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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 ...



ArticleWhy can’t I be OK with where I am?

Why can’t I be OK with where I am?

As a Founder, no matter what I've ever accomplished I've never been OK with where I am. It's weird, too, because I started out with so little that accomplishing anything was a huge win. And yet, I find that my anxiety exists in nearly ever Founder I meet.

It almost seems like the very drive and ambition that makes us great Founders also makes it very difficult for us to just kick back and enjoy the status quo. It's as if we're Kevin Arnold constantly reaching for the car door handle of accomplishment while our asshole older brother Wayne keeps hitting the gas pedal when we try.

"Why wasn't my last accomplishment enough?”

When we had nothing but a dumb idea and a dream, the idea that this could turn into our day job was a massive milestone. ...



ArticleWhy No One Tells Founders "It's over, move on."

Why No One Tells Founders "It's over, move on."

No one tells Founders "Hey, you know what, it was a good run but you should probably stop killing yourself and just take the mulligan on this one." No one ever actually tells us it's OK to quit.

Instead, we build up this narrative in our head that we've got to burn through all of our savings, exhaust our health, and basically run ourselves into the ground to prove we didn't give up. But here's the problem — everyone else gave up a long, long time ago. They just never told us — and never will.

Investors Have No Incentive to Tell Us What's Up

When we were kids playing sports, and we were obviously winded, our coach would pull us out and tell us to take a breather. If our investors were our coaches, they'd hand us some amphetamines and tell us...



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...



ArticleWhat’s the Least a Founder Should Know About Finance?

What’s the Least a Founder Should Know About Finance?

A Founder that doesn't understand startup finance is a liability to the company.

The very survival of a startup comes down whether we have enough cash to survive. If the Founder can't answer that question, it'd be like hopping on a jet with a pilot that doesn't understand how to read the altimeter, compass, or fuel gauge. They might be a great pilot, but without knowing the fundamentals, that trip is going to end poorly.

Fortunately, Founders don't need an MBA in finance to be competent, we just need to understand a few basic principles very well. While I'm the Founder + CEO of Startups.com, I'm also our CFO. That's because I learned long ago that with a solid understanding of just a few key principles, we can make (and avoid!) really criti...



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...



ArticleWhat Founders Learn From Growing up Broke

What Founders Learn From Growing up Broke

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...



ArticleHow to Create Career Paths at a Small Startup

How to Create Career Paths at a Small Startup

The old days of having to grow our staff by promoting them into a management pyramid are (thankfully) wasting away. Startups can do way more with fewer people, which means fewer management layers and more a more empowered staff.

Yet, we're still stuck in the old thinking of "I can only progress if people are reporting to me." It's a dying notion, yet one we struggle with as startup Founders to replace. But we have to figure out how to recast the career paths of our teams if we're going to learn to work in a new world of smaller teams doing 10x more than they used to.

Growth Needs to be Unpacked

When our staff talks about growth, they are really talking about three things — money, recognition, and empowerment. Money is easy — we can always p...



ArticleWe Need a Strict Definition of Personal Success

We Need a Strict Definition of Personal Success

As Founders, we spend an inordinate amount of time setting and pursuing goals, yet the ones that truly matter — the ones that affect us personally — are often amorphous. If we're spending every waking moment working toward a goal, it stands to reason that our goals should have an insane amount of fidelity.

We Tend to Suck at Goal Definition

If you ask a startup Founder what their goals for the startup are, they may say something like "To sell for a billion dollars!" But that's a pointless goal unless that Founder needs exactly a billion dollars (or their percentage of it) to achieve their goals. Also, if you have a plan for spending a billion dollars please call me - I want to hang out.

A better goal would be "I need $281,520 to pay off my ...



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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