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We need to treat every successful startup like it's our last — because statistically speaking, it probably will be.

In the startup biz, there are tons of second and third acts (I'm on my 9th) but there are very few that are ever equally successful. That's a problem for us as Founders, because we can easily lose sight of how important a single success is, and waste the opportunity thinking there will simply be another.

What if there isn't? What if this startup success, in whatever form it has right now, is the last successful startup we'll ever build? Shouldn't we treat it like gold versus assuming this is "one of many"? What happens if we get this wrong?

The Odds are Stacked Against Us

The first thing we need to understand is that the odds ...

Every good startup dies a thousand deaths before it ever lives.

We don't like to believe that because it sounds awful. Who would get excited about doing anything that sounded like it was going to die a bunch of times? Yet death — in the form of setbacks, restarts, and in some cases implosions — is kind of what we do for a living as Founders.

Pretending like we're going to get through this whole thing unscathed is like picking up a video game on the hardest setting and thinking we're going to beat the entire game without ever losing a life. It just doesn't work that way.

So just like our blinking Super Mario coming back to life for the 1,000th time, we've got to learn how to play through the whole game while pretty much expecting to lose a f...

The only thing harder than making a ton of money is giving it away to family.

On paper, it sounds easy. We've finally got some dough and now we can hand it out like Robinhood to all the people in need. What could feel better than helping our family with a little extra cash?

That's until we find out what a giant tangled mess of problems it tends to create. What we are thinking about is how helpful we can be, but what we're not thinking about — and where most Founders live in regret — is what a can of worms we open from here on out.

It. Never. Ends.

The problem with giving away money once is that once we open those floodgates, they are nearly impossible to close. All it takes is a single act of kindness to send those gates crashing open.

Here...

Venture-funded startups grow way beyond their means because they have to.

Time and time again we get asked by (typically bootstrapped) Founders about why in the hell venture-funded startups love that so-called "fake growth."

You've seen this before, when a new startup raises gobs of venture capital, hires hundreds of new people, burns through tens of millions of dollars (or more!), and then later on has to crash and burn the whole thing because it never actually made any money.

From the outside, it seems insane. What Founders don't realize is that this whole "fake growth strategy" isn't just some bizarre misstep - it's an actual playbook. We look at stories like WeWork and ask "How could anyone let that happen?" Well, it turns out, there's...

Legendary Founder stories are great — unless you're the poor bastard who had to live through it.

As Founders, we're regaled constantly of comeuppance stories of our fellow Founders who risked it all... almost lost it all... and then won it all in the end. It's entertaining, inspiring, and sometimes even true.

Often we wish we could have such an epic story ourselves. But what we rarely comprehend in those stories is that in order for the story to be so epic, someone had to go through a massive amount of pain to be able to tell it.

The reality of that pain and suffering is not only overlooked quickly but entirely justified by the outcome. But does that make it all OK?

The Against All Odds Legend

Recently a good friend of mine shared a tale of...

It turns out middle schoolers may be some of the best Founders I've ever met.

A little backstory. My kids go to a small school in Ohio that only has 208 students in the whole Middle School (grades 5-8). The school is very innovative, but one of the things that they do is allow the teachers to each pick one topic they would love to teach, no matter how weird, and pitch it to the entire Middle School.

I got invited to this pitch, totally unprepared as usual, and watched all of the other teachers pitch their classes. It was everything from "How to be a Pirate" to "How to Create your Dungeons and Dragons character." There were some seriously academic ones in there, but I was "sold" on the D&D course for sure! Where was this stuff when I was a kid...

As a startup, customer acquisition is essential for success. It requires careful planning and execution to ensure that your efforts are successful and cost-effective. In this introduction, we will explore key topics such as building relationships with potential customers, tracking success metrics, leveraging digital marketing channels, testing different campaigns, and more. With the right strategies in place, customer acquisition can be an exciting opportunity for startups to grow their customer base and expand their business.

Overview of customer acquisition for startups

Why Customer Acquisition Matters for Startups

Customer acquisition for startups is an incredibly important process that can mean the difference between success and failure. A...

There is absolutely a point where the cost of building our startup is simply too high.

The problem is all of our startup lore tells us otherwise. When I talk about building my new startup I talk about not taking a vacation for 7 years, not seeing my family for 3 years, and eating nothing but Ramen Noodles for a decade.

OK, the last part isn't true, it was Chocolate Pop-Tarts dipped in Nestle Quick (I was living big all along!)

We've built a culture around respecting the sacrifice, which is only somewhat helpful. What's dangerous is when we wind up taking it too far. How far is too far? That's the $0 question.

The Hard Truth of Being a Founder

One of the most difficult things about being a startup Founder is that you have to be willing to sac...

As a founder or leader in a startup, it's easy to get caught up in the day-to-day grind of running your business. But if you want to achieve real success, it's important to take a step back and consider the bigger picture.

In his essay "Growth," Paul Graham argues that the most successful startups tend to be those that focus on rapid growth.

But what does it mean to have a "growth mindset"? Simply put, it's the belief that your company can and should grow quickly, and the willingness to take on new challenges and opportunities as they arise.

This means being open to trying new things, even if they come with a risk of failure. It means embracing change and constantly seeking out ways to improve and expand your business.

Company Culture: A Key Dr...

Most funded Founders get to a point where their current deal sucks.

It starts when we take (and keep) salaries well below market, then it extends as our position in the cap table gets crushed, and explodes when we're in Year 8 and nothing has improved.

We now run a company that isn't good for us — and probably not good for investors either. So how do we propose a change in our deal when so much time has elapsed?

Whatever we think our new terms should be, whether it's an increase in base salary, a cut of the profits, or an increase in our stock position, what matters is how we propose it. There's a specific path we need to take to insure we stand the best chance of a reset.

Make it a Binary Decision for Board Members

When it comes time to ...