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How do we maintain focus and order when everything else is going to hell?

There are two skills we need as Founders trying to lead chaotic startups — the ability to solve problems and the ability to focus our attention. As it turns out, the ability to focus our attention tends to be the most important.

You see, chaos is pretty much standard fare at any startup. Yet, if we're not able to organize that chaos, no matter how capable we are, it will consume us. When everything is in chaos, we need to be the steady hand that guides us through the storm, even in cases where we're the only person in that storm!

Over time we start to realize that we can't "end chaos," but we can learn to control it in a way that allows us to systematically assess and...

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...

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...

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...

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 Startups.com 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...

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...

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...