ArticleThe Case Against Full Transparency

The Case Against Full Transparency

Startup Founders love the idea of full transparency when it works for them.

At first glance, it's hard to argue against the idea of "full transparency" in our startups. Who wouldn't want the inside information about what's really happening at a startup? Doesn't that make everyone feel more informed, safe, and supportive?

But try running a startup for long enough, and you'll quickly start to see that the concept of full transparency only works when things are good. The reality of running a startup quickly devolves into lots of shitty situations where going "full transparency" is more likely to sink our startups than improve them.

We Want Transparency When it's Positive

Startups often love the idea of full transparency in the early days when ...

ArticleWhy Do We Still Have Full-Time Employees?

Why Do We Still Have Full-Time Employees?

For as much as we startup Founders love to innovate business models, we sure have done a lousy job of innovating on the employment model. Our salary lines tend to be our single largest expense in a company, and yet the biggest innovation we've had to date has been moving to a remote work system.

We've agreed that we don't need offices or "40-hour work weeks" anymore, so why haven't we agreed that we don't need the "full-time salaries" that came with them?


Yeah, I said it. Yeah, I'm about to be exponentially less popular. And, well, I wasn't that popular before, so… But seriously, why haven't we reconsidered compensation in an era where everything has become fractionalized?

Full-Time is Dead

Very few people actually work full-time an...

ArticleThis is Probably Your Last Success

This is Probably Your Last Success

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 ...

ArticleHow Many Deaths Can a Startup Survive?

How Many Deaths Can a Startup Survive?

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...

ArticleHow Should I Share My Wealth with Family?

How Should I Share My Wealth with Family?

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.


ArticleWhy Do VC Funded Startups Love "Fake Growth?"

Why Do VC Funded Startups Love "Fake Growth?"

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...

ArticleLiving the Founder Legend Isn't so Fun

Living the Founder Legend Isn't so Fun

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...

ArticleYouth Entrepreneurship: Can Middle Schoolers be Founders?

Youth Entrepreneurship: Can Middle Schoolers be Founders?

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...

ArticleHow to get Customers for Startups

How to get Customers for Startups

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...

ArticleAt What Point Have I Sacrificed Too Much?

At What Point Have I Sacrificed Too Much?

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.

How Much is Our Health Worth?

Invariably the first casualty of sacrifice is our health. It comes as the perfect trifecta of destroyin...

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