« Part 1: Reality Check
“It was just so off-brand for you guys.”
I didn’t really go for the marketing-speak, but I knew what she meant.
It was late April in 2011, and Jenni and I were sitting near the fireplace at the Great Britain Hotel, the delightfully offbeat pub in the inner Melbourne neighbourhood of Richmond, that had been my sanctuary and playground during my chaotic period of a few years earlier. Jenni, one of the people I’d come to rely on to tell me what I needed to hear, was home from London for a brief visit over Easter.
She was talking about the How Much Do You Heart Me? microsite we’d launched a couple of months earlier for Valentine’s Day. Until that moment, not a single person had straight-out told me they thought it was a bad idea. But Jenni was telling me something I’d known deep down all along.
The journey to How Much Do You Heart Me? had started back in November 2010, about three months after the launch of our new website version and our Techcrunch & Lifehacker coverage. The message we’d taken away from the feedback after that launch was that our flight search product was amazing, and that all we needed to do was add more airlines and destinations so it would be useful for everyone.
The version we’d launched carried just 13 low-cost airlines. It enabled good functionality in Australia & Southeast Asia, and moderate functionality in Western Europe and the US. But the confinement to low-cost airlines meant there was barely any inter-continental coverage. We were positioning Adioso as a flight search tool for adventurous travellers, but you couldn’t get from the US to Asia, or from anywhere to Latin America or Africa, and it was completely unusable to Canadians.
The problem was, the search engine we’d spent the previous eight months building could only handle low-cost airline flights as individual one-way segments. To offer more comprehensive coverage, we needed to add full-service airlines. These airlines structure their fares in a completely different way. So it wasn’t a mere case of continuing to develop the engine we’d already built. We had to start building a new platform again.
As we set about the task, we were all confidence; we’d have the new engine built within a month or two, and as soon as it was done we’d be able to offer comprehensive global coverage, and even start making revenue out of all the transactions we’d refer for full-service airline flights.
But by late November, almost three months later, we seemed barely closer to the finish line. Some of our core technology assumptions were turning out to be flawed and the task was becoming increasingly complex. Estimates of “four more weeks” were floated, but there was no real way of knowing with any kind of certainty.
To complicate things, our burn-rate had us looking at only about another five months before we’d need to have another funding round closed. If we could announce the launch of the new engine in a month, and if that would start growing the traffic, we’d be in good shape, though the timing would be tight. But if it took two, three or even six more months, which for all I knew was just as likely, we’d be screwed.
During a company hacking retreat in New Zealand, a team member suggested a different approach. We’d take a break from building the new flight search engine, and try a new project that would be much more achievable and fun. A simple microsite that matched flights with hotels to create packages for spontaneous romantic weekend getaways was proposed; it seemed to have merit. It was much more of a known undertaking than the new flight search engine. We’d need to build a hotel search component, but we’d been planning to do that anyway; everyone knows the only way to make money out of flight search is to add hotel search. This would give us the incentive to get a minimal implementation done quickly.
A Christmas theme made sense; it was a pretty tight deadline, but we wanted to make the timeline short to keep it lean. It would be social and sharable, it would hook into Twitter and Facebook, and it would totally go viral, especially if we offered a $1000 travel prize to whoever came up with the coolest tweet about it.
Something else about it appealed. We needed to have something exciting to show our existing investors. We’d been getting concerned questions about our traffic and our development progress. And some were wanting us to hurry up and start generating revenue. One investor seemed to reply to each of our slavishly prepared update emails with the same question: “Do you have a business model yet?”.
The microsite idea would put all those problems to bed. It’d be wildly popular, make us some money, generate lots of hype and drive loads of traffic back to Adioso, giving us the momentum we’d need to raise our next funding round. Fenn briefly put forward a dissenting view, but he was outvoted. The getaway package microsite was going to be our salvation. So we got to it.
It was all mostly working with about nine days to spare before Christmas. All we were waiting on was the accommodation distributor. There’d been a delay. We’d needed their Europe-based engineering team to do some customisations, but with some of the team unable to get into the office due to the record-breaking snowstorms, they were even more under-resourced than usual.
Christmas came and went. No accommodation. No microsite launch.
No matter, we thought. It was always going to be cutting it fine. We could just come up with a new theme and try again in a few weeks.
Valentine’s Day seemed like the perfect theme for a site to let couples find romantic getaways. A sexy 50s-esque flight attendant would ask you to choose a budget, representing how much you loved your lover, and you’d then be shown a series of weekend getaway options. With howmuchdoyouloveme.com already registered, it became howmuchdoyouheartme.com.
