The Seven Signs Your Entrepreneur Friend Is Going to Fail

There are several stages of the entrepreneur’s progression into the pit of hell that is a startup company, and I am here to be your guide through each one.

Every time a startup dies, a talented young person has to re-prioritize. Pexels

Many times people assume that because I love computers, I must love startups too. Those people are very wrong.

I didn’t used to be such a grump. You see, I came of age in suburban Connecticut in the late ’80s and early ’90s, looking to the nascent Internet to find the tribes I couldn’t find IRL: fellow Bette Midler fans; women who seemed impossibly sure of their sexuality; people who worked with computers every day as part of their actual jobs without being ridiculed as nerds. I even became a tech journalist world who writes about technology and the Internet for a living.

But I’ve realized that asking a person who worked at a startup about “what it was like to work for a startup” is like asking your friend who got blackout drunk to detail their thoughts on the later portion of their Saturday evening. The far more reliable witness, in my opinion, is the friend of the person at the startup, the boringly employed observer witnessing the hideous spectacle from afar. If that friend is a remotely decent person, at a couple of crucial junctures they attempted to talk their friend out of the startup, advocating any other kind of job or activity in its place—even grad school, even a useless MFA. There are several stages of the entrepreneur’s progression into the pit of hell that is a startup company, and I am here to be your guide through each one:

Stage One: So You’ve Got a Friend Who Really, Really Likes Startups

  • DURATION: one to four years
  • DANGER LEVEL: When you hear noises in the walls of your apartment each night but you’re still able to convince yourself that those noises are definitely not mice

Working at a company is so lame and boring, your friend Rory or Chad is saying! There are so many things that make companies so lame to work at, like benefits and office supplies and a boss who gives you regular feedback. Wouldn’t life be much better at a startup? Startups are in business magazines. People who work twenty-four hours a day at their startup feel much more freedom in their lives than people who work at nine-to-five jobs. Just like what’s his name, Horatio Alger. That guy would definitely be the cofounder of a startup, along with an engineer named Boris whom he’d never met in person because Boris lives in Russia and also maintained a side business as a club promoter.

Dangerous influences for your friend at this stage include seeing pictures of the Google cafeteria, reading the poetry of a then-unknown twenty-something Jack Dorsey, and/or meeting other people who also have ideas for startups but have not suffered the isolating hell of actually forming a company themselves. All of these things will solidify your friend Rory or Chad’s beliefs that it’s a good idea to build a wooden spaceship bound for the moon, also known as a startup.

Stage Two: You’ve Noticed That Your Friend Has Bought Some Books by Famous Venture Capitalists That Are Full of Advice About Startups

  • DURATION: One week
  • DANGER LEVEL: SpaceX ship bound for Planet Delusion

Once your friend is really wading in deep, it will be time to start reading the books and tech blogs of startup land’s most revered figures: the venture capitalist.

A venture capitalist is like a member of clergy in the Catholic Church: he uses his power to prey on young boys and then forces them to keep the particulars of their relationship a secret. (Examples of startup-founder-and-venture-capitalist special secrets: this startup will never make any money / this startup is technically designed specifically and only to lose money / this startup has lost even more money than it wants to tell its investors about because it is just that much money.) The venture capitalist also expects patently ridiculous things in return for their involvement in digitally savvy young men’s lives, namely a return on investment of “100x.”

The other thing venture capitalists have glamorized in their books—almost as much as the idea of 100x—is a new, more positive emotion around the notion of “failure.” Success is success, sure—that’s why we have the whole 100x thing—but failure is success as well.

Before you know it your formerly normal friend is absolutely devouring these books, highlighting the shit out of the pages of The Hard Thing About Hard Things.

Stage Three: Oh God, They’ve Narrowed It Down to One Idea

  • DURATION: six weeks
  • DANGER LEVEL: Taco Bell “Fire” Hot Sauce plus the all liquid garbage from an outdoor music festival

In the earlier stages Startup Friend will entertain several equally useless ideas for new mobile app companies. Let me try to guess for you right now what they are: so one is about food delivery, right? A specific snack they like when they’re high? And one is about a very specific problem that they experienced while traveling (“I was flying to Indonesia last year when I noticed that there was nowhere to buy GMO-free insect repellant”), and one is about sharing fashion with like-minded strangers. How close am I right now?

In the Narrowing It Down To One Idea stage, things get dicey. An argument for all choices—quitting work, gambling on a startup, the hobo’s logic that their startup will end up in the less than 1 per-cent that are successful—will not be successful at this stage. You’ve already lost your chance for at least a year.

Stage Four: Time to Write a Pitch Deck for All Your Lucky Future Investors!

  • DURATION: endless
  • DANGER LEVEL: Gravity has ceased to exist.

The purpose of a pitch deck is for the startup founder(s) to select a centuries-old industry that they plan to “disrupt” by means of their digital “innovations.” Food is a $90 trillion industry, a typical pitch deck will begin. And by our calculations, if can capture even 10 percent of that industry, it’s a $20 billion opportunity. Simplistic, highly designed pie charts will accompany these decrees, with all the data points very creatively sourced. (“According to the website Chartbeat, the attention economy of the food universe is growing by over 96 percent!”) Later on, in the section labeled “Our Team,” photos of young men jamming out at Coachella, standing next to surfboards, or skateboarding down a public staircase will accompany their biographies, with these photos intended to increase an investor’s confidence in the group’s overall money-making capabilities. Somehow this works.

