My First Day at Sonder

Tuesday was my last day at Uber. Wednesday was my first day at Sonder.

In just a dozen or so hours, my life took a drastic turn towards a new direction. And so began my next big adventure; a new chapter of growth and learning.

My first day at Sonder was unlike any other, and as the day progressed it became increasingly clear that I’d made the right choice. From the very start, I was drinking from the firehose, barely able to keep up, and loving every minute of it. When the day ended, I felt invigorated by the influx of new information. On the train ride home, my mind raced and I couldn’t stop thinking about my experience.

Reflecting back, my first impressions of Sonder were:

1. The business is incredibly complex.
2. Process and automation is a key part of their DNA.
3. They made me feel extraordinarily welcome.
4. Sonder is going to be huge.

Meanwhile, my phone had been blowing up all day with messages from friends and folks on LinkedIn about my next move. Catching up on all the threads, I found they centered around a few questions:

1. No break after 4 years of Uber? Are you f***ing crazy?
2. What the heck is Sonder?
3. Why Sonder?
4. Can I join you? :-)

Let me unpack all of this.

Are you crazy?

The short answer is, well, yeah, it’d be fair to call me crazy.

I don’t think you can do truly big things unless you’re, at a minimum, a little crazy; ideally, you’re a lot crazy. Startups are really hard, and the vast majority don’t know what they’re getting into. Being overly reasonable might make you hesitate just enough when it counts and let that multi-billion-dollar opportunity slip through your fingers.

Of course, I didn’t forego some well-deserved R&R simply to prove that I’m crazy. Once I discovered Sonder and realized its enormous opportunity and incredible challenges, I simply couldn’t wait. I had to dive in head first.

After I gave notice, my manager replied, “Wow. Why not take a break?” I joked with him, “I don’t need a vacation. I need inspiration.”

As soon as I finished saying it, however, I realized it was actually true. It wasn’t a joke at all. Uber is a revolutionary company with plenty of upside remaining, but I think things got far too comfortable for me. Sonder was the inspiration I needed to step way out of my comfort zone. I had to jump, and there wasn’t a moment to spare.

What is Sonder?

My pitch is still being refined as I’m brand new to this, so bear with me for a bit. Here goes my attempt to put it as succinctly as possible without losing the color.

Sonder is reinventing hospitality. Your stay should be magical and unforgettable. You should feel intimately connected to the city; as if you’ve lived there your entire life. Anything you need is just a few taps away and delivered instantly. All at an amazing price.

Every inch of the space should be beautifully crafted by professional interior designers. It should capture the character of the city, yet remain functional and flexible, especially if the little ones are in tow.

There is no check-in. Step out of your Uber, let the smart lock open the door, and walk in as if it was your own home. There’s high-speed wireless and your phone connects automatically. The full kitchen is sparkling and the bath is stocked like a spa, but you’re ready to sink into the award-winning Sonder mattress to have the sleep of your life.

And this shouldn’t be limited to vacations only. Arrange a long-term stay for that summer internship or big project that just came up; we’ll make sure housekeeping takes care of you. In fact, you can say goodbye to apartment life entirely if you want and hop from Sonder to Sonder as you please; your bags will be packed and delivered for free.

This is Sonder’s grand vision. Far from room sharing. Light years ahead of hotels. It’s hospitality, highly evolved. A new way of living.

We have a huge vision and it’ll take a lot of work to get there. We’ve already made tremendous progress. See for yourself here.

Why Sonder?

Believe it or not, I had no intentions of leaving Uber. In fact, I was planning to take advantage of the sabbatical policy and go on a months-long bike tour in Japan this summer. And if I’d stayed, I certainly would’ve enjoyed a good chunk of change once perf closed out in March; not to mention an impending IPO and a whole lot of equity left on the table.

Sonder fell on my plate by pure chance. The recruiter action was particularly hot around November. Likely coinciding with my nearing the 4-year mark, and of course the ever mounting press barrage on Uber. Even though I rarely reply to recruiters, I somehow got it in my head that I should “practice just in case.” So, I decided to reply to one message. Then another. And another. Until shit got real and I had a dozen companies wanting me to come on-site.

