Failure is an opportunity

is the lie you tell yourself when your startup fails.

The harsh reality is that failure fucking sucks.

Don’t let the startup mantras and hashtags fool you. Failure is emotionally draining, physically exhausting and psychologically frustrating. In some circles, it’s externally glorified, and in others, overwhelmingly demonized.

I know this. Today, better than most days because today, we shut the doors down on OutTrippin, our company, our baby and the love of our life for the past two years. Notice how I struggle to even say the word failure in that sentence? It’s not a strategic choice of words; it’s just agonizing to say the words: My company failed.

I keep telling myself that failure is an opportunity. Based on the generally positive demeanor I’ve had over the past few days, many might think I do believe it. Sometimes, I think I believe it too. I can logically draw the lines and understand why failure can be, and should be an opportunity, but sometimes logic just goes out the window. Because when I dig deep, behind the pleasant demeanor, behind the words, behind the actions, late at night as I lie awake, tossing and turning, a paralyzing realization starts to sink in and the “truths” you keep telling yourself during the day can no longer mask the reality:

Failure. Fucking. Sucks.

It’s a funny little world. I remember when we started this adventure 2 years ago. Indi, my cofounder, and I met in a hostel in Buenos Aires. Traveling through, we became fast friends and when we happened to find ourselves in the same beautiful city a few months later, this time to live, ended up as flatmates and eventually as co-founders. We’ve been all over the shop, from Buenos Aires to Santiago, Melbourne to New York, and San Francisco to Dubai. We put it all on the line to realize our vision of what this world may look like if each person traveled more, traveled better and found experiences that they found truly amazing and eye opening. We think it would make us a happier people, a more understanding civilization, a more loving race. And so we tried. And try hard we did. We started OutTrippin, to build products that let people get personalized recommendations for truly amazing experiences on their travels. Our first product was a service that let travel experts compete to build your vacation. We took investment, we moved continents, we dealt with visa bullshit, joined an accelerator, found mentors and experimented with product, partners and business models. We failed, we learned, and we got up and tried again. And never thought that one day, we would get up to try again, but OutTrippin would not. We never thought OutTrippin would fail.

90% of startups fail. That’s a statistical fact (uh, more like just an estimate). And yet, every account from an entrepreneur with a failed startup, the recurring theme always is: ‘I never thought my startup would fail.’ It’s the combination of the narcissistic nature of entrepreneurship (that I, as a single human can change this world of 7 billion people) and the stressed importance and almost glorification of hardship (airbnb and their one thousand days of failure) that has allowed us to create this magical bubble of optimism where we allow ourselves to reach for unimaginable heights, work our asses of, all with the belief that we are the outlier, we are not the 90%. Even if statistical reality says otherwise.

And boy that bubble is simply amazing. It’s energizing in the face of impossible (improbable) odds. It’s invigorating even in the darkest hours, when all seems lost, and it gives you permission to go after goals that most others have deemed impossible. Because, you, your beautiful, intelligent, passionate self is the person to achieve the impossible (improbable).

And. it. is. glorious.

Right up until it all comes crashing down. And 90% of the time, it does. And today, it came crashing down for my startup and my life for the past 2 years.

People ask me, what happened? It all seemed to be going so well, I thought?

I was back in Santiago, Chile in April 2013 when I was skyping with Indi on a Wednesday evening, who was stopping by Melbourne for a friend’s wedding. She said I’d love this city. She said I’d love all the cute hipster girls (she knows me well) and that we should totally think about moving there. I considered it for half a second and thought I’d see who’s investing in Melbourne on AngelList. After a few messages with Adrian Stone & Nathan Sampimon, by Friday morning just 2 days later, Indi was pitching OutTrippin to a crew of angels. We all got on a Saturday group skype, and by Monday AngelCube invited us to join their 2014 batch. The only catch, move to Melbourne in 4 days, by Friday morning. For many, that’s a no way, that’s absolutely ridiculous. For us, it was a no-brainer. A day of packing, some serious hustling for visas and few tearful and sudden goodbyes later, we were off to Melbourne, myself from Santiago and João from Portugal, just one week since Indi suggested we consider Melbourne as the next stop on OutTrippin’s journey.

