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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...

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...

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 if all the sacrifice we're making for this startup isn't worth it?

There's a bit of a compact we make with ourselves that it's OK to sacrifice our time, money, and life experiences for a big payoff later. The most important part of that assumption is that we're absolutely certain that the things we'll get with that payoff are worth the sacrifice.

But how do we know for sure? What if we go through all of this sacrifice, get everything we ever thought we wanted, and wind up no more satisfied than we are today? What if our dreams are an illusion?

The Cost of Being Wrong

The cost of us being wrong is significant because, as Founders, we sacrifice a lot for our goals. By comparison, if we work a regular day job, we get paid for our time. We...

It doesn't matter if we have a "big opportunity" if it never really accomplishes our personal goals.

Yet it's hard to avoid starting a company without thinking in terms of the market potential or the ultimate outcome. If we run around saying that our new startup could one day be a "$1 million business," we're going to get very few high fives. Yet, if we say we're going to be a "$1 billion business," we'll have people lining up to talk to us. Why is that?

The difference in that balance becomes who benefits from that outcome. At $1 million, it's almost entirely the Founders. At $1 billion, it's investors, staff, and everyone else that's joined in the party. What we need to consider is who we're really building this business for and, as such, ...

There are tons of famous Founders who have built world-changing companies in less than 40 hours per week — I just can't name a single one.

I'm not talking about the later stages when a company is already successful. I'm talking about the "garage band years" when it's just the Founder(s) doing every possible job and scraping to get a single paying customer.

The idea is that we can simply put in our 40 hours, work really hard, then turn it all off and live a regular life. Which sounds awesome. So why is it that every time we hear the origin story of a Founder, it's always the same — they worked insane hours for an insane amount of time to get to an incredible outcome?

Time is Money

Let's start with the correlation of hours to our success and...