"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...

How could we possibly be "right" as Founders when literally everything we are doing is unknown?

Think about it — we're building a startup that has never existed with a product that's being invented run by a team that's never worked together delivering to a customer who has never heard of us. Oh, and did I mention as Founders we've probably never done this before?

What about that formula drives certainty?

Separating Mistakes from Failure

Let me start by saying this — there is no possible way, NO possible way, that as a Founder we could possibly make the right decision over and over. In fact, the only way TO make the right decision is going to be to make tons of mistakes until we figure out which decision is correct.

We need to learn that whe...

Most of us Founders have never raised capital, so when we dig in for the first time, we're mostly guessing at how the game is played. And friends — it is indeed a game. The problem with this game is that as Founders, the odds are stacked way against us.

We actually make matters worse when we don't understand the rules, and instead revert back to our base instincts, which range from carpet bombing the investor with follow-ups to trying to translate "I think it's interesting" into 50 potential meanings, like a 16-year-old after their first date.

What we need is to be able to read the signals for what they are, and when we do, take our foot off the pedal if the signal says "stop" and jam the pedal when the signal is "yes."

Anything that's not ...

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...

Craig Newmark is the man behind craigslist —a website that today is among the 40 most visited websites in the world, is found in 70 countries, and can best be compared with Exchange and Mart in the United Kingdom.

Craig started craigslist back in 1995, and today he is reportedly worth more than DKK 3 billion. However, the last impression you get when talking to him is that of an entrepreneur guru. On the contrary, Craig is completely down to earth, something of a nerd (his word), and deeply passionate about using technology to make the world better.

He no longer heads craigslist but has dedicated his life to charitable work via Craig Newmark Philanthropies, which supports and connects nonprofit communities and drives powerful civic engageme...

As Founders, when we give away equity determines how much we're going to lose.

That's because the equity game, and our job of holding on to it for dear life, is really about vulnerability. The more vulnerable we are, the more we give away. The stronger our position is, the more we retain. It's really that simple, and yet, especially if this is our first startup, it's hard to realize when we're giving up too much too early.

There are really three moments in time where we have to really consider our timing and our approach — when we add co-founders, hiring early employees, and when we take on seed capital. What we often don't realize is that there is a lot of strategy to when and how we pull these triggers, while a lack of strategy has massiv...

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...