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Founders ask the big questions for our startups. Customer service answers them.

In nearly every startup I've ever built, I've always stayed incredibly close to our customers. In fact, if you're reading this via our email list, which goes out to over 250,000 Founders like you every week, you'll notice that's my name on the reply button. That's actually me. If you're one of the brave souls who have attempted to contact what you were probably assuming was a bot or some customer service queue, you were probably surprised to get a message from me instead.

We've got over 200 people, a team of marketers, a team of customer support folks, and an insane amount of infrastructure. I also own a personal assistant business in Zirtual.com — so why am I a...

Growing up broke was one of the most valuable assets to shape me as a startup Founder. At the time it didn't feel too valuable (it sucked) but I'd come to learn later that it burned specific traits into my behavior that served me insanely well in building startups from scratch.

Many of us have had the same challenges, coming from disadvantaged upbringings that felt like a setback at the time but also became crucibles of learning and adaptation that actually made us far more capable when our skills were put to the test later on.

We're Forced to Become Experts

When we're broke, we can't afford to pay anyone to do anything. Plumbing breaks? We become a plumber. Car won't start? We become a mechanic. We just don't have a choice, so it forces us...

Startups.com marketing technology stack

What is a Martech Stack?

First up, what even is Martech? This is an abbreviation of “marketing technology.” It’s the tools and software you use in your day-to-day sales and marketing.

The reference to the “stack” has been used by developers for years, in reference to the technology and codebases they use within the products they build. Martech Stack references the marketing technologies and tools you use within your marketing infrastructure set-up.

By stacking these tools together and integrating them you create a consistent, automated flow of data between your tools.

The benefits of setting up a Martech Stack

The likelihood is that you already have some form of Martech Stack in place, even without...

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...