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I never expected to be an entrepreneur. My first business, the mobile user interface (UI) company The Astonishing Tribe (TAT), was set up by six friends who wanted to work with something we loved and learn from our own mistakes rather than from others’. I am not even sure that it actually felt like a startup. TAT became a completely unexpected giant success both personally and financially (the business was bought by Blackberry for $150 million).

When I started my second business, I wanted more than financial success; it had to mean something to me. I believe that an entrepreneur’s true purpose is to try, learn, and experiment rather than follow more conventional ways of achieving success. Therefore, there is more room for failure, which is ...

One of the challenges we've been tackling internally at Startups.com, and I'd imagine lots of other startups, is breaking down how we communicate in a diverse workforce. We feel that diversity shouldn't just be about hiring, it should be about understanding.

In fact, it stands to reason that the more diverse our workforce becomes, the less implicit understanding we will have amongst ourselves. Our backgrounds will become so different that what we say and how we respond will have less and less common ground.

I wanted to share one step we're taking to address this challenge in hopes that others will share their experiences too (by the way, the "reply" button on these goes directly to me, the Founder). One of our focus areas has been creating ...

Most of us Founders have never raised capital, so when we dig in for the first time, we're mostly guessing at how the game is played. And friends — it is indeed a game. The problem with this game is that as Founders, the odds are stacked way against us.

We actually make matters worse when we don't understand the rules, and instead revert back to our base instincts, which range from carpet bombing the investor with follow-ups to trying to translate "I think it's interesting" into 50 potential meanings, like a 16-year-old after their first date.

What we need is to be able to read the signals for what they are, and when we do, take our foot off the pedal if the signal says "stop" and jam the pedal when the signal is "yes."

Anything that's not ...

Investors — As Founders we love you, need you and appreciate you. But the relationship feels very one-sided when we're pitching for capital. As Founders, we just need a better way to communicate not only the evil word "NO", but the equally evil word "Maybe." "Yes!" we seem to have figured out.

All we're asking for here is to be treated with respect and dignity. We don't need to be coddled, we just need a clear "No" when the time is right and ideally some basic kindness along the way. It doesn't take much, but we could really use some shifts in how we communicate these days.

Don't be a Dick

I've met with and pitched hundreds of investors. If there's one thing that I could never figure out, it's why so many act like raging dicks. Not all of t...

I sent the following letter to our entire team at Airbnb.

Hey team,

Our next team meeting is dedicated to Core Values, which are essential to building our culture. It occurred to me that before this meeting, I should write you a short letter on why culture is so important to Joe, Nate, and me.

After we closed our Series C with Peter Thiel in 2012, we invited him to our office. This was late last year, and we were in the Berlin room showing him various metrics. Midway through the conversation, I asked him what was the single most important piece of advice he had for us.

He replied, “Don’t fuck up the culture.”

This wasn’t what we were expecting from someone who just gave us $150 million. I asked him to elaborate on this. He said one of the r...

When entrepreneurs are successful, we are enormously interested in what made them become entrepreneurs. It’s as if their main achievement is the decision to say goodbye to the secure and safe life — the sure job, the safe pay, and the good CV. While the choice of taking the plunge is definitely a precondition for success, it is quite far from being the primary achievement. The difficult part is not becoming an entrepreneur but remaining one when things look hopeless and everyone around you has lost faith. We love stories about how two 15-year-old kids in a basement have a good idea, get a breakthrough on the first day, and become a global success a year later. In reality, however, building a business and generating real value takes time. It...

At Startups.com, we built an 8-figure business by saying "no" — a lot.

We knew going in that if we’re going to have 100% control of our destiny now and in the future, that would only work if we could constantly say "no" in a disciplined manner.

But you know what? Saying "no" sucks. Just like saying "no" to delicious glazed donuts sucks. We know that we want them, but we also know the cost of saying "yes"! Now I'm hungry for a glazed donut. See what I mean? We knew that controlling our destiny would mean an insane amount of discipline, across the entire organization. In order to prepare ourselves for this discipline, like any good regimen, there were a few things that we'd have to stay incredibly focused on.

We had to be OK with things takin...

In 2008, the world got a new music streaming service named Spotify. It was developed in Stockholm, Sweden, and provided digital rights management-protected content from record labels and media companies. It may have started out as a local thing, but the freemium service quickly expanded. Today, Spotify has more than 140 million monthly active users and over 50 million paying subscribers.

I had the pleasure of meeting up with Andreas Ehn, who was Spotify’s first employee and CTO. Andreas was responsible for the product and platform architecture as well as hiring a world-class engineering team, of which many have gone on to become successful entrepreneurs on their own.

After Spotify, Andreas founded Wrapp — a mobile online-to-offline customer...

Our Founder careers aren't defined by the size of our positive outcomes, they are defined by whether we've had one at all.

Therefore, if our outcomes are so important to us, shouldn't we first start with optimizing for the most likely outcome that will be meaningful to us? Is our idea more likely to become a $3 million business earning $1 million in profit or a $100 million business that could go IPO?

We need to start our journey, which implies an insane amount of tough decisions, aligning our path with outcomes that will not only be meaningful but those that we have the highest probability to achieve.

Optimizing for a Billion Dollars is Silly

To be fair, the "It has to be a billion dollars" is a mantra directly driven from the VC community...

“May you live in interesting times.”

 — Chinese proverb 

This (somewhat liberally translated) Chinese proverb is something you hear often in Silicon Valley these days. Some say it is a curse. Regardless, nobody denies its truth when it comes to the changing technology brings to our world.

Driven by the exponentially accelerating rate of technological progress we now have (literally) supercomputers in our pockets, can access the world’s information at our fingertips, can sequence genes in our kitchen labs, and 3D print prototypes on our desktops. Gordon Moore’s 50-year-old prediction that “the number of transistors in a dense integrated circuit doubles approximately every two years” (know commonly as Moore’s law) holds up to this day and h...