Let’s jump straight to why I accepted. I’ll save the topic of interviews for a later post. Suffice it to say, I’m an eager student of the art of interviewing.

It may seem like I made a rash decision to jump, but in actuality, I had very specific criteria in mind. The company that would pull me from Uber would have to meet a very high bar.

1. Consumer-facing — Being able to talk about what you do and having it resonate with ordinary people (i.e. those outside the Valley) is truly rewarding. Uber in the early years was like this and it felt wonderful. I remember one plane ride where the man sitting next to me got so excited to learn I worked at Uber he wanted to take a selfie with me. And when the flight attendant found out, she brought us a free round of cocktails.
2. Strong product-market fit — There’s nothing more frustrating than having no users or customers. It can be extremely demoralizing, and every day becomes a grind. When you do have product-market fit, it’s night and day. You have a clear line of sight to success and it’s just a matter of working your ass off. I have enormous respect for startups who’ve crossed this chasm and love helping them grow.
3. Huge opportunity — Any company that isn’t going big, or thinks too narrowly, will quickly lose my interest. Hotels are $550B globally. Corporate housing adds $3.2B in the US alone, so let’s say $10B globally for all furnished apartments. If hospitality and living (home ownership) are truly redefined, then the opportunity becomes massive and we grow the pie as Uber did with transportation.
4. Physical and hard to scale — At Uber, I got hooked on the complexity of the physical domain. It takes a whole lot of creativity and hustle to succeed here, and it’s incredibly challenging, which is why it’s so fun. With the proliferation of infra-as-a-service and competing cloud platforms driving innovation up and prices down, achieving technical scale is not nearly as hard as it used to be. Bridging the physical and digital world in order to improve peoples’ lives; now that’s really hard. A million things can go wrong from the moment you open Uber to request a ride to the moment you’re dropped off at your destination. And people always overlook international; it gets dramatically more complex in terms of payments, regulations, fraud, safety, labor, culture, and, most critically, physical infrastructure. Uber created the magical ride — globally — now Sonder must create the magical stay.
5. High cash flow business — Honestly, I’m tired of working at companies that don’t make money. I spent a lot of time there, and I’ve decided it’s simply not for me. I don’t like the idea that my customers are the product (to advertisers). I do, however, like the idea of my customers finding so much value in my product that they part with their money many times over to use it. That opens up so many possibilities and interesting challenges.
6. Small (<500) but growing rapidly — I’m not a very good politician, so I’m useless at 15,000+. Cutting off at 500 is largely arbitrary, but is based on my experience at Uber (I was employee #529). My biggest wins and happiest times came well before 5,000, so I figured getting in right before 500 would be even better. But size isn’t the only thing that matters; the business needs to be growing, ideally experiencing hypergrowth. I love growing teams; that’s my sweet spot.
7. I won’t be “the old guy” — Two important things: 1) my family and 2) diversity. The truth is, I’m not the only one joining this company and taking on risk; my family will also be dragged along. They’ll be rooting for me, supporting me when I’m down, and also dealing with any hardships the company faces. I’m extremely fortunate to have a family who stands this firmly by my side, and any company I join will have 110% of me because of that. Travis Kalanick may have asked us for the impossible on a daily basis, but he always recognized the people at home who supported us. Knowing there are people from different stages of life tells me a company values experience and diversity, and they should have the requisite open-mindedness and empathy to build a truly amazing company.

To my amazement, Sonder checked every single one of my boxes, with flying colors. I don’t know many companies today that can (if you do, please share).

As you can see, Sonder stood out among the lot, and I’m thrilled to be part of this great company.

How is Sonder different?

As I mentioned before, the business is incredibly complex. “Airbnb clone” was my first thought upon hearing about Sonder, but in actuality, they’re nothing alike. That first day opened my eyes as we visited the teams on the ground and got to see how the sausage was made.

