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:

1) Do you have a clear plan for how to spend the money?  

Investors aren’t banks: they’re not in it to get a few percent back.  They’re investing in you to get a massive return, and they expect you to generate that return by spending the money they just gave you.  This means from the moment you get the cash, it’s burning a hole in your pocket – so if you don’t spend it fast on *something*, your investors will get angry.  To avoid that, makes sure you know as clearly as possible how you’re going to spend that money, and make sure your investors understand that up front.

That said, in practice you probably won’t be in a strong enough position to really make use of that advice.  Rather, it’s likely you’ll likely be so desperate that you’ll say anything to get it, and investors are surprisingly happy to turn a blind eye.  So as fallback advice, just be sure to write down your spending intentions even in the most general terms, and email them to your investors in a way that is non-confrontational.  This gives you *something* to work with in the event there’s disagreement down the road, which will almost certainly be the case.

2) Is it enough investment, without being too much?

There’s a Goldilocks zone to how much you raise.

  • Don’t raise exactly 1x what you need, as everything takes longer and is more expensive than you expect.
  • Don’t raise less than 1x with the intention of going back for more, because raising is extremely distracting and it gets harder to raise the next round if you don’t perform.
  • Resist the temptation to raise more than 2.5x what you think you need, as investors will press you to spend it — and once gone, it’s gone.

Rather, raise enough to get the job done with a reasonable cushion against the unknown, but not so much that you get too comfortable and start making stupid decisions.

3) Do you fully appreciate and accept the strings attached?

Let’s be honest, investors are more savvy than you when it comes to this sort of thing.  You sell coffee: they sell money.  You know more about coffee than them, but they know way, way more about money than you.  Just as you could pass off day old coffee on most customers without them realizing, investors have a thousand tricks for how to tie all sorts of clever strings to the money they offer you.  Accordingly, make sure you understand every little term in the contract, and have it reviewed by a competent attorney.  They’ll say “oh, don’t worry about that; that’s just boilerplate and we’d never actually do that.”  Assume every single term will in fact come to be, and get comfortable with that possibility.  If you can’t, walk away and find someone else.

Taking on an investor is like hiring a boss; make sure hire well because it’s a decision you can’t undo.

Have you ever wondered what it feels like to live with 30 of your coworkers?

For Expensify, that’s crossed off our bucket list! We do our annual offshore abroad, but it’s never been on this level in size and scope (not to mention, we don’t all live together under one roof on the offshores). Last week, we spent seven days in the Upper Peninsula, Michigan eating, working, sleeping, and then some; fun was just the tip of the iceberg.

From arriving at the local airport on the 8-seater Cessna Grand Caravan to hiking the Black River Falls, we had a blast in the Ironwood area and couldn’t have been more surprised with the welcome we received from our hosts Chris and Anne at the Powder Hound Lodge. Here are a few snapshots illustrate a day in the life of our week in the Upper Peninsula.

*Photos by Robert Chen

Powder Hound Lodge Welcomes EXPENSIFY to the UP

Our new home for the week

8 AM (sometimes 10 AM): We start off each (most) day(s) bright and early with a team breakfast. On this particular day, Anne from Powder Hound made us the works: bacon, eggs, pancakes, sausage, and buttered toast. Yum!

Getting the day started with some breakfast and conversation

Starting the day started with animated breakfast. Hot sauce anyone?

9 AM: After breakfast, the team is ready to tackle the day’s work for a solid few hours. Just look at that concentration, everybody is in the zone!

Expensify Working at the Lodge

The spacious living area was big enough for all 30 of us, and then some!

12 PM: Lunch is served! In this photo, we took over a local restaurant downtown serving delicious organic Italian food. Gotta support the local businesses while we’re here (sorry, Burger King!)

Expensify takes lunch in downtown Ironwood

Which one of these is not an Expensifier?

2 PM: Once we finish lunch, we go back to work in the lodge on most days with a few breaks in between. Wednesday was a special case – the local Expensifiers decided to take the SF team out to explore Michigan’s beautiful outdoors.

Team Expensify at Rainbow Falls

Team Expensify hike victoriously to Rainbow Falls

On the Black River Parkway Falls hiking trail

*On the Black River Parkway Falls hiking trail

David Barrett pausing for a break

David pausing for a break. /swag

Enjoying Lake Superior

*Contemplating life while enjoying Lake Superior

6 PM: Every night we’d have something fun to do. Whether it’s a job fair happy hour, a company-wide barbecue or something else, there were plenty of things to keep us occupied.