Startup founders get used to living on the knife’s edge because anything can happen. In fact, anything happens all the time. For every amazing thing I tell you is happening, there is an equally destructive thing that could also happen to the company. For every potential ascension and growth opportunity, there is a deep dark valley we could plunge into. Things can be amazing and terrible at the same time. For every huge deal we close, it can all fall apart before we’ve even had a chance to finish the champagne. So we learn to drink up quickly. We learn to manage the constant threat of things falling apart. We mask it behind the amazing potential. But masking it doesn’t make it go away. It’s always there. It’s a condition without a cure, the best we can do is manage it, mitigate it, and accept it.

And that’s just how it goes. Sometimes it all comes crashing down like a house of cards.

So what went wrong?

I don’t believe that only one thing going wrong can kill a company. Usually it’s a catalog of things that go wrong that brings any company to this point. It was no different for us. Every thing that could have gone wrong, went wrong. That includes everything from business model failure, partial failures in team dynamics, general tiredness of doing this thing this long and go through yet another product and biz failure, a difficult investor climate in the travel industry, but most of all, the market dynamics that pushed us onto a mountain that we kept trying to ascend, only to eventually realize that that mountain was not our Everest.

It wasn’t our Everest.

Startups are hard. And it’s not made easier when life things happen. Back in 2013, we were going through AngelCube, an intense 3 month accelerator program that essentially takes over your life. Similar to other accelerators, the non-stop ferocious nature of the program requires you to park your life entirely for 90 days and focus on your company and company alone. But life, as you might expect, makes other plans. 7000 thousand miles away, I got a call no son should ever get. A hysterical sister and mother, trying to tell you that your dad, the man who you could always turn to, the one man in your life that’s always been there, is no longer there. And suddenly, everything changes. Everything that you knew to be true, no longer is. Every thing that you knew about life, is shrouded in doubt. Everything you were, you no longer are. I left immediately to return home (obviously), leaving my cofounders to keep the company going while I tried to simply accept what had just happened. You never realize the strength of the bonds you create with those who you start a company with until it’s put to the test. We fought through what was the worst moment of my life and my co-founders Indi and J0ão helped me put myself back together in a way that made me think that nothing could stop us from ascending our Everest, all because we had just survived the worst moment of my life.

With all the sleepless nights, grey hair and the financial disaster that is your personal bank account, you’d think we’re nuts to go after the impossible (improbable) odds. But the truth is, when it’s a vision you so passionately believe in, everything else fades away. You say, ‘who cares about the grey hair, I’m on the George Clooney aging plan’. You say, ‘you’ll sleep when you’re dead.’ Money, schmoney, this is why you have credit cards. It’s all good if you can keep going after your vision. It’s all good as long as you have your Everest. And that’s why, it’s so very, very, very crucial to find your Everest.

Because no other mountain is worth climbing.

OutTrippin was our Everest for a long time. But we were also open to following the market to wherever it might lead us. And this time, we were led astray.

In the world of travel planning, finding a business model that works is like hunting for unicorns.

It’s why there has been little to no competition to TripAdvisor on the travel planning front for the past decade. We’ve always had an amazing community of travel writers and bloggers and we’ve always had a concept that got people really excited. The problem has always been to find a business model that could scale. From OTAs to airlines, from content companies to hotels, we experimented for a sustainable route to create high quality expert generated travel content at scale. What a mouthful, I know.

With a recently launched b2b (business to business) product targeting hotels, we came damn close too. But it dragged the company to a place where we dealt with slow moving behemoths and a b2b sales cycle that makes movements of glaciers look like that of a Ferrari. We could make peace with that, I think, but we couldn’t make peace with the fact that this wasn’t the mountain we wanted to climb. We wanted to focus on creating more magic with our apps on the consumer side. But without the revenue from hotel partners to cover content costs, it would all come crashing down like a house of cards.

The travel industry’s investor climate is colder than the arctic.

It is notoriously difficult. There are fair few success stories (Airbnb, HotelTonight are the only ones that come to mind and are essentially in the accommodation booking space) and there hasn’t been a legitimate challenger to TripAdvisor in over a decade. Investors are skeptical and rightfully so. Many don’t understand the space and those that do know exactly how hard it is. Either way, doesn’t make quite the savvy investment, does it?! What that means is that most travel startups are going to have to prove 10 times more than their counterparts for similar valuations and investment, all in an effort to overcome the industry bias. Doesn’t make it impossible, just a whole lot harder.

