Archives For CEO Friday

Crazed ramblings by the CEO.

myths about great leaders expensify

To be a great leader, you can’t just put on a mask…

So much reading on the internet today revolves around what makes a good leader, what characteristics a good leader has, and ultimately, how to be a good leader.  What we forget is that leaders are inherently part of a team, and without a team of supporters, leaders don’t exist.  A true leader relies on his or her peers and surroundings to help be the most effective they can be.  Bulldoze over these myths and avoid common misconceptions when trying to identify the leaders at your organization.  You’ll be glad you did.

Myth #1: Leaders are Assigned By Management

As much as they might like to think that’s the case, in practice leaders are nominated by peers, not selected by management.  Accordingly, you don’t need anybody’s permission to become a leader — just start leading.  You’ll know it’s working when people follow.  A good company aligns top-down management with bottom-up leadership, and thus will recognize your leadership and promote you for it.

Myth #2: Great Leaders are Larger Than Life Personalities

While there are obviously some clear examples of that (e.g. Steve Jobs), there’s many who would argue that he succeeded despite his personality, not because of it.  Rather, it’s generally accepted that the best leaders quietly enable others to be their best, rather than driving everybody toward the leader‘s own vision.  Perhaps the earliest recognition of this is in the Tao Te Ching:
The Master doesn’t talk, he acts.
When his work is done,
the people say, “Amazing:
we did it, all by ourselves!”

Myth #3: Leaders are Born, Not Made

I think this fallacy is more damaging than any other.  Leadership is a series of learnable skills — mostly around effective listening, communication, and an empathetic creativity to truly seek out and understand another person’s position, even if it’s not very clear to them.  Ultimately, leadership is the end result of anybody seeking to increase their (hopefully positive) impact on the world beyond what they can achieve themselves.

Whether you’re an aspiring leader or searching for the right person to lead your team, keep these common myths in mind so as to find a leader that truly does what he or she is intended to do: lead.

Want to work in an environment that encourages personal growth and leadership development? Check us out – we’re hiring web and mobile engineers!

David Barrett Travel Expensify

With the faithful sidekick, Lemony, of course! Photo by Robert Chen

Every year, I spend 1-2 months overseas, with probably a trip every month in between. In the last four weeks alone, I spoke at conferences in Norway and Tunisia, before heading to Portugal with the team for our 2014 Offshore. Currently, I’m writing this on a 30-hour journey from Portugal to SFO — which due to the miracle of timezones, happens in a mere 16 hours.

With all this movement, you can say that I’ve had my fair share of both delightful and horrifying experiences in business travel. Along the way, I’ve developed some core nuggets of knowledge that I live by, and I’m passing them along to the next travel-savvy entrepreneur (aka YOU). 

1) Pack Light

Obvious advice, but I mean, really light.  Buy the smallest suitcase you can — if it has wheels, it’s too big.  I travel with a bag slightly larger than a tennis racquet case.  Aim to travel light enough that you can carry everything with you at all times — to the conference, to dinner, to the meetings, everywhere.  It’s a business trip after all, and to make the most of it you need to be out shaking hands, not ferrying back and forth to your hotel room.

2) Get a Spare Battery

I carry a ChugPlug for my MacBook Air and USB charger for my phone, both of which I use them all the time.  Even if there are outlets where you’re going (and why take that chance?), it’s never cool to fumble with cords at the start and end of a meeting, or be stuck huddled around a conference’s lone “charging station”.  The technology to go cordless exists and is readily available, so enjoy it!

3) Use Modern Tools

We are living in a golden era of great services for business travelers, such as Clear for skipping security lines, Uber for getting where you need to go, Expensify for scanning receipts and managing your itinerary, Airbnb for feeling like home while on the road, Gogo wireless for staying connected in the air, etc.  Make a point to really give them a shot, even if it means developing new habits to go with them.

