I Asked Listeners for the Most Random Ways They’ve Made Extra Money

Last month, I put out a call for listeners to share the most random ways they’ve made extra money, and the responses did not disappoint!

Some side hustles start with a business plan. Others start with a stranger in a parking garage asking if you want to get paid to drink beer.

That one actually happened to me in Atlanta. The woman worked for a market research company, and they needed taste-testers for a product that hadn’t launched yet.

I invited a couple of friends along, and we each made about $75 sampling what turned out to be Miller Chill.

Later we lived near a place called the National Food Lab, so I went over and did a few more paid taste-testings.

Tune into Episode 751 of the Side Hustle Show to learn:

the strangest things listeners have been paid to do
how a few of those random gigs turned into real businesses
where to find unusual rental and marketplace opportunities

1. Loading Chicken Trucks

Joe Saul-Sehy from Stacking Benjamins kicked things off with a story from his teenage years. He got hired to go out to a farm and help load chickens onto a truck.

The job sounded simple. Reach into the coop, grab a chicken, put it in the travel coop, but real life was different.

The birds panic and escape, and you chase them around a farm apologizing.

The “right” technique (grab both legs, pull hard, wing damage optional) was enough for Joe and his brother to quit at the first break.

As Joe put it, “that is the weirdest and the worst side hustle I ever had.”

My own one-day teenage gig was cutting out organic dog biscuits in a commercial kitchen for about $10 an hour. Tedious, and it didn’t smell great. But no chickens were involved, so I’ll take it.

2. Uber Eats Delivery, But on a Bike

Cody Berman, author of Retire by 30 and host of The Financial Independence Show, moved to Australia for six months while his wife studied abroad.

Rejected from 15+ jobs in Australia, Cody signed up for Uber Eats — but with no license, he switched to bike delivery, and with no bike, he bought a too-small, single-gear pink bike for $25 on Gumtree, in a hilly suburb.

He earned a few one-star reviews for sweating on people’s food.

His tips:

Get a bike that actually works
Go electric if you’re somewhere hilly
Or just pick a different hustle

3. Selling Snacks at School Lunch

Chandler Bolt from Self-Publishing.com got his start at Scout Camp. His mom sent him with a bunch of snacks, and he came home with a wad of cash and a switchblade knife.

In high school, he turned that into a business for his entrepreneurship class. Every two weeks, he and a friend loaded up a Prius at Sam’s Club until the wheels almost scrubbed, then worked the lunches selling drinks and snacks.

They made $8,000 in profit in about two and a half months. Chandler kept $2,000. As he said, he got paid to go to school. It worked so well that the school shut it down the next year.

I did the same thing at Scout camp, loading up at Costco and undercutting the camp trading post. And our youngest just sold $3 shave ice with a friend on a hot day — about $25 each for an hour’s work.

4. Selling Empty Smartphone Boxes

Jason Butler runs My Money Chronicles, a site about personal finance and side hustles. He’s flipped plenty of normal things: clothes, toys, board games.

The surprise was empty phone boxes. He’d read that someone online was selling them, so he listed a couple of Samsung boxes. They sold within a week.

There’s a whole economy in “worthless” items apparently. An original box can double or triple a resale price (used iPhones, Jordans, LEGO sets), so resellers pay $20-$25 for an empty one.

Same with vintage manuals. (A Charizard-shaped Cheeto once sold for $350, then resold for $87,000 — so check the snack drawer.)

5. Buying Out a Yarn Shop

Donna Westerkamp from DonnaWesterkamp.com walked into a yarn shop that was going out of business.

She asked what they’d do with leftover inventory, got a call from the owner, lowballed a price — and suddenly owned the whole stock.

She resold it on eBay and Craigslist, roughly recouping her cost. “The inventory was atrocious… but I made a ton of money,” she said.

Donna was already in the crafting niche, which matters. That’s what Shannon Jean recommended in Episode 731: start with what you know.

6. A $5,000 Yard Sale (and a Free Facebook Strategy)

Bill Fortenberry of Fortenberry Marketing built his company around a strategy he created for his dad’s business, which had a Facebook page and no marketing budget.

He calls it the 1-10-10 strategy:

1 post a week
10+ photos per post
shared in 10+ local Facebook groups

Bill needed test cases. Around the same time, he and his wife were downsizing and raising money for a missions trip to Ukraine to help at a youth camp for kids affected by the war. So they held a yard sale.

He took 30 or 40 pictures, put them in a single Facebook post, explained what the money was for, and shared it in local community groups. That one post brought in more than $5,000.

Jeff Rose covered another angle in Episode 706 — the Facebook content monetization program, earning $1,000 a day.

7. E-Bike Rentals

Wanting something to run around a full-time job, Brian Sadler from Wisconsin delivers e-bike rentals to nearby trails, campgrounds, and resort areas.

