What’s scarier than the sugar hangover from eating a whole bag of candy corn??

These real life startup stories.

BEWARE, MY FRIEND.

No, no, no! Do not enter! Don’t do it! It won’t end well!

A startup founder just walked into the haunted office building despite all the warnings.

Let’s find out what happens next…

Ghosts of cap tables past!
Skeletons in the swag closet!
I know what you did last summer quarter!

Here are 6 terrifying (no, actually) startup stories to keep you up at night…or learn from!

Will you survive to tell the tale? Better to just avoid them in the first place!

Share your own terrifying experiences (or favorite Halloween wordplay) in the comments!

Build It And They Don’t Come

I have seen this haunting tale too many times to count.

Thousands or even millions of dollars spent building an app. No one uses it. Zero dollars in revenue.

SAVE YOURSELF!

Former Founder (or Investor) Comes Back To Haunt You

I know many stories of extremely messy ex-founder or ex-investor situations. Often it’s relatively gracious or maybe a little tense but amicable overall.

But sometimes these situations result in legal battles, (very) unattractive cap tables, and conflict that hurts the company irreparably.

Founder Gets Kicked Out

I’ve heard the reverse too. Founder gets pushed out and ends up with nothing.

  • Date before you marry! (especially true for investors, do they have a history of replacing founders?)

  • Review legal documents carefully – AI is amazing here!

  • Work with an executive coach on leadership, communication, culture to head off issues and grow with your company

Now You See Them, Now You Don’t

We’ve all heard the lines:

  • “I definitely want to buy that.”

  • “Build it and then I will buy it.”

  • “Do this work for me, then I will pay you.”

Or maybe it sounds like:

  • “We have this enterprise customer who is about to sign.”

  • “We’re doing just one more free trial, then it will be a paid contract.”

And then…nada. They ghost you. They decide to not move forward. They build it themselves. They export the helpful data.

Not Alive, Not Dead Either

Sadly, this is a real term in the startup world.

A company that’s still around but stalled out. The company is operating but not growing.

Enough revenue, capital, or hope that they haven’t shut down. But there’s no future.

The scariest (and saddest) part is the opportunity cost. What if all those smart, entrepreneurial people used their talents for something else?? What could they be building now instead??

A World Lost In Time (and Money)

You know that creepy scene of lost cities or sunk ships at the bottom of the ocean?

That happens to startups too.

Raised more money than the company is currently worth. Usually raising during a boom. Never growing into the valuation.

The company is “underwater” and it is gut-wrenching for everyone involved — founders, investors, employees have all poured in years, dollars, heart, soul with little to nothing to show for it.

Will this give you nightmares for weeks?? 😬👻🎃 I’m sorry if it was too scary! Next year will be only tricks and treats!

Do you have any scary startup stories?? How did you escape the mortal peril??