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Warning: This isn't intended to be a political statement. It's intended to explore the entitlement of earnings by Founders, regardless of where in the world they live or what system of government they are in.

Do successful Founders deserve the profit for their invested risk?

For a long time, this question seemed almost rhetorical, but in the past few decades, the entitlement of Founder profit in the world has come under serious scrutiny. As the cultural and economic divide among workers continues to increase, the notion of who "deserves" profit has become incredibly volatile.

Not surprisingly, I'm wildly biased on this topic because I’m so passionate about startups! I believe Founders earn and deserve every penny of the profit they make, a...

Everyone loves to glamorize the Founder who risked it all — until they are the Founder who lost it all.

Recently I was watching the History Channel series "The Toys that Made Us" with my kids, where they documented the inventors of toys from Barbie Dolls to Trivial Pursuit. Within the documentary are conveniently scripted scenes where actors dramatize key moments where the Founders "risked everything" to bet on their big dream, which of course, went on to become a huge hit.

When my daughter turned to me and asked if that's what it's really like - to risk everything to become successful — I turned to her and said, "Yes, if you're lazy." I said "lazy" because I didn't want to say "stupid" but when she's an adult, I'll be sure to add that part...

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...

There are a ton of jobs we can hire for — a "Founder" isn't one of them.

Nearly all of us, at some point, dream of replacing ourselves with someone else, ideally someone that's a big level up, so that we can take the pressure off of us and enjoy the good life. But over time most of us arrive at the same conclusion — back-filling the role of "Founder" is nearly impossible.

Why is it so hard? Clearly, there are more people out there substantially more qualified than we are to run our companies. Yet, time and time again, Founders try to recruit the "perfect replacement" only to find themselves right back in the leadership chair before they know it.

The answer lies in the fact that while we can hire capabilities beyond our own, there are a few ...

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...

All startup hype aside, actually getting paid kinda matters.

The short line of highly visible, massive startup successes is vastly overwhelmed by the long, long, long line of Founders (and their staff) who racked up all kinds of debt with nothing to show for it. That's the part of the story no one likes to talk about — actually getting paid.

Building a startup is synonymous with deferred compensation and equity fortunes, but it masks a very real truth which is very few of those paper fortunes every become liquid. As Founders, while we benefit from amassing those paper fortunes, we need to be entirely focused on the real paper — getting paid with cash money.

Watching Monopoly Money Millionaires

It's so easy to get caught up in the value of "...

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...

Founders — at what point is the problem our ability to manage versus the capability of the talent we manage?

Our entire startup is fundamentally limited by the quality of our talent and the quality of our management. So how do we know when we're tapped out on either? If we don't have a firm understanding of where our team is limited, we can't address fundamental issues that prevent us from growing.

Yet it's easy for managers to blame talent and for talent to blame managers. How do we as Founders assess both to determine who needs attention? First, we need to understand what the limiting factors are.

Turning Water Into Wine

At some point, no matter how good of a manager we are, we cap on the quality of our talent. For example, if LeBron Jame...

Most people think they work hard when, in fact, they hardly work.

If you ask the average person if they work hard, most will tell you, "Yes!" with a combination of pride and resentment. The idea of working hard is generally associated with a measure of self-worth and contribution, so naturally, we'd all like to believe we're part of that.

But what is the cost of "thinking" we work hard while actually being fairly shitty at it? What happens when everyone around us (including us!) genuinely believes they work super hard, even though their actual output and productivity aren't that great?

As startups, we live and die by our productivity and that of our teams, so if we're all operating under the illusion of "working hard" without having any met...

"Never tell anyone how much money you have. They will only judge you by it or try to take it from you."

That was some of the best advice I've ever gotten from the son of a well-known billionaire after my first startup just started to take off. At the time, I had just started to make some money, and like any poor kid who just came into some cash, I wanted the whole world to know just how well I had done.

So yeah, I was the douchebag posting pictures of my Lamborghini, only social media didn't exist yet, so I guess I was just emailing them, which is way worse! Little did I know at the time how much trouble my personal PR campaign would create for me.

They Will Only Judge You by it

One of the things I first started noticing was that everyone w...