Here We Go

On October 29, 2018, after months of planning and preparation, Expedia Group’s communications team came alive. At 6AM pacific time, their press release hit the wire. Shortly thereafter, embargoed news outlets ran the story. One of the world’s largest travel companies announced to the world it had acquired two short term rental startups.

One of them was ours.

They had scheduled our day in fifteen minute increments. The legal team briefed us about what we could and couldn’t say. Expedia was, after all, a public company, subject to all sorts of regulations, and no one, especially us, wanted to mess this up.

We participated in a handful of interviews. We made personal calls to our most valuable customers. We sent emails to our users and posted notices on our website informing visitors of the news.

After months of keeping this huge secret, our phones lit up, and the congratulations poured in. Our family and friends expressed excitement and disbelief. Our thousands of new coworkers offered cheerful greetings and optimism. Our industry contacts delighted in a non-RealPage acquisition and displayed a curious fascination that Expedia Group, a huge new player, had entered the multifamily industry as a counterpunch to the much-maligned Airbnb. (More on that later).

Announcement day peaked with a third quarter earnings call during which the CEO of this multibillion dollar machine answered questions about what the acquisition meant for Expedia’s alternative accommodation ambitions.

And there we were. A tiny, eleven-person company named ApartmentJet. My cofounders and I had casually, and not without amusement, agreed to the name while drinking beer at Buffalo Wild Wings two years earlier. Now it pulsed in giant letters on the scrolling NASDAQ board in New York City’s Time Square. We became a Wall Street Journal headline. Chicago tech outlets cheered the news of big West Coast companies finding value in the midwestern startup community.

That day would prove to be the midpoint of the entire ApartmentJet saga. Eighteen months after product launch. Eighteen months before product shutdown. We had survived the odds. We had achieved an outcome most people only get to read about. We were determined to disprove the old adage that most acquisitions fail, but that didn’t make us unique. We had spent the previous month asking ourselves, “What happens next?” Was the hard part over? Or was it still to come? Several of us had been through acquisitions before. We knew no matter what an acquirer tells you during the process, you never really know what they have planned.

Over the course of the next few months, I plan to chronicle the adventure.

Having been part of half a dozen startups, I’m always drawn to tales of entrepreneurial success and failure. There’s such a fine line between the two. I find motivation in every story, even when the circumstances are different than my own, because the struggles are similar. Lack of capital. The need to convince others of your vision. The uncertain decision-making. The constant balancing on the edge of failure. I believe there’s something to be learned in every one of those stories. And while we may not have built the deep moat described in Jim McKelvey’s The Innovation Stack or the political intrigue of Nick Bilton’s Hatching Twitter, maybe there’s a nugget or two in our story that will prove motivational or instructional to anyone struggling through the startup grind.

Four years in startup life is like twenty in normal life. All day every day, your thoughts center around one goal. Sometimes those thoughts are unproductive worries that keep you awake at night. Sometimes that goal is, to borrow a word from compatriot Dan Palumbo, ephemeral. You make good decisions and bad, and you must objectively review them if you hope to learn anything.

Books and articles talk about how much effort goes into starting a company or building a business, which can lead to the idea that hard work will overcome all difficulties. But the greatest challenges are not the hours you put in physically. The true antagonist is your own mind. The worries. The educated guesses. The whims. The hopes. The work life balance. The onslaught of new problems, the euphoria of surmounting them, and the disappointment of not. Outcomes are never as certain as they seem in retrospect. Therefore, it’s difficult to effectively convey the emotions of any struggle when recounting it years later. Hopefully I can do this one justice.

My plan here is to offer a high level summary of events. I had originally intended to conduct interviews and include perspectives from many of the people involved. Instead, for various reasons, I decided to tell the story as I experienced it, right here on my blog, which means all mistakes or misrepresentations are mine alone. It’s my own therapeutic exercise. A retrospective analysis.

Startup life is a whirlwind of contradictions. Depleted creativity, soaring inspiration, exhaustion, opportunity, despair, elation, purpose, aimlessness, and, we must never forget, the stomach-knotting need to make payroll to avoid destroying the lives of people who depend on you.

Amid so many emotions, hard work becomes the escape, not the challenge.

This is the story of all that hard work, all that fear, all that excitement. It’s an abridged Rise and Fall of ApartmentJet told in five parts. I plan to break each part into multiple posts, with a new entry every week or two.

Part one dives into how it all began, from concept to product launch. Part two discusses funding, growth, and constant peril. Part 3 covers the build-up to acquisition. Part 4 recounts the difficulties of integrating our little startup into a massive company undergoing its own integration struggles. And in Part 5, we enter the year 2020. I shall say no more about 2020 for now, knowing the year itself effortlessly conveys an abundance of ominous foreshadowing.

So thanks for hopping on this rollercoaster. Hope you enjoy the ride.

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