Startups - When to Stop

Relentlessness can become self-damage. How can we startup lunatics strike a balance when we have to reach beyond normal, beyond reasonable, beyond even do-able to prove it can be done?

Intentions and Balance

My CEO intentions:

  • I will move mountains, redefine international boundaries, and ride solar flares for my team.
  • My investors will soundly sleep, warm with the understanding I will do anything to prove them right for supporting my team.
  • Customers, too, will feel my conviction and become our sales force because of our unending drive.
  • Everyone will know every time they look in my eyes and hear my voice: I will not let you down.

This philosophy hasn't changed despite failing.

The shadow of this attitude is Burkowski-like self-destruction.

How can we startup lunatics strike a balance when we have to reach beyond normal, beyond reasonable, beyond even do-able to prove it can be done?





The Romance of Pain, Death, and Destruction

Oh, that moment! You meet your competition for the first time and they know, they grok you and your team are different.

Hannibal is here.

I never saved anything for the swim back.

  • Vincent via writer Andrew Niccol

Customers, too, they know and they want to experience riding on a Juggernaut.

Most of the people I dig have similar traits, and find themselves on difficult, long, artistic paths.

I descend from the sky and land on things really hard, and I go at everything with that amount of fury.

...and if it burns my body to a crisp I'm happy to go right now.

  • Henry Rollins

Doug Stanhope, Louis CK, Henry Rollins, Ricky Gervais, Werner Herzog, and others all trust their passion.

Doing so without perspective hurts.

Passion is that which destroys reason.

So keep your goddamned perspective, and watch for siren songs.

Check Yourself: I Doubt They Want You Dead

Even with an all in approach, I doubt your team wants you dead.

Which of your investors asks of you: Please kill yourself for my bank account?

Which of your teammates says: Damage yourself permanently.

If you believe anyone on your team does and you want help talking to them, contact me. I will gladly correct their thinking or your perception.

Check Yourself: Death is Easier than Destruction

When you are dead you no longer have to work.

When you are destroyed, you have to get out the broom and the mop and the greeting cards and rubbing alcohol and the hardcore scrubbing tools.

You have to tidy your dignity and ego and reputation and credit score.

The club is boring.

"Now he's gone and joined that stupid club. I told him not to join that stupid club."

Check Yourself: Vices

A beer with a buddy can be better for you than a workout.

Funny as the joke is—too much of a good thing is a damned good thing—it's a lie.

Start with a small test if worried: What's my coffee intake?

Some personal rules to keep me on the cliff.

Rule: No Permanent Damage

Penn & Teller, in How to Play with Your Food spell it out with clarity: N.P.D. No permanent damage.

Some pain, some discomfort is okay, useful in fact, however, incurr no permanent damage to either reputation or health.

Doing so severely limits your opportunity to try again, and you already know how bloody tough it is to start something.

Do not hurt your future self.

Rule: Get Outside Yourself

Yes, we fight against the status quo and continually need to explain to folks their reality is limited, it really can be better.

This willful delusion serves us.

To a point.

Seek opposing minds who understand this paradox, and can share insight from outside.

Sometimes this comes from a board of directors, sometimes from a bulletin board of anonymous founders, sometimes from the kindness of the other noodles out there.

Rule: Play

Non-competitive play, yo, with the goal: laugh and remember it's just a ride.

For me, it's:

1) guitar and singing
2) non-competitive softball
3) friendly poker
4) drawing
5) trail running
6) watching standup
7) purring from the cat

I still play softball and poker competitively, though I cordon it off.

Respect your hobbies. They're fuel.

Rule: Audit Yourself

My perception, too, is bullshit. Audit myself, because while I am special, I am also not special.

1) What exact day does revenue come in?
2) How much?
3) Where does it go?
4) Can my team eat?
5) Can I eat?
6) Is this sustainable?

Really, jackass?

Rule: Track It

Another way to get an external perspective, this is why I created meometer in late 2011.

Track reality and predict where I'm heading.

Rule: Listen

Friends, family, and peers will provide hints I am steering left when I should point straight.


Sometimes their faint, soft words get drowned by my own inner voices.

Listen harder.

Practice quietness.

Rule: Winning at 60 is Just as Cool

It's a decade or two or three of work to become an overnight success. Slow movement is still movement.

Have patience and start the next thing. Integrate the lessons from last time.

Where was I 10 years ago? Wow. That's quite a distance.

Rule: Stop

Sunk cost fallacy?

Stop, for fuck's sake. Be a janitor in Alaska again and recalibrate.

Rule: Learn

What am I missing? I know this territory is vast and I only see so far.

I don't need to be right, this needs to be right.

Let me know.