The secret experiment behind the Expensify Lounge

TL;DR: The Expensify Lounge was a wild experiment. As of November 1, 2023, it will be closed until further notice.

When we first launched the "Expensify Lounge" –  with plenty of seating, an amazing view, fresh cappuccinos, hand-mixed cocktails, and to top it off: a nightly sabered Champagne sunset toast, right downtown in the middle of San Francisco's financial district, all for free – people couldn't help but ask "Why are you doing this?" and "How long can this possibly last?"

As the first expense reporting mobile app, we were already very familiar with the mobile workforce.  But for the first decade of the business, most work still happened in a traditional office.  COVID changed all that overnight.  Kitchen tables replaced cubicles, and everyone was a digital nomad… whether they liked it or not.

For many, this was a transformational time.  People discovered the joy of working in their PJs.  Then slowly, explored local cafes.  As the horrors of COVID waned, the joys of telecommuting grew, and the conversation slowly shifted from "when can we go back to the office?" to "... should we?"

Granted, we were already a "remote first" company long before COVID on account of our culture of traveling around the world together as a company (Curaçao, Italy, Iceland, and Indonesia this year alone).  So being forced to work from home wasn't disruptive.  It was just boring.  But we recognized that we were living through a transformational time for the rest of the market, and decided to fix up one of our offices and run a little experiment around a very simple question:

Can anything bring workers back to the office voluntarily?

Before COVID, your office had a monopoly on your time: you had to go, or you got fired.  It didn't matter if your office sucked, you just had to go.  But COVID taught everyone that it's entirely possible – and often preferable – to work on the beach, at your home office, in a cafe, or literally anywhere in the world that isn't your office.  We all stumbled awkwardly into the light of day, and can't quite remember why we ever chose to live underground in the first place.

Going to the office is no longer a necessity.  It's a choice.  And we wanted to know what, if anything, would cause people to voluntarily choose to go back to the office when the entire rest of the world (including the comfort of their bed) beckoned.  And we're happy to report that the results are in:

Mostly no.

Recall that we went absolutely all out – we did everything possible to make the office as attractive as we possibly could.  Drinks delivered straight to your desk.  Gigabit wifi.  Call rooms.  We took this concept further than any company reasonably could at scale, to leave no stone unturned.

And don't get me wrong, it was epic.  The only comparable experience I can think of is in the early 2000's, a legendary entrepreneur named David Weekly hosted giant working parties in his literal mansion – the geek equivalent of the Great Gatsby – where a hundred random hackers would show up with their laptops to drink beer and work all night, side by side.  It was a funner, simpler, happier time in Silicon Valley, where everyone was focused on genuinely pursuing their dreams, where you could still be the first to try something, where everyone was working together to imagine a better world.  The Expensify Lounge had a similar kind of magic, where people chatted about large language models and business models interchangeably, cocktails in hand, looking out over the city where dreams are transcoded into reality.

An Expensify Lounge barista kicking off the daily sabering tradition.

Additionally, by many other measures, the lounge was a wild success.  It was an incredible brand experience: despite how lavish it seemed, from a cost perspective it was orders of magnitude cheaper to fix someone a cocktail in our own bar than to try to talk to that same potential customer at a conference booth.  In a way, it was like the most amazing conference booth you've ever seen (and if you've seen our booth, you'll know that's a high bar), but open every day of the year, with no competitors milling about, and for far more guests at a far lower marginal cost.  It had a line out the door and we had to turn people away earlier and earlier every day.

It was also a fantastic laboratory for new product innovations.  We launched our revolutionary Expensify Chat in the Lounge, as it's so much easier to test when you have a large group of new people experiencing the feature for the first time right in front of you every day (and now it's powering conferences around the world, directly informed by that testing).  We learned the dark arts of wifi capture portals (shudder… so messy).  We learned so much about how collaborative communities form, about how to manage the downsides of semi-anonymous co-working spaces (to the dude who shoveled cans of Liquid Death into his bag every night, I'm looking at you).

