Archives For CEO Friday

Crazed ramblings by the CEO.

At the intersection of yes and no

At the crossroads of yes and no

As a small business owner that caters to small business owners, I can say with extreme confidence: Yes!  Yes, absolutely turn down any investment unless the following three things are true:  Continue Reading…

Uber partners with Expensify to bring SmartRides to business travelers worldwide

I think it’s safe to say Uber is one of the most significant startups of the decade. Their vision is to make arranged transport so cheap and convenient that you literally don’t need to own a car: it’s so audacious, when Travis told me I straight up laughed. After our last startup together, I started Expensify, and he started Uber, and I wished him the best of luck in an incredulous sort of way. Well the time for luck is over. This is happening folks, and woe be to all who stand in Uber’s way.  Continue Reading…

Cloud Computing

With ambient services, companies will be able to predict where you’re headed, before you get there.

This is a pretty popular topic, and since I’ve been asked this question a lot, I wanted to share my thoughts on paper.

The future of cloud computing is what I would call “ambient services.” What this looks like in real life: over time, cloud services will look less like Google Search, and more like Google Now.  Continue Reading…

This is my guest post written for LinkedIn Pulse, enjoy!

boss-hoggEverybody loves to rave about the bossless workplace, but it’s far more easily said than done. I’ve already written about the perils of the “flat management mutiny” — which comes as you emerge a leadership structure out of flat chaos — but it’s even harder going the other direction: dismantling an over-managed “top-heavy” structure and getting back to its roots. Here are some tips to pull it off in your organization:  Continue Reading…

What do you mean we can't build it?

What do you mean we won’t support that customer?

Note: This is my guest post, originally published in Pando Daily.

Flat management structures are all the rage, and with good reason: innovation is the lifeblood of a startup, and nothing kills innovation like micromanagement. But scaling a flat management structure is harder than it seems. Plenty has already been written about the risks of accidentally creating the stuff of highschool nightmares, but even if you dodge those bullets you’re in for a little discussed treat: full out mutiny of your team.  Continue Reading…

But with less walls and and more coding.

Our challenges have fewer walls and and more coding, but same idea.

It’s widely repeated that “great people are 100x more productive than average people.”  But while everybody says it, most companies just hire 100x more average people. At Expensify, we try very, very hard to hold the line and only hire people we think are truly great. This means that despite ample resources and more than enough work to go around, we hire extremely slowly — and spend an enormous amount of energy doing it.  A lot of that energy is directed toward refining the hiring process itself, with a major recurring topic being: what makes someone great?  Continue Reading…

Imagine you ran a coffee shop with great coffee, a cool vibe, comfortable seating… and no customers.  Not an uncommon problem, and the classic solution promoted by social media experts would be something like:

“Create a Twitter handle and offer discounts to customers who follow. Broadcast weekly events and promotions via Twitter and engage with your audience to encourage them to come and bring their friends.  More discounts to people who get their friends to follow.  Create a mailing list; Tumblr; Facebook page; etc, etc.”

Continue Reading…