Archives For Thought Leadership

We lead.. with our thoughts.
Just kidding, but we do have some thoughts we’d love to share with you.

Speaking live on nationwide TV is about the most chaotic, stressful, underwhelming, and anti-climactic thing I've ever done

Speaking live on nationwide TV is about the most chaotic, stressful, underwhelming, and anti-climactic thing I’ve ever done

When I started Expensify, I had no idea being a CEO involved talking so much, to so many people, on such a wide array of topics.  Whether it’s a chance encounter in a hallway, keynoting a conference, or being woken up by CNBC with an offer to debate Howard Dean about whether the FEC should accept Bitcoin (answer: yes), you never know what opportunity will come up — and it’ll pass you by if you aren’t ready to jump on it without notice or preparation.

Prior to Expensify, I don’t think I’d ever been on stage or spoken to more than two people at the same time, but here are some tips I’ve come to swear by:  Continue Reading…

Most VC pitches hinge on a key number:

Return On Investment (ROI) = LifeTime Value (LTV) / Cost to Acquire a Customer (CAC)

And I can’t blame them: VCs are in the business of selling money.  They want to know that if they sell you their money (paid for with equity), it’ll be put to good use.   This is more true today than ever because startups are so cheap to run anymore, meaning the only realistic way you can spend millions of dollars is on customer acquisition.

But the open secret that has taken me years to learn is this: it’s all bullshit.   Continue Reading…

It’s very fashionable to quantify every aspect of your business to the N-th degree.  It sounds great in cocktail conversations to rattle off CAC, LTV, retention rates, magic numbers, and a host of other variables — and to extol the virtues of A/B testing every single thing from day one (or even before).  But beware getting too reliant on data, because when it comes to your most important and difficult decisions, it won’t be there to save you.  This is because startups are trapped between a rock and a hard place:  Continue Reading…

masterapprenticeI gave a talk this week at DreamForce called “The Entrepreneurial Instinct” (they picked the title) largely about the importance of trusting yourself and doing your own thing, and expanding on the ideas in this TechCrunch guest post.  One of the attendees wrote me with this question:

One thing I wanted to ask you was if I work in a company where I am not a senior level exec, capable of making the decision to experiment on ways to get our product to rapid adoption, how do I go about convincing them to just try something out?

Here’s how I responded:  Continue Reading…

Expensify is unusual in many ways.  But one of our most well documented oddities is our habit of taking the whole company overseas for a month.  There are a huge range of reasons to do this: to work, to play, to finish off the year before, and to get inspired for the year ahead.  But regardless of your reason, here are some hard-learned tips for making the habit work for you:  Continue Reading…

The Road Not TakenThomas turned me on to a great article from Tim O’Reilly about things he’d do differently had he the chance to do it over.  I sent the response below to Thomas, and forwarded a copy to Tim — who encouraged me to share them with the world.  So, here we are:  Continue Reading…

Expensify in the News

Wow! April was a big month for Expensify in the media. Our Bitcoin Reimbursement announcement drew a large amount of attention. Our CEO, David Barrett was asked to speak on 3 different news programs: FoxBusiness, SkyNews, and CNBC! In addition to television appearances, we had a multitude of tech blogs write up on why our Bitcoin adoption was a big deal. Here are some highlights:  Continue Reading…

"You have no reason to trust me except that I said you should."

“You have no reason to trust me except that I said you should.”

Nearly everybody in Silicon Valley agrees on how a company is supposed to be run. These are codified into a nebulous set of “best practices” — the pre-packaged advice that is handed out to nearly every startup, in nearly every market, under nearly every set of conditions. But if there’s one thing I’ve come to believe is that “best practices” generally aren’t.  Continue Reading…

A little over a year ago we did a post entitled, How to Sell it to the Man. (The Man = your boss, their boss, your accountant, your colleagues, etc.) Since we didn’t spend the last year just twiddling our thumbs, selling Expensify to the Man is even easier for you and we thought we’d give you some updated ammo for the good fight.

Expensify is easier on your wallet.

Expensify vs. our Competitors 

Expensify bills $5/$10 (depending on plan) per active submitter per month, plus the first two for free. What’s the difference? The “active submitter” part. We only charge you for a user if they actually used the product that month – that is, if they submitted an expense report. At the end of the month, no matter how many employees you have signed up, you will only be billed for your active submitters. Each active submitter can submit an unlimited number of expense reports at no extra charge.

Compare this to your current expense reporting costs and you’ll find that in the overwhelming majority of cases our price is simply unbeatable.

Expensify vs. your wasted time

Don’t have an expense reporting software? Using Excel or cut/paste documents? Let’s do the math. Your salesperson earns 50K per year, which translates to roughly $20/hour. It takes them 4 hours and a lot of frustration to fill out expense reports each month.  That’s $20/hour x 4 hours = $80. If it takes them 20 minutes to submit a report with Expensify, that’s $20/hour x 0.3hrs + $5 or $10 for Expensify = $11 or $16, frustration-free.

Expensify is easier on your employees.

Stop making your employees dread that envelope stuffed with receipts that just sits on their desks. No more endless papercuts as they scramble to find that one report your accountant wants to review, NOW.

  • Accessibility: Submit, access, edit, and submit all of your expense information to your Expensify account from anywhere with an internet connection (mobile or web).

  • Organization: Filter your expenses, receipts, and reports by date, type, category, and a multitude of other parameters for quick lookup.
  • Security: We use bank-level security to keep your sensitive financial data safe.

Expensify is easier on your accountants.

Does your accounting department use NetSuite, Microsoft Dynamics, Oracle, Sage, another accounting package? Not a problem, Expensify allows you to export expenses and reports into custom CSV formats, acceptable by your accounting package. Perhaps they use QuickBooks? Awesome, because Expensify connects to your QB account to sync everything back and forth. Save your accountants hours of manual input, save your company money.

