« Part 1: Reality Check
« Part 2: Stunts
I stood in the middle of the street at the top of the hill, taking giant, euphoric gulps of air. I grinned with delight as I watched the moon shining through the scattered clouds and onto the rippling surface of the ocean. All I could hear was the wind in the trees and the waves gently lapping on the beach. With May ushering in a winter chill that normally lasts till about October, the seaside town of Lorne, packed with tourists during the summer months, had returned to its permanent population of less than a thousand. But with the locals all tucked up in bed, I had the town to myself. I gleefully trotted and skipped down the steep hill to the bottom, turned around, then sprinted back to the top.
Suddenly, the world seemed full of promise and hope. The problems were still on my mind: the panicking investors, the aggrieved former team members, the outstanding bills. But they weren’t tormenting me now. They were just steps that needed to be taken, ordinary business issues that could be worked through calmly and methodically.
“This,” I thought triumphantly, “is what it means to be full of life!” It was a state I’d been desperately trying to achieve for years. Somehow, my iron-pumping, triathlon-training self of years earlier had become so lethargic that just getting out of bed was a huge effort. I’d tried so many things to get my energy back: every diet, supplement, detox procedure and mind-hack I could find. But whatever improvements there’d been, they weren’t enough.
Yet here I was, after just a week of solitude in a friend’s beach house, running and skipping and shadow-boxing like a lunatic, exploding with vitality like never before. And it wasn’t as if I had to drag myself off the couch and out into the chilly, windy night to sprint up steep hills. I wanted to do it. I needed to do it. I just couldn’t sit still. And doing it felt amazing. Exhilarating and euphoric and calm and peaceful all at once.
The plan for Lorne had been to adopt a lifestyle of perfect health: strict diet, nutritional supplements, daily meditation, sauna sessions, and long walks on the beach, filling my lungs with fresh seaside air. Was that all I’d needed to cure five years of fatigue? It seemed improbable; I’d been doing most of those things for more than a year. Apart from the solitude and the seaside location, there was really only one other thing that had changed: the overwhelming sense of dread I’d felt for the past few months had been replaced by relief. Could that have been it? Was relief the magic ingredient?
Of all the emotions running through my mind that week in early May 2011 when I arrived in Lorne – the week Adioso’s funds finally ran out – relief was the dominant one. Relief that the many months I’d spent worrying about running out of money were finally over. Relief at the thought that things probably couldn’t sink any lower. Relief that now that failure had unequivocally arrived, I could stop fearing it and start focusing on positive steps to get back on track.
It helped that we’d found a way to keep ourselves fed. Having created a popular open-source library used by Twitter developers, Fenn had picked up some remote contracting work for a well-funded US startup. He thought he could do a couple of solid days a week contracting to bring in enough to cover our basic expenses, while still allowing time to work on Adioso. I wouldn’t have minded if all he did for Adioso was keep the servers running. I was worried about his own stress and fatigue, and felt guilty about having him toil to pay both our living expenses. It wouldn’t be for long, I told myself. I was going to figure out how to get us some real money.
Aside from recovering some health and emotional balance, what I most hoped for in Lorne was some clear time to think everything through. Was I still up to the job of being a founder of this company? What about Fenn? Was he up to it? Did he still want to do it? Did he even know? Could we function as a team? What about Adioso? Was it worth persisting with it? Did we even want to be in the travel industry? Over the weeks I spent living in Lorne, I rolled all of these questions around in my head, often during long walks along the beach, or sitting on the verandah watching the kangaroos graze on the grass in front of the house.
Though that surge of energy after the first week was cause for optimism, I couldn’t get ahead of myself. So many times before, some perceived breakthrough had led me to euphorically proclaim that from that moment forward, everything would be different, only for the lethargy to return within days. Even if this really was the beginning of a sustained improvement, I still had major doubts about my capabilities. What was it, I’d increasingly been wondering, that I was actually good at?
Fenn’s talents were clear. He was a brilliant programmer; probably one of the best in Australia. He was also unusually socially competent for a programmer. He enjoyed the company of others; people liked being around him, and other great hackers loved working with him.