With the help of our designer and two front-end developers, we had it ready for launch on the Monday a week before Valentine’s Day. By then the project had taken far more time and money than we’d initially envisaged, and with the end of our runway in sight, we needed this to be a success. But everyone who’d worked on it or previewed it was convinced it was a winner.
We published the blog post announcing the launch at about midday. We tweeted it and Facebook-posted it, then sat back and waited for the hockey-stick graph to take shape. People who knew us responded with exactly what we wanted to hear. The Melbourne Twittersphere was abuzz. People with personal connections to Adioso and the others involved with the project were euphoric.
Within about 30 minutes, the traffic and social media buzz flattened off. It wasn’t spreading much beyond our own networks. I waited for a few more minutes to see if it picked up, but it remained flat. A wave of dread swept over me. I went out for a walk, alone. I thought back over the two and a half months since we’d made the decision to take this direction, calculated that we’d bet 75% of what had remained of our runway to get here, only to find that it had moved us no closer to funding. For the first time since our last fundraising a year earlier, I was starting to panic.
Over the next couple of days, the campaign scored some media hits, with coverage in Lifehacker Australia, Tnooz, and Notcot, and we heard the campaign had been on everyone’s lips at a Melbourne advertising industry networking event. People were talking about how beautiful the design was, how fun the concept was, and how cool the use of HTML5 was. In total it generated just over 10,000 visits – about 5 days’ regular Adioso traffic. And not a single revenue-generating transaction.
I knew it wasn’t an outright failure. I knew the people who loved it had good reason to love it, and everyone who’d worked on it had done a wonderful job. But it was just like any new startup idea. To become truly successful, it would have to go through months of testing and improvement. There was no time or money left for that.
Six weeks later, as we were returning to Melbourne from our bubble-bursting trip to the Bay Area, Fred Wilson caused a stir in the startup world with the publication of a post lamenting the fact that he’d passed on an early-stage investment in Airbnb. In the post, he recounted the legendary tale of Airbnb funding themselves through a cash drought by selling novelty Obama-themed breakfast cereal during the 2008 election campaign. He explained that in retrospect, Airbnb’s ability to survive a crisis in this way was the most powerful indicator that they’d turn out to be a good investment.
Over the following weeks, as our cash situation became increasingly desperate, I became fixated on the idea that this kind of campaign could work for us. I scoured Alibaba for ideas for Adioso-themed travel accessories, like neck-pillows and eye-masks. Fenn suggested a one-off comedy event as part of the upcoming Melbourne International Comedy Festival, where comedians would tell travel stories. Ned had been toying with the idea of importing fixed-gear bicycles from China, and thought perhaps we could get them painted in Adioso orange and promote them to the unconventional traveller.
I started thinking t-shirts would be the way to go. Yeah, t-shirts! But it wouldn’t just be a plain ordinary t-shirt sale. We’d make it a Kickstarter-like affair, tied in with the new features we were proposing to build on the site. People would pledge their support for a particular feature, and fund development of it by buying a limited-edition t-shirt. We’d rinse and repeat as we worked through more and more awesome features, funding ourselves all the way to greatness with t-shirt sales.
I bounced the idea off my housemate Cris, then to Fenn in a late night call. They both responded with something like “er, yeah, I guess that might work”. It was good enough for me. The next day I put it to Ned in a walk’n’talk around the park near our office. I hadn’t slept much the night before, and was in a pretty overhyped state as I explained it to him. He contemplated what I’d said for a few moments, then stopped, turned to me and said “Fuck dude. Do you really think you can get through this?”
The question had been nagging at me. Because there was one major flaw in all these ideas that revolved around selling products to our community: we didn’t really have a community anymore. We used to. Not a huge one, but the community we’d had was devoted and passionate. They’d email us, and excitedly tell us how refreshingly simple and delightful the site was. They’d tell us about the trips they’d been able to take only because the site existed. They’d suggest features, and respond with excitement when we quickly implemented them. They’d ask if we had t-shirts they could wear, or if they could just send us a donation out of gratitude for all the time and money we’d saved them.
To these people, Adioso had represented what travel search should always have been; a way for people who wanted to travel as often as possible to learn about where they could go, and find the best flights as quickly and easily. They’d seen Adioso as their saviour from the exasperation they’d felt towards the antiquated travel search sites they’d always been forced to use.
