Why I joined HotelTonight
Last week I started a new role as a Marketing Manager at HotelTonight, a white-hot startup based in the heart of San Francisco. After some time apart from startups, I feel like I have been released back into my natural habitat.
Back in April, a blog post I wrote entitled Rate-of-learning: the most valuable startup compensation ignited the largest response of any post I’ve written, in part because it validated the rationale for joining startups and because it aligned with real experiences of those in the startup community.
The key takeaway? The single most important reason to work at a startup is not salary or stock options but the chance to learn at an incredibly fast rate and generate compounding interest on those learnings over time.
Ironically, I wrote this post nearly a year and half removed from working at a startup—the last one I’d worked for, ThisLife, was acquired by Shutterfly at the end of 2012. I hadn’t realized it at the time but the piece was one part love note to startups and another part subconscious resignation letter.
Launching a new brand at a public company with financial resources and massive distribution channels at your disposal is a dramatically different experience than hustling to drive growth on a shoestring startup budget. But part of what working at a non-startup taught me is why I love startups so much in the first place: their abhorrance of bureaucracy, their aversion to mediocrity and a direct connection with the customer that comes from having proved nothing and being paranoid about getting your ass kicked.
This is why startups are able to win despite having fewer resources—and why it was time for me to put my money where my mouth was and hunt down the kind high rate-of-learning role I had advocated others to do in my post. To grab a seat on a rocket ship and never look back.
Download HotelTonight here
After talking with startups of varying size and scale, I was and am most supercharged about HotelTonight. An emerging powerhouse in the on-demand economy, HT makes the hotel experience sexy by letting consumers book a room on their smartphone in 10 seconds or less. Hotels love HT because of its focus on last-minute hotel reservations (which don’t cannibalize future bookings) and consumers love it because they get great deals on amazing rooms—making spontaneous weekend trips or last minute accommodations a cinch. At the highest level, I think there is something magical about a company with an incredibly simple, customer-facing front-end that is powered by a sophisticated logistics engine on the backend to make the magic happen.
Throughout the interview process—an adventure in itself — HotelTonight had all the attributes of a company with escape velocity growth. Three in particular sealed the deal for me:
Every company talks about the importance of culture—but talk is cheap. Culture is when you have a two hour interview late on a Friday afternoon right before Outside Lands and everyone still looks excited to be at work. Culture is when employees meet up with you for drinks during their off-hours to help you prepare for your new role. Culture is when you have an open work-from-home/time-off policy and everyone comes into the office anyway to be part of the action.
Walking into the HotelTonight lobby, you immediately see the words Build. Question. Respect. emblazoned on the wall. Usually these types of mottos are pretty meaningless because either A) they don’t line up with reality or B) they are just a series of cliches that fail to differentiate your culture from any other. But these words popped off the wall and became real for me as I connected with the company.
The HotelTonight office bar. Every employee puts a bottle on the shelf. Mine is the Fireball.
Build means thateveryone in the company is a builder, no matter their role. No matter if you’re in marketing or finance (i.e. not an engineer)—you find your own way to build the company, improve the product and make customers happy. The builder mentality is contagious; once it’s got a hold of you, it’s hard to be a part of any company where builders are scarce.
Good questions are a way to make sure you are building the right things. Should I be spending my time on X? Should the team be spending their time on Y? Is there a better way to do Z? Questioning helps you identify the things that matter and eliminate the things that don’t.
Questions demonstrate respect not only for your coworkers who are joining you on the mission, but the customers and the partners you are there to serve. Fuse all three values together, and you have an organization that’s laser focused on building the right things well. Many companies attempt this, but fall short on one dimension or another, and only the rocket ships are able reach the outer limits of space.
HotelTonight CEO Sam Shank gave a talk at SXSW Las Vegas about design being the ultimate differentiator in mobile commerce. In a world where the marketplace has shifted from offline to online, and from web to mobile, the stakes for design have increased exponentially as thousands of square feet of retail space are sucked into the 1136 X 640 pixel screen of the smartphone. A halfway decent design may be tablestakes for launching any new business on mobile—but great versus not-so-great design is the differentiator that allows consumers to sort the winners from the losers quickly and decisively, using their thumbs and powerful pocket computers to vote yes or no on your company’s existence.
Great design, however, can only be born out of great cultures because design is not a commodity, but rather a value, cultivated and sustained over time. You can see the value of great design not just in the craftmanship of the product a company ships but in the place where that product is built. Pick any company with a beautiful app. What you’ll see when you walk into their office is a space where aesthetic matters, filled with people who care about getting the details right. HotelTonight is that kind of place.
Inside HotelTonight headquarters in San Francisco
Paul Graham talks about “building something people want,” which despite sounding simple is insanely hard to do. Most startups never get lift off in this respect; they push their product into the market, but the market is unmoved. Over the last few weeks, I’ve told a dozen people about HotelTonight and nearly all of them downloaded the app and several have either booked or will book a room soon. Getting people over the hump of installing the app was my anecdotal test for determining how much product-market fit the product has, and in this case the readings on my PMF meter were off the charts.
As a marketer, I’m only at my best when I’m delivering something people actually want. A lot of marketing is removing barriers that keep people from adopting a product worth loving. Sometimes you’ll hear talk about “growth hacking” as a vehicle for taking rocket ships to the moon, but it’s a fantasy if the underlying product isn’t solid because they eventually run out of gas. When you have true product-market fit, the market will pull value out of your company as fast as you can build it because they genuinely want more. And that is the only fuel you need for the trip.
We choose to go to the moon, not because it is easy, but because it is hard.
As a mobile-only company, taking the hospitality market by storm is no small undertaking. Competitors dump millions into acquiring customers on the web and many of these tactics don’t work with a mobile app. Despite these headwinds, HotelTonight is riding a gigantic, cresting wave because consumers are mobile. Like the Great One, Wayne Gretzky, HotelTonight is “skating to where the puck is going to be, not where it’s been”.
I believe the HotelTonight rocket ship will go to the moon, remake the hospitality industry, and become the number one most loved hotel app in the world—and I can’t wait to be a part of that journey. To the ThisLife team at Shutterfly, I have enjoyed working with all of you and am rooting for you to win. To the HT team, thanks for welcoming me aboard and making me feel at home already. And to everyone who is seeking out a high rate-of-learning, take the risk to find the rocket ship that will get you there, not because it is easy but because it is hard. And it matters. Because when you hop on a rocket ship, it becomes a launch pad for everything else you will ever do.
Special thanks to Tammy Han from First Round Capital for putting me in touch with HotelTonight and helping make this happen.
Want to get hooked up on HotelTonight? Use my code KYLET for a $25 credit towards your first booking. You can download the app here.