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ArticleEven in Failure, Founders Deserve True Respect

Even in Failure, Founders Deserve True Respect

From time to time I find myself working with a Founder who's in the unfortunate position of having to shut down a startup. It happens way more often than people realize, yet each and every time it leaves the Founder very alone, wondering what the hell they just put themselves through.

They feel dejected. They feel ashamed. They run countless "what if" scenarios that consider what the startup would have been like if they had chosen a different path. In the end, they just regress further and further into a position of failure and all the shitty emotions that come with it.

I only know this because I've done it — it sucks — and I don't wish that soul-crushing epilogue on anyone. What I have learned, however, is that from that pile of rubble the...



ArticleThat Founder Sold For Too Little!

That Founder Sold For Too Little!

"Did you hear about the Founder who sold their startup and 'only' made a million dollars?!"

Ah, the popular refrain of startup haters everywhere when they gleefully recount the supposedly "shitty" outcomes of hard-working Founders. They get almost giddy with speculation. Nothing excites the people who don't start companies more than trying to belittle the outcomes of those that do.

Well, startup haters, this one is for you. This is a not-so-subtle reminder that not only do your opinions not matter — at all — but how wrong your position is, to begin with.

"What Startup did You Sell Again?"

Before we even dig into how wrong their analysis even is, and it's almost always wrong, let's begin with who is even making this analysis. 99% of the tim...



ArticleForget "Big Ideas" — Start with your North Star

Forget "Big Ideas" — Start with your North Star

The most impossible task for a Startup Founder is to "invent a big idea."

It's not because we lack creativity, it's because we wind up focusing our energy on the wrong thing. Big ideas, by themselves, are nearly impossible to corral in our minds because they are inherently either "not big enough" or "too big to tackle."

We tend to go about this all backward. We assume that once an idea is incredible enough, it will guide all of our actions thereafter. But that is like putting a map down on a table and saying "We want to go west!" without making this is the most reasonable path.

"What Do I Want This Idea To Achieve?"

Any idea can become a "big idea" if you work at it hard enough. What we should be more focused on is a step beyond that — wha...



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...



ArticleWho's Qualified To Be A Founder?

Who's Qualified To Be A Founder?

Being a Founder is a job that anyone can get and no one is qualified for.

My 9-year-old daughter became a Founder last year within 60 minutes of forming her own company online (she didn't even need my help). I'd argue she's about as qualified as most of the Founders I meet at Startups.com, and that's not a knock. It's to say that none of us are "qualified" to be a Founder, not because we're not smart enough, or capable enough, or experienced enough — it's because fundamentally it's impossible to be qualified for this job.

We Can't Be An Expert At Everything

The difference between a Founder leading a startup and a CEO leading an established business is that the Founder has to be there from the start when no one else is there. That means the...



ArticleStartups are Built at the Expense of Founders

Startups are Built at the Expense of Founders

That's not how this works. We don't get the benefit of sitting on our thrones and commanding our armies until much, much later in life — and in many cases, never. What we are guaranteed along the way is a wraith-like drain on our life force (D&D reference there, fellow nerds) in every possible facet.

What we need to understand, and accept, is that our startup's future can very easily come at the expense of everything we hold dear. It's very much hard-coded into how the Founder Journey works, and damn, do we pay a lot of bills along the way.

First, We Pay With Our Savings

Long before we raise money or earn some revenue, 100% of our "income" is just our personal savings. We use terms like "sweat equity" as if working for free somehow mag...



ArticleBeware the Absentee Landlord of Equity

Beware the Absentee Landlord of Equity

What's the worst equity holder we could possibly have in our cap table? The one who isn't even here any longer.

We all know this, and yet for generations, we've built cap tables loaded with "absentee landlords" who provide no ongoing value but reap all the benefit of those that continue to drive the ship. Until recently the notion of "dead equity" has been just accepted and rarely challenged, leaving those that still work for the company to carry those that don't.

I'd like to poke a giant, trident-sized hole in this argument once and for all. And for my fellow Founders who are dealing with this issue at present, or soon will be, I want to provide you with some ammunition toward what will invariably be a tough and painful conversation.

Great...



ArticleHow to Make Potential Failure Less Scary

How to Make Potential Failure Less Scary

I've failed numerous times and watched countless other Founders do the same. We kept ourselves awake nonstop worrying about the outcome of our failures. We took years off of our life and put ourselves in horrible places mentally and physically.

And you know what we learned in the end? It generally didn't matter.

That's right, our "fear of failure" was always 100x worse than how the failure itself played out. And so we took desperate measures to avoid failure, like clearing the last of our savings, running up debt, and going yet another year without pay. At some point, we became far more intent on "not failing" than succeeding.

What we need is a method for dissecting failure into actionable bits.

Failure needs to be Unpacked

If we think ab...



ArticleHow We Leave is How We're Remembered

How We Leave is How We're Remembered

The one thing everyone remembers about a relationship is how it ended.

As Founders, if we're around long enough, we're going to see the end of a boatload of relationships, and as such if we're not keenly aware of how important it is that we end those relationships gracefully, we're going to end up with a whole lotta angry exes.

There's really no way around this. Unlike our lives as an employee, where it was just us and our boss, when we are the boss, we're at the center of so many important relationships. Whether it's investors, staff, customers, partners, even the media — all of those relationships have a cost, and when they end, those costs actually multiply.

Later on in life, we learn how important it is to have "good breakups" because w...



ArticleWhen Can I Feel Good About Taking a Break?

When Can I Feel Good About Taking a Break?

Founders need to be as militant about recharging as they are about working.

Yet, nothing in front of us suggests slowing down or taking a break to do it — at all. We have a mountain of work, no one to help us, and we're burning through what's left of our cash and credit. The last thing any of that suggests is "Let's plan a sweet vacation!"

What we're missing in this mess is the fact that it's not about whether or not we want to take a break — it's that we have to. If we're going to run the marathon that is the startup journey, we can't just go full sprint 24x7 and pretend it'll all work out. Instead, we have to become highly regimented in our plan to recharge all the time, and treat that recharge as seriously as we treat our startup.

Move t...



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