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What's the least we need as Founders to be happy?

For as much time as we invest in building our startups to achieve our goals, we spend shockingly little time in identifying what those goals actually mean. The danger in not defining our minimum viable happiness goals is that we wind up hoping to "find happiness" but never really defining how to get there.

And that's a pretty big problem when we're in the early stages of building a startup when very little helps fill our "happiness meter."

It's easy to make big, lofty, far away goals, but frankly, that's pretty useless right now. What we need to do is identify the shortest term, minimum goals that will make us happy so that we do everything in our power to get there as quickly as possible.

What happens to funded startups that can't raise any more funding?

We enter the funding "No Man's Land" where startups go to linger and eventually die a very long, unceremonious death. No one talks about it — certainly not the Founders who are left with the breathing corpse that was their once-hot startup. Certainly not the investors who have written off their investment long before anyone else.

Yet everyone knows we're digesting in the Sarlacc pit for a thousand years without any idea what to do about it.

Having been in this fiery wasteland more times than I care to admit, I learned that at some point Founders have pretty much three options to escape, and "we'll just hold out for funding" isn't one of them.

Buy it Back

Let's start with per...

Startup culture has gone from glorifying victory to glorifying effort.

"Hustle Porn" has become more and more popular, particularly on social media, where would-be champions of entrepreneurship proclaim their insane personal sacrifices to the Gods of Startups. We're constantly wooed with tales of Founders putting in insane hours, risking it all, and coming away with the spoils of success to show for it.

How much of this is really a celebration of hard work and is how much is just the equivalent of giving ourselves a Participation Award for effort?

"I just put in 100 hours this week!"

Let's start by debunking the myth that working 100 hours in a week is somehow a victory to be lauded — it's not. The intention is that we're SO dedicated to ou...

Celebrating adding staff is like celebrating the cost of a wedding — it's the liability, not the achievement.

It seems like everyone loves to champion the importance of "scaling our staff," whether it's the media or our local government talking about job creation (when is the last time a startup was successful because it met a job creation metric?) Of course, we proudly announce we're hiring because it implies that our business is doing well, right?

While that may be true, the reality is adding staff still falls under the cost bucket of our income statement, and while those important hires may help us grow revenue, the important distinction is that they are not, in fact, revenue.

They are actually a massive cost, and in most startups, by fa...

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...