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Our most broken assumption in Year 1 is that anyone will stick around for Year 2.

Spoiler Alert: They won't, and the cost of giving away a ton of equity and responsibility to people who won't be around for long is incredibly expensive.

I see this play out all the time, especially with First Time Founders who naively think that everyone who promised to help launch their startup in Year One will actually stick around to do it. It’s easy to make that mistake — when everyone’s talking a big game and acting just as excited as we are to build something amazing, we can’t help but believe them.

But all of a sudden, people stop showing up. That Co-Founder CTO whom we thought was going to build the whole product for "free" goes MIA. That mentor who ...

At what point do we find out if all of our startup sacrifice was worth it?

The prevailing theory is that as Founders, we can justify our sacrifices of time, money, and emotional energy for the bounty of riches we'll enjoy on the other side. It's almost hard-coded into all of us the moment we take the plunge to start something.

But what happens when we're on the other side and we're forced to come to terms with whether or not those sacrifices were justified? Can we truly replace what was lost in getting here with what was gained through our efforts? What if we straight up made a bad bet?

Let me tell you a personal story about my journey as a Founder over 30 (very long) years of building startups and my assessment of a mountain of sacrifice o...

The value in our startup in an acquisition is usually a fraction of what we think it is — not a multiple.

That's not because our startups lack value; it's because we often misunderstand how that value actually gets calculated. In the past 30 years, I've spent a tremendous amount of time on both sides of these transactions, both as a Buyer (we bought 6 companies at Startups.com) and as a Seller (I've sold 5 of my own companies).

What I've learned is that Founders have really unrealistic expectations of how our startups are valued at the time of a sale. Frankly, it's not because we're not smart, it's because there simply isn't a lot of guidance on how startups get valued at all.

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Our Founder ambition is our greatest source of strength — but can also be our greatest enemy.

While being a startup Founder and having ambition are nearly synonymous, that doesn't mean the very same ambition that drives us to climb mountains can't also push us off a cliff!

I know this because I've lived it many times. I wasn't born the smartest, the most privileged, or the most talented. But I was born with two gifts — ambition and a willingness to work insanely hard. When you're starting from nothing, those gifts mean everything. Yet, what we tend to overlook is that those "gifts" have some major drawbacks that come back to haunt us later on.

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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...

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...

Today's investors are like the dinosaurs of old, looking up at the sky and saying, "Hey, look at that bright shiny thing cruising right at us..."

Back then it was a meteor that created an extinction-level event for the T-Rex. Today those dinosaurs and their Patagonia vests are watching AI about to make them extinct. What it means to be a VC investor is about to change forever, not because of anything the VCs have done wrong, but because the need for them is quickly evaporating.

For a very long time, building a startup company was insanely expensive and risky. We had to pay for a ton of people, marketing, and infrastructure in hopes that the upfront investment would be worth it. But what happens when those costs plummet? What happens when we...

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 ...