We are still struggling with a broken right thumb, or boo-boo, considering that Halloween is upon us. Scary that it’ll take a few more weeks to heal, and speaking of scary, we decided to consider what lessons Halloween might have for founders.

First, a bit of history. “Some say the festival has its origins in pre-Christian traditions that mark the changing of the seasons,” according to MSN. “The ancient Celtic festival of Samhain, was also a pagan religious tradition that welcomed the end of summer harvest, and the changing of seasons… The Celts reportedly believed that around this time of the year, the veil between the living and the dead was thinner, and spirits could walk the earth. This is where the costumes came in, worn as disguises by festival-goers so they could “avoid being terrorized by all the evil spirits walking the Earth during Samhain.”

“Halloween just has that open world magic that you don’t get any other time of year. It’s this one day where everyone is encouraged to dress up as whatever wild thing they want, and go walking around town together while other groups of kids/teens do the same thing. It’s this wonderful, connected community that doesn’t exist for anything else,” a fan on Reddit commented.

Halloween is, above all, a social holiday. People love donning costumes and yea, even in this era of newfound sobriety, getting together and ‘boos’-ing it up!

Like most holidays, it’s also big business. NRF Consumer Survey Finds Halloween Spending to Reach Record $13.1 Billion and Pet costumes are an $860m business. This is something to think about, founders. While investors seemed to have tightened their belts, time to think outside the box. Example: Spirit Halloween is making short-term leases cool.

“The key to success has been Spirit’s commitment to scooping up short-term leases,” Morning Brew reported. “The store that kinda just appears one night in your local mall like an apparition only has a few months to make a year’s worth of revenue. Moody’s Ratings recently estimated that Spencer’s (which acquired Spirit in 1999) and Spirit made about $1.9 billion in 2023—with Spirit bringing in more than Spencer’s.”

Orange may be the color of the holiday, but that’s a lot of green! And note, we have a friend who made quite a tidy living making custom covid masks during the lockdowns and selling them on Etsy.

Next, think scary movies. Broadcasts and streaming services are rife with them the entire month of October. Our personal favorite: The Shining. We’re not a fan of gore and guts but if you want scary, Kubrick does not disappoint. In our opinion, The Shining and The Exorcist are to Halloween what Die Hard is to Christmas.

According to Gallop, Paranormal Phenomena Met With Skepticism in U.S. Two-thirds of Americans are skeptical of paranormal beliefs, yet more people go to see scary movies than they do comedies or dramas. Here’s the Box Office History for Horror. While you’re not a Hollywood studio, think AI user-generated movies or shorts and note to self: With more viewers than Netflix and Disney+ combined, YouTube is now TV’s biggest player, Quartz reported. And like other holiday entertainment, Halloween movies are evergreen (and orange), so during this – let’s call it – investor cold spell if not winter, time to start thinking outside of the box office as you’re bootstrapping your way to traction. There are plenty of holidays besides Halloween to contemplate, but if you’re moved to get those creative juices going and are casting about for Halloween entertainment ideas, consider: there’s nothing scarier than – pun intended – undertaking a startup. Onward and forward.