David Barrett of Expensify Giving a Toast

*David giving a quick thanks to all our Job Fair attendees!

Expensify Company Barbecue

*Hanging out at the company barbecue

11 PM: We’re a pretty work-hard-play-hard kind of team, so it’s not unusual to see some of us working until 10 or 11PM. But when the laptops close, it’s time to have some fun!

Supporting the Hurley, WI bars

Supporting the local bars in nearby Hurley, WI

Bonfire fun

*Expensifiers have a number of talents, including fire throwing!

Needless to say, we survived a full week of intense Expensify-ing with Expensifiers from both SF and the UP. We’ve created some irreplaceable memories that have only brought the growing team closer than ever before.

Next stop, Portugal!

Check it out, you ain’t seen nothing like this before!

During our UPshore in Michigan, we took some time to do our version of the Ice Bucket Challenge to raise awareness and #StrikeOutALS.

We’re also doing our part by donating to the cause; learn more about ALS and donate here!

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.

Since then I’ve been dazzled on the sidelines like everyone else, as uberX became a near-daily part of my life. But today we’re doing more than just sit idly by while the world of transportation is reinvented around us. We’re doing our part to build the future, and I couldn’t be more excited.

I’m very proud to present to you: SmartRides, the first product of a long partnership with Uber (who is also an Expensify customer worldwide) to help automate not just your expense report, but your business trip itself.

Expensify already tracks your travel itinerary — just forward reservations to and we’ll give you live flight updates, put confirmation numbers and key addresses at your fingertips, and even automatically create your whole expense report for you.

But with SmartRides, we’ll put that information to work and begin automating the physical side of your journey, too. When we see a flight is coming up, we’ll have a car pick you up and take you straight to the airport. When your plane arrives, a car will be waiting outside baggage claim to take you straight to your hotel. When your return flight lands, we’ll pick you up and take you home.

We’ll do all this without you ever needing to look up any addresses, describe where you want to go in a city you don’t know, or make any complex decisions after a long and tiring flight. Just say ‘Yes’ when prompted, and we’ll take care of the rest. There’s nothing to enable, and no extra fee — this is just a new feature built into Expensify that will appear when you need it most.

This is all part of our long term vision for the company that I’m still struggling to describe, but sometimes call “ambient computing” — an always-on service that combines information from the physical and digital world to create a comprehensive understanding of what you’re doing, to anticipate your needs and take care of all the mundane details on your behalf. (Totally optional, of course, and with the utmost respect for your sensitive personal data.)

Anyway, it’s exciting stuff, and I can’t wait to hear your feedback as you experience it for yourself. Feel free to drop me a line at if you have any questions (though please be very patient, as it can take me a long time to respond). Thanks for using Expensify, and let’s build the future together!

Expensify Partners with Uber to Bring SmartRides to Business Travelers Worldwide

Traveling Can Suck. SmartRides Don’t.

Traveling can be brutal. Delayed flights, trying to find a cab, fumbling through your phone for your hotel address — it’s all a huge headache. Those headaches are now a thing of the past because Expensify has teamed up with Uber to trade your boarding pass for hotel key with a single tap.


So What is It?

Expensify already provides live flight updates for any reservation forwarded to, and creates your expense report along the way. We call this feature “Trips”, and we’re taking it one step further: starting today the Expensify app will detect when you land and have an Uber driver waiting outside baggage claim to escort you straight to your hotel — all prearranged from your itinerary without you even needing to look up the address.  We call it “SmartRides”; the VIP travel experience for everyone, brought to you by Uber and Expensify. 


Expensify Uber



Think This is Magical? We’re Just Getting Started.

As great as SmartRides is, it’s just the beginning of our partnership with Uber. Next up is an expansion of SmartRides to take you to the airport at the start of the trip, and back home after. After that, we’re launching our integration with Uber for Business, which allows companies to centrally pay for their employees’ Uber trips and automatically sync up the receipts. After that we’ll take Realtime Expense Reports out of beta such that expense reports are a thing of the past once and for all, and then… well, you’ll need to just wait and see.

We didn’t just set out to make “expense reports that don’t suck”; we’re aiming for a total reinvention of the expense management space. Call it ambient computing, call it crazy, call it whatever you want.  But we’re doing it, sooner than you might expect, and it’s going to be awesome.

Have you tried SmartRides yet? Let us know what you think!


