ArticleWhy No One Returns Our Sacrifices

Why No One Returns Our Sacrifices

We all want to do right by the people connected to our startup, but when do our sacrifices ever get paid back in kind? Or more specifically, do they?

I recently had a tough heart-to-heart with a fellow Founder where they talked about having to move on personally from the startup. They were burnt out, they had diluted all of their upside in multiple rounds of investment, and they felt "stuck."

They were stuck because they felt that if they left, they would first need to do right by all the people around them — their team, their investors, and their customers. All of these people were incredibly hard to convince to work at their startup, so the idea of "leaving them" seemed like an impossible leap.

My advice was blunt: "Do you really think an...

ArticleWe Are Animals With Tools

We Are Animals With Tools

When I (Jonathan) read the book Exponential Organizations 3 years ago, a whole new world opened up for me. Up until then, I didn’t know Salim Ismail that well—just like a lot of other people, I guess.

Today, Salim Ismail is one of the hottest names in the business world. He has spent the last 7 years building Singularity University as its founding executive director and current global ambassador. Prior to that, Ismail was the vice president at Yahoo, where he built and ran Brickhouse, the company’s internal incubator. His last company, Ångströ, a news aggregation startup, was sold to Google in 2010.

Salim Ismail has founded and/or operated seven early-stage companies, including PubSub Concepts, which laid some of the foundation for the real...

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...

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?...

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