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ArticleHow We Built an 8-Figure Business by Saying “No”

How We Built an 8-Figure Business by Saying “No”

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...



ArticleLeadership From The Trenches

Leadership From The Trenches

Ben Horowitz recently published his book The Hard Things about Hard Things. It’s no exaggeration to say I love it. As a third-time founder having experienced many of the challenges firsthand, I wish that book had been written 15 years ago, when I was trying to build my first company (although I’m not sure I would have read it back then; learning seems to be easier in hindsight). One of the great things about Ben’s book is that it focuses on sharing the hard lessons when it’s not all smooth sailing.

Inspired by this, I thought I would add some of the lessons from Tradeshift. Just like Opsware, Tradeshift is a company in wartime, as are most B2B companies try- ing to break into highly entrenched software markets controlled by incumbents with ...



ArticleWe Want to be Safe, Not Just “Rich”

We Want to be Safe, Not Just “Rich”

How much money do we need to be rich?

It's an important question as Founders because our financial goals and appetite for risk are inextricably tied to the decisions we make in building our startups.

The problem with determining what "rich" is to us is that there's rarely a hard limit on how big that number can be. In some cases, we may even feel ashamed to state it out loud, for fear that we're either too high ("you jerk!") or too low ("slacker!").

The thing is — it doesn't matter. In most cases, we're really not talking about "being rich" as a goal, what we're really talking about is being "safe". We want to know that our bills will get paid, our loved ones will get taken care of, and if shit hits the fan (because eventually, it always do...



ArticleMusic for Everyone

Music for Everyone

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...



ArticleOptimize for the Probability of Outcomes, Not Size

Optimize for the Probability of Outcomes, Not Size

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...



ArticleMoney Doesn’t Define a Successful Startup

Money Doesn’t Define a Successful Startup

It's really hard to convince people that money isn't the most important metric of a startup's success. Especially if those people happen to be investors, in which case, it actually is the most important metric.

But what we're talking about, as always, is what's important to Founders, and by extension to the people that work within that startup.

The broken part of the startup narrative has become this — "If it's growing fast and making money, it's successful, no matter what other costs are incurred."

I'd like to just go crazy for a moment and offer a new narrative — "If it's making everyone's lives geometrically better, then it's successful, and hopefully that means it's making money."

Focus on Making Lives Better? What?!

I know, I know. W...



ArticleWhere was the entrepreneurial dinosaur when we needed him?

Where was the entrepreneurial dinosaur when we needed him?

When I’m listening to Naveen Jain describing his plan to create big business on the moon, it’s hard for me to grasp that he was once a poor child in India.

Today, Naveen is a billionaire and a very successful entrepreneur. His own recipe for success is, among other things, not knowing much and not being very good at anything. To me, that sounds like the opposite of what business life normally requires, yet Naveen isn’t joking, and his track record proves that he is not wrong either. After all, the young boy that grew up in poverty in India is today changing the world as we know it and has Sir Richard Branson and Google founder Larry Page as two of his good personal friends.

Jonathan: Naveen, I find it so inspiring that you have used entrepr...



ArticleWhy Our Founder Reputation Matters

Why Our Founder Reputation Matters

Long after our startup is done, no matter what the outcome, our Founder reputations will live on.

And for many of us, that could actually present a real problem.

Unlike our resumes, which present essentially one dimension of our lives (our job performance), our Founder Reputation is built on how our performance affects so many people — employees, investors, customers, the media, and even our personal relationships.

Founder Reputations are Easy to Tarnish

From the get-go, we have two huge obstacles working against creating a great reputation.

First, we're about to build an organization that will likely (statistically) fail. It's sort of hard to build a winning reputation on the back of a potential failure that could result in the loss of job...



ArticleForm an Advisory Board to help Raise Capital

Form an Advisory Board to help Raise Capital

Capital raising isn't about pitching investors, it's about getting in front of them to begin with. But how do we get introductions from investors if we don't know any?

We start with forming an Advisory Board.

The suggestion here isn't to form an Advisory Board specifically for raising capital — since there are a ton of benefits to having an Advisory Board. However, as a first step toward raising capital, it makes a ton of sense to surround ourselves with smart, well-connected people who believe in our product but also have been through the very gauntlet we're entering into. In the same way we'd hire a dev team to build an app, why wouldn't we round up a team of smart, well-connected Advisors to build our capital raise?

We don't need to be s...



ArticleHow do I leave my Startup Stress at Work?

How do I leave my Startup Stress at Work?

Decoupling startup stress from our "regular life" is one of the biggest challenges we deal with as Founders. Running a startup isn't like working at a job. The startup is a part of who we are, so our stress feels like it's imprinted into our very DNA.

Yet, at the same time, if we can't decouple our startup stress and our home lives, we risk destroying both. What we need is an actual strategy for freeing up our minds so that we can actually enjoy both sides of our lives.

Isolate and Attack the Problem

As Founders, we are awesome at attacking problems all day long at our startups. So why is it that we never isolate the problem of our "take-home stress" and attack it with the same intensity?

The first step is to isolate the problem as an actua...



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