4) Learn Four Key Phrases

You don't need to go all out, just learn a few key phrases

You don’t need to go all out, just learn a few key phrases

Wherever you go, learn how to say “please”, “thank you”, “excuse me”, and “one”.  If you’ve got those down, you can say “Excuse me, one cappuccino please? Thank you!”  It’s not at all productive because odds are they speak your language far better than you speak theirs, but there’s something very satisfying about having a full interaction in another language — even if it’s as insignificant as ordering coffee.

5) Treat Yourself

Even on the best of days, business travel pretty much sucks.  It’s a strange combination of incredible stress: discovering your flight is delayed and you must sit in an uncomfortable chair for hours, awaiting the privilege of sitting in a different uncomfortable chair for hours more, followed by a sterile hotel in a town you don’t have time to explore, a single long-shot meeting that will probably amount to nothing, and then the whole thing over in reverse.  It’s not a fundamentally glamorous endeavor, so take your luxuries where you can.  Even if it’s just you, go to a steak house and order a nice bottle of wine.  Splurge for an overpriced movie.  Go down to the lobby bar for a nightcap and order top shelf.  You deserve it.

Have you tried any of these tips yourself? Want to share some advice or fun stories from your travels? Write to us in the comments below!

You just started your new job and you want to make a good impression.  You’ve been working at the same job for years and want more responsibility.  In either case, how do you step up your game and make a difference?  What can you do to get yourself noticed?

Set a Goal

Not a career goal, a life goal.  A goal so big you likely can’t ever fully realize it even with a lifetime of effort, but something you genuinely want to devote your life to trying.  Figure out how to make your current role into a powerful stepping stone on the long and often murky path to however you personally define success.

The bigger your goal and the more you can align your position to achieve it, the more naturally motivated you will be to work hard, resist distraction, and keep finding ways to move forward even when everyone else would have given up.  This will all have an immediately noticeable impact on your job performance even if you keep it secret.  But, if your boss is any good, his or her goal is to help you succeed in your life’s ambition. So, do them a favor and figure out what that is and then tell them so they can help steer your career in that direction.

Be a Force Multiplier

There is no such thing as a long-term career path that involves you remaining as an individual contributor forever.  The most important skills you will ever develop involve collaborating with those around you to achieve more as a team than the sum of what you can each achieve alone.
  1. Be the person that keeps the meeting focused on the topic at hand.  Write down decisions as they happen, and email them out when done — along with a photo of the whiteboard.
  2. Master the art of being able to argue both sides of the topic to the satisfaction of all involved, demonstrating you are making a real effort to remain objective in your recommendations.
  3. Speak up for the silent majority whenever you see a vocal minority hijacking the discussion or taking it in unproductive directions.  Don’t ask permission or wait to be told, just start doing it.  Your boss will definitely notice.

Be a Carbon Fuel Rod

Keep calm and be awesome

You heard right.

When everybody else is dramatically melting down around you in the heat of the moment, be the one who absorbs and neutralizes the anxiety of your peers, rather than reflecting and magnifying it.  Separate the smoke from the fire and get everybody calmly focused on proactive, realistic solutions.  Remind people forcefully about the many supposed problems that don’t actually exist.  A huge amount of your boss’s time is spent unwinding needless anxiety from unnecessarily high amounts of workplace drama, and your help here will be extremely appreciated.

Employers are looking for the best of the best, and those people tend to exude ambition, collaboration, and focus.  Stepping up and helping your boss is a surefire way to make the case that yes, you are the one they need and can’t live without. At Expensify, we love it when candidates exhibit any, if not all, of these traits because honestly, there is so much to do and we just need to Get Shit Done.
Interested in our GSD mentality? We’re hiring! Drop us a note and get in touch or email

At lunch with the Tunisian Minister of Technology, M. Tawfik Jelassi, at the International Innovation Summit of 2014, the topic of the day was: how do you bootstrap a startup ecosystem?

Don’t Reinvent What’s Already Been Done

To be clear, the question isn’t “How do you recreate Silicon Valley?” I think Alberto Sillitti (Free University of Bolzano, Italy) has answered that question best: Silicon Valley simply cannot be replicated. It is the unique product of 100 years of risk, return, and reinvestment, starting with vacuum tubes and leading to the present. Silicon Valley is a petri dish of large corporations, startups, and industry/university partnerships, concentrated into a 100 km strip of land, and fueled by a global base of private investors. The conditions that created Silicon Valley exist nowhere else in the world, and probably never will again.

