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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 ...

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...

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...

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...

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...

I had the pleasure of talking to Blake about his ideas and experiences as a social entrepreneur. I started by asking him about how TOMS started.

Blake: I started TOMS after a trip I took to Argentina in 2006. I noticed that many of the locals wore shoes that I learned were alpargata. I also noticed that in rural villages there were many children who were without shoes and how that was affecting their daily lives. I had to come up with a way to help and knew that relying on donations alone was not a sustainable solution, so I used my knowledge of business to come up with an idea. The result was a for-profit business model that empowers customers to help children through their purchases. For every pair of shoes purchased, a new pair is given ...

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...

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...