Jan 31, 2013 · 4 minutes

When I was a high school student, I had the best friends that any teenager could ever want. We did the usual cool stuff that cool teenagers do, like drive around in our cool cars, drink cool drinks — like a cool glass of beer — and we watched a lot of cool sports. We were pretty cool.

But here was one of the coolest things about my friends — they constantly called me a “fat ass."

And what, exactly, was so cool about my best friends repeatedly pointing out that I was thirty pounds heavier than I needed to be?

It made me lose weight.

The summer after sophomore year, I decided that I didn’t want to be called “fat ass” anymore. But if I told my friends to stop calling me “fat ass,” it resulted in them calling me “fat ass” with double frequency. So I ran every day on my dad’s treadmill and ate ridiculously healthy. And when I returned to campus three months later, I was in the best shape of my life.

It was awesome. I felt like such a stud. But somewhere along the line, my friends changed.

No longer content to highlight one another’s deficiencies, they started doing things like telling me how much they liked my new sweater, or they praised my restaurant selection as “terrific." And when I did or said something objectively stupid, they would hold their tongues.

And, even to this day, when I talk about my dwindling gym attendance, I am rebuked with a chorus of “Stop it, you look great!” or something to that effect.

I liked it better when they called me a “fat ass."

No, I don’t need every asshole on the street or in the coffee shop to call me a name. Nor do I want my parents to do it. But — for the love of God — somebody needs to step out from the pack to tell me the truth, and remind me that stuffing my face is a bad idea. My friends should be the guys to do it.

So, with that in mind, let me get to the point of this article: You probably shouldn’t fail.

Your investors don’t want to hurt your confidence. Your wife and parents want to encourage your dreams. Your co-founders don’t want to acknowledge the possibility. The Silicon Valley establishment wants to foster collective risk taking. Your pets love you no matter what. And even though your grade school teachers don’t remember you, they would probably be encouraging.

It’s a good thing — no, a great thing — that all these people in your life and in the startup ecosystem have rallied around a message that failure is ok. Failure happens. A lot. And Silicon Valley’s attitude towards failure is one of its greatest assets.

But, since you and I are friends, and we can talk to each other like friends, I am going to let you in on a little secret...

Do not fail.

As it turns out, the same friends who called me a “fat ass” when I was a young teenager went on to be my co-founders when we started our company together. That’s right, I started a company with my high school friends.

And my group of friends had not a single asset when we went out to raise our angel round. We had no money in the bank. None of us could code. Our collective work experience was the sort of crap that looks bad on a founder’s resume — finance, etc. Even our pitch book was laughably clunky in its design.

But we had one asset that carried the day: we had never heard the “Failure is ok” mantra, probably because we never went to any Silicon Valley networking parties. It also helped that TechCrunch barely existed back then.

Our image of failure was one in which we marched into our lead investor’s office, lowered our heads in shame, and heard him scream — with red eyes the size of saucers — “You did what with my money?!” Then we were marched at bayonet-point to some dark, damp cellar with a chorus of faint whimpers accented by the occasional shriek. Half-starved Rottweilers skulked behind, waiting for their chance to feed upon the wretched founders who sucked so badly at driving user engagement. We were lashed for every page view milestone we failed to achieve. The man in the leather mask who grunted orders though his thick cockney accent, would drag our lifeless bodies to some opaque corner, and chain us to a cold, jutting rock… our mothers and fathers deemed us unworthy of missing.

That’s the image of failure that I think about so fondly.

Because that was the image that scared us into working nights and weekends, and when something went wrong, we cared so deeply about the misstep. I lost a lot of nights’ sleep, and sometimes I didn’t go to sleep until I had fixed the things that were going to cause my nightmares.

Vacations weren’t even very fun, because I felt helpless on the Cabo San Lucas beach without my laptop... I needed it to identify bugs and think about enhancing the user experience... or it was the dungeon for me!

Those were the good old days.

Negative reinforcement is very powerful, and I encourage every founder to identify at least one person who can be his or her pointy bayonet in life. Have that person give you shit every time he sees you drunk at a barbeque or occasionally text you something mean about how lazy you are.

It will help.

And — for the next 48 hours — you can send me an email at FailureIsTotallyOk@gmail.com, and I will make you feel three inches tall about how soft and feeble you are.

You can send me some advisor share grants when you close your Series A.

[Illustration by Hallie Bateman]