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From Zero to Side Hustle
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9 days ‘til Halloween!
👻 “Monster Mash” hit No. 1 on the Billboard chart in October 1962. It climbed back into the Top 10 in 1973, and every October, it returns without anyone having to reinvent it.
A song about a lab party became a seasonal fixture. It doesn't need to be popular all year. It needs to be the obvious choice for one month.
We look for businesses built the same way: demand that returns on the same date every year, from customers who already know it's coming.
Service is on.
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First Up, Our Sponsor
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You are sitting on $100k to $2 million of data
OpenAI, Micro1 and Anthropic have paid out billions of dollars to partner with companies on their operational data. It's creating a new revenue stream for businesses over 20 people and pays anywhere from $100k - $2 million a pop.
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Backyard Blockbuster
WHAT’S THE PROBLEM?
Every homeowners association (HOA), PTA and parent planning a birthday wants an event people will actually show up for. A giant movie screen on the lawn does that.
They want the big-screen night. They don't want to buy a screen, figure out a projector and sound, and stand in the yard at 11 p.m. packing it all up.
That's the gap: people want a movie night, not movie gear.
WHAT’S THE BIG IDEA?
Rent out the whole night: inflatable screen, projector, speakers, setup and cleanup. Backyard Movie Theater in Dallas charges from $375 for a backyard night and $650 for HOA and school nights, with a free rain date.
The business makes money on movie nights. But it grows from the same customer list, because those families also book indoor theaters and party add-ons.
►Derek Sharp, a North Dallas dad, started with a $250 to $300 Amazon screen a relative gave him. His first paid booking was $290. He told IBTimes the business did about $40,000 in its first full year and is on pace for $90,000 to $100,000, at 70% to 80% margins.
Zooming out: the screen pays for itself on the first night. The best customers book more than once.
Think: HOA summer series, school end-of-year nights, church groups, apartment complexes.
🥢The winners will be the ones who get on the community calendar. One HOA or PTA board can book a whole season. A standing spot on the calendar beats chasing birthdays one at a time.
🍜 The risk is weather and paperwork. Sharp's first job went wrong when wind damaged his cheap screen. And a movie shown at an HOA or school night usually needs a public performance license, which can cost $250 to $1,000 a film.
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What's your take?
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Hat Bars Turn Trucker Hats Into A Party
A trucker hat used to be something you grabbed at a gas station. Now groups pay to sit at a table, pick patches, and watch their own hat get pressed on the spot.
It's an activity and a souvenir in one, so bachelorette parties, birthdays and company events book it. A heat press, a hot plate that fuses a patch onto the hat in about 30 seconds, keeps the line moving.
At the big end, the branded-merch company Stitchi runs hat bars at company events for $58.33 a person, with a 100-person minimum. At the small end, Remix Trucker Hat Bar in Asheville charges $40 a guest with a 20-guest minimum, and a real estate agent opened Hat Over Heels on her Utah town's main street in 2024.
Where the trend branches next:
Company events, with the company logo on a patch
Bachelorette and birthday groups in a storefront
A mobile tent at bars and farmers markets, like Howdy Hat Bar in Milwaukee
Monthly pop-ups inside someone else's boutique
► The money is in group bookings with a per-person minimum, not in single hats.
If you try this, buy 30 blank hats and a bag of patches, run one free hat bar at a friend's birthday, and time how long each guest takes.
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Don't Miss This
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NVIDIA's Founder Says Farmers Should Absolutely Use AI
“If I were a farmer, I would absolutely use AI.”
That’s Jensen Huang, founder and CEO of NVIDIA.
He’s pointing to one of AI’s biggest untapped opportunities: farming.
DIT AgTech is already putting AI to work with 500+ units deployed and 370,000 head on-platform.
𝘐𝘯 𝘮𝘢𝘬𝘪𝘯𝘨 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯, 𝘪𝘯𝘷𝘦𝘴𝘵𝘰𝘳𝘴 𝘮𝘶𝘴𝘵 𝘳𝘦𝘭𝘺 𝘰𝘯 𝘵𝘩𝘦𝘪𝘳 𝘰𝘸𝘯 𝘦𝘹𝘢𝘮𝘪𝘯𝘢𝘵𝘪𝘰𝘯 𝘰𝘧 𝘵𝘩𝘦 𝘪𝘴𝘴𝘶𝘦𝘳 𝘢𝘯𝘥 𝘵𝘩𝘦 𝘵𝘦𝘳𝘮𝘴 𝘰𝘧 𝘵𝘩𝘦 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨, 𝘪𝘯𝘤𝘭𝘶𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘮𝘦𝘳𝘪𝘵𝘴 𝘢𝘯𝘥 𝘳𝘪𝘴𝘬𝘴 𝘪𝘯𝘷𝘰𝘭𝘷𝘦𝘥. 𝘋𝘐𝘛 𝘈𝘨𝘛𝘦𝘤𝘩 𝘩𝘢𝘴 𝘧𝘪𝘭𝘦𝘥 𝘢 𝘍𝘰𝘳𝘮 𝘊 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘚𝘦𝘤𝘶𝘳𝘪𝘵𝘪𝘦𝘴 𝘢𝘯𝘥 𝘌𝘹𝘤𝘩𝘢𝘯𝘨𝘦 𝘊𝘰𝘮𝘮𝘪𝘴𝘴𝘪𝘰𝘯 𝘪𝘯 𝘤𝘰𝘯𝘯𝘦𝘤𝘵𝘪𝘰𝘯 𝘸𝘪𝘵𝘩 𝘪𝘵𝘴 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨, 𝘢 𝘤𝘰𝘱𝘺 𝘰𝘧 𝘸𝘩𝘪𝘤𝘩 𝘮𝘢𝘺 𝘣𝘦 𝘰𝘣𝘵𝘢𝘪𝘯𝘦𝘥 𝘩𝘦𝘳𝘦: https://bit.ly/4bzuWCi
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How Pet-Sitter Software Found Its First Customer
Most people who build a tool for a trade build it alone and then go hunting for customers. The founder of a pet-sitter scheduling tool did it backwards: he called the customers first, and the first one who paid became his partner.
What they uncovered: Kyle Thielk, a software engineer in Austin, started Time To Pet in 2014: scheduling, client messages and billing for pet sitters and dog walkers. He reached out to hundreds of local sitters and walkers. Mike Grenier and his wife, who ran a pet-sitting business and couldn't find software that fit, tested it, and Grenier became Thielk's co-founder. Today Time To Pet says 4,500+ pet-care businesses use it, and a solo sitter pays $25 a month for the cheapest plan.
The usual mistake is building for an imagined "pet industry." Thielk built for one real business with a real calendar problem, then sold it to thousands more like it.
A $25 monthly price only works at volume, so the tool had to fit the daily routine of small sitters exactly. A partner who ran that routine every day was the shortcut.
What they learned: whatever tool you build for a trade, find one business owner who will use it every day and let them shape it. Other owners in the trade trust a tool that one of their own helped build.
His first customer was not "pet businesses." It was one Austin couple running a pet-sitting company who were tired of their scheduling mess. If you're building a tool, your first buyer is one owner in one trade who already complains about the problem.
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Hungry yet?
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Enough talk. Go cook.
That's the plate. Reply and tell us what your HOA would pay for one great night. Forward this to the neighbor who always runs the block party. See you tomorrow.
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