The 10 Biggest Lessons From 10 Years of Endless

Endless is 10 years old. I still can't believe it. I crossed one side of the bridge in San Francisco, landed on the other side a decade later and lived to tell the tale.?

I posted a retrospective on the big day, but I want to go even deeper into our Endless history. I’m going to take the time to write it well, shipping a post every month for the next year.

There are many ways to live a good life and many ways to build a company. These are the lessons I’ve learned from my attempt to do that over the past decade.?

1) If you don't go, you'll never know

Ideas come to us in many ways. I'll talk about how I came up with my specific idea later, but in my case I knew that it was going to gnaw at me unless I got an answer as to why it wouldn’t work. Ultimately, it all came down to whether people in emerging markets wanted computers.?

In between my first and second years of business school, I got an offer for a dream internship. I wanted to take it, but I couldn’t stop thinking about my travels, the people I met, and how my idea could impact them. I knew there was only one way of knowing whether it was worth doing: get on a plane and meet my users. I couldn’t predict what people in emerging markets wanted while sitting in a room in Silicon Valley.?

I asked an advisor what to do: take the safe option or dive into what felt like a risky leap? His words were, if you don't go, you'll never know. That sentence changed my life. I printed the poem Ithaka, a gorgeous poem depicting the epic road to discovering one’s purpose, and set out to find mine.?

The person who took my dream internship at that eight-person startup called Thumbtack became their VP of Product. That company is now worth $3 Billion. But I would have chosen my path again and again. I found my purpose on that trip. It is one of the great blessings of my life.

If there isn’t an idea calling you, that’s okay. But if something is calling you and you’re intimidated, remember that if you don’t go, you’ll never know.?

2) The truth is in the field

There is a philosophy that permeates Stanford. Its premise is so simple: Speak to your users. Birth your products from understanding your users so well that they become the soil from which your company sprouts. I have interviewed thousands of people in our market through the years. That first summer, I traveled through six countries, 19 cities, and spoke with hundreds of people. When I started Endless, five of our first seven employees were hired to go into the field to do user research. We had a mantra: The truth is in the field. We called it Ground Truth. It was gospel.

I am still in love with Endless today because of how deeply I came to understand our market. I cannot give up because of the conviction that all of my time in the field has burnt into my brain. The big insights of Endless always came from talking to users. My advice? Spend time in the field. Read the Human Centered Design Toolkit. And come with more questions than answers.?

3) Exist for your users

There are a lot of motivations to start a company. I can only tell you what has worked for me. What we build changes lives. And has the potential to change millions of them. Our number one value is that we exist for our users. Many people talk about how “the customer is number one,” but at the end of the day those companies exist for their shareholders. Endless’ only reason to exist, from day one, has been to change the lives of our users. It’s the reason I founded Endless. If my goal were to exist for shareholders, I would have given up long ago.?

4) Impossible is not always impossible

I have been told that so many things would be impossible. They weren't. In future posts, I'll describe why we built an entire desktop operating system to go head to head with Windows. When I set out to do that, I sought the advice of many people. One was a prominent venture capitalist. He was intrigued by the spark in my eye, so he invited me to his home for advice. He told me that it would be impossible to build a desktop operating system. When I pushed back, insisting that others had done it, he walked me to his driveway and asked me to leave. We now have that operating system and one of the best Linux teams in the world running it.?

When I met with the world’s best Linux contracting firm, I told them that I was going to need to ship Endless OS on the laptops of the big PC manufacturers. Their CTO took me into a room, separate from my team. He spent 2 hours talking me through a 300-line spreadsheet, telling me all of the things that I would need to do and how it would be practically impossible. I was also told it would be impossible to make a desktop OS run on ARM processors, the type of processor that powers smartphones. When manufacturers wouldn’t ship our operating system on their computers, we had to build hardware ourselves and many people told me that we couldn’t do it.

In each of these cases, I knew that these were things that were technically possible. Challenging? Yes. Expensive? Much more than I had anticipated. But all possible.

That CTO now runs Endless OS. Together, we built our own ARM-based computers. It was the cheapest production computer in the world. We’ve had our operating system ship on millions more laptops with four of five largest PC manufacturers in the world. We went from a leading VC telling us that we would never be able to make an operating system to being one of the most influential organizations in the Linux desktop community. It was all possible.

