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Most people think they work hard when, in fact, they hardly work.

If you ask the average person if they work hard, most will tell you, "Yes!" with a combination of pride and resentment. The idea of working hard is generally associated with a measure of self-worth and contribution, so naturally, we'd all like to believe we're part of that.

But what is the cost of "thinking" we work hard while actually being fairly shitty at it? What happens when everyone around us (including us!) genuinely believes they work super hard, even though their actual output and productivity aren't that great?

As startups, we live and die by our productivity and that of our teams, so if we're all operating under the illusion of "working hard" without having any met...

"Never tell anyone how much money you have. They will only judge you by it or try to take it from you."

That was some of the best advice I've ever gotten from the son of a well-known billionaire after my first startup just started to take off. At the time, I had just started to make some money, and like any poor kid who just came into some cash, I wanted the whole world to know just how well I had done.

So yeah, I was the douchebag posting pictures of my Lamborghini, only social media didn't exist yet, so I guess I was just emailing them, which is way worse! Little did I know at the time how much trouble my personal PR campaign would create for me.

They Will Only Judge You by it

One of the things I first started noticing was that everyone w...

The only product that makes sense right now is the one that makes dollars.

We all want to believe that in the formative days of a startup, all we should be building is the exact product vision in our heads. We should be turning a blind eye to anything that doesn't directly contribute toward that vision. Everything else is a distraction... right?

While that does sound wonderful, it's not only rare, it's also somewhat delusional. The reality is most startups (who aren't funded) need to focus on building stuff that makes money, regardless of whether it's directly contributing to the product vision. And guess what? Sometimes that winds up being the best product investment we can make.

Money = Runway

Let's start with the obvious — we need to get...

TL;DR: "Oh Sh*t!! My competitor just raised a bunch of funding to do exactly what we're doing. We're done for, right? How can we possibly compete with someone who now has the resources to do all of the things we wished we could do?"

Yes, a competitor just raised some funding. No, it probably doesn't matter.

"Wait, what? How could my competitor raising money be anything but my own personal Armageddon?"

Well, it turns out that when the pixie dust settles after those big announcements, our competitors often have a whole new bag of problems to deal with that we don't. We need to look past the upside of that new capital to understand how most funded startups actually sink themselves with an anchor of funding.

All Fat and Bloated

The very first t...

Here's a crazy idea — what about a startup that just makes money?

I know, I know — crazy talk! But it turns out that while 1% of the startup world is busy chasing venture capital and trying to create outsized returns, 99% of the rest of businesses are just trying to build a business that consistently turns a profit.

"How dare you question the wisdom of VC!" — echoes the startup world.

But seriously, it turns out even grizzled veterans of the startup world, especially those who have raised venture capital before, are getting really excited about building companies that guarantee a profit versus potentially generating an exit.

What Happened?

It's a confluence of factors, really. When the Nuclear Winter of Funding hit in 2022 and beyond, an aw...

There's no perfect to know if you've found a great Co-Founder, but there are some really obvious ways to tell you're about to recruit a bad one!

Yet picking Co-Founders isn't something many of us will do more than once in our lifetime, so how could we possibly know what to look for? There's no absolute checklist, but there are 3 categories where most Founders don't press hard enough — Selection, Shared Cost, and Commitment.

Technically there's a fourth, which is "personality type," but that's so incredibly hard to determine in the early stages (see: all of dating and marriage) that it's almost not worth mentioning compared to the Big Three. If all of these start to sound way too familiar, it may be worth thinking about an exit strategy.

"Oh...

The most ambitious companies grow their products, not their teams.

Back in 2002, I was invited by (now) Managing Partner Roelof Botha to come pitch the partnership of famed venture firm Sequoia Capital. While I was sitting in their lobby I noticed two things that I'll never forget.

First, like most venture firms, they had a giant list of "tombstones" on their wall, which are the plaques they create after a company goes IPO. The list was already impressive back then which included companies like Yahoo!, Electronic Arts (EA), and Cisco among many others. It was the "who's who" of venture investments globally at the time.

The second was that there were maybe 20-30 people in the entire office — and this was back when everyone was in the office....

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...

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...

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...