11 Points of Advice from an Honest CEO


November 26, 2019



Whether you build technology or inspire those who do, you have the power to change the world.  But only if you make a genuine effort to try.

On Tuesday, November 12th, students in the audience of the Newton Lecture Series were given a strikingly blunt lecture from Expensify Founder & CEO, David Barrett.

Unlike most speakers who talk for an hour and take 20 minutes of questions, Barrett spoke for 5 minutes then took 80 minutes of questions. To listen to a live recording of his lecture, click here.

Barrett’s core philosophy was profoundly straightforward: identify the biggest problem you can and then try to solve it.

Two days after his lecture, David sent out a ‘special message’ to his audience.

Here, and with his permission, we give you that special message. 11 Key Takeaways from Founder, CEO, and Richard A. Newton distinguished Lecturer, David Barrett.

“1) More than anything, the future will be defined by technology — if you have the ability to build it, you are literally building the future.  This makes you one of the most sought-after people in the world, and the world is going to fight *dirty* for your attention. Prepare to be lied to, by everyone. They will overcomplicate everything, and try to convince you that you need their sage wisdom to make sense of their deliberate obfuscation. They will label and bucket you, to keep your vision narrowly focused on what they want you to see — and what they want you to do. And odds are, you will fall for it. You will probably even thank them for absolving you of the responsibility of making up your own mind.  You will celebrate their fawning appreciation of specialization (in the skills they need at that moment), secretly appreciating the excuse to learn less about more under the largely-false guise of learning more about less. You are the most valuable resource in the world, and if history is any guide, those closest to the resource generally gain the least value from it. Beware.

2) If you do *not* have the ability to build technology, then know that your ability to influence the world is almost entirely determined by your success in recruiting and inspiring those who can.  But you will be up against a tremendous amount of competition against those who are trying to recruit and inspire those same people to do something else. Start looking around you right now and ask: which of my tech-savvy friends should I invest most of my attention?  Because right now is when you have the most differentiation — you have the inside track, but it won’t last. Once they get out into the real world, they’ll pop onto the radar of *millions* of others who will compete for their attention. Make the most of that edge while you have it.

3) In either case, the imposter’s syndrome you feel will be overwhelming. We have built incredible networks whose sole purpose is to inundate you with images and stories of people who appear to be faster, smarter, more beautiful, better connected, and overall more successful than you.  Just turn that shit off. Deep down in your heart you know it’s all vacuous postering, bravado, and fearmongering. When was the last time something genuinely good happened by signing into whatever social network du jour the kids are up to these days? Take your eyes out of the gutter and start looking toward the horizon.

4) Whether you build technology or inspire those who do, you have the power to change the world.  But only if you make a genuine effort to try. And the first step towards trying is simply devoting the time.  Create a spreadsheet with two columns: date, and hours. Every day, put how many hours you spent on that day trying to change the world.  Just one number, updated as you go throughout the day. It doesn’t matter if you *did* change the world in that time — success and failure feel exactly the same after all, right up to the end — it only matters if you *tried*.  Every day that cell is 0 is a day you opted out of the future; make those days as few as possible.

5) Odds are you have a vague desire to change the world, but no idea how.  That’s fine — even having the desire puts you head and shoulders over the rest (and actually taking the time to try puts you further ahead still).  Get used to this feeling. Most of your journey will feel like this: a vague desire to try, and no idea how. Resist the temptation to say “I can’t focus; I’ll do this later” or “I don’t have any ideas; I’ll do this later”.  Later will never come: focus only happens when you are excited about an idea, and ideas only happen when you actually sit down to think about them. Turn your phone face down, pull out a blank piece of paper (paper works better than a laptop, because it will tempt you with fewer distractions), uncap a nice pen that feels good to write with, and then just start writing down whatever you are thinking.  Even if it’s “Wtf should I be writing?” — write that. Then write whatever comes after that. Writing forces you to slow down your whirlwind of ideas and commit them in a tangible form; it forces you to claw your way forward through a blizzard, one cold and lonely step at a time. But then you start to see footsteps behind you — you start to realize that you are going *somewhere*. Even if the only evidence of your effort after a hard day’s work is a long series of footsteps (recorded as hours spent trying to change the world), and even if you don’t know where those steps are taking you, it’s better than the *nowhere* you were going before the exercise started.  Just keep walking, then start running, then start flying. But you’ve got to start somewhere *and refuse to stop*.

6) Don’t worry about your plan — start first with your dream, and dream big.  Start with the biggest problem you can possibly imagine, and then start trying to genuinely solve it.  Not by reading some book about how someone else is going to solve it: for any interesting problem there are bound to be a thousand different books, each with a different conflicting solution.  Just trust your instincts and write down on paper everything you already know about the problem (as little or as much as that might be). Define what you think the problem is, and what causes that problem, and your best ideas off the top of your head to solve that problem.  Ask yourself “Why aren’t others doing this solution? Is it because I’ve defined the problem wrong, or is the solution infeasible? Or maybe nobody has tried it? If not, why not? And what stops me from trying it myself?” Challenge your own ideas — don’t talk to your friends, don’t talk to your family.  Talk to yourself, as you need to be your most powerful critic. Pose an idea, then critique that idea, tear it apart. Then from its ashes, create a new, stronger idea.