People will tell you that many things are impossible. When they do, question whether it really is impossible, or if it’s just difficult. And if it's the latter, ask yourself whether the challenge of doing it is greater than the stakes of not doing it. For me, it is clear. Having spent so much time so close to users, I know the most important thing: our users need it. It is like a maze: just because we haven’t found the end doesn’t mean there isn’t a way out. There is a way. We’ll find it.

5) The idea you start with probably won’t be the idea you succeed with

We started with a profound conviction that smartphones could be plugged into TVs to make them full PCs, effectively making computers free for anyone with a smartphone. Ultimately, our conviction was driven by our perceptions of the core need. But what we do today has nothing to do with smartphones. Researching that idea - engaging with users - turned into discoveries of real solutions. The insights in the Endless Vision - games can teach the skills which power 21st Century jobs, device cost is best solved with a top up financing mechanism, and the internet access gap can be addressed by harnessing storage - were all discovered on the journey.?

Harvard Business school’s top entrepreneurship professor says that of the 2,000 business plans he’s witnessed become companies, only five percent followed their original business plan. This is freeing. It means that you don't need to know everything at the start. Just get started.?

6) Cocooning and Traveling

Our VP of engineering used to tell me that the best engineers he ever worked with went through a chapter of cocooning. They would hole up for a period in which their whole world was coding. They lived, breathed, and dreamed it. I look back now and realize that I was cocooning as well.?

For years, the only thing I thought about was Endless. This time wasn't spent in one room. In fact, it was spent traveling hundreds of days a year, following the vast web of connection points around the world that it took to connect people in emerging markets to the power of technology. I was incapable of talking about anything other than Endless. That obsession gave me so much. It gave me the insights that power what we do today. It built our incredible team. It allowed us to run through walls. It has also stamped some of my most formative lessons into my brain.

Looking back, those travels were also magical. The places and experiences I had, the whole journey, was magic to me. I was living life on its frontier, in the dusty fields of India, dancing Carnaval in Rio, getting drunk beneath a flickering lightbulb with factory workers in China. If I could design a happy, fully-lived life, it would include that. So many moments felt like I was smelling the perfumes of the ancient cities of Ithaka. There are chapters of life when it is possible to live so vigorously, cocooning in total immersion, and living life on the frontier. I got to do that and I feel blessed. Live yours.?

7) Move to Guatemala

One of my biggest regrets during this journey was that I didn't move to Guatemala. When our COO was reading Delivering Happiness by the founder of Zappos, she told me, “we need to move our entire company to Guatemala immediately.” She had read the part where the founder, Tony, realized that the company would live or die based on what happened in their fulfillment center, which was in Las Vegas. He moved the entire headquarters next door.?

Our small sales team was building channels in Guatemala. I would pop in there once a month and unblock whatever bottleneck was in place, but invariably another would appear. I’m still left wondering how things would be different if I had listened to her. We could have solved sales there.

Someone recently told me, “first time founders focus on product and second time founders focus on distribution.” I was 80% focused on the product. I knew that users loved it and I thought distribution would take care of itself. I wish I had put everything into distribution.

8) Build a team of shining stars

Two things powered the joy that I felt in those early years: the mission and a team that I loved.

I have so many fond memories. Of us being arm in arm in a huddle shouting “Endless!” Of the favela party that we threw for VCs. Of the vigorous debates. They were beyond talented, like superheroes, each one of them - one person had synesthesia and could literally smell code. Each person had a shining soul that drew him or her to Endless. This team was on a mission.?

I remember being at an offsite, putting up post-it notes of words that defined our culture. Someone put up a note with the word “DRAMA” with an X across it. “I’ve never seen a place without any drama.” Someone else described it as a unicorn of a culture.

Then things started to change. We grew. I was spending more time on the road, our teams were expanding, and it became a war of attrition, of persistence, of blending new hires with the original crew. With so much to do, we ended up making hires that didn't match the values of the team that had built our vision, and we thought we could paper over those cracks. With my attention spread so thinly, with offices and users across the world, those cracks turned to giant chasms overnight. The culture started to change, and people who I started this journey with, people who shaped the vision, started leaving. Drama became the core of our team. It was as if the DNA of the company totally changed overnight. It took years to rebuild that culture.?

