How #Startup CEOs Can Keep Moving During The Unthinkable

Is there ever a time during a #startup CEOs tenure where you aren’t in crisis? I know it never FEELS that way. There’s always an overwhelming amount of things weighing heavily on your shoulders. The needs of your investors, your employees, your customers, your significant others and your family. The weight is always heavy and even though good things will happen, it still usually feels like you’re living your life in crisis mode. And that’s during the good times.

But what happens when things get real bad? Things that you didn’t…

I’m Not Here to Make Friends. I’m Here to Build a Business.

“Sometimes, no matter how hard you try to do the right thing, there’s always someone who thinks you’re an asshole.”

That’s the exact content of one of my most liked and retweeted tweets from last year. Unfortunately, you won’t find it if you search my feed because someone ‘suggested’ I take it down. I regret that decision deeply now. But at the time, I was pressured into being a good corporate player. But I shouldn’t have, because the resonance it kicked up among friends was significant. It echoed…

There were very few moments in my life that were scarier than the very first time I went into a Board meeting as a CEO. That’s hard to admit, but it’s true.

I had been part of Board meetings before as a Founder, but never as the CEO. I was never the one on the hook for the meeting before. I was never the one who was scared shitless of looking like an idiot who didn’t know what the hell he was doing in front of his investors before. Imposter syndrome had never been so real for me before.

After…

As CEO, every single thing you do matters…

Thoughts on culture, leadership and power.

The Fish Stinks From The Head. I’ll never forget learning this phrase from a member of my leadership team at one of my previous companies, a former Chief Marketing Officer for numerous global luxury brands, and as smart and thoughtful an executive as anyone I’ve ever worked with. Simply put, it means that when an organization and its culture are consistently and profoundly dysfunctional, those deep issues can almost always be traced to the most senior leadership. — @ElieFinegold from his recent article on WeWork.

Here’s…

A framework for managing difficult team discussions.

I’ve had two calls in the last week or so from CEOs I speak with often, both related to the same thing — not acting quickly enough to defuse real turmoil within the executive team. That’s just in the last week or so. This is an incredibly common issue that can have disastrous effects on a startup.

Most of us have a tendency to shy away from difficult issues between people. They’re messy. They’re scary. We don’t want to confront our friend(s) with things we’re not happy about. These are natural feelings, And we use them to justify a delay…

I was out walking my dogs today.

It’s a beautiful day here in Boulder — one of those days between summer and winter (most people call this fall, but here in Boulder, it’s really just a transition day) where as long as you’re in the sun, it’s summer, but if you’re in the shade, it’s winter. You end up either over dressed or under dressed several times over the course of the walk. Great colors outside and lots of new smells for the dogs to enjoy.

I have two dogs. They are both rescues.

Sydney is the oldest. She’s ten…