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...

There's no paycheck in starting companies. It's the finishing part that matters.

I say this because many of us simply love the thrill and idea of starting another startup. There's always this thought — "Boy, if I could just launch this one idea that I can't stop thinking about (while forgoing my existing startup), it'll be amazing!"

Here's where the logic in that breaks down over, and over, and over.

It's Gonna Cost us 7-10 Years to be Right or Wrong

Every single time we start something anew, we reset the clock on how long it will take to make it successful. No matter how good we are, the maturation rate of a company will almost always take 7-10 years — if we're actually successful with it. That's the successful timeline, not the un-success...

Yesterday I was talking to one of my good friends, a Founder, who built a wildly successful startup doing 8-figures in revenue that said "The company is doing great, but after all of our rounds of investment, I've got a tiny sliver left of this company. I feel more like an employee than a Founder now."

What many Founders don't realize, is that this happens all the time. I've gone through it myself. In our efforts to grow our startups and in some cases just trying to keep them alive, we sacrifice that juicy "Founder equity" that we disproportionately award ourselves and all-too-often plunder in the name of growth.

Do Most Founders Lose Tons of Equity?

Not "most", but certainly an awful lot, even in what looks like a successful startup. This ...

The following is a piece of really bad advice. If you follow it, there’s a large risk that you’ll be cheated, deceived, run over, and on the whole look like an idiot. I’d regret that, of course. But it is also really bad advice to urge good people to become entrepreneurs, as it’s almost dead certain you’ll fail. So if you nevertheless have taken the chance and thrown yourself into a new adventure, you may just as well place all your jetons on red and follow my advice: Trust everyone.

Trust is a mirror.

In 2002, I was a young, newly trained journalist with a blank CV and without much chance of a job in that branch. I, therefore, chose to change direction, and I called Morten Lund, a well-known Danish entrepreneur (co-founder of Skype), and a...

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 ...

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. ...

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...

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...

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...

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...