ArticleCan I Lead Without Being Liked?

Can I Lead Without Being Liked?

We're all probably a lot less liked than we think — and that's probably OK.

As Founders, we're automatically put on a pedestal, and that pedestal is sometimes used to praise us, and other times to set us up to have rotten tomatoes thrown at us! Either way, we tend to stand out in the organization. In a perfect world, we'd be universally praised and admired. Our staff would love everything we do and only talk nicely behind our backs. But the world isn't perfect, startups are a grind, and the constantly changing floor beneath our feet creates a metric ton of resentment.

But instead of worrying about whether we're going to be universally loved like Kanye, let's talk about what to do about it in the infinitesimal chance we're not.

It Comes With...

ArticleWhen To Admit “I Messed Up”

When To Admit “I Messed Up”

There's absolutely no way to go through the startup journey and not screw something up — OK, a ton of things. So why, as Founders, are we so bad about admitting our mistakes?

Unlike many other aspects of life, both personally and professionally, admitting we're wrong appears to have much more painful consequences to Founders because so many more people are involved. When I worked at a job and I messed up, the only people that were affected were my boss (who was unsurprised) and potentially my co-workers (who definitely didn't care). The consequences of my mistakes were tiny.

But now I have 200 people that rely on me. If I make a mistake, it affects all of them, and in some cases all the people that they are connected to as well. As Founders...

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, 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...

ArticleHow Do I Sell The Vision?

How Do I Sell The Vision?

Communicating a bold vision isn't just about how it's delivered, it's about how it's crafted.

As Founders, we live and die by the quality of our visions. We use it to inspire people to join us, to convince customers to buy from us, and to attract investors to fund our ridiculous ideas. Visions are the lifeblood of what we do, and yet, a lot of us don't really understand how to create them.

The common misconception is that our vision is simply a grand statement we make about the future. While that's partially true, it doesn't really explain what separates a good vision statement from a great one. To create a great one, we have to understand the three underlying mechanics.

Sell the Problem

Selling a vision is really about framing a problem be...

ArticleManage Downside First, Big Opportunity Second

Manage Downside First, Big Opportunity Second

Who cares how fast we can scale if we're not around long enough to do it?

That was our motto at since Day One. While it's a ton of fun to think of grand growth strategies to take over the world, it kinda helps to be solvent enough as a company to see them through (at least that's what we've heard). What we've developed over the past decade are essentially two strategies for every major initiative — a "Downside Strategy" where we plan out the worst that could happen and an "Upside Strategy" which considers growth.

Most startups don't actually do this. Instead, we have basically a growth strategy and then in the back of our minds, we sort of formulate this "Oh Shit! Strategy" which loosely envisions what could happen if this does...

ArticleWhy Money Can't Buy Happiness

Why Money Can't Buy Happiness

As Founders, so many of us have joined this marathon because we believed there was our own version of "happiness" on the other side of it. The problem for many Founders, once they've "made it" is that they don't realize that money was never going to buy more happiness. In fact, it wasn't the problem they were solving for, to begin with.

Think of it like getting a big, honking bruise. In this case, that bruise is a metaphor for debt. When you have a bruise, you're constantly worried about it — it's super painful. So we think about how great it will be when it goes away. And eventually, it heals (we have some money). But all we did was get rid of the pain, we don't actually become "more healthy" than we were before.

The same goes for debt. Wh...

ArticleHow Transparent Should I be With Staff?

How Transparent Should I be With Staff?

If most early-stage Founders were being completely transparent with their staff, their company updates would probably look something like this:

"Hey everyone, good to see you all on Zoom. So my quick update is this — We don't know if we have enough runway to make it to our next funding round. Also, I'm getting a lot of personal emails from folks saying they don't see the vision anymore. And personally, I don't really think this was the right decision for me or my family. So.. who wants to lead with OKR updates?"

That's the kind of truth that exists for us as Founders every day, and yet we find ourselves "hiding" that truth from our staff on a daily basis. Does that make us horrible people? Do all Founders leave this kind of information out?...

ArticleNever Tell People How Much Money You Have

Never Tell People How Much Money You Have

When I was just starting my startup career and had a little bit of success, I got the best advice ever from a friend of mine whose family had started a $50 billion company. He said:

"Never tell anyone how much money you have. Only two things will happen — they will either try to take it from you or size you up by it — either way, you lose."

I give that advice to every newly minted exited Founder I meet, and at this point, I've given that advice so many times I figured it was worth a detailed explanation. It actually doesn't matter how much you have (or don't have), the advice is just as valuable.

The Money Matters

Like it or not, we are judged by our money. If we have it, people judge us because they don't have it, and if we don't have it, ...

ArticleIs this the "Right" Co-Founder?

Is this the "Right" Co-Founder?

Imagine getting married to someone you hardly knew just because you "really needed to get this marriage thing going, and they seem qualified enough at the time." Does that sound like the recipe for a healthy long-term relationship? Probably not. But that's pretty much how most of us select our future spouse for our startups (aka "The Cofounder").

At some point, we inevitably step back and ask "Is this really the right person to be my long-term co-founder or did I just do a shotgun wedding with this weirdo?" Which invariably leads to "How can I tell if this is the 'right' co-Founder, and if it isn't — how do I unwind this thing?

To be fair, these are questions most Founders will end up asking, and if we're not, it doesn't mean our co-founder...

ArticleWhy Isn't Anyone As Committed As The Founder?

Why Isn't Anyone As Committed As The Founder?

It's ridiculous to think that anyone will ever be as committed to a startup as the Founder.

And yet, we're constantly beating ourselves up trying to find just the right combination of great hires, strong incentives, and attractive growth to convert all of this raw talent into the committed, startup-building machine that we've become.

But it's 3 a.m. and we're sitting in bed staring at the ceiling completely engrossed in nothing but the future of this startup. Why isn't everyone else? Is there some sort of magic formula that would convince the rest of the staff to also be sitting in bed staring at the ceiling? (In this scenario we're assuming we'd want people to do that...)

It's time we realize, as Founders, that expecting the same level of ...

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