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What if our current startup success can't be repeated?

As Founders, we're ridiculous optimists, and for all of our "vision" we're pretty damned short-sighted. In our minds, if things are going this good now, it stands to reason that they will go even better in the future. It has to, right? We'll be better connected, more experienced, and way more prepared than we were for our current startups!

But that's not how startups work. The startup game isn't chess, where the conditions are similar and we're just more experienced. It's more like blackjack, where we know a little bit more, but the variability changes on every hand.

Don't Know What You Got, Til It's Gone

(If you sang this last headline in a Cinderella power-ballad, you are my people). ...

We all want to do right by the people connected to our startup, but when do our sacrifices ever get paid back in kind? Or more specifically, do they?

I recently had a tough heart-to-heart with a fellow Founder where they talked about having to move on personally from the startup. They were burnt out, they had diluted all of their upside in multiple rounds of investment, and they felt "stuck."

They were stuck because they felt that if they left, they would first need to do right by all the people around them — their team, their investors, and their customers. All of these people were incredibly hard to convince to work at their startup, so the idea of "leaving them" seemed like an impossible leap.

My advice was blunt: "Do you really think an...

If most early-stage Founders were being completely transparent with their staff, their company updates would probably look something like this:

"Hey everyone, good to see you all on Zoom. So my quick update is this — We don't know if we have enough runway to make it to our next funding round. Also, I'm getting a lot of personal emails from folks saying they don't see the vision anymore. And personally, I don't really think this was the right decision for me or my family. So.. who wants to lead with OKR updates?"

That's the kind of truth that exists for us as Founders every day, and yet we find ourselves "hiding" that truth from our staff on a daily basis. Does that make us horrible people? Do all Founders leave this kind of information out?...

When I was just starting my startup career and had a little bit of success, I got the best advice ever from a friend of mine whose family had started a $50 billion company. He said:

"Never tell anyone how much money you have. Only two things will happen — they will either try to take it from you or size you up by it — either way, you lose."

I give that advice to every newly minted exited Founder I meet, and at this point, I've given that advice so many times I figured it was worth a detailed explanation. It actually doesn't matter how much you have (or don't have), the advice is just as valuable.

The Money Matters

Like it or not, we are judged by our money. If we have it, people judge us because they don't have it, and if we don't have it, ...

Imagine getting married to someone you hardly knew just because you "really needed to get this marriage thing going, and they seem qualified enough at the time." Does that sound like the recipe for a healthy long-term relationship? Probably not. But that's pretty much how most of us select our future spouse for our startups (aka "The Cofounder").

At some point, we inevitably step back and ask "Is this really the right person to be my long-term co-founder or did I just do a shotgun wedding with this weirdo?" Which invariably leads to "How can I tell if this is the 'right' co-Founder, and if it isn't — how do I unwind this thing?

To be fair, these are questions most Founders will end up asking, and if we're not, it doesn't mean our co-founder...

Most Founders get rich without ever exiting their business. Yes, you read that right. We don't have to build a rocket ship that takes on gobs of funding for an IPO in order to have everything we want.

We just need to keep making money (and not even that much!)

While to most people this may sound obvious, in the startup world we tend to forget how this simple fact works. We keep thinking in terms of this big liquidity event where we get handed a giant check like we just won the Powerball. We picture ringing the bell on NASDAQ wearing the only nice outfit we own shaking hands with bankers and smiling for the camera.

And in the end, we picture having enough money to just do whatever the eff we want.

The Stacking Effect

I spend a ridiculous amo...

There we are, once again, sitting at yet another Founder get-together while everyone tells us how great their startups are doing. Oh shit, that woman just said that they raised a massive round of funding. That guy just said he just surpassed 100 employees. The other person (I'm losing count) just claimed they are growing 50% per month.

"WTF? I thought I was doing great and now listening to everyone else I feel like a total loser."

And there it is. The age-old startup-sizing "competition" where we indeliberately one-up each other with how amazing our startups are doing. In the process, we all make each other feel miserable about ourselves.

What's that? You don't do that at get-togethers? Well, if you're like most, you're doing it anyway in s...

There's no golden age to start a company, but there is definitely a timer on when we can withstand failure. The question is — when does that timer expire for us?

As it happens, our numeric age isn't really what's driving our "Founder Expiration Date" — it's about how our age may reflect our relative appetite for risk. That's really a nice way of saying "What's the oldest I can be before I'm too old to recover from failure?"

Age Erodes Risk

Every year that goes by is another year we can't get back. When we're in our 20's and starting a company, we have our entire adult life to make up for the risk of failure. In many cases, we may not have a family or even a mortgage to worry about. At most, our failure may result in some lost years and a sh...

Every startup dies a few deaths before it lives forever.

But that's not what they tell us in the startup Founder brochure. Instead, we make up this fairy tale that our startup must be a great idea that instantly takes off, leaving customers and investors standing in line to hand us their cash. We keep making great decisions while we struggle to stay on top of our meteoric rise. Our days are jam-packed between photo shoots for magazine covers, headlining major conferences, and giving powerful speeches at company retreats.

Sound familiar?

No, of course it doesn't. Because that's not how any of this shit goes. The real version of a startup involves failing incessantly, sometimes to the brink of shutting down, until we rise back up and finally ...

At Startups.com, we built an 8-figure business by saying "no" — a lot.

We knew going in that if we’re going to have 100% control of our destiny now and in the future, that would only work if we could constantly say "no" in a disciplined manner.

But you know what? Saying "no" sucks. Just like saying "no" to delicious glazed donuts sucks. We know that we want them, but we also know the cost of saying "yes"! Now I'm hungry for a glazed donut. See what I mean? We knew that controlling our destiny would mean an insane amount of discipline, across the entire organization. In order to prepare ourselves for this discipline, like any good regimen, there were a few things that we'd have to stay incredibly focused on.

We had to be OK with things takin...