Aug 27, 2015 · 4 minutes

Last month, we hosted a webinar on “Good problems to have." You can watch it here.

You know the kind of thing: Those challenges of building a startup that you don’t worry about at the beginning because you figure if you get there everything will be going so well, you’ll be swimming in a pool of gold like Scrooge McDuck without a care in the world.

Then you get there and are smacked in the face with the hardest challenges you’ve ever faced as a founder. And now investors, customers, and employees are all counting on you to make the right decision. “Good problems to have suck just as bad as bad problems…. maybe worse because you’ve had some measure of success,” Phil Libin said during that Webinar. “You have more to lose.”  

Libin continued:

At the beginning of your company when you are always a couple of months away from going out of business and every crisis is an existential crisis, because all you’re trying to do is optimize for staying alive. That is the happiest and simplest time in your company… everything else is in the good problem to have category, which is like “Good news, you’re kind of successful that’s why you’re having it. Bad news is it’s more stressful than anything else before.”

Today, we're launching a new editorial series -- also called "A Good Problem To Have." In it, we’ll be writing more about founders facing and tackling these “good problems,” sharing their tips to get through them. We hope it’ll make you all feel less alone in what can feel like the loneliest job on the planet.


But first, I wanted to share what Andy Dunn of Bonobos and Phil Libin said on the webinar about one of their greatest “good problems to have.” This year, both of them realized their businesses had grown large enough that they both felt they had to fire themselves as CEO. Both described it as one of the hardest and most bittersweet moves they had to make.

Replacing yourself as CEO is particularly emotional these days because of the overwhelming cult of the founder, the sense that founders should never be replaced because they have an intrinsic understanding of their companies that no one can replicate.

But what the cult of the founder is really a reaction to is a board replacing a founder against his or her will. VCs scared of being viewed as “anti-founder” will hesitate to make the decision for a founder, so that leaves it up to you to fire yourself in many cases. How do you know when it’s normal self-doubt and how do you know when you are holding  your company back?

In the case of Evernote, Phil Libin has always said he wants to run his company for 100 years. So… he kinda knew this was inevitable. “If I'm the last CEO we've failed in our mission,” he said. “I fully intend to be alive in 100 years, but I will be a disembodied head in a robot spider body with laser beams or something and that may not be the best thing to have as a CEO.” He called it a “deeply weird and painful decision even though it’s intellectually the right one.”

Andy Dunn replaced himself this past year too. He talked about Bonobos’ long journey from software ecommerce platform that happened to sell pants to divesting all that and focusing on becoming a fashion brand. Bonobos sort of stumbled and iterated its way into guide shops-- which became its best performing customer conversion channel. As it became clear that was going to become a big part of the company’s future, Dunn knew he wasn’t the guy to build it out.

Here’s what he said about the difficult decision, and how at some point the things that can make you a good founder can distract from a company’s growth:

As a founder your instinct is to put something new in the world... you start a company because you are irreverent. You start a company because you want to create something out of nowhere, and the paradox is that if you are successful with that, and then a job evolves from an act of creativity and irreverence. Focus and execution and scaling become equally important as [creativity and irreverence]. You have to ask yourself am I a fit for what the job requires?

Stay tuned all month for more stories of when founders lucked their way into problems and how they got out of them.


SPONSOR MESSAGE: Cloud-based HR partner for growing startups. Learn more at