Olá from Portugal!

We’re halfway through our first week in Lisbon, and oh, what a beautiful city it is!

Traveling abroad with an entire team is exciting, but it also requires a higher level of patience to work together as we’re all in a state of ebb and flow. To stay as productive and on task on the offshore as we are in the office, we follow these few simple guidelines.

Avoid Complex Solutions to Simple Problems

Expensify Morning Standup in Lisbon

Morning 10AM Standup in Lisbon

Aim for the simplest possible solution to the problem at hand. Think paper to-do lists, daily standup meetings, writing a priorities from scratch on a blank whiteboard and emailing out a photo, etc. Most productivity issues result not from inadequate tools, but from a lack of discipline.

In Portugal: We meet every morning at 10 AM in a central location near Baixa to go over larger-picture projects, questions, and other details that help us get the day started. Each person also sends a daily 10 AM email that lists our tasks for the day. Both practices improve accountability and focus within the team throughout the entire trip.

Tip: Start the day off with a team meeting to get everyone on the same page. Review goals and projects for the day, figure out a lunch location or other logistics, and identify then nip problems at the bud to prevent them from snowballing into something bigger later on.

Emphasize Project-Based Work

Portugal Working Team

Lots of cross-team collaboration going on here.

Nothing is more stressful than looking at a list of a thousand “must do” things that you’ll probably never get to. Not only that, but to-do lists only capture checklist tasks, not overarching, bigger vision goals. On the offshore, we focus our work around projects so that we have deliverables that can drastically improve our product by the end of the trip. Think fWOW projects, but on a larger, more ground-shaking (in the product sense) scale.

In Portugal: Because we’re Expensifying 24/7 on big trips like the Offshore, it’s the perfect time to get big things done, and especially in teams. Everyone in the company has a project to work on that can be ‘delivered’ at the end of the trip; in the past, projects have included a website and mobile redesign, SmartScan, and Expensify Trips, among others. This year, we’re focusing on real-time expense reports and travel.

Tip: Before the trip, create a list of the projects everyone is involved in and have periodic updates throughout the trip so that everyone will be on the same page. The check-ins lead to greater transparency in each project, so that the entire team can watch the project progress.

Stay Calm and Carry On

A major drain on productivity is needless drama in the workplace. Odds are, everybody around you is at least as busy as you (even if you don’t understand why), so resist the temptation to aggravate things further. You are not an island; just like others affect your productivity, you affect theirs. Take that responsibility seriously.

In Portugal: Being transparent about projects makes it easier to understand what other people are working on. As a result, we tend to be more mindful and considerate of each other’s time.

Tip: Schedule meetings in advance and set a clear agenda – this helps maximize efficiency in the meeting. Alternatively, travel from cafe to cafe and work with a group of people who would most likely be doing similar tasks or projects; that way, you’ll all be on the same page and won’t need to shift from one project mindset to another.

Have you ever worked remotely with an entire team, or participated in something similar to the offshore? Want to work with us? We’d love to hear your experiences! 

Think back to all the jobs you’ve ever had in your life. In those roles, when did you finally get handed some real, capital-R Responsibility on the job?

Individuals are generally hired at a company based on what they’ve done in the past and how that translates to potential at the new position. Even after a rigorous interview process that should have proven the candidate to be a very capable person, a new hire still has to prove themselves before getting some real responsibility. Why is that?

Trust Begets Trust

Riding a bike

Learn the ropes and before long, you’ll be able to do it on your own.

As a new hire, onboarding feels a bit like learning how to ride a bike. Before you’re allowed on the bike, you have to learn from various sources the best practices of how to ride a bike. After this storm of information passes, you finally hop on the bike…only to realize there are training wheels attached.

Don’t get frustrated; training wheels are important in learning the ropes. The better you understand the basics, the easier it’ll be to find ways to insert creativity into the process.

When the training wheels come off, it’s time to ride like a big kid. Unfortunately, this is where processes start to get murky. Managers might still feel a bit nervous about you even after weeks of training, so they keep a hand on the bike handles to help steady the transition. The problem is that when a hand goes on, it’s hard to let go. Managers are afraid that if they let you go off on your own, you might crash and hurt the company, yourself, or both in the process.

It’s a very cautious position to take, but it’s not always unwarranted; take a look at a number of social media blunders that have happened due to poor judgement or lack of knowledge. On the other hand, micromanagement and overprotection might prevent the new employee from ever learning how to ride the bike properly on his or her own.

How to Give (Well-Earned) Responsibility to Your Team

Cultivating trust between you and your supervisor takes time, but being active early on can expedite that process. Don’t just go through the motions; ask questions and show that you’re thinking about and seeing the larger picture. Trust also leads to more responsibility, which helps cultivate the feeling of value, and culture helps with feeling a sense of belonging. But what does this look like in practice?

During my interview, I had discussed the potential of inbound marketing and restructuring the blog as something I’d like to focus on if I were hired into the team. After getting an offer and signing the t’s before dotting the i’s, the blog was handed to me to carry out my vision. Shortly after, the first thing I did was systemize the writing and publishing process by creating an editorial calendar. My previous work and the work I did during the interview process was enough for the team to say, okay, we trust you with your ideas on how to improve the blog.

From Varun Varada, one of our newest Software Engineers:

Varun, Software Engineer

Varun Varada, Software Engineer

“The best way I can describe it is that there is a seed of responsibility that’s planted into Expensify’s culture. The freedom that has been given to me allows that seed to grow organically so that I end up having more responsibility the longer I’m here. Going with this metaphor, the freedom is the soil that’s helping me grow. For example, I’m currently working on a fWOW project that came out of necessity, but I’m passionate enough to fix it that I’ve taken it upon myself to do so. Once that project is done, I’m going to start on another one that I designed myself.”

The lack of trust in new employees is not unwarranted, but if you hired someone based on the responsibilities they were given at their last job, chances are, they’re probably not an idiot. Spend the time onboarding and training them, but don’t deny new employees the chance to take on bigger projects either.

How do and when do you dole out responsibility to new employees? As an employee, what do you think? We’d love to hear from you in the comments section below!

Raising money or starting your own business? Then you might want to continue reading!

David recently spoke at the Silicon Valley Innovation Summit (SVIS) about the cultish view of customer acquisition amongst startups and the myths of performance acquisition. Check out the video for tips and tricks on how to avoid the CaC trap:

The keynote touches upon a few key points:

  • Customer acquisition is almost synonymous with raising money, why?
  • Theory (V = R * $ *LTV/CAC) vs. Practice (V = R * $ * hope)
    • Curious? The video explains in detail where hope “fits in”
  • Making money should be a requisite for making money
  • The nouveau enterprise: introducing disrupter (we know, very overused word) economics

While the keynote itself is about 11 minutes long, stick around for the Q&A session afterwards, where David explains exactly how his view on CaC has fueled our strategy against our biggest competitor.

Got something to say? We’d love to hear your reaction and thoughts on the subject in the comments section below!

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 (totally optional) 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 offshore). 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!

Although the trip was optional, everyone was excited for the week-long retreat/meet-and-greet that created some irreplaceable memories. The team’s excitement and enthusiasm for crazy things like this is what makes us love what we do and all the amazing people we work with!

Next stop, Portugal – we’re ready for ya!

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 receipts@expensify.com 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 dbarrett@expensify.com 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!