7) When you truly get stuck — and *only* when you get stuck — pull out your laptop and do some research.  Don’t ask for advice, because it’s going to always be in the form of “I’m not sure, have you tried reading what others have thought?  After you’ve read everything that has ever been written about it — then consider thinking an original thought. But definitely don’t think right now, whatever you do.  Thinking is a huge waste of time when there is something available to read (and given that more is being written in a day than you can read in a lifetime, this means the time to think is precisely never).”  So don’t ask for advice, ask for *data*. Figure out what tangible data materially affects your understanding of the problem and proposed solution, and dig in to find that data. Once you have it, close your laptop (to turn off its distractions), then go back to paper.

8) Repeat the above about a million times throughout the rest of your life, each time understanding the problem a little better, and getting a little closer to a viable solution.  As you go, always be on the lookout for a more impactful problem, or a more radical solution. Sometimes you are crossing a desert, where you plod forward unobstructed, but bored and parched.  Other times you are climbing a mountain, with exciting twists and lots of backtracking. But don’t agonize over how slow you seem to be progressing, how little you seem to be accomplishing, or how frustrated and disappointed you will inevitably get in your peers for thinking ideas that you realize are patently, obviously false and counterproductive.  Again, success feels exactly like failure for 99% of the journey, so don’t worry about anything except how many steps you took in the genuine pursuit of changing the world.

9) Over time you’ll start to get a sense of what’s going on.  Initially, it’ll be a vague sense of what direction you want to go.  Then it’ll be a slight glow on the horizon, then a blurred light through the clouds.  When you are lucky, the clouds will part for a moment and you’ll get a flash of your own North Star — a crisp and perfect idea that is so pure, so strong, you cannot find any fault in it.  You challenge it, but it stands up to all your scrutiny (and by this time, your scrutiny of ideas has gotten pretty good). You glimpse it between the trees, mountains, and clouds separating you from it, but even when it’s temporarily obscured: you know it’s there, waiting for you.  You just need to get through this forest, over the next ridge. You just need to keep clamoring toward it.

10) Can you imagine how nice it would be to have a North Star to your life?  Some idea so compelling to you that you literally want to devote the rest of your life toward it?  Just think how useful it would be to have the ability to evaluate every single decision in your life based on whether it takes you closer or further to your goal.  This is the point where uncertainty melts away — you’ve long since stopped caring what people think about you or your ideas, and you can’t even remember why you were so concerned what the experts thought, long, long ago.  You are on a mission, to change the world, and nobody can stop you.

11) The clearer your North Star, the more obvious the rest of your life becomes.  Which friends to associate with? Which major in college (or even whether to go at all)?  Which job to take? Which books to read, movies to watch. Everything becomes so easy when you know what you want out of life: knowing what you want dramatically increases the odds of getting it.  Decide this, and you will never work for anyone again. Even if they’re paying you, you know that you are there because it’s the shortest path to your destination. You control your own destiny and work for yourself, changing the world, as you see fit.

Anyway, that’s the long and short of what I wanted to communicate.  As for why I wanted to communicate that, it’s because my goal — my North Star, if you will — is changing the world by recruiting, inspiring, and empowering as many people as I can to change it together.  That’s fundamentally what Expensify is: a group of people each on a journey toward their own North Star, where those journeys happen to overlap right now in this moment in time.

I don’t know how you want to change the world, and honestly, it doesn’t matter.  Whatever you think right now will likely change somewhere over the next 80-100 years of your life, so I don’t actually care that much.  All I care about is finding people who want to *try*. I want to bring them together so we can all collaborate on figuring out the best way to change the world, together.  Because even if we don’t agree on the exact goal, so long as we agree on the immediate next steps, they’re easier to take together than apart — we don’t need to agree on whether we’re going to Portland or Seattle if we both agree we’re going North.

As such, Expensify is a special place for those who take a serious interest in changing the world.  Everything about the company is designed to encourage you to figure out your purpose in life, and to better equip you to pursue it — not only with the vast resources of a highly profitable company at your disposal, but by surrounding you with the finest group of humans we have figured out how to assemble.

Expense reports were never my calling, nor anybody else’s in the company.  It was just the fastest path from point A to point B — and now we power a mission-critical, recession-proof service that is insanely profitable and used by more businesses than the sum of all our competitors combined.  And while doing that, we recently did a Superbowl ad (along with a full-length music video), just because it was awesome.  We travel as a team (plus families, including kids) around the world for a month a year.  We just launched a corporate card, into an insanely noisy and competitive space, and 10,000 companies signed up in the first month.  I’d tell you what else we’re going to do, but you simply wouldn’t believe me.”