Breaking up with investors at the end of a failed startup journey is basically every Founder's worst nightmare. It's that awful conversation we did everything in our power to avoid. We rehearsed it over and over while starting at the ceiling at 3 AM. And yet, here we are.

How we break up with investors is as important as how we built the relationship to begin with. That's because in the startup world, building long standing relationships among key players, including investors, is all about treating those folks with respect at every step of the journey — even the shitty ending part.

We need to own the outcome

This is no time to point fingers. It was our job to create a successful startup; it didn't work out — we have to own that. This is th...

Founders are rarely prepared for how to handle a legit crisis, like when the whole world turns upside down overnight.

I lived through 9/11 with 700 employees, raised multiple funding rounds in the middle of the 2007 Financial Crisis, and just for "funsies" oversaw the overnight shutdown of a startup with 450 people.

So yeah, I have some experience here.

What I've learned is when crisis hits, a solid approach to communication is one of the single most effective tools we can employ.

Cut the Bullshit

In times of crisis, no one wants to hear the sugar-coated version of where things stand.

"Hey Team, I know half of you have turned into flesh-eating Zombies, but the good news is there's way more La Croix for those of you who have survived!"

No...

Would you rather make $200K with a shitty quality of life or $100K with an awesome quality of life?

In the startup world we all seem to understand that $200K is better than $100K, but we do a really lousy job of qualifying that difference based on what actually matters — our quality of life.

When we step back for a second, we may come to find out that "compensation" in strictly monetary terms, is a broken metric. We're all really trying to translate those dollar signs into how it will impact our quality of life.

So why don't we just start with what improves our quality of life and then figure out where money comes in?

What we really want is time.

Years ago at Startups.com, we instituted a work from home policy. At the time we were all sti...

8 years ago I decided that whatever startup I was going to launch would be the last startup I ever did.

I made this decision after launching 8 startups and realizing that creating a company as a "means to an end" was a shitty way for me to live.

I found myself in this constant cycle of being wildly preoccupied by "the next thing." Raising money for my startup was a means to a quicker exit. Killing myself meant I could finish this chapter faster, more successfully.

I had endless justifications for compromising my life because I could always "make it up later."

But what if there was no "later"?

This time around I decided to change it up.

I asked myself, "What if I picked what I wanted to do for the rest of my life NOW?" So instead of maki...

During the early days of my first startup I stumbled upon a huge liability that was killing us quickly — me.

What's funny is no one else needed to have this discovery. The rest of the organization had figured out long ago that I was immature, combative, prone to anxious tirades, and generally a pain in the ass to work with.

And looking back, I'm probably being kind.

As a Founder (and CEO), every single one of those idiosyncrasies becomes amplified a hundred-fold because my liabilities to the organization become rooted in every decision we make, every interaction we have, and the entire morale of the company.

If we don't exercise some serious self realization — and do it quickly — we may be creating one of the biggest hurdles our organiza...

There's an incredible amount of magic in having very little time to get things done.

That's why at Startups.com, with over 200+ people, we manage our entire workload based on what we plan on getting done by Friday. That's it. No long term planning sessions, no confusing Gantt charts or Trello boards. Just 5 days to get stuff done.

And damn it's effective.

Less Time = Less Room for Excuses

The problem with creating longer planning cycles is that every additional day, week, or month decreases the visibility and accountability for a single day of work. Our focus needs to be reducing the amount of time we can cheat on our time.

Imagine we wanted to lose 10 pounds this year. At lunch, we can order a cheeseburger, because hey, we have all year t...

While the novelty of creating the next Facebook sounds amazing, the truth is we don't need to necessarily invent a product to bring a new innovation to market.

If we look closely, we'll see that some of the fastest-growing companies out there — Uber, Casper, Dollar Shave Club and dare I say it, WeWork — are all based on ancient business models with a new twist.

Start With This: "What's Wrong With Current Products?"

Look, Uber didn't invent taxis — they just simply asked, "What's broken about the taxi business?" (Well, the limo business initially but who's tracking?) Any of us would be hard-pressed to find an existing product or service that couldn't use a ton of improvement.

What customers care most about is the improvement. Maybe that's ...

Startups feel like sprints in the beginning, but for any of us who have done this before, we've learned that it's a marathon.

We're judged by our speed when we start — and our endurance when, and if, we finish.

When Does "Pacing" Ourselves Start to Matter?

Not in the beginning. In the beginning, it's full sprint all the time — or at least that's the way it feels. We've got a headful of energy and we're ready to tackle every problem with longer nights and more stress.

But it doesn't take more than a year or two before those late nights and sustained stress start to run us down. Getting fired up over every last problem, and the stress that comes with it, begins to burn our cortisol levels to a dangerously low point.

At that point, the spr...

Let me first admit: I am a recovering long-hour champion.

For nearly 3 decades, if you asked me how many hours I work, I would just say "All of them." I wore it as a badge of honor. For almost 20 years it never occurred to me that you could drive to or from work in daylight. For my first three years of my startup career I didn't see my family or celebrate Christmas.

Now let me admit what a colossal flipping waste of energy that was.

Yes, I created great startups and had some success. Yes, a lot of that "hard work" was necessary. But now, with the benefit of history and having watched thousands of startups go from zero to something, I've come to learn something:

Those long hours were a symptom of inefficiency, not a default badge of honor ...

We're all freaked out about sharing our flaws.

We're worried that employees, investors, customers and just about anyone else will think less of us. Maybe they won't invest, maybe they won't buy our products, or maybe they won't come to work for us.

Sharing our flaws is terrifying. But it's also one of the most liberating things we can do not just as Founders, but as the weirdo humans we all are.

You're the Founder/CEO of Startups — do you have flaws?

Geez, where do I begin?

I've been building startups for nearly 3 decades and I have tons of flaws. I've got massive ADHD (I can't even proofread this sentence without losing focus), terminal pain, crippling anxiety — and I can't dance to save my life.

For a long time I would have never even...