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What if we had a passion that consumed us more than our startup?

Being a Founder means thinking about your startup constantly. It’s not just work—it’s identity. And over time, it quietly starts to absorb more and more of our energy, attention, and sense of self.

For most people with “normal” jobs, the solution to burnout is taking a break—a vacation, a long weekend, a few nights offline. That works because their jobs stop when they walk away. But for Founders, our jobs never really stop. Our minds don’t clock out at 5pm. Even when we’re technically away, our brains keep running the simulation—funding, hiring, product, growth.

We can’t pretend like we can just flip the switch and shut it off. But what we can do is create a counterforce—somet...

The startup world is in a "Silent Recession" that no one is talking about, and it's a real problem.

Most of the Founders I speak to in private say the same thing — their business isn't going well. It's a combination of a weird economy, a Nuclear Winter in startup funding, and sky-high interest rates. Economists can tell us that the stock market is at an all-time high, unemployment is down, and inflation means people are spending too quickly. Yet if you talk to enough Founders honestly, they will tell a very different story.

If you're at a point where you're trying to understand why things aren't quite going as well as they should, let me shed some light on things my friends. We're in a Silent Recession among startups, where secretly they ar...

Most startup Founders never get rich — and it's 100% our own fault.

I'm not talking about not getting rich because our startup failed — that one is obvious. I'm talking about having a startup that actually worked and still not getting rich. And when I say "rich" I don't mean "Powerball Rich" I'm talking in most cases, making any money at all. As a whole, we tend to suck at making money for ourselves.

The reason for this is that the startup ethos is riddled with fallacies about how we should approach profit and wealth. We've constructed a narrative that glorifies sacrifice and risk while somehow completely overlooking common sense and profit.

Founders need a reality check. We need to remind ourselves that treading down the most dangerous pat...

Every Founder wishes they had more money, but we often don't realize what happens when we spend it.

There's this fascinating transition point that we go through as Founders where our problems start with income (because we always start with zero) and then quickly transition to debts (because someone always needs to be paid).

We put ourselves in this dangerous loop where instead of getting ahead on that next round of income, we actually dig ourselves deeper into a hole by adding exponentially more costs—and those costs aren't just financial.

We don't just grow income; we grow problems, and sometimes, way faster.

The Weight of Zeroes

When I was building my first startup with just a couple of college kids on payroll, I was terrified that I woul...

Some investors may be considered "angels" — but they are no saints!

That's why when it comes to getting "bailed out" by future investors, whether it be compensating us personally for money we've lost or helping to get our startup out of debt, we're entirely on our own. We've helped thousands of Founders raise capital, and invariably, many ask whether new investors would be willing to cover their previous losses or investments. The short answer is "absolutely not." But the longer answer may help you understand exactly why.

What Debts Are We Talking About?

The most common debts Founders ask about are personal debt they've created in financing the company or forgone compensation. The question often looks like, "I've put in $100,000 of my own m...

Most startups launch with $0 in funding, but no one ever really explains how the hell they do it. We keep saying, "They bootstrapped it," as if that explains anything other than "They didn't take on investors." What the heck does that even mean? What it is intended to mean is that we find creative ways to compensate people and buy things that don't involve using cash in the bank.

We can't possibly cover every use case of how startups find resources for $0, but let's take a look at the most popular categories that people run around looking for money for and see how we make it work.

Paying for People

Figuring out how to compensate people is where we're often stuck first. Most of us are familiar with paying folks with equity, but that's not th...

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...

There is a ton of hidden treasure in failed startups — you just have to know how to look for it, and ultimately, how to capture it.

After my first (not last) venture-funded startup tanked, everyone pretty much ran for the hills. Investors bailed, the team got other jobs, and customers found better solutions. But I kept thinking "We just spent a ton of money to build all of this, can't I capture this value back?"

Then it occurred to me — the same thing is happening for countless other failed startups. All of the assets that they spent millions to build just get buried. Everyone tries to make a last-ditch effort to sell them off, but in most cases, it never works and they just evaporate.

But what if we were the ones looking to dig up that bur...

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...