Download the Expensify App and start enjoying SmartRides here:

Download Expensify on the App Store  Download Expensify on Google Play

While thinking of fun, creative projects that would also WOW our customers, software engineer Carlos had the AMAZING idea of integrating Expensify with Silicon Valley’s newest darling, Yo.

The 411:

To set it up, go to Settings > Connections.

Scroll down until you see the Yo integration, and enter your username before pressing ‘Connect’.

Expensify & YO! integration

Voila, you’re all set!

After connecting, you’ll get Yo’d as soon as you get reimbursed.

Why Integrate with Yo?

People want to be notified when they’re reimbursed. Yo is a simple communication system that works perfectly in context. Once Yo opened their API, an Expensify integration was a no-brainer.

Have a question? Email us at or give us a shout-out on Twitter!
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.

The Cloud – Past, Present, Future

Stepping back, the evolution of computing can be summarized as an inexorable trend away from systems “reacting” to your input and more toward systems “proactively” anticipating your needs. The original mainframe systems were “time-sharing” and only had time to answer one question for one person at a time, in tiny slices. Desktop computers gave their full attention to a single user, but only so long as they were powered on and you were sitting in front of it. Cloud services gave rise to 24/7 services catering to your needs, and then mobile made these services accessible everywhere.

From these services, I believe the next step in that evolution are services so pervasive, so aware, and so reliable that you simply forget they’re there. They’re not some “cloud service” operating somewhere far away; they’re “ambient services” that surround and assist you continuously.

Apple vs. Google: The Past

In an ideal world, Siri would already know. Photo credits: Apple

In an ideal world, Siri would already know.
Photo credits: Apple

Siri was the first serious attempt at creating an ambient service; inspirational in its vision but falling short due to a lack of context. On the other hand, Google used its massive trove of information to create Google Now, the first truly ambient service. Google Now has so much latent awareness — of what you are doing, what you’ve done in the past, and what you’re likely to do in the future — that it doesn’t need to wait for you to ask it a question; it anticipates and resolves your needs before you know you have it.

Apple vs. Google: The Present

The problem with ambient services is that very, very few people can do them right. Google succeeded where Apple has failed (and continues to fail) because of data. Apple has by far the best user experience, making it fast, easy, and fun to find the correct button to press to accomplish what you want. In contrast, Google Now has no buttons, it’s just there. Google Now doesn’t need to ask you to press any buttons, because it already knows what button you would press — so why even show it?

Apple vs. Google: The Future

Pre-ambient systems like Apple will continuously get ever more complex, because more functionality means more and more buttons. However, ambient services like Google Now will get ever simpler: the more the service knows, the better it can anticipate your needs, and the fewer questions it will need to ask you to do *more* for you.

Who Will Lead the Charge?

So if “ambient services” are the next big thing, who will lead the charge? Google, obviously, but who else? I’d look to any service accumulating a trove of valuable data so massive and boring that nobody would pay attention to it otherwise.

Take search for example. Today we see search as “obviously” the most valuable real estate on the internet, but it wasn’t at all obvious when Google started. Recall that Google was the 25th search engine, launched when Yahoo dominated the skyline. Google didn’t even attempt to compete in the public search engine space and instead was focused on enterprise search appliances (a business model that failed spectacularly, by the way). They couldn’t raise money, and couldn’t sell the company, not for even $1M.

It was only in desperation that Google was forced to see what we now realize is obvious: an individual’s search history for tells us an enormous amount about their past preferences, their current concerns, and their future needs. This realization led not just to AdWords, but to a company built on data aggregation and normalization — a company that scours the internet (and the physical world) for anything it can possibly learn, indexing it for easy access, and offering it back to the user at a keystroke. That in itself is why Google would be the first to develop a true ambient service as they’re the only ones with enough data and awareness to pull it off.

What’s Next?

As for who does it next, clearly other search engines will follow suit. However, none of them currently know more than Google, so none can really hope to compete with Google Now. Rather, you need to find someone who is aggregating and normalizing vast sums of previously inaccessible data — data that Google isn’t indexing — and presenting it back to the user for action wherever they are: at home, at their desk, and on the road.

As you can imagine, I feel my own space is a pretty good candidate for ambient services. We’re working hard to make that future come true, but I’m sure we’re not alone. Regardless, somebody’s going to crack ambient services – probably several parties – and optimize it for different contexts based on the ambient awareness those parties have already obtained. Whether in a few months or a few years, who can say, but someday soon we’re going to look back on today’s cloud services in the quaint way we look at yesterday’s desktop applications.

Personally, I can’t wait.