And that just meant that we had become a company that did things the bootstrapped way. A specific conversation I had with my cofounder still rings out in my mind. I told her of a random idea I concocted in the shower the night before. It combined the tinder swipe concept, amazing things to do in the city, and an ‘algorithm’ that would put together a timely version of an itinerary with the things you like most with the time constraints you had. Groundbreaking? Not at all. But her response is what was most telling. She asked:

“How do we make money from this?”

It wasn’t one sided, there were many conversations where I played the role of ‘show me the money!’ We had just become a company with a ‘show me the money’ culture. Remarkably, it helped us become self-sufficient and we probably made more revenue than most travel startups our stage, mostly because we had no choice but to keep on hustling. But it also left no room for errors; And it meant that any new idea came constrained with the question: How do we make money from this?

And that, ultimately stifled our creativity.

All that pressure took it’s toll on the team too. It did us no favors that part of the team, mainly João, was on the other side of the world with a 12 hour timezone difference. Sure, tools like Github, Google Hangout, Slack, Basecamp and countless others, help you manage team workflow no matter where they are, but there are no tools to help manage emotions and morale. And startups are just as much an emotional journey as anything else. When the person you work with day in and day out sits next to you, you can see how they feel, when to push, when to support and when to get them a glass of wine or a gin & tonic. But when you have a 2 hour window in a day to work together, you barely have time to get past work to really get to know how they are truly feeling and how you might help.

I caught up with Indi last week after her trip to visit family in Sydney, and mine to visit family in Dubai. It seemed like a moment away from the home base of OutTrippin had helped us clear our heads and understand who we were and what we believed. We had a glass of wine and our thoughts and, dare I say it, “feelings” just seemed to come rolling out. We talked about how this b2b product we created for hotels as the revenue and content driver for OutTrippin had become the bane of our existence. It seemed to have pushed us in a corner of the market we had no interest in. How the god awful b2b sales cycle with hotels made me crave a shot of vodka simply to answer an email. We talked about how it was convoluted that we never believed in this new product but were willing to do it if it made it easier to pursue our core vision. About how the reality was that it didn’t. It didn’t make it easier to pursue. It didn’t follow our core vision. And it certainly wasn’t our Everest.

Eventually, it became clear to us that it was tiresome to even feign excitement over this new direction we were taking, all to keep surviving as a company.

We spent the past two years of our lives on OutTrippin because we were driven by the magical memories that we helped create. From sci-fi themed honeymoons in New York City to diving trips in Malaysia, from bachelor parties in Austin to a girls trip to Iceland, these stories and countless others that we’ve helped make are absolutely epic. And for this we are prouder than a dog with two tails.

But the more we moved in this new direction to keep surviving, the more the magic faded. And that was the straw that broke the camel’s back. It was the stark realization that in an effort to keep surviving as a company, we had started climbing a mountain that wasn’t our Everest. And that wasn’t fair to our users, our customers, our community and it definitely wasn’t fair to us.

There is no logic in building a company whose direction you no longer believe in.

And so, it’s time for us to find a new challenge, and bring this crazy train we’ve been on, to it’s final destination. As I sit here, listening to Frank Sinatra lay down some truth bombs, I can’t help but resonate with ol’ blue eyes:

“I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king. I’ve been up and down and over and out but I know one thing: Each time I find myself flat on my face, I pick myself up and get back in the race.”

And that, ladies and gentlemen, is life (and I can’t deny it). I feel a surprising ease that I cannot explain. Considering all of the above, one would think that I would be a wreck but it’s quite the opposite. I’m energized by the decision as opposed to burdened by it. There isn’t a trace of regret. Maybe it’s because I’ve made my peace with it. Maybe it’s because I don’t know what’s next but that excites the living hell out of me. Maybe it’s because I get to restart the search for my Everest, because I am just as thrilled to climb it now as I was when I started OutTrippin. Or maybe, just maybe, failure is just another opportunity to start again. This time, faster, better, stronger, and (most importantly) more intelligently.

This article originally appeared on kalro.net