So by many measures, it was a wild success.  We are so much better equipped to navigate the years ahead with what we've learned. 

But did it reliably compete with the rest of the world?  No, it did not.  Expensify Lounge 0, Rest of World 1.

In practice, the lounge was a place that people would generally visit, marvel at, work for a bit, and leave.  They would tell their friends, who would come in (typically around happy hour for a cocktail), they would be astounded… and then leave.  Yes, we had a hard core group of daily visitors.  But by and large, it was an ever changing group of people who viewed it as perhaps the best place in the city (in the world?) to work – but by no means the only place to work, and not the place they want to work every day.

So what do we do with this knowledge?  Our business depends on understanding how business works – and where it works.  We build tools for collaboration, both inside and outside the office, and if the office is changing, that means our market is changing.  And as a self-styled "long term business", that means always looking beyond the next quarter or next year to identify the underlying trends shaping the market over the next decade – and a total disruption of the place most of our customers spend most of their time doing most of their work.

Two coworkers at the Expensify Lounge discussing strategy.

Accordingly, based on this experiment, I think it's safe to say that anyone going to the office every day is likely going because they feel pressured to (either by their boss or their peers), not because it's actually their preferred place to be.  Which isn't to say there's no place for offices going forward – far from it.  Rather, we're just never going back to a regular 9-5 office culture, a staple of not just our modern culture, but also the foundation of most urban planning.

More pertinent to our business, we expect all those billions of daily in-person meetings, watercooler chats, physically printed materials, whiteboard sessions – they're all going online.  All those tools that presume you sit on a gigabit LAN right next to your local file server, or even have a reliable connection to some global server – they are going to buckle under flaky connections and high packet loss.  All the business processes built around talking out loud in realtime to the people you depend upon – they're all going asynchronous.

Not immediately.  But inexorably.  If the best office in the entire planet can't compete with the local coffee shop, the tightly-closed Pandora's box of "work from anywhere" has burst open, and will never be resealed.  No amount of begging or coercion is going to work in the long run: the businesses that demand it are fighting a losing war of attrition against an infinite universal energy.

You heard it here folks:

The office is dead.

But that doesn't mean collaboration is dead, or that community is dead.  It just means it's broken free from its stuffy, sterile confines, and is becoming something so much bigger, more dynamic, and more exciting.  Cafes and beaches and airplanes and kitchen tables around the world are the new office, and as someone who works from one of those every day, I couldn't personally be happier.

So what is next for the Expensify Lounge?  Unfortunately, as our experiment has concluded, we are shutting it down.  We might reopen it again in the future when we have a reason to, but as of 11/1, it's an exciting but finite chapter in Silicon Valley lore.  I hope you were there to enjoy it – it was epic.

As for us, we are shifting our "physical world" attention to our next bold experiment: the Midtown Beer Garden, powered by Expensify, located next door to our global headquarters right smack in the middle of the growing tech hub of Portland, Oregon.  Similar to the Lounge, it's best viewed as an open air laboratory for answering questions that guide our long term strategy – but this time, with 10x the daily visitors, at a tiny fraction of the cost (or no cost, as we expect it soon to be profitable).  What is the secret question being tested by the MBG?  I can't wait to share.  But for now, I hope you will visit and experience it.  There's nothing else quite like it.

But all that is really just a tiny subset of what we've got cooking.  While we love to think about the long term, and we love experimenting with the creation of physical communities, the our immediate focus is entirely on building a virtual community atop New Expensify – which we describe as a "superapp" due to its ability to seamlessly blend personal and business payments, along with bill splitting and realtime chat.  It's basically a lovechild between Venmo, WhatsApp, and Splitwise, optimized for groups of traveling friends (think bachelorette parties and Burning Man camps), community groups, side hustles, and startups.  It's getting better and better every day (we just launched SmartScanning and receipt splitting so you can get paid back for picking up the tab for your group of friends, all within Expensify!) – check it out, and more is on the way!