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ArticleRetiring Early is a Broken Concept

Retiring Early is a Broken Concept

"I want to put $50 million in the bank by the time I'm so I can retire early and never have to work again!"

Ah, the common refrain and justification of every startup dreamer, from the Founder across to the earliest employee. If only we could put that magic pot of gold into our coffers, then we could do what we really want to do.

Except it begs the questions:

  1. How much of what we really want to do can we already be doing?
  2. Do we really not want to work or do we really just want to feel safe?
  3. What the eff are we going to do at (whatever age) with nothing to do all day?

Time and time again when I query Founders, beyond the surface level stuff, about how hard they have thought through this lifetime goal that they are sacrificing everything for...



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...



ArticleWork is love made visible

Work is love made visible

“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...



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...



ArticleGiving is Our Future

Giving is Our Future

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 ...



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