Archives For CEO Friday

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Nobody likes to talk about firing.  It’s not something to celebrate: if you need to fire someone it means you screwed up.  Either you hired the wrong person, or — more common — you hired the right person, but failed to enable their success.  Either way, the blame falls on the company (not the individual), so it’s no surprise that companies tend to avoid talking about their failures.

But despite that discomfort, firing is an important topic because in the long run, careful application of firing is actually more important than hiring.  To understand why, consider this simple chart:

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There’s an old adage in Silicon Valley:

A people hire other A people, while B people hire C people.

Said another way, great people want to work with other great people, but not-so-great people prefer to work with people worse than themselves.  This is because great people love to be challenged by their peers, while not-so-great people prefer not to be challenged at all.

The Vicious Cycle of Mediocrity

It’s easy to agree with the above in theory.  But building a company that adheres to this in practice is very, very hard.  So hard that extremely few companies actually do it, despite the best of intentions along the way.  You can tell if your company is doing it by seeing if it’s followed this path:  Continue Reading…

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One of the greatest perks of working at Expensify is that you are surrounded by passionate, mature people naturally motivated to do the right thing.  This works because we hire people who have three key characteristics:

  • Extreme natural talent
  • Long term ambition
  • Deep humility

All three matter in different ways, but the third is particularly relevant here because it’s what ensures everybody has an appreciation for the limits of their knowledge — which translates into a low-drama, super collaborative environment.

Now, when people hear “collaborative environment”, they typically think about the various off-the-shelf management techniques, like Scrum, Agile, Holacracy, or whatever the pop-business gurus are selling these days.  We don’t use any of those.  Rather, we try to live by two main principles:  Continue Reading…

There are no shortage of challenges and problems running a startup, but by far the most difficult of all is hiring.  Attracting, retaining, and inspiring truly excellent people is the lifeblood of any startup, and Expensify is no exception.  But what I think is exceptional about Expensify is our commitment to maintaining and even raising the bar on hiring as the company grows.

That might not sound exceptional.  Indeed, it might even sound cliché.  But make no mistake: despite how easy it is to make this claim, it’s very difficult to actually put it into practice.   Continue Reading…

Last week Expensify hosted its very first conference, eponymously named ExpensiCon.  We are still stunned and humbled by its tremendous success, and I need a bit more distance before I can really talk about it in a broad way.  (Read “Expensify is the Slack of Accounting” if you want a taste.)  But I wanted to quickly share a chart that was created at the very last moment, and which became the central focus of the entire conference:

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There’s a lot in that graphic, so let me unpack it:  Continue Reading…

no cockroach signI won’t lie: it’s flattering and vindicating for the low-burn, efficient-growth strategies we’ve been championing for years to come into vogue.  For years we’ve watched quietly on the sidelines as low-interest rates and market doldrums have fueled massive investments into “Unicorn” startups, operating unsustainable business models at a massive loss.  And I can’t deny we’ve envied their shocking valuations.  So I’ll admit satisfaction that the mythical creature’s shine is wearing off, and that there’s enough appreciation of our sustainable, profitable models that startups of our class have finally earned a name of our own.

But “cockroach”?  Seriously?! Continue Reading…

I’ve been trying to wrap my head around Common Table Expressions for a while, and all the tutorials I’ve read started out with “simple” examples that were way too advanced for me to follow. Here’s my attempt to write a tutorial that starts as simple as possible.

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