He did it the smart way:

built the website first
borrowed a neighbor’s bike to test the concept
and befriended campground owners who loved having a new guest amenity (some via paid partnerships).

The lesson: go where your customers already are. We have a scooter episode with Lenny Tim, who spent a couple of years on local SEO before buying a single scooter.

8. Renting Out Your Backyard to Dogs

Marie Frey from Nova Scotia has three kids four and under, including twins, so passive income was the goal.

She found Sniffspot, which works like Airbnb for dogs. Dog owners book her backyard by the hour. Setup took a couple of pictures and a price. Bookings are accepted automatically, so there’s no management, and she can block off times when the family wants the yard.

They made about $500 the first year and a little less the second. For something this passive, Marie says any extra money is a win. There’s no labor either — no dog walking, no boarding.

Similar marketplaces worth a look:

Swimply — rent your pool (hosts earn $5k+/yr; insurance included)
Neighbor — rent storage space (garage, shed, side yard, attic)

9. Board Game Rentals

Trish is in Kitsap County, Washington, near Seattle. She rents out board games, in her words, “like their DVDs from 2004.”

She runs it through her local Board Game Geek guild and rents through the Libib app. She’s building a subscription where people pay $20 a month to borrow four games.

She’s up to over 300 games, all labeled, scanned, and organized like a tiny Blockbuster.

It started because she loves board games but can’t read rule books at night, so she’s building a business around daylight gaming.

I like the subscription model better than per-rental. There are challenges to solve — shipping, missing pieces — but it’s a great niche.

10. Renting Out Baby Gear

Ariana Johnson became El Salvador’s first BabyQuip provider — renting car seats, cribs, and strollers to visiting families.

Chatting with them during deliveries, she spotted a gap and launched the blog El Salvador Kids Guide, which now brings sponsored reels and paid trip-planning consultations.

The two hustles feed each other. Some families find the guide and then rent gear; others rent first and come back for advice.

If you’re already the go-to travel planner in your circle, that’s a skill you can monetize — see Episode 670 with Bailey Richert.

11. Digital Nomad Co-Living and Retreats

Danny Flood had been traveling for years as a digital nomad, selling courses online through a partnership with AppSumo.

A friend in Greece invited him to a villa in the countryside, and Danny started organizing co-living retreats there.

The first one had three people, four including him. The next year he expanded to Nepal. Two years later, roughly 35 or 36 people came to the co-living in Pokhara.

Then people suggested a summit. He hosted one with more than 120 participants, with the Nepali government and tourism board attending. He’s back in September for the co-living and a second summit at digitalnomadsnepal.com, with about 40 speakers.

His advice: find a location that isn’t saturated, run it in shoulder season, pick a clear niche, and use good photos. Some of his first posts were just on Reddit.

If events appeal to you, try Episode 634 with Chloe Winstanley, or Episode 297 with Hung Pham on The Culture Summit.

12. Online English Lessons

Monica is the founder of English with Monica. She went from 524 TikTok followers to 70,000 in a year by going live four times a week and actually engaging.

That audience unlocked bootcamps, digital products, and memberships.

There are dozens of sites where you can teach English online, but it’s usually one-on-one, and typical rates might be $10-25 an hour.

If you build your own audience like Monica did, you become a market of one — and that changes what you can earn from the same skill.

13. Turning “Can You Help With My Resumé?” Into a Business

Two callers, nearly the same story — both started by request, not marketing:

Cyril (DareToCloud.com)

Cyril, a guitar teacher, was asked by a student’s mom to help with her CV.

He was great at it, got her up to speed on a required CRM, and she landed her dream job.

His realization: the real skill was communicating clearly to a specific person — “a CV is basically a landing page for a human.”

That’s now what he does for a living (website maintenance and SEO for B2B companies).

Balkisu Fidelis (Kisu’s CVs Collection)

Balkisu started by helping a friend apply for a job. Later that month, the friend referred someone else. Before long, people were paying her to write and improve CVs and cover letters.

Both started by request, not from marketing. That’s a great sign — if people ask for your help without you even trying, that’s real perceived expertise.

Years ago, Austin Church from Episode 417 told us to pay attention to what wants to happen. There’s also the Tim Ferriss line: what would this look like if it were easy?

If a project has sat on the back burner for years, maybe it doesn’t want to happen. And that’s okay.

14. Affiliate Marketing Without an Audience

Anthony Smith makes money recommending digital marketing products — no big audience, funnels, or paid ads.

His first sales came from simply sharing useful info with people already looking to grow their businesses.

His takeaways:

People respond to authenticity — you don’t have to be an expert
Consistency beats perfection

That’s sales 101 — be a listener first and a problem solver second.

Your Turn

Big thanks to everyone who submitted a clip. I’m sorry I wasn’t able to air all of them.

If you have a fun, random, or creative side hustle to share, I’d love to hear it and possibly feature you in an upcoming episode.

Episode Links

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