Bonus: We also integrate with your payroll solution!

We’re happier to provide you support

You will also have email access to one of the best support teams in the business. With a 24 hour turn around time on emails (and usually quicker), we can get any issues you have sorted out quickly.

Care for a second opinion?

Check out our Twitter feed some time. I don’t know about you, but this is the first company I have worked at and been comfortable saying THAT to a potential user. Our users can’t seem to stop showering us with love! With the usual state of public discourse towards companies being rather negative this is something we are quite proud of.

Do you have a complex, outrageous expense reporting setup?

Not only can Expensify manage it, we can make it simpler and more intuitive for you, your employees, and your accountants. Email our support team and tell us about your current setup. We’ll tell you how we can make expense reporting a quicker, easier necessary evil.

At some point, a startup outgrows its lack of structure, but isn’t yet ready for the real deal. What do you do? There are some lessons to be drawn from how P2P networks grappled with the same problem.

1. Fully Connected (2-4 people)
When a P2P network is very small, every node sits next to every other node. If there’s something you need, you just directly ask the nodes around you, and they can give it to you in one step. This is akin to the early days of a startup: just turn to the left or right and every problem is solved.

2. Gossip Protocol (5-10 people)
As the network grows, not every node sits next to every other. But this is fine, because the network is still small: even if your peers don’t have the answer, odds are they just need to ask one of their peers, and the answer is found. So every question can be answered in 2 steps, which is still pretty good.

3. Supernodes (10-20 people)
However, as the network continues to grow, sometimes gossip isn’t effective: it’s possible that there are nodes sitting more than 2 steps away. In startup terms, this means peers who are off in their own direction, and nobody knows what they’re doing. But because everybody has already accepted there are things both they and their peers don’t know, it’s easy to assume that somebody else knows what they’re up to — when in fact nobody does.  Accordingly, people can be overlooked: they don’t get the support and oversight they need to be effective.

To solve this problem, a small group of well-intentioned employees — generally without any formal acknowledgement — steps up to take on greater responsibility. They don’t have any formal titles; nobody technically reports to them. But everybody knows they are doing far more than being individual contributors: they are “supernodes” who just take it upon themselves to pay attention to more than most. They are the people who walk around and ask questions.  They notice when people are unhappy, overwhelmed, unsupported, or unsupervised. They are the people everyone turns to when nobody knows the answer.  They are the unsung heroes who keep a startup from imploding under the weight of success.

But inevitably, the supernodes themselves burn out. After all, they’re consciously doing more than anybody else — but without any real extra incentives, resources, or authority. And when a supernode burns out, the whole network they support burns out, too.

Up until very recently, that’s where we were. So we’re moving on to the next stage: DHT.

4. Distributed Hash Table (21-?? people)
Because supernodes are volunteers, they don’t necessarily have any formal accountabilities — being a supernode isn’t a job, it’s a calling. And though over time supernodes tend to focus on certain areas, and though all nodes tend to learn what those areas are and act accordingly, those focuses aren’t documented or even formalized. This means new employees don’t know who knows what; people don’t know who is more qualified to make a decision than the next person. A supernode can only do so much as a volunteer: at some point your organization needs to upgrade to a DHT.

At a high level, a “distributed hash table” is a data structure where given any particular question, you can determine who knows the answer — in one step.  No searching, no gossip: just ask the right person and they will know.  In organizational terms, it’s kind of like an org chart: it documents which people are in charge of which areas. Ideally anybody can look at this chart and immediately determine the correct person to ask any question.

But it’s only a partial org chart: only the supernodes are put into the chart, and all the other nodes are left ambiguous. It’s not about strictly defined teams operating under a chain of command — it’s about a mob of people, where some people carry megaphones. Anybody can switch who they follow at will, depending on what they’re trying to accomplish. But those carrying the megaphones coordinate to ensure that the mob overall continues heading in the right direction.

That’s where we are today. Expensify is a mob, with megaphones. Naturally, I reserve the loudest megaphone for myself (as would any benevolent dictator), but more and more it’s the jobs of the supernodes to keep the mob moving forward — with me just helping coordinate behind the scenes.

How long will this last? I’m not sure. Like so many things, our lack of overt structure has worked much longer than I think anybody realistically thought was possible. Indeed, I attribute how well things have worked so far entirely to the fact that we only hire a very particular sort of person who can thrive in this environment. But I’m confident that it’ll keep us moving forward at our already astonishing rate, to whatever level comes up next.

Q: Why not a strict hierarchy; isn’t that more efficient?

A: In content delivery terms, that would be a “broadcast tree” — you have a single source, which broadcasts to the first set of nodes, each of who broadcast to the second set, out until all nodes get the content.  It’s a top-down control network, and yes, it is optimally efficient.  In an established company where all the kinks of the business have been ironed out, everyone’s job is well defined, and the success of the organization rests upon minor tweaks applied top down — yes, it’s ideal.  Most large companies are structured this way for a reason.

But a startup is nothing like that.  At least, our startup isn’t anything like that, and we all quit places like that to come here.

Rather, it’s more like I throw a flaming torch way out ahead of us, and we all try to figure out how to get there.  Sometimes it involves building bridges, blowing up mountains, and occasionally burning our boats behind us.  But my job is only to figure out (roughly) where we need to be: how we get there is up to the mob.  So our structure is optimized to put maximum control into the hands of the most people.  It can be chaotic, confusing, and sometimes a bit scary.  But it’s a lot more productive, and infinitely more fun.

Founder and CEO of Expensify
Follow us at @expensify