Maverick Traveler

Location Independence, Geo Arbitrage, Individual Freedom

Business Lessons From Silicon Valley’s Most Disruptive Companies

Last week I sat down and read The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, which chronicles the rise of Uber and Airbnb from simple ideas to multibillion-dollar businesses. These companies are widely credited with ushering the era of the new sharing economy and were also one of the first companies to be called “unicorns” (a startup that’s worth more than $1 billion).

I had two reasons for reading this book. First, I wanted to understand how these companies came about, learn about their challenges, and understand how they overcame them to become who they are today. After all, these weren’t just regular businesses. Their business models were designed from the ground up to disrupt well-entrenched (and well-funded) incumbents.

The second reason was more personal. As someone who spent a decade living and working in Silicon Valley, I wanted to reacquaint myself with the part of my life where I came to work at 9 in the morning and sometimes didn’t leave until 11 in the evening, stumbling towards the exit while doing my best to avoid stepping on an array of empty pizza boxes laying on the floor. It was a fun flashback to a time in my life that I don’t particularly want to repeat.

Here are some lessons learned:

Create something that people want

There are lots of reasons why companies fail: poor execution, poor work ethic, run out of money, lack of experience, lack of mental toughness to persevere, poor partner fit, etc. While all of those can be responsible for the company failing, I think the number one reason that companies fail is much, much simpler: they create a product that nobody wants or needs.

This is precisely why Uber and Airbnb had such massive success. Airbnb was born because there weren’t any rooms available for the  2008 Presidential convention. Uber was born because some guy had trouble hailing taxis in San Francisco.

The main take away is that, while the solution you’re developing doesn’t need to be super disruptive or global in scope, you must be able to carve out yourself a little niche that nobody else is doing or not doing well enough. Even if you decide to do a YouTube video or write a blog post, it needs to provide value in a way that isn’t currently being done. This is called having a unique value proposition. Regardless what you call it, you must make me care in some way or form.

Make it so good that people tell others about it

Marketing creates demand for a product or service. There are lots of ways of doing it. One way is to give out flyers on the street. Another way is creating ads on platforms such as Facebook or Google. Nevertheless, one of the best ways is when a product is so good that it advertises itself fairly old school: word of mouth. If I’m using a product that delights me, I will surely tell others about it.

One of the main things that these companies got right is that people enjoy using them so much that they recommend them to others. In this way, everyone acts as an ambassador for a product’s brand. I’ve personally used both services extensively in Eastern Europe and Asia, and have never hesitated to recommend them to others.

The main takeaway is that you want to make something so delightful or interesting that others never hesitate to recommend it to others. It doesn’t only apply to products and services. It can be as simple as a blog article you write or a YouTube video you record. Make an impact in people’s lives and they’ll have no choice but to react one way or another.

Obsession is good

One of the interesting parts of the book is when one of the co-founders, and the future CEO, Travis Kalanick, finally understood that Uber has massive potential. Before that, he was juggling several projects that included advising and investing in other companies. As soon as he realized that Uber might be a massive company one day, he dropped everything else and focused on the business with unparalleled tenacity. He became obsessed with the company.

I had similar experiences. Long ago, I used to think that going from a 9-5 employee to an entrepreneur was as seamless as changing the sneakers you wear or enrolling in a different Yoga school. I was wrong. Actually, becoming your own boss is one of the greatest mind-shifts you can experience. Few things can top it.

Being surrounded by other entrepreneurs helped cement this new mentality. One of my friends whom I’ve known for many years now runs a super successful business. When we meet for lunch, the only thing on his mind is business and not much else. I have no doubt the only things he thinks about are improving and scaling the business. Another old friend, who’s now a doctor with his own private practice in Manhattan, wakes up every day at 4:30 am and begins planning his day. He usually doesn’t leave his office before 8 pm. One thing is for sure, unlike being a regular employee, where you’re free to do anything you want after 5pm, running your own business means constantly brainstorming of ways to grow and improve it.

The main takeaway is that, while you can’t control many variables like whether you succeed or fail, you can control things like your own discipline and work ethic. Then, if you fail, you’ll at least know it wasn’t for lack of effort. Otherwise, you’ll spend the rest of your life wondering if the only thing that stood in the way of success was being more disciplined.

Business can be war

This is my favorite part of the book. It’s also one of the most controversial aspects of both these companies, perhaps more so of Uber than Airbnb. Both companies were controversial from the start because they brought heavily regulated services directly to the people. In the process, they upended entire industries that existed for a long time. Many have said these industries were long ripe for disruption. I definitely agree.

While Airbnb was more flexible with the authorities, Uber was more combative. Its CEO famously declared early on that, “traditional taxi companies are the real enemy.” While that may sound belligerent and even unethical, you really have to read the book to understand that they had no other choice. In most cities around the world, taxi companies have tight relationships with city authorities and the number of taxis on the streets is kept artificially low in order to ensure high demand and high prices. In fact, Uber wasn’t even the first company to introduce ride-sharing, where you hail a private car that isn’t registered with the city authorities (i.e., UberX vs. Yellow Cab). The other ride-sharing companies that decided to play nice with the taxi mafias quickly discovered how futile it was and thus no longer exist today.

Long ago, I reached the conclusion that you can’t do anything meaningful if you’re not controversial. Controversy is polarizing. Polarization sets you apart from everyone else. If you don’t make a real difference in people’s lives, then what you’re doing probably doesn’t matter much. That’s especially true in a crowded market that, thanks to the Internet, enables people to build a company in days instead of months and transforms every individual on the face of this planet to a personal brand who are vying for limited attention.

The main takeaway here is that business can be war, at least in the beginning while you’re establishing a beach head, so you must be ready to fight if you want to be noticed and recognized. That doesn’t mean you must be unethical and hateful; there are many ways to structure your message in such ways that you’re being exposed to a huge audience and not hated by the entire planet.

Closing thoughts

As a permanent traveler, I’m probably exposed to Airbnb and Uber more than most people. I’ve used Airbnb in over 20 countries and Uber everywhere its available (I also used Lyft in America). These services have improved traveling tremendously. Although I’ve never had trouble booking accommodations in foreign countries, it was always a hassle to take a taxi from the airport. Most taxis in third world countries are overpriced and unreliable. Uber (and other ride-sharing companies) fixed this. Now, I can easily get on a plane, land, request an Uber, and get to my Airbnb without any hassles. Even ten years ago this wasn’t possible.

Whether you hate it or love it, these services and the sharing economy are here to stay. Despite the controversy, rolling back these services are as practical as eliminating the Internet. In fact, this is merely the beginning of a new era where more of our time and space will be packaged and monetized for use by others. It’s given rise to lots of new opportunities.

Although I don’t plan on starting a multi-billion startup anytime soon, the lessons learned from understanding the rise of these companies are no less applicable to starting any kind of business, whether it will be a $100 billion startup or a location-independent business that’ll generate several thousand dollars per month while letting you live anywhere in the world. Freedom is cheaper and more attainable than you think.


  1. A true guide from real trenches.

    Normal people get only average results.

  2. Another fun observation:

    “…Create something that people want…”

    Recently, I had a discussion with my older brother who works in IT sector. Funny thing, we both came to the same conclusion. If Mark Zuckerberg offered to sell me for 50$ the rights for facebook code before launching it, I would tell him: “50 bucks? Are you nuts?
    We finally have a way to say whatever we want to anyone anonymously. Why on earth would anyone wanted to use Fb?”

    Even bigger surprise for me (and still is) the success of instagram.

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