By the time you’ve read a dozen of these presentations, they go from being comical to the new normal of business communication. Startup pitch decks’ most definitive trait is that they reduce profoundly complicated macroeconomic situations into folksy binaries, making any system’s problems seem surmountable by a small team of mobile software engineers. In a typical pitch deck a problem-solution statement will go something like this:

Finance is broken.

Followed by:

But Moneybong can fix it.

You try to see the good intentions in these presentations, at least for the first couple of years. You try to believe all the hype. Young people want to change the world with their companies, you think to yourself. Isn’t that nice? However, the flaws in the optimism become ragingly apparent somewhere around years two and three of hanging out with your friends who have committed themselves to starting startups: your sleepless, constantly worried friends who believe they’ve deftly avoided the hell of working for a big company all while failing to recognize that the pressure placed upon them as a startup person may indeed be killing them. Is finance broken? Yeah, sure. But is the team at Moneybong really the exact assortment of minds that the world wants guarding its retirement funds? And can the whole of “finance” really be “hacked” by a team of children in a coworking space who have never so much as applied for a car loan?

Stage Five: A Tech Team Has been Assembled (Sometimes in New York, Usually in Kazakhstan) and a Product Has Been Released

  • DURATION: one to four years
  • DANGER LEVEL: Your kid’s pregnant hamster is hiding somewhere inside your apartment building.

The product is done! Hasn’t the whole world been waiting with bated breath for this exact kind of product to come out? By the way your friend is talking, you would think so. The email flow at this stage will be daily. Your friends will want you to promote their product and believe that you “owe it” to them to promote said product. Because if you had a product, they would definitely redirect their lives to promote you.

This is when the blogs will happen.

This is the time when your friend will get a big ego but believe they are “staying humble” as they now carry no fewer than three different cell phones everywhere they go. The myriad cell phones will exist to both test the product on different hardware and also to field numerous calls from powerful people. One of my startup friend’s signature hangout moves is to casually-not-casually lay down their three to four cell phones on the table and then sit down behind them, like a king in front of his bowing subjects. Once I watched an actual doctor witness this ritual and then shrug ever so slightly with understanding: Hey, that guy has to do Internet, his inner monologue seemed to say, I’m only a doctor.

Secretly, by this stage, no matter how much capital your friend has raised, they are running low on it by now. They are starting to get nervous, and all the stuff they blathered to Fast Company was just an attempt to win some venture capitalists for a few more days, give them something to tweet to their fans.

Stage Six: Your Friend Has an “Office”

  • DURATION: one year, give or take a year
  • DANGER LEVEL: Low, because this will drain the money from the startup venture capital coffers and potentially return your friend to you.

When young people are allowed to design their own offices, awful things happen. I’ve never worked at a startup, but I have worked at an office designed for and by young people, and that was pretty close. Every employee had a locker with his or her own name written on it. This office smelled like toast, dead rodent, candy, perfume, and burning plastic. Each employee had approximately two feet of personal working space, and then someone else’s working space began, which of course made it impossible to work. There was also an office dog named Lola, who was a small, Wizard of Oz–looking animal acquired on a drunken impulse, and she was decidedly not house trained. Lola smelled like wet bacon and ate a steady diet of cigarette butts and stickers off our office floor.

Sometimes Lola barfed and then ate it during conference calls. It was impossible to make points while Lola gagged loudly, producing a blob of what looked like Campbell’s Chunky Soup and then, cautiously sniffing at her own creation, would begin to lick it. We were begging her not to do what we could see her considering next, muting the phone and loudly yelling. Children, inhabiting an office.

The other thing I remember most about working in a startup-like office was just how many days could go by without anyone doing any work. Points and debates that I can recall from this office include:

  1. “I can’t believe they let newscasters fly a helicopter and do the weather. Does anybody remember the 1980s, when Jane Dornacker flew into a bridge?”
  2. “Oh my god, I just sprayed Raid on my glasses.”“I think I have psoriasis of the liver.”
  3. “Does Zicam even work? What the fuck is dissolving inside my mouth right now?”
  4. “I’m glad we’ve given Guy Ritchie a twenty-fifth chance at directing.”
  5. “Picture this game: it’s a blending of Twister and Battleship called Battlestrip.”

Because it’s impossible to work in young-people offices, often nothing gets done. And for startups that’s when the money trouble starts. And ultimately money trouble is a problem that’s impossible to stop

Stage Seven: Reality Sets In

  • DURATION: Quick yet long at the same time
  • DANGER LEVEL: Of course having a bunch of debt is stupid. Of course it is.

Funding is running low. Very low.

This is because “venture capitalism” is just a fancy name for “debt.” The Silicon Valley/Alley response to running low on funding is simply to spend more of the existing funding on some “big ideas.” (Read: things that have not been thought through, which makes any-thing seem big. Dave Morin and the team at Path thought they could steer their dying social network toward profitability by selling people digital stickers. That’s what I mean by “big idea.”)

At this point the final stages will happen in rapid succession, sometimes within the constraints of a single week. They are: Back out. Never apologize to anyone for all the downloading, tweeting, emailing, Facebook liking, reviewing, and using that you made everyone do.

And finally…

Bonus Stage Eight: Good-bye

Every time a startup dies, a talented young person has to re-prioritize. And to these young people, I say, don’t become a bald, old white man standing over a barbecue, thinking you’re a part of the solution.

Jess Kimball Leslie is a technophile, futurist, and author of I Love My Computer Because My Friends Live in It: Stories from an Online Life (available now). Jess‘s writing on tech and media has appeared in The Atlantic, TechCrunch, Elle, The Hairpin, Anthem Journal, The Awl, and The Tribeca Film Festival blog. The Seven Signs Your Entrepreneur Friend Is Going to Fail