 

The other side is doing things that are short-term positive, long-term negative. Simply put, this is where you do something that feels good now, but hurts you in the long-term. This includes things as simple as overspending on credit, eating junk food, or doing heroin. While these things may feel good in the moment, they usually result in long-term detriments. 

Doing the hard thing of making short-term negative decisions with an expectation of long-term benefits is difficult because we’re often short-sighted. As humans, we have a tendency to be too focused on instant benefits that pertain to the moment. Our survival instincts take over and we usually end up doing something that can truly wreck us down the road.

We’ve all seen this. People agree to bad term sheets, make poor hiring decisions, and keep under-performing team members around, all because they don’t want to do the hard things. These long-term negative decisions build on themselves, causing far more problems in the future. 

My advice for those starting out with founding a company: establish a culture of short-term negative / long-term positive decision making. As a leader, you’ll need to set an example every day. 

This means you’ll occasionally want to throw up. So, throw up. Then, have the hard conversation. I promise, doing the hard thing now will be much better than what you’ll need to go through later. 

Expect the journey to be difficult

Doing something extraordinary is just that, extra-ordinary. It’s beyond what everyone else is doing, that’s why you’re here creating something out of nothing.

The reason why there is this giant glob of median-ism in the middle is that things get more difficult as you reach for more rewarding endeavors. This causes most of the population to abandon the rewards and settle for something more common. 

This isn’t a bad thing, only a part of the economical-physical laws of risk-return.

Given this, don’t be surprised when you encounter extreme difficulty. 

There will be days when it feels like the world is completely against you. You will feel alone, shunned, exhausted, disrespected, and like this world was made so that people like you can’t succeed. 

Good news, you’re right. 

Bad news is, that doesn’t change anything. 

The fact is, doing hard things is hard. It’s emotionally taxing and physically draining. Even so, if you want the reward, you’ve got to take some risks and deal with some pain. You’re never going to do anything extraordinary if you don’t do the “extra”.


These last few years have taught me not to run when the going gets tough. Stick it out, stay in the discomfort, go back to my values to stay on the path, and keep pushing forward. So far, this strategy has served Coterie fairly well. We’re still here and we’re continuing to grow.  

I know I have a lot more to learn. Even three years in, we’re just starting on this journey and while we’ve accomplished a lot, we’ve yet to truly make a dent in this massive space. I truly believe the best is yet to come. Inevitably work will be hard and I’ll make mistakes, but that’s how the journey is. And I’m thankful to be on it.

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