In 2003, Fenn had asked me to start a company with him because we seemed to look at the world in much the same way; I could program well enough to help him build things, and I also had a degree in business and experience in sales and marketing. He’d thought I’d be able to do all the messy business stuff to turn his talents into commercial success. As we progressed, I’d worked as a programmer on some major projects, at times excelling enough for Fenn to comment that I was closer than anyone else he’d met to being as capable a programmer as himself.
But that was years ago. As we went through Y Combinator in early 2009, my energy levels collapsed, my programming output ground to a halt, and my contribution as the business guy wasn’t nearly enough to compensate. As the months passed after YC, and we started to comprehend the magnitude of the technical and commercial challenges Adioso faced, I found myself feeling as though any contribution I could offer was like pissing on a bushfire.
Was I incompetent, and out of my depth? Was it a mistake that we’d been backed by such eminent investors like Y Combinator, Paul Buchheit and the Reddit founders? That wouldn’t be particularly remarkable; even for the very best investors, most of the startups they backed turned out to be mediocre or outright failures. But we weren’t meant to be one of them. PG seemed to have had particular belief in us, telling us before demo day he thought we could one day be IPO material, and strongly recommending us to VCs and angel investor friends. It was shameful to consider what they’d think if they knew how little I was getting done. Or how long it took me to get out of bed every day. This wasn’t how I was brought up. What would my parents think, or my late grandfather?
It had been comforting to think that my problems were the result of some curable – or at least definable – physiological condition. I’d spend endless hours consulting Dr. Google, scouring mainstream medical journals and wacko alt-med discussion boards and everything in between. ADHD, Asperger’s syndrome, depression, anxiety, chronic fatigue, bipolar, metal toxicity, poor liver & kidney function, adrenal fatigue, low thyroid function, digestive disorder, mitochondrial dysfunction, glutathione deficiency and more; I’d pore over whatever I could find, trying to find common threads and pointers to the next plausible-sounding treatment option. “You’re fine, it’s all in your mind,” well-meaning friends would scoff. I’d heard the same from doctors, back when I used to think they might be able to help. Even if it was all in my mind, I’d reasoned, it still meant there was something wrong with my mind.
But while the health fixation was a distraction, it didn’t stop Adioso from being on my mind at every moment. I seemed to be constantly turning over our conundrum in my head: we needed funding; to get funding we’d need a growing audience and revenue; to get a growing audience and revenue we’d need inventory and technology; and to get that we’d need funding. I’d endlessly be trying to work out what I could or should do, and willing myself to do it. And while I waited for an answer, I’d be reading anything that seemed to offer a glimmer of insight: the history of the travel industry, economics, consumer psychology, user-interface design. I was able to tell myself I was learning a lot, but tangible output was sparse. Was I simply a downright lazy person? The accusation had been levelled at me plenty of times in my life. It just didn’t make sense. I was trying so hard! How can someone so lazy be so stressed and exhausted?
Still, I didn’t accept that my flaws alone were holding us back. I’d always been driven by determination, passion, and camaraderie. Even at my lowest points, I’d always loved discussing big ideas, and imagining ways that Fenn and I could both become better, stronger, more capable people. In the good old days, we could keep each other going like that for hours. But these days, Fenn just didn’t have much spark. It seemed he was only interested in problems he could code his way around; beyond that, he just didn’t seem to care very much. I didn’t even really know what he was spending his time doing anymore. He always seemed to be busy doing something, but I couldn’t see how it was moving the company forward, and I doubted he could either.
Somehow, we’d gotten out of sync. The very fact that I was in Lorne by myself seemed to symbolise the distance that had formed. I’d hoped that Fenn would join me for at least a few days so we could spend some time to bond and refocus. But he’d just wanted to stay put in Melbourne, where he could at least look forward to spending his evenings with his girlfriend, Hannah.
I wondered if it was the travel industry’s fault that we were burned out and drifting apart. The travel thing had been Fenn’s idea; I’d been lukewarm on it initially. My reaction when Fenn first suggested it was, “Why would we want to build a travel search website? They all suck.” It wasn’t as silly as it sounded. Even as a layman I could sense that it was an industry controlled by monolithic old companies that would make it tough for new entrants. But I thought it would make for a good trial run at building our first consumer web product, so I was willing to go along with it. Fenn would soon realise it was a futile pursuit and we could move onto one of my better ideas.