But as enviable a proposition as that might be, recreating Silicon Valley is also not necessary; just as there’s no need to reinvent electricity or the internet, bootstrapping a startup ecosystem isn’t about starting from scratch. It’s about starting from today, and all that today has to offer. With that in mind, here are three ideas gleaned over multiple days of discussion with government ministers, corporate giants, university professors, and local entrepreneurs about how it might be done in Tunisia, or anywhere else in the world.

1. Evangelize The Fact That Local Success is Possible

Expensify: How to Bootstrap a Startup Ecosystem

Don’t need a map when everything you have is already here

Wherever you are, you’re there due to the generations of entrepreneurs that came before you. Many of them are probably still there, and countless more are surely in the wings, ready to take off. But it’s likely they don’t know each other, meaning few will have have personally seen someone truly succeed – a critical moment in any entrepreneur’s life to prove that success isn’t a mirage, a miracle, or a luxury enjoyed only by unknown geniuses on the other side of the world. Rather, success is the inevitable result of sustained hard work and repeated failure. Create a community that recognizes and celebrates local success, and that exists to spread knowledge about best practices for success in your local region.

Set the wheels in motion: Create a monthly dinner series where you identify one prominent local entrepreneur to come and tell their “origin story”. Not the “exit story” about how great it is to have succeed, but rather the story of the hard times before success, and how they got through. Keep it very private and intimate — 10-20 seats, hosted at an unreasonably nice restaurant that most entrepreneurs will never go to otherwise. The limited attendance not only controls cost, but also creates an exclusivity that makes tickets extremely sought after. Accumulate a database of potential local entrepreneurs and actively curate the list to invite the best and brightest: it needs to be an extremely “talent dense” meeting for people to walk away impressed. Have an open application process so anybody can apply for a ticket, and then seed the database by canvassing all local universities to identify their top students, as well as asking business leaders for their rising star employees. Once started, focus on nominations. Make a point to have a good mix at every dinner of vocal and enthusiastic people from past dinners, as well as new people who have never come before. Aim to make the event so interesting and so exclusive that every local entrepreneur looks forward to their invitation with anticipation. Once a year, invite everybody in the database to an annual entrepreneurship conference full of the best local and a select group of global speakers.

2. Eliminate Barriers to Global Investment in Local Startups

Expensify: How to Bootstrap a Startup Ecosystem

Work on a streamlined process that works for everyone. Photo credit: Financial Times

Most discussion on global investment seems to focus on very large, abstract issues like trade agreements, import tariffs, and other issues that only really matter to enormous multinational corporations. The barriers that affect startups are quite different and generally much more mundane. Make a point to talk to the smallest of entrepreneurs — the lone individuals with an idea and enthusiasm but no idea where to start — and give them a clear roadmap from zero to success.

Pro-tip: Hire a prominent Silicon Valley law firm – with a name every investor would recognize worldwide – to come up with a legal corporate structure that addresses the common concerns of an investor while meeting the needs of local entrepreneurs. There are a huge range of small, arbitrary issues that few people seriously care about but just need to be decided: where is the company incorporated (possibly in multiple jurisdictions), which corporate entity owns which types of assets, how to employees get paid, how investors are protected, who gets what in the event of failure, and how is everything split up when there is a success.

Work with that law firm to boil this down into a streamlined, repeatable process, and then promote this legal structure to every VC you can find, everywhere in the world. Negotiate a deal with that law firm to represent your region’s startups at a highly discounted rate (because it’s been so standardized) – possibly even subsidized to help offset the enormous legal expenses that cripple a small startup. Make sure the structure has genuine teeth that are enforced aggressively against startups who attempt to commit fraud against foreign investors: even a few bad apples can ruin the entire initiative, so demonstrate up front that you are not just an advocate for the local entrepreneur, but also a local representative of the foreign investor.

