Growing Up, Growing Out

Photo Credit: Igor Ovsyannykov

There are an infinite number of unique moments in a founder’s life. They stem from the unique attributes of their startup, their team, their customers — all perfect prisms to guarantee the uniqueness of your experience above everyone else’s.

There are, however, a very common set of moments that all founders share:

  • First time talking about the idea that is about to become a startup
  • First time talking to an investor, then waiting for a yes, then getting a no
  • First time interviewing someone, making an offer, getting rejected, then pleading for a yes
  • First time talking to a customer, bullshitting on pricing or features, getting a no

Yep, there’s a number of things that all founders have in common, even if the only thing they want to be is a unicorn. Above and beyond all these exciting moments, though, there’s an equally terrifying set of freak out moments:

  • How am I going to pay my rent?
  • How can I possibly do what I just said?
  • How do I fire someone?
  • Should I fire myself?

I have been living and breathing all these moments for my entire adult life. Today, I want to talk about that last one — firing yourself.

I’m the proud co-founder and CTO of Chute, a YC-backed startup that’s been building and delivering software to marketers since January 2011. In that time, we’ve raised rounds, been through Y-Combinator, pitched endless customers, won and lost many of them, and even hired and fired dozens and dozens of employees. Basically, the works.

As of February 2017, I no longer work at the company I co-founded. Feels weird to finally say that out loud, in public — but there are a few important lessons in there, to say the least.

Note: Chute and its team continue on with my full confidence and support

Growing Up

I’ve had almost every hat at Chute, much like most founders I know. From developer to designer to marketer to product manager to sales rep — whatever is needed, you do it, and you better like it. And like it I did.

In my 6 years at Chute, I spent the bulk of my time working with Engineering and Product to deliver our platform. While I was always ready to pitch, over time, it became my responsibility. First, I was our Chief Evangelist, spreading the company gospel. At the end, I was actively working with the sales team and leading solutions.

End of the day, it was very rewarding. My product brain loved seeing customers find solutions to their problems. My entrepreneur brain loved helping deals happen. I learned a lot about the parts of a business I hadn’t previously driven.

Without a doubt, I’ve expanded my skills and matured in my thinking in a very short time.

Growing Out

The secret to being an entrepreneur is to find a way to fund your ideas without interrupting your pursuit of those ideas. At no point in your life as an entrepreneur will you feel you have all the time, energy, money or people to get everything done. That’s the rub.

As our company grew, so did our team. A band of generalists gave way to roles and responsibilities. Our company finally had more bandwidth to take on new, interesting challenges. For a long time, of course, there was still plenty to do for everyone, and everyone did everything that there was to do.

From our first hires, I knew that my job, in particular, was to replace myself. Looking around, it was clear that my mission was accomplished. Looking back, we outgrew each other a long time ago.

At first I didn’t know it. Then, I ignored it. Finally, I accepted it.


The best thing you can offer your startup is everything you’ve got, at least until it’s got everything it needs.

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