How to Kill a Startup: A Short, Ten Step Guide

Never be afraid to laugh at yourself, after all, you could be missing out on the joke of the century. —Barry Humphries

*Above: Potential movie posters, were films ever made about Glyph’s untimely demise.*

Longtime readers may know that before the long, circuitous route to my current “portfolio career”—one comprised of writing, investing, thinking, advising, consulting, researching, speaking, ghostwriting, and more—I failed as founder.

Alongside my younger brother and older cousin, I worked to give rise to a simple, though compelling, concept. Per our long-dead website and iOS app circa 2014:

Glyph was born from a simple idea: we love family games.
We love the fun banter, absurd quips, and clever taunts that occur during a boisterous game night. Unfortunately, at present there exists no way to recreate that experience on a mobile phone.
We set out to change that.
Glyph’s platform offers a way to play one of our favorite games—charades—using emojis, all while seamlessly chatting with your friends We strive to redefine the group chat experience by building a platform that finally offers a proper integration between games and group messaging.
Let’s change the way we talk.
Let’s make group chats more fun.
Let’s make games more interactive.
Let’s make social media more social.
Let’s Glyph.

Given the Cambrian explosion of both social messaging apps—iMessage, Facebook Messenger, WhatsApp, Snapchat—and silly games—Angry Birds, FarmVille Candy Crush, Clash of Clans—since 2014, I still believe the idea behind Glyph was both solid and timely. (To say nothing of our lovely logo, designed by my friend, the exceptionally-talented Steph Wulz.

That said, our collective execution was anything but. If a gif, it would have resembled the following:

Put simply—per Khalid’s catchy hit—I was young, dumb, and broke; a twenty-one year old intoxicated by the seductive mix of blissful ignorance and fatal naïveté.

Though this experience deserves a more thorough postmortem (stay tuned, dear reader, that is a longer post for another day), recalling it brings to mind two germane quotes. Each relates to a classic entrepreneurial axiom:

If you assume, you make an ass of you and me.
- i.e. Not all personal problems are venture-scalable businesses.
It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.
- i.e. Seek—and listen to—feedback from your ideal customer in order to make something people want.

And so, inspired by Late Night Great David Letterman’s Top Ten Lists of old…

…I cobbled together a Top Ten List of my own.

How to Kill a Startup: A Short, Ten Step Guide

X. Utter those famous last words: “How hard can it possibly be?”
IX. Opine about the wonder and virtue and joy of “being one’s own boss.”
VIII. Look in the mirror and see a self-styled, Irish-American Mark Zuckerberg. Name him something stupid, something like Mark O’Zucky.
VII. Bootstrap your business and pay yourself a middling salary — thus incurring unnecessary taxation.
VI. Assume PMF stands not for Product-Market Fit but rather Pretty Much Finished. In hindsight, this was incredible foreshadowing.
V. Launch a rebrand before a product.
IV. Order all of the swag—socks, fidget spinners, sunglasses—in the name of “marketing” and “customer acquisition.”
III. Fall victim to Shiny Object Syndrome — chasing new superfluous features and wasteful widgets like a moth to a bug zapper.
II. Spend more time playing your game (with your two cofounders, no less) in the name of “market research” instead of promoting said game to potential customers.
I. Take a job at a Big Tech firm, thus immolating any last shred of entrepreneurial ambition.*

*For a time, that is. Stay tuned and watch this space.