3. Create incentives for people to stay

Support your local rockstars.

Support your local rock stars.

The key risk if you succeed with (1) and (2) is that Silicon Valley will instantly poach your best entrepreneurs; rather than invest in a remote entity, they’ll immediately move the team to Silicon Valley. A sustainable startup ecosystem requires entrepreneurs to succeed locally and stick around to mentor new entrepreneurs, invest in local startups, and become serial local entrepreneurs in their own right. This is likely the most difficult of the three, and failure here is likely what keeps most burgeoning startup ecosystems from taking off.

Set the wheels in motion: Make your successful entrepreneurs rock stars. If they left and succeeded elsewhere, give them a hero’s welcome and encourage them to come home. Invite them to meet government ministers and foreign dignitaries or have them on stage at key functions, including not just the annual entrepreneur conference outlined in (1) but also at local fairs and holiday festivals. Give them positions as guest lecturers at universities, put them on local TV, and give them a monthly column in a local newspaper. Very little of this actually costs money, but all of it is something nearly impossible to obtain in Silicon Valley due to the sheer scale of the ecosystem. Local entrepreneurs should be seen as a national treasure to be nurtured and celebrated.

Granted, some might question whether it makes sense to celebrate an app developer more than a fireman, but the question at hand is how to encourage more startups and not more firemen. Whether or not it’s fair is open to debate, but I wager a country that does elevate entrepreneurs to national hero status will have more entrepreneurs that a country that doesn’t.

These are just three of what I’m sure are countless possible ways to bootstrap a startup ecosystem. Some of the ideas are crazy. But part of being a startup is being a little crazy — if it were safe and obvious, someone would have done it already. Really, every city and country in the world is its own startup. If you want your city-startup to attract more entrepreneurs, it needs to act like an entrepreneur itself.

A mobile app is a necessity for any company trying to make it in the big league. At Expensify, we’ve built apps for iPhone, Android, BlackBerry, and Windows Phone – and even had a Palm Pre app too, when it mattered.

Compared to mobile web usage, mobile app browsing time has increased by 6% from 2013 to 2014. It’s no wonder that companies are vying for a mobile user’s attention by building a native app. Developing a mobile app isn’t easy, but avoiding these three common misconceptions can drastically increase your reach and adaptability.

Expensify mobile app development on Android and iOS

We know iOS is shiny and beautiful, but don’t forget about Android!

1) iOS is Enough

If you’re making a consumer product for individuals, then you might be right: iOS users install more apps, and use them more reliably. If you’re selling a business app – especially one used in groups – then you absolutely need *at least* an Android app, and you might consider BlackBerry and Windows Phone as well.  Because even if most of your target audience is on iOS, there is the idea of the “tyranny of the straggler”; if one key person in the group needs something other than iOS, that person will push the whole group over to an app that supports everyone.

2) Cross Platform Layers Make Shitty Apps

It’s true that for the best user experience, native controls are critical; an HTML5 solution as almost never adequate. Most modern cross-platform layers wrap portable “business logic” with native controls, giving you the best of both worlds. In practice, as much as you’d love to spend all your time tweaking out the UI to make it smooth and glitzy, most of the complex logic that eats up all your development time actually has nothing to do with the UI. Writing your business logic in a way that can be shared across platforms prevents you from needing to re-write (and repeatedly debug) your most complex logic once for every platform.

3) You Don’t Need a Website

Mobile + Web = Love

False: Mobile + Web = Expansion

It’s called “mobile first” not because there is only a mobile app, because it’s just *first* – you still need “web second” for growth. This is because you depend on knowing your users’ email addresses, sending them messages, and giving them something to click through to. You need your users to invite friends and colleagues, and they need someplace to send them that is more powerful and engaging than a link to an app store. The most important feature you will ever build is the one that helps you sign up the next user: that’s the feature that ensures every new user is slightly easier than the one before; otherwise you’re facing a long hard slog for every single download.

What are some other common myths or misconceptions you’ve experienced regarding mobile app development? Leave a comment and share your thoughts!

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.

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!