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Newsletter #19 - My Top Ten Seasonal Businesses That Print Money
Nikolas Hulewsky
October 26, 2025
One Halloween business did $1.1 billion last year.
Another guy I know clears $15K per snowstorm with a crew of 4 people.
Seasonal businesses aren't just side hustles—they're cash-flow machines hiding in plain sight while everyone's chasing their startup fantasy. The best part? You can start most of these for under $10K.
This week, I'm sharing my top ten seasonal businesses that could fund your next acquisition (or replace your W-2), including:
What you missed this week on Nikonomics
BUT FIRST, I want to create better content for you. Please take 2 minutes (if you haven’t already) and fill out this survey. You deserve awesome playbooks, business plans and tools just for YOU!
Why Seasonal Businesses Are Perfect For First-Time Entrepreneurs
How seasonal businesses can turn into money-printing machines.
Listen, I know these businesses aren't glamorous. You won't be pitching VCs or posting about your SaaS metrics. But here's what you will be doing:
Making money… FAST
Here's why seasonal businesses are criminally underrated:
Low barrier to entry: Most can be started with less than $10,000, some with just a few hundred dollars.
Massive demand: People need these services, and they need them NOW.
Simple operations: There is no complex tech stack and no inventory nightmares. (mostly)
Sweaty startup magic: You're trading elbow grease for cash, which means less competition from the bros that just want to "work on their laptop".
Scalable: Start solo, hire a crew, then manage multiple locations as you get more holidays under your belt.
Hear me out… One Halloween business alone did $1.1 billion last year. Let that sink in.
My Top Ten Seasonal Businesses:
1. Halloween Pop-Up Shops (Fall)
The costume and decoration industry is massive. Rent empty retail space in September, stock up on costumes and decorations, and ride the October wave. That $1.1B company I mentioned? They proved the model works at scale, but there's plenty of room for local operators.
2. Porch Pumpkins (Fall)
Buy pumpkins wholesale from farms, sell them retail in high-traffic areas. It's agriculture meets arbitrage.
Bonus: You could pair these with hay bales, mums, and cornstalks for higher margins.
3. Fireworks Stand (Summer & New Year's)
Let’s be real, Americans love blowing things up. This business has two busy seasons, which means two opportunities for massive markups. Permits can be tricky, but the margins make it worth the hassle.
4. Pool Cleaning (Spring, Summer & Fall)
Pool owners hate maintenance. Which is great for you because it means demand is insane for this business. You’ll have recurring revenue, low startup costs, and you can build a route that prints cash for 6-9 months a year.
5. Leaf Removal (Fall)
Every suburban homeowner's nightmare is your opportunity. All you need is one truck, some equipment, a few employees, and BAM, you're in business. You can charge by the yard or the hour, the world is your oyster.
6. Christmas Tree Farm/Lot (Winter)
This one is a little tricky to start, but I really love this business. The farm itself will require land and patience (trees take years). But four weeks of controlled chaos can net you $50K-$200K+.
7. Christmas Lights Installation (Winter)
Homeowners want the Christmas cheer that comes with a fancy light setup. But few people have the time to Clark Griswold their house. Luckily, that’s where you come in! They don't want to risk their necks on a ladder. Charge $500-$5,000 per house for installation and removal. Scale with a crew.
8. Snow Removal (Winter)
The original side hustle of every ‘80s kid looking for a few bucks. But if you turn this into a business, one snowstorm can easily mean $5K-$20K in revenue if you've lined up commercial contracts. However, residential driveways add up fast too.
9. Backyard Ice Skating Rink Installation (Winter)
Niche, but profitable in the right markets. You’ll find families that will pay $1,500-$5,000 to have a backyard rink installed for a few weeks of winter magic with the kiddos. The setup is straightforward once you learn the system, and it could be an easy way to make seasonal money.
10. Shaved Ice Stand (Spring, Summer, Early Fall)
This business is the definition of low overhead and high margins. People will line up in the heat for this sweet little treat. Whether you are mobile or stationary, this business practically runs itself once you dial in your locations and recipes.
The Question You Need to Answer: Which one would you start or buy?
Here's my advice.
Pick the one that matches your climate, your skills, and your risk tolerance. Then go all-in for one season. Test it and see what works, learn the problems you can solve in the next season if you want to scale. Or, if you hate it, move on and pick another.
The people making their first million aren't always building the next big thing. Sometimes they're just showing up with pumpkins in October or a plow in December.
The opportunity is there, and the demand is proven.
The question is: are you willing to get your hands dirty?
This Week on Nikonomics:
Every week, I dive deep with entrepreneurs who've cracked the code on building real businesses. Here's what you might have missed:
The $1.5k Per Job Drone Hustle You Can Start Today ($1M+/Year)
Guest: Chris Koerner
Drone Roof Inspections are exploding. The industry’s growing 15%+ CAGR, half of insurance adjusters are retiring, and drone tech is stepping in to fill a 400,000-job gap.
Chris and I break down how a $2,000 drone + FAA license can turn into a six or seven-figure operation because:
The margins are massive
The labor crisis = your tailwind
Regulation = your moat
Listen Here → YouTube
Is OpenAI’s Agent Builder Ready For Work? Honest Review + Demo
Guest: Elizabeth Knopf
OpenAI just launched Agent Builder, and for the first time, non-technical founders can create autonomous workflows that think, remember, and act, without needing to write a single line of code. In this episode, we cover:
How automations follow rules, but agents make decisions.
Why guardrails protect your data (and your brand).
Why usage-based pricing is a double-edged sword.
The $4.5 Trillion Reason This Doctor Quit The Mayo Clinic
Guest: Dr. Sandeep Palakodeti (aka Dr. Deep)
Dr. Deep’s company, Velocity Health, is flipping American medicine on its head by treating longevity like a KPI, not an afterthought.
Dr. Deep and I break down:
How his precision medicine clinic is scaling nationally using a SaaS-style subscription model
Why Healthspan is quickly becoming the next trillion-dollar industry
How subscription healthcare works
Ask Me Anything
Every week, I answer questions sent to me via Twitter, Speakpipe or [email protected]. |
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Nik Hulewsky