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The startup world is all about moving fast — but at what expense?

We've built this narrative for ourselves within startups that we're constantly under the gun to move quickly or else. If we don't move quickly, we won't attract more funding, we'll lose ground to all of our competitors, and we'll be perceived as being "slow," which is considered the death knell for any respectable startup.

But what if all of that is bullshit?

What if there are real costs to moving too quickly that will far outweigh whatever perceived benefits we're told we're getting? We stand to lose a lot if we invent a false notion of urgency that prevents us from making good decisions for the long term.

Pleasing the Wrong Party

Let's start with who we're moving fast for. ...

There's a reason the only way to get the "Founder" job title is to start the company — because there's no way to hire for it otherwise.

When I was running my first company, I was in my mid-20s with a hilarious lack of experience. The company was growing quickly, and we went from "a few people in a room" to "a few hundred people in a room," and soon my lack of experience (and pimples) was becoming very evident.

I was scared, so I set out to find a replacement for me, someone who could not only bring more experience but more confidence to the staff in executive leadership. We found an "old guy" who, at the time, I think was maybe 38, probably less, but he had some gray hair and was orders of magnitude more mature than the lot of us.

Try #1: C...

What if we're all competing in a game we can't actually win?

That's not because our startups aren't good enough or that some evil competitor will ruin us. It's because before we even get out of bed in the morning, we've already set ourselves up to fail by tirelessly running a gauntlet where we're guaranteed to lose every time.

Our mistake was setting ourselves up to compete with aspects of our Founder life that we can't actually win at in the first place. Our perception of ourselves is supposed to be our greatest asset, but in fact, it tends to be our greatest weakness because we are constantly moving the goalposts on ourselves.

Our Peers

It's easy to use our own peers as a benchmark for our own success. When I get into a room full of Found...

Investors want to believe that we're on the same side of the table and are interests are aligned — but it's all bullshit.

The pitch from investors goes something like this "We want all of our incentives to be aligned, so that a big win for us is also a big win for you. We're on the same side of the table!"

That sounds wonderful, but what's missing from that pitch is the fact that only a tiny number of outcomes wind up with both of us having the same upside. Like when you hear about a company getting acquired for a giant sum or going IPO — that's what investors are referring to.

But statistically, that's not how it actually goes. Less than 1% of funded startups are going to have that kind of outcome, which means we should be way more concer...

When times are good at our startups, we think it will never change; when times are bad, we think it will never change.

Yet the only constant with startups is change.

The challenge for many Founders is that this is likely the first time we've had good or bad times, so we have yet to see a full cycle. That makes it difficult to know whether this is a short-term blip or a long-term trend. As such, we tend to grossly overcompensate by spending too much in good times and running for the hills in bad times.

How Startups Actually Grow

We all have this fantasy that our startups constantly grow "up and to the right!" on our beautiful charts. The reality is way different. The best way to think about our startup journey is a constant cycle of "feast o...

Demo

What if I told you that selling a company for $40 million could net you more money than if you sold it for $200 million?

On its face, it sounds ludicrous, I know! But what's missing in that formula isn't the exit price, but how much of that exit we get to put in our pocket as we raise more rounds of capital.

More importantly, our opportunities to sell for $40m are dramatically more abundant than selling for $200m (or more!). That means every time we raise capital, while it sounds like we're improving our chances of an outcome, we're also reducing our options to find an exit at all.

Real Founder Dilution Numbers

CapShare released a study of 5,000 startup cap tables to determine how much equity Founders have at each stage of a funding round. ...

Yes, AI is actually going to change everything, and No, we're not all totally screwed.

Why? Because every time we embrace change as Founders, we create exponentially more value than has ever existed before. And every time things change, everyone freaks out and thinks the "old ways" were the only way things should have been done.

I'm an avid carpenter — I build tons of stuff with power tools. Every time I'm zipping through a piece of lumber with my portable saw I think, "Some poor bastard used to have to do this by hand. I bet the moment he saw an electric saw, he figured he'd be out of a job!"

What we're missing with that line of thinking isn't whether we'll be displaced — it's whether we should have been doing that work by hand, to begin w...

What happens when our main customer becomes our investor?

This is fundamentally the rabbit hole that nearly every startup goes down when fundraising. At some point, we start to realize that we're no longer building a startup for the needs of our customers; we're building it for the perceived needs of our next investors.

At any given time, our startup needs vastly more cash than we have, so we're always looking for the shortest path toward filling that gap. The very nature of investor capital is that it comes dramatically before customer capital (revenue), so in most cases, our early "customer," as it relates to cash, is an investor.

So what happens? Our investors become who we're building the company for.

We Optimize for Their Needs First

T...

Startup Founders are like top athletes — if we don't keep working that startup muscle daily, we get out of shape fast!

Normally while we're building our startups, that's not a problem — we get all the "exercise" we need in the form of unrelenting stress and anxiety (hey, it's burning calories, right?)

But seriously, being active in our startup keeps us relevant, connected, and engaged in our business worlds. The moment we disconnect, whether it be from a sale, a wind-down, or even just a career change, we start letting that muscle atrophy, and it's very hard to get it back in shape.

We Lose Our Relevance

When we're in the middle of building our startups, one of the things that we can take for granted is how relevant we are at the moment. We...