But before we knew it we had users loving our product more than anything we’d done before, and Y Combinator was inviting us for an interview, and we had to get serious about travel after all. It was OK with me; I could see how travel would be a pretty exciting world, especially if YC could make it easier for us to gain traction. Though I’d not travelled extensively, I’d loved all the travel I’d done, and wanted to do more of it. It was during my first trip to Thailand a few years earlier, then a trip around Europe the following year, when I’d started to feel more alive and free than I’d ever felt before. The idea of living a life of abundant travel, and extending that opportunity to others, was giving me the sense of purpose I needed.
The problem, we’d discovered, was that this kind of passion alone didn’t get you funded. The travel startups that did get any funding all seemed to be founded by sports-jacketed, middle-aged MBAs from other big travel companies. There didn’t seem to be any successful travel startups founded by nerdy outsiders. Fenn and I were just a couple of scruffy geeks from Australia. We’d tried to recruit some travel veterans as investors and advisors, but it always seemed we were talking a different language. Though everyone was polite and supportive, you just got the feeling that we just seemed too crazy or feeble for anyone to believe we could succeed. Now we were learning that many prominent investors refused to invest in travel startups at all. It was easy to see why; usually the founders just wind up broke and burned out. In our present state, we epitomised the very reason why smart investors steered clear.
But for me, now, the thought of just walking away and letting the establishment win was too infuriating for me to countenance. It wasn’t so much the prospect of our own failure that was upsetting. It was more that what we were trying to build would not be built by anyone, and that the kind of product and company we’d envisioned would never actually exist. At least if there was another company trying to build something similar, we could just go and work for them. At the very least we could use their product. But nothing on the landscape had any appeal. When we entered YC back in early 2009, it had seemed we were the only startup trying to do anything ambitious in travel. Since then there’d been an avalanche of travel startups getting solid coverage and funding. By now enough time had passed to see if any of them were going to pull off anything like what we had in mind. No one had come close.
Why was it, I wondered, that there wasn’t a company that had huge appeal for the talented people who wanted to build brilliant travel products? So many of the most talented engineers and designers are crazy about travel. Why wasn’t there a travel company as attractive as Google and Facebook? In this era when company culture is considered so crucial to success, could there be a better platform on which to build an amazing culture than travel?
Reflecting on the minimal impact there’d been from other travel startups, it didn’t seem we were quite such miserable failures. Sure, our internal and personal issues had hampered our progress. But we’d still achieved a huge amount for a small team. And we knew people really wanted our product. In Australia, where we had near-complete airline coverage, people still loved what we’d built, even if they thought we weren’t improving fast enough. And we’d frequently get enquiries from people all over the world, asking when we’d extend coverage to their location or desired destinations. What we’d failed to do was to figure out how to scale out and cover the rest of the world – but the barriers in the travel industry made it impossible for anyone to do that.
We’d now spent the past three years of our lives trying to build a product that gave a good answer to the question, “Where can I go to a tropical beach for about two weeks in late October for under $1000?” It had taken us till now to understand that there was 50 years of travel industry infrastructure standing in the way, and it certainly wasn’t going to move for us, or anyone, really.
Yet, just as I was wishing we could turn back the clock three years and do something more sensible, signs of hope were appearing on the horizon. Two ambitious startups in Europe were starting to offer new kinds of flight data services, which may have been just what we needed. Google had acquired the leading flight data company ITA Software. One could only speculate about what they’d do in travel, but who knew, maybe that would help us somehow. At the very least, maybe it would motivate the established flight distribution companies to get more serious about innovation.
Maybe we’d just been too early. It was said that being too early was one of the most common causes of startup failure. I could understand why that would be true for VC-backed startups with millions in funding and a mandate to move fast. But we’d only taken a couple of hundred thousand dollars from angel investors. We didn’t need to hurry. If we’d been too early, that was OK, we could just wait.
But should we? Would it really be a good idea to persist when we were both so exhausted? Well, I could think of one reason why: when I did a stocktake of what I had to lose, there wasn’t much there. My finances, my health, my social life; they’d all taken a battering. I didn’t feel like I had to worry about losing much more, yet I could still see a pretty huge upside if I could make the right moves. And as if like magic, since I’d arrived in Lorne, new ideas seemed to be coming at me from all directions. It seemed that only now that we were out of money and my back was to the wall, my creative inspiration was flowing more richly than ever before. Maybe Adioso was the kind of company you can only build when you have nothing to lose. If it was, we’d only just arrived at the starting line.
