What Does Founder Success "Feel" Like?

Founder success is almost never what we picture it to be.

When we think of wildly successful Founders our minds easily jump to billionaires like Branson, Blakely, and Musk, balancing a life of magazine cover story photoshoots with keynote presentations and TV interviews. Our most "successful" Founders often have this air of glamour around their success.

But as it happens, Founder "success" feels way less glamorous. In fact, the most exciting success milestones are often so mundane when they occur that we don't even realize they happened. But this success is a culmination not of a single event, but a series of tiny events that we later look back and realize was when our success was truly defined.

We Always Make Payroll

For most of our journey, we feel like we're living week to week, month to month. During those periods we're constantly trying to run around raising just enough money, selling just enough customers so that we can once again cover costs and live long enough to do it all over again.

It's fucking exhausting.

Then one day, our salespeople actually sell something. Our marketing channels start to convert. Cash starts rolling in, and lo and behold, we finally make payroll without having our weekly heart attack. And then it happens again, and again, and again until one day we actually get a full night of sleep and realize that in fact, this business is going to continue to make payroll without killing us in the process. That's what success feels like.

We Aren't Personally Leveraged

Since the beginning, we fought this constant battle between company growth and our dwindling personal finances. Every day it was "Do we increase our marketing budget or do I pay down my college loans?" Every round of financing wasn't just filling the company coffers, it was preventing our own from being further depleted.

At some point we just got used to it — we associated company growth with personal destruction, whether monetarily, emotionally, or physically. We forgot there was a time when we used to get paid to go to work, not the other way around.

Then something weird happened — we made some profit. That business which had been a torrent of everything we had to offer did this bizarre thing and offered something back. We were so surprised by the turn of events at first we thought it was a fluke. Then, the business did it again, and again. Then it started paying us more money than we could have ever made at a job, and in some cases, more than we thought were even worth. Then everyone wanted to take it from us (a subject for a different time...)

Someone Says "Thank You"

We spend the majority of our early Founder careers saying "Please" and asking for something. We're leveraged in so many ways, and everyone expects something from us. We hire staff and they want to make sure they get paid (seems reasonable!), we take on investors and they want a return (we promised), and we sell to customers and they get super, super, super demanding (suck it up!).

We spend so much time asking for things, trying to make everyone happy, trying to deliver on so many promises that we forget that all of our efforts is in the service of helping all of these people — staff, investors, customers and damn near everyone. We're everyone's mule, and we just take it.

Then one day, we're at lunch with a co-worker, and we find out they just bought their first house. We're enjoying a great meal with so much pride that all of the work we've put in together was able to make this dream happen. Not our dream — their dream. And at that moment, they look us straight in the eye and say "Thank you." Everything we've done, all the sacrifices we've made, the promises we've kept, has earned us those two simple words.

At that moment, we feel success. From that point on, nothing else compares.

In Case You Missed It

Let's Define Success By What We Don't Have To Do Anymore Why do we measure startup success by money? Is it the money we're truly talking about or the freedoms that money buys? If it's freedom, then how much of that freedom comes from money, and how much of it comes down to choice?

How Much Should I Be Working? (podcast). Wil and Ryan take a deep dive into the benefits of thinking quality and not quantity when it comes to your weekly punch card.

We Need a Strict Definition of Personal Success Every moment we spend pursuing an undefined goal is a complete waste of time — especially personal goals.