Evaluating Delusional Startups

April 28, 2016 holman

We’re proven entrepreneurs — one cofounder interned at Apple in 2015, and the other helped organize the annual Stanford wake-and-bake charity smoke-off — who are going to take a huge bite out of the $45 trillion Korean baked vegan food goods delivery market for people who live within one block of Valencia Street (but not towards Mission Street because it’s gross and off-brand), and we’re looking for seasoned rockstars to launch this rocket ship into outer space, come join us, we’re likely backed by one of the venture capitalists you possibly read about in a recent court deposition!

Okay, so they’re always not going to come at you like this. If you’re in the market for a new gig at a hot startup, it’s worthwhile to spend some time thinking about if your sneaking suspicions are correct and the company you’re interviewing with might be full of pretty delusional people.

Here’s a couple traits of delusional startups I’ve been noticing.

I’m gonna make you rich, Bud Fox

After a long afternoon of interviews, I sat down with some head-of-something-rather. Almost verbatim, as well as I can remember it, he dropped this lovely gem in the first four minutes of the conversation:

Now, certainly you’d be joining a rocket ship. And clearly the stock you’d have would make you rich. So what I want to aaaaahhHHHHHHHHHH! thhhwaapkt

The second part of whatever he was saying got swallowed up by the huge Irony Vortex From Six Months In The Future that zipped into existence right next to him, as the Rocket Ship He Was On would promptly implode half a year later.

In my experience, people who promise riches for you, a new hire, fall into two camps:

Both of those camps are fairly delusional.

Many leaders — unfortunately not all, but that’s life — that have a good chance at striking it rich tend to be pretty realistic, cautious, and optimistically humble about it. In turn, having those personality traits might also lead them to making more generous decisions down the line that would benefit you as well, so that’s also a bonus.

Lately I’ve heard something specific come up from a number of my close friends: the bonus they just received in the first six months from their new job at a large corporate gig far dwarfed the stock proceeds they made from the hot startup they had worked at for years.

People have been saying this for decades, but it’s always worth reiterating: don’t join a startup for the pay, and if someone’s trying to dangle that in front of your eyes, you can tell them to shove their rocket ship up their you-know-where.

The blame game

A company I was interviewing at borked a final interview slot with a head-of-something-such, so I rescheduled them for coffee the following week.

Sipped my tea for half an hour… no show. Hey, it sucks, but miscommunication happens so it wasn’t much to fret over.

The rescheduled phone call another week later started off with an apology that quickly turned into a shitstorm. The main production service was down he said, and therefore he could not attend our coffee, nor could he look up and send me an email about it, even though he did notice it and did briefly feel bad about it. The fucking CEO shat on my team the next day in front of the whole company which was complete bullshit because his team Had Done All The Necessary Things and really it was The CEO’s Dumb Fault The Shit Was All Broken Anyway right? Christ. In any case the position we were interviewing you for has been filled do you want to try for anything else?

So there were a lot of things to unwind here, and I truly do have stories from interviewing at this company that will last me until the end of the sixth Clinton administration, but the real toxic aspect is the:

Cultures that throw each other under the bus — in either direction, up or down — don’t function as well. The wheels will fall off the wagon at some point, and you’re going to end up with a shit product. You can even be one of those bonkers 120-hour work week startups, grinding hard at all hours of the day, and still be good people to each other. You’ve got to bounce back from setbacks and mistakes. Blameless cultures are better cultures.

On a related note, it’s amazing what you can sometimes get people to admit in an interview. While chatting with another startup, I informally asked what the two employees thought of one of the cofounders. Total shit was the flat response. Doesn’t do jack, and really doesn’t belong in engineering anymore. Props for their openness, I guess, and maybe it helped me dodge a bullet, but how employees talk about others behind their backs says a lot about how cohesive and supportive the company is.

We’re backed by the best VCs, we’re very highly educated, we know product, we have the best product

I don’t understand how you can love your startup’s product.

For me, the high is all about what’s happening next. Can’t wait to ship that new design. The refactoring getting worked on will be an order of magnitude more performant. The wireframes for where we’re hoping to be two years from now is dripping with dopamine.

I don’t understand people who are happy with what they’ve got today. Once you’re happy, you’re in maintenance mode, and maybe that’s fine if you’ve finished your product and are ready to coast on your fat stacks, but by that point you’re beyond building something new anyway. These startups who eagerly float by on shit they did years ago, assuming that rep will carry through any new competition… I just don’t understand that.

Stewart Butterfield has a healthy viewpoint when he talks about Slack:

Are you bringing other changes to Slack?
Oh, God, yeah. I try to instill this into the rest of the team but certainly I feel that what we have right now is just a giant piece of shit. Like, it’s just terrible and we should be humiliated that we offer this to the public.

Certainly he’s being a bit facetious here, since I don’t imagine he thinks the work his employees have done is shit — rather, a product is a process and it takes a long time to chip away the raw marble into the statue inside of it.

The other weird aspect of this that I’ve noticed is that there are some companies who truly hate their competition. I really dig competition, and I think it brings out good stuff across the board, but when it flips into Hatred Of The Enemy it just gets weird. Like c’mon, each of your apps put mustaches on pictures of fish, y’all gotta chill the fuck out, lol.

Asking people what they think about their competition can be a pretty decent measurement of whether the company twiddles the Thumbs of Delusion. If they flatly espouse hatred, that’s weird. If they take a nuanced approach and contrast differences in respective philosophies, that’s promising, because it means they’ve actually thought through what makes them different, and their product and culture likely will be stronger for it.

It also likely just means fewer dicks at the company. You can only deal with so much hatred in life before it sucks you up into a hole.


I get that startups are supposed to be — by definition, really — delusional, in some respect. You’re building something that wasn’t there before, and it takes a lot of faith to build a nascent idea up into something big. So you need a leader to basically throw down so everyone can rally behind her.

Maybe I’m an ancient, grizzled old industry fuck now that I’m nearly 31, but I’m weary of seeing the sky-high bonkersmobiles driving around town these days. That’s part of the reason I’m cautiously optimistic about this bubble that will certainly almost certainly okay maybe it’ll pop again soon — it’ll get people a little more realistic about their goals again.

I still think startups are great and can change the world and all that bullshit… I just think it’s worthwhile to stop and think hard about what your potential company is promising you. Catching these things early on in the process can help save you a ton of pain down the road.

And if you’re hearing these things at your current company, well, good luck! You’re assuredly already on a rocket ship, surely, so congrats!