Today I look back with so much gratitude for the team that we have and the team we have had. Thank you, all of you. You know who you are. We are alive today and we can change the lives of so many people in the future, thanks to you.?

9) The wick is only so long

God did I burn brightly. I felt so alive. Unstoppable. I was working 100-hour weeks and traveling 200 days a year. I remember the conviction, the feeling that if there were brick walls in the way, I would go through every single one, because there wasn’t a choice. And we barreled them down, one after the other. Year upon year. I felt I could go on forever. Until I couldn’t anymore.?

It turns out that the brighter you burn, the faster you burn out.

They say that being a CEO is a deeply lonely job. I would get home on the heels of some long trip and stare at the wall. It was utter emptiness. The stress and the loneliness were like acid burning my nervous system. Someone asked me why I used the word “fight” so much in a post I wrote. That’s what it felt like. I suited up in my armor each day, preparing for a fierce struggle.

I knew it could stop if I just let go. But I couldn't. There were (and still are) so many people who need the power of a computer to unlock their lives. I got through it with prayer, meditation, church, and meeting the users who reminded me of the difference we were making. It was a question of who would give up first: Me or the obstacles.

I am proud that I didn’t give up. It took years to restructure Endless to be sustainable. We went through rounds of layoffs. We restructured our capital structure. We changed our management. And when it was all in a good place, I eventually, finally, took a few months sabbatical to reset. I’ve built a new and more balanced life, with my ever-loving wife and my two radiant kids, with a morning routine of meditation, yoga, and journaling. Everything worthwhile comes with a fight. It was all a rite of passage for me to be ready. Now I feel prepared for the decade ahead.?

10) What got you here won't get you there

You will need to keep reinventing yourself. We seem to believe that we should just keep doing whatever got us here. It turns out that isn’t true. Every phase needs something different from us. There is a book whose title says it best: What got you here won’t get you there.?

That is true for us personally and for our organizations.

Endless isn’t the company that it was for most of its journey. Endless is now an umbrella brand. It encompasses a game studio that teaches kids to code and a digital access team that is trying to take everything inside of Endless OS and make it available on every platform. We are not limited to our own products. We want to manifest our vision of every kid as a creator in any way we can. So we also support others who are pursuing that same goal by investing in and donating to them.

Everything has changed: my leadership style, my lifestyle, our strategy, our products, our team. Everything has changed but the vision: the whole world, empowered. That we hold onto.

My Parting Wish

I write this as someone squarely in the middle of his journey. I am right here, between the starting line and the finish line. I’m asking myself what advice I want to keep close to my own heart.?

As I set out on my Endless summer, I printed that poem Ithaka and carried it with me. The poem is about getting to a fabled destination and its very first words are my parting advice. “As you set out for Ithaka, hope your road is a long one.”?

It has been ten years for us, with decades ahead. May we cherish the long road.?

Godspeed.

Ithaka

As you set out for Ithaka

hope your road is a long one,

full of adventure, full of discovery.

Laistrygonians, Cyclops,

angry Poseidon—don’t be afraid of them:

you’ll never find things like that on your way

as long as you keep your thoughts raised high,

as long as a rare excitement

stirs your spirit and your body.

Laistrygonians, Cyclops,

wild Poseidon—you won’t encounter them

unless you bring them along inside your soul,

unless your soul sets them up in front of you.

Hope your road is a long one.

May there be many summer mornings when,

with what pleasure, what joy,

you enter harbors you’re seeing for the first time;

may you stop at Phoenician trading stations

to buy fine things,

mother of pearl and coral, amber and ebony,

sensual perfume of every kind—

as many sensual perfumes as you can;

and may you visit many Egyptian cities

to learn and go on learning from their scholars.

Keep Ithaka always in your mind.

Arriving there is what you’re destined for.

But don’t hurry the journey at all.

Better if it lasts for years,

so you’re old by the time you reach the island,

wealthy with all you’ve gained on the way,

not expecting Ithaka to make you rich.

Ithaka gave you the marvelous journey.

Without her you wouldn't have set out.

She has nothing left to give you now.

And if you find her poor, Ithaka won’t have fooled you.

Wise as you will have become, so full of experience,

you’ll have understood by then what these Ithakas mean.