Forums Search

Offices are a relic that we keep using to justify work.

Think about it like this — if offices had never existed, and a bunch of us were building a startup, do you think anyone would agree with this proposal:

"Let's find a spot that's inconvenient to get to, separates us from our lives, requires us to work in the least comfortable setting, and leaves us doing essentially the same thing we did at home."

"Oh, also, let's pay a fortune for it."

Whoever made that insane proposal would probably get booted off the management team! And yet, here we are, clinging to that relic of a working environment like it's a badge of honor.

"But We Need Them to Build Culture"

Culture is incredibly important, but let's not hard code the concept of "having cultur...

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...

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...

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...

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...

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...

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...

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...

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?...

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...