Airbnb is a platform. Guests can peruse rooms or entire units for their next vacation. Hosts are (mostly) regular people looking to make a few extra bucks. It’s hit or miss on amenities and service, so much so they even have different classes of hosts. You’re taxed 6–12% for the privilege of using this platform.

Sonder is not a platform. It does not do room shares; if you want to stay in someone’s spare room in an RV in the middle of nowhere, you should definitely use Airbnb. Sonder gives you your own private space and is focused on quality and reliability of experience. You will always get 4-star units with 4-star service.

Sonder is not a platform, and it doesn’t want to be. It’s the “host” (or rather “superhost” given the quality) and owns the experience end-to-end. Let me draw an analogy to explain the challenge.

Imagine you’re a host on Airbnb, and you list an entire apartment. You handle inquiries and bookings yourself; you clean and stock it yourself; you’re a one-woman show. Things are going well, so you decide to list a second unit. You’re stretched a bit, but since it’s only two units you manage OK. You scrounge furniture and such to stock this second unit; you ask friends to help you with cleaning and miscellaneous things.

This works, and you could add a 3rd or 4th unit. Theoretically, you could expand much bigger and still be profitable. The problem is, you can’t possibly manage that. What if you wanted to scale up to 100 units? 1,000 units? Heck, make it 1,000,000. It would take a massive army and a fuckton of money. But that’s not even the hard part. How would you even get a million beds, dining tables, towel sets, etc into these units, assembled, and arranged to be even modestly hospitable? The logistics are mind-bogglingly complex; and while you’re trying to figure it out, you’re bleeding $100M every day those units are vacant. Yet, you haven’t even gotten to cleaning, maintenance, and support, the gnarliest parts.

You’d be right if you said this sounds essentially like running a hotel (a massive and distributed one at that). Sonder’s operations do look very similar. But you’re thinking, What makes you think you will win?

1. Best of both worlds — Sonder combines the best of hotels (consistency, reliability, service, amenities, location) with the best of Airbnb (local, unique, homes, tech). It’ll be very risky and difficult for hotels to morph into Airbnbs. It’s been 9 years since their founding and hotels have not evolved. Likewise, it’ll be very risky and difficult for Airbnb to switch from being a platform to being a host itself. Airbnb is simply not an operational company.
2. Tech-ingrained DNA — Hotels aren’t in the software business. They stitch together various off-the-shelf software, which they pay dearly for. Tech will eat everything, and Sonder is a tech company at heart. Every employee — from operations to recruiting to human resources — live and breathe technology. To double down on tech, the entire company was recently moved internationally to San Francisco, where we will accelerate the engineering team’s growth.
3. Innovation — Despite the surge of technical innovation in the physical space, hotels have not changed much if at all. This industry is ripe for innovation. The way people travel and experience the world is changing. We all have smartphones and use them for everything. We expect things to be magical and we want low prices. What if Sonder did to hotels what Amazon did to retail?

Great, can I join?

Absolutely. Sonder is growing rapidly and is hiring across the board. Let me help you land your dream job at this amazing company, just like I did.

Here’s how:

1. Check out our jobs posted here.
2. Connect with me and leave a note including 1) which role you’re interested in and 2) your email. If we’re already connected, just send me a message.
3. Like this article and share it with others interested in hot startups.

For the engineers out there, I invite you to join me on the ground floor of the next big thing.

Together we’re going to tackle complex problems across logistics, supply chain, data science, and machine learning; all in the name of transforming hospitality. At times, I’m going to ask you to jump into unknown territory or take on highly nebulous projects, but I promise I will be here to support and empower you. You will be continually challenged and given the autonomy you need to learn and grow.

On your first day, the team and I will give you a warm welcome and make sure you feel a strong sense of belonging. I will make sure you have access to mentorship, including from those in my personal network, to help you along your path. And whatever you need, I will be there for you.

If this sounds like a place you’d like to work at, let’s connect!