ArticleWhy I'm Either Working or Feeling Guilty

Why I'm Either Working or Feeling Guilty

I have two modes — working all the time and feeling guilty about not working all the time. There's no third mode.

I'd love to say this is a new phenomenon or that I've got some monopoly on this curse, but having spoken to countless Founders just like me, it appears I'm certainly not alone.

Now, part of that might just be self-selection. Perhaps the people who tend to work tirelessly often want to do it for themselves, or at the very least, have more motivation than the people they left back in their cubicle farm. I can't think of anyone who works harder than a Founder without anyone telling them to do it!

How Did This All Start?

Everyone's origin story comes from somewhere else, so I can't pretend to triangulate the genesis of this afflicti...

ArticleAre Founders Driven by Fear or Greed?

Are Founders Driven by Fear or Greed?

Most Founders are driven by pure fear — greed is something we can only "hope" to achieve.

Our pop culture loves to opine on the greedy nature of famous Founders, from Elon Musk to Cornelius Vanderbilt. It's easy to say, "Oh that Founder was only driven by greed — look at all they have that they don't need!"

But that often overlooks where it all started, where most of us are. It's kind of hard to be labeled a "greedy Founder" when you're living in your parents' basement applying for 24.99% interest rate credit cards just so you can keep the business alive!

The general population fails to realize that greed is a luxury we can only hope to achieve.

It Usually Starts with Fear... Lots of Fear

The reason being "greedy" is a luxury for most Foun...

ArticleWhat if I'm Building the Wrong Product?

What if I'm Building the Wrong Product?

We're all building the wrong product — we just don't know it yet.

Every great product is really just a bunch of bad assumptions that get shaped into the right ones. The idea that we could define exactly what our customer wants with all the perfect features is mostly a myth (unless we got lucky!)

What's tricky as Founders is that we have a very short window to get this right, and let's face it, our livelihoods often depend on that window. We don't have countless months and years to "tinker" — we have to get this thing right really fast.

So we end up beating our heads against the wall, trying to compress time and get the perfect product to the market so we can build and scale a successful company. But what if the time we're trying to compress...

ArticleHow Startups Actually Get Bought

How Startups Actually Get Bought

We're not in the business of selling our startup; we're in the business of making it something worth buying.

Contrary to popular belief, we don't just build a startup and have a bunch of big companies start calling on us to make offers. Yes, it's happened to some really incredible companies, and no, it probably won't happen to you (or me).

That's fine, so long as we understand how the process of selling our startups actually works in the real world. At we looked at over 100 startups before we bought 6, and I can tell you from experience that 90% of Founders have no idea how this process works. Why would they?

Startups are Bought, Not Sold

The first thing to understand is that we actually don't have a ton of control over when o...

ArticleQuitting vs Letting Go

Quitting vs Letting Go

How can we tell the difference between quitting and just "letting go" of our startup?

The outcome is the same, but how we feel about each path dramatically changes how we approach it. When we think about "quitting," we feel like a big loser. "Quitting is weak!" we may tell our alpha brains. We associate quitting with giving up, and that feels like a deeper, more humiliating version of failure.

Conversely, letting go feels kinda zen by comparison. It sounds like we've thoughtfully weighed our options and made a mature, worthy decision to move forward on a healthier path.

But are we just kidding ourselves because we're really giving up, or should we be proud of ourselves because we've made a sound decision?

Hello, Dr. Ego

Whenever I contempl...

ArticleActually, We Have Plenty of Time

Actually, We Have Plenty of Time

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. ...

ArticleWhy Can't Founders Replace Themselves?

Why Can't Founders Replace Themselves?

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...

ArticleWho am I Really Competing Against?

Who am I Really Competing Against?

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...

ArticleInvestors are NOT on Our Side of the Table

Investors are NOT on Our Side of the Table

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...

ArticlePlan for Bad Times, Budget in Good Times

Plan for Bad Times, Budget in Good Times

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...

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