Somehow, over the eight months since we’d launched our new version, we’d stopped hearing from them. I couldn’t really pinpoint when it had happened; you don’t really notice these things at the time. Well, not if you’re not paying attention – which I guess is why it had happened.
As I thought things through I realised we’d been paying attention to the wrong people all along. It had started when we’d taken the message from the Techcrunch/Lifehacker/Hackernews crowd that the most important thing we had to do was enable global airline coverage. Not that we shouldn’t have been thinking about that; our community had been asking for months for us to improve our international coverage and to include full-service airlines.
But that was only one of several things they’d been asking for. Being so fixated with the huge task of enabling complete global coverage in one big hit, we’d been ignoring lots of other, far more achievable things, that would at least have shown our users and investors that we were making progress. But when things started going wrong, rather than calmly reassessing the situation and correcting back onto a more sensible path, we panicked and made a huge bet on something completely new and untested.
I realised it had been out of fear of letting down investors that we’d chosen to pursue the microsite idea, only to end up letting them down anyway. And I realised that in seeking the plaudits of the social media crowd, we’d made it impossible for the people who’d loved us and supported us from the early days to know what we stood for, or where we were going.
That night, an old friend was having his 30th birthday party. I had some Airbnb guests coming to stay in my bedroom, so before going to the party, I went home to make up the room and pack up my things. I’d be spending the next few nights in a single bed in my old bedroom at my parents’ place. As I filled the back of my car with what seemed like all my worldly possessions, I thought “I guess this is what it means to live out of your car.”
I went back to do a final tidy-up and check for any important items or valuables. I noticed my passport on the bookshelf, thought perhaps it was safer to have it with me rather than leave it with strangers, so I picked it up and tossed it into my laptop bag before heading off to the party.
The party was fun and I was in good spirits, given how uncertain our business situation seemed to be. My friends were always interested in how things were progressing with Adioso, and I was frank about our troubles whilst still maintaining an upbeat stoicism. “We’ll get through it” I assured them, and myself. “We always have before”.
As the night drew to a close, I offered my friend Keir a lift home. We said our goodbyes to the others, and walked up the street to the car. As Keir walked around to the passenger side of the car, he stopped abruptly, pointed at the rear window and said “did you know about this?”.
As I walked around to inspect, my heart sank as I predicted what I was about to find. Sure enough, the window was smashed, with broken glass covering the back seat. Only one thing had been taken: my laptop bag, containing my 12-month-old Macbook Pro and my passport.
As we drove back to Richmond, the late-night chill of the descending winter billowing through hole that was once my rear window, I dwelt on the perversity of it all. Normally I’d never leave my computer in the car unattended. It was only there because I was staying at my parents’ place. And I was only staying at my parents’ place because I was broke. Too broke to have any ability to buy a new computer.
Rather than going straight to my parents’ place, I decided I needed to head back to my home to think things through. When I got there I was relieved to find Cris still up. “You wouldn’t believe what happened”, I said. “My computer was just stolen out of my car.”
“Oh dude.” He jumped up and gave me a long, consoling hug. Then he turned around and pointed at the old black plastic Macbook that he’d been using as his music machine. “This” he said. “I don’t need it, it’s all yours, give me half an hour to move stuff off it and you can have it.”
I went into the living room and collapsed on the couch, staring at the ceiling for a few minutes. It was almost 16 months since I’d last had a sip of alcohol, and only a couple of weeks less than that since I’d last craved one. But right now, the temptation to pour myself a Scotch was becoming pretty powerful. I opted instead to hunt through my media server for something to take my mind off things. “Curb Your Enthusiasm” seemed to fit the bill.
Without being much of a superstitious guy, it was hard to escape the feeling that the universe was trying to send me a message. I’d spent the past six months trying to bluff my way to the appearance of business success, but I’d been found out. Until I’d learned my lesson, I couldn’t travel overseas, and I couldn’t have nice new things. And the tool I’d have to use to try and work my way back was a 32-bit plastic Macbook made in 2006.
And so, three days after the theft of my Macbook and my passport, as Jenni summed up the past eight months of my life in one swift blow with the marketing jargon-term “off-brand”, I felt I finally had to acknowledge where we’d gone wrong. We’d stopped paying attention to the people who mattered most, and as a result we’d nearly sunk the company. The only way back was to stop pulling stupid stunts and to start listening.
Photo by Hannah Koelmeyer
I’m publishing this series as an eBook via Leanpub.