It was one thing for me to think like that. But what about Fenn – back at his desk in Melbourne, clocking up the hours to pay not just for his own rent and groceries, but for mine too, while I pranced around on the beach, basking in my latest epiphany? Could I get him believing that our miserable predicament is in fact a giant opportunity? Or more importantly, should I?
Fenn had seemed pretty disengaged and miserable for a while. Always the kind to suffer in silence, I was worried that it was all getting too much for him. He and Hannah hadn’t been able to take a holiday for a couple of years. In a few months, Hannah would be travelling to the USA to attend Burning Man for the first time. Without some kind of windfall in the next couple of months, Fenn wouldn’t be able to go with her. It was weighing heavily on me. Perhaps it was time to stop holding Fenn hostage to my delusions, and let him go and do something less stressful, and more lucrative.
But what if there really was a way through this? What if we were actually quite close to pulling it all together? Would it be the right thing to do, to let Fenn just walk away from the best opportunity he’d ever have to build a world-changing product and truly great company? And would Fenn really find a better career somewhere else, with someone else?
Maybe, maybe not, but I was pretty confident about this: I’d yet to meet anyone as determined as I was to build a better life. That was all I really cared about. Adioso had just become the medium, the motivator, and the benchmark. I wasn’t attached to Adioso as an end in itself, I was attached to Adioso as a conduit to the most enjoyable and fulfilling life I could create, for myself, and for anyone else who cared to join me in that quest.
Adioso was the natural progression of a journey that had started six years earlier, when we’d read How to Start a Startup, then The Game, then later The Four Hour Work Week and The Dip. Each of those texts had awakened something in us, triggering intense discussions and excited proclamations about what our futures may offer, which were all underpinned by one fundamental realisation: that you had choices about what kind of life you could live, and even what kind of person you could be.
Among the most profoundly moving experiences I’d had during the Adioso journey were the approaches we’d had from a couple of friends in our social circle in Melbourne. They’d come to us quite independently and unbeknownst to each other, asking if they could invest. Neither of them were particularly close personal friends, they weren’t wealthy, they had no experience investing in early stage companies, and they weren’t even expecting big returns. They’d just witnessed the journey that Fenn and I had been on, they could see the determination that drove us and the potential for Adioso to become something wonderful, and they were willing to contribute substantial portions of their modest savings to be a part of it.
In my darker moments, it was the faith that those people had shown in us that gave me the resolve to carry on. I couldn’t bring myself to let them down. But for the most part my thinking wasn’t so grim. It wasn’t so much that I couldn’t let them down; I just knew we didn’t need to. There was going to be a way we could get this company back on track. I didn’t know exactly what it was going to be, but it was going to start with recapturing our motivation for starting Adioso in the first place: to build a life for ourselves that involved a lot of travel and a lot of fun.
So I’d convinced myself. But could I convince Fenn?
I’d realised that at the very least, what I had to do to make things better for Fenn was to give him options. In our present state, he was trapped. Sticking with the company was no fun, but walking away and letting it collapse would have involved plenty of hassle and misery too. Maybe he would be better off going and doing other things, with other people. I’d be disappointed if he did, but I couldn’t claim to want the best for him while standing in his way. So at least I could try to get the company into a state where it could survive whether Fenn wanted to be a part of it or not.
Of course, he’d only want to stay if I could make it fun for him again, if I could give him support, and if I could become the co-founder he’d wanted in the first place; someone who saved him from having to worry about annoying business bullshit and gave him the freedom to write brilliant code and build amazing products.
Could I do it? I wasn’t sure what it would take. But for the first time in months, I had optimism. Just a few days by the beach was all it took to overcome years of lethargy to be leaping off the couch and sprinting up steep hills at midnight. Who knew what else could be within reach?
Without that surge of vitality, I wouldn’t have been nearly as positive. But the way forward was becoming clearer. Despite everything that had happened, Adioso was still the only thing I really wanted to do. Maybe it could again become what Fenn most wanted to do. Or maybe it couldn’t.
Either way, there was only one way to give us both what we needed. We needed to start building a new team. Now that our funds were at zero, it was time to start hiring.
Image credit: The Coastal Descent by BMcIvr
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