Calling Charon: When it’s Time to Send Your Venture Across the River Styx?

In the faux-alpha-male world of scaleups where one has to endure seemingly endless yarn from self-proclaimed entrepreneurial macho types who allegedly have Sequoias of the world begging them to invest in their fiftieth disruptive unicorn while they’re on the phone with Mr. Larry Google about the acquisition of said unicorn, it’s seldom we talk about shutting ventures down.

Previously I discussed the monomyth and the structure of epics to navigate the entrepreneurial waters, but what if your venture isn’t a Hero’s Journey? We all know 90% of ventures are not Greek epics, but dramas and tragedies.

I’ve decided to try to address this topic after the melodramatic fallout of a video game studio and their project called Police 1013. Alas, I still have a (hopefully fading) relationship with this industry where dramas and tragedies are always plentiful and juicy — you see, this is a potent mix of sensitive geeks and the brutal world of entertainment.

So, how come a CEO at the tender age of 47, with four kids, a brain tumor, mental health problems, suicidal thoughs and a game that is in development for almost a decade, wouldn’t call it quits sooner? It’s obviously a difficult question: psychologically, financially, morally, ethically…, but if there’s a tl;dr here, it’s quit before this happens to you

I should know; my business partner at the game studio I ran suffered a massive heart attack and almost died before calling it quits.

Ask the Hard Question

Do you feel like no matter what you do, no matter how much you invest in marketing, how much money you raise, how many times you pivot, how many bad apples you fire, or how much you try to fit your product in that market, has little effect and the venture just won’t hockeystick?

Do you always wind up killing your father, marrying your mother and gouging your eyes out, no matter what?

If your answer is “yes”, or even “well, I wouldn’t say it’s that bad, but”, it’s time to call that guy Charon at Uber Boats and set your venture sailing across the river Styx into the Underworld to join Juicero, Beepi, Yik Yak, Doppler Labs (dare I say Theranos?) and a pile of other Hades’ favorite scaleups that didn’t know when to throw in the towel and quit.

Alternatively, but similarly worrying, if you run a zombie venture, that is to say, a venture that won’t die but won’t grow fast enough, you’re in a very bad spot. You’re not interesting for investors which would help you grow, you’re not interesting to your top talent, which would help you grow and you’re not in enough trouble to go Chapter 7.

You’re in limbo, the worst place a company could be in.

Note: this only goes for scaleups. If you’re running a lifestyle business, this blog is not for you.

It’s Quiz Time!

So, instead of another long-winding blog that goes nowhere, let’s instead take a quiz! Answer the questions below and let’s see what I think you should do. Which is in no way, shape of form what you should actually do.

But, before you start tapping away the answers, here’s a pair of pro tips before you pull the plug on your business.

Don’t worry about investors. It shouldn’t be a surprise to them if they’ve followed the venture’s situation — if they haven’t, well, they weren’t doing their job. In any case, they are professional investors, so they should expect to lose money.

Take care of your employees — deal with them with empathy. Losing a job sucks. Do all you can to find work for them, help them with CVs and referrals, talk to them individually and see if there are any serious existential problems and help them find solutions. But most importantly, never blame them for shuttering your venture. They are doing what you ask them to, and if not, they are working in a dysfunctional company you are running and have set up.

So, the quiz! Simply answer what you feel is the most correct answer, and tap Submit.

Are you passionate about your business?


What’s your growth rate (CAGR)?


Do you like working with your cofounders?


Do you know how to drive growth profitably?


How is your LVT vs CAC ratio?


When fundraising or just casually approaching investors, what was their feedback?


Are people leaving the company?


Do you have problems attracting top talent?


Do you sleep like a baby — by that I mean do you wake up crying every two hours?


How’s your health, if you don’t mind me asking?


How many times a week do you feel like not going to work?


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