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

Random Ways to Make Extra Money - Random Ways to Make Extra Money Cover

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 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 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’s also a real estate investor, and author of The First 3 Doors: Lessons From Our Rookie Years in Real Estate Investing.

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). Our Neighbor review.

9. Board Game Rentals

Trish is in Kitsap County, Washington, near Seattle. She rents out board games, in her words, “like they’re 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 as a hobby 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. Here’s an example of his Stan Store.

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

Looking for More Side Hustle Help?

Start Your Free $500 Challenge. My free 5-day email course shows you how to add $500 to your bottom line.
Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.

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Filed Under: Uncategorized

We Bought a “Boring” Business. Running it Was Another Story.

Andrea Palacio

Buy a boring business, they said. It’ll be easy. It’ll be fun.

That’s the dream Andrea Palacio and her husband chased when they bought a landscaping company.

The road got bumpy fast, but they still added around $300,000 in equity value in just a couple of years.

Andrea Palacio runs AndreaPalacio.ai, where she helps other business owners put AI to work.

But before that, she and her husband lived on a sailboat for 4 years while running an e-commerce business selling pet supplies on Amazon and Shopify.

When that business stalled, they sold it and went looking for something new. They landed on a South Florida landscaping company, thinking it would be steady and mostly hands-off. Instead, almost everything went wrong at once.

Tune in to Episode 750 of the Side Hustle Show to learn:

how Andrea rebuilt after losing most of her team and clients
how simple AI tools gave her back 20+ hours a month
what buying a business taught her about leadership

Why a Landscaping Business?

After 4 years on a sailboat, Andrea and her husband felt their e-commerce growth stall.

To keep competing with big pet-supply sellers, they would have needed to invest hundreds of thousands of dollars. They didn’t want that risk, so they sold and looked for a new path.

Andrea watched a lot of YouTube videos about buying businesses. The pitch was simple: buy a company that already works, put a manager in place, and step back.

They wanted something that fit both of them. Andrea is strong online with marketing and customers. Her husband is very hands-on.

Landscaping felt recession-proof, since in Florida everyone has to keep their lawn cut, so they went for it.

The Deal That Fell Apart

They bought the company for $470,000, paying about a 2.3x multiple on net income.

To fund it, they used an SBA loan and put their personal assets, including their home, up as collateral. Quitting was never an option.

Then things unraveled. The seller was supposed to train them, but he disappeared just 5 days after the sale.

Soon after, the manager quit and told the crew they were better off finding other jobs. The team dropped from 12 employees down to about 2.

A Brutal First Month

At the time, Andrea had a 7-month-old and was pregnant with her second son.

She was fielding 50 calls a day while handling marketing, admin, and customer service.

Revenue fell from $70,000 a month to $40,000 a month, and her husband had to do the labor himself.

Digging Out of the Hole

The first move was running Google Ads to win back clients. It was expensive to learn, and they wasted money before getting it right.

Finding workers was even harder. Andrea says she might interview 100 people, have 5 show up, and find just 1 who was decent.

Taking over an existing business and then improving it is its own skill.

Jono Santamaria took the same approach with a laundromat, making a series of changes to grow revenue once he owned it.

Learning to Sell

About half their revenue was recurring lawn care.

The other half came from bigger custom and enhancement jobs, which they didn’t know how to sell. They lost their large commercial clients, like shopping plazas paying $2,000 to $3,000 a month.

Andrea’s husband learned sales the “fake it till you make it” way.

Over about a year, they rebuilt revenue to $60,000 to $65,000 a month, sometimes hitting $70,000, while working 80-hour weeks.

Using AI to Get Time Back

The 80-hour weeks left Andrea feeling like she couldn’t be present for her kids. Something had to change.

Her sister mentioned that ChatGPT had just come out.

AndreaPalacio.ai

Andrea, who calls herself tech-curious, started playing with it and imagined AI handling her phone calls and chasing late payments.

Trial and Error

She first hired an Upwork freelancer to build her idea. Five months later, she had nothing.

A second freelancer built an automation on Make that sent clients a photo, pulled from their CRM, after every service, plus a follow-up text.

Happy clients were sent to a Google review; unhappy ones went to a complaint form.

They also switched from paper scheduling to a CRM called Jobber.

Then Andrea taught herself Make on YouTube and built the AI receptionist she first imagined, which booked appointments right inside Jobber.

She notes tools like Claude Code make this even easier today.

How She Trained the AI

Andrea says the setup is the easy part. Tools like VAPI or Retell AI can spin up an AI receptionist quickly. The real work is training it to say the right thing every time.

So she listened to every call, found the problem spots, and updated the prompt to fix them.

Her big mindset shift was to think in steps and systems, and to train the AI like a junior employee.

If a client calls upset, the AI transfers the call to her. If a client wants an estimate, it books the visit on the calendar. Just two automations gave her back at least 20 hours a month.

Listed for Sale — and a $750,000 Offer

With calls handled and time back, they listed the company for sale. They also hired a friend Andrea had known for 20 years as operations manager in December 2024.

Around the same time, they got an offer of $750,000, well above their $470,000 purchase price.

They also bought a small fertilization and pest control company for $170,000, with the seller financing half.

In the end, they decided not to sell, since selling would leave them without an income source. The business was finally stable and running without them handling calls.

When It Fell Apart… Again

In January 2025, the family moved abroad for six months and left the manager in charge. But the business started sliding. Andrea had also stepped away in September 2025 to focus on her own AI company.

When they returned near New Year, their bank account had $2.50 in it. They discovered the manager, a friend of 20 years, had been stealing.

Five days later, a full truck of equipment worth $10,000 to $15,000 was stolen. The lesson Andrea took away was painful but clear: they had not learned how to lead a company.

Rebuilding Leaner with AI

They let the manager go. Good replacement managers wanted $100,000 or more a year, which the company couldn’t afford. So instead of hiring, they automated more.

Now Andrea’s husband goes to the office just one day a week for sales. AI handles the marketing, which brought in so many leads that May was their biggest month ever.

They also built a dashboard to track their real numbers:

which crews are efficient
how long jobs take
and pay versus what each client is charged

For people, they simply promoted their longest-tenured worker to organize the crews each morning. Andrea says missing those key numbers is exactly why they got robbed without noticing.

What Andrea Learned About Buying Businesses

Andrea’s top warning is to never buy a company unless the seller finances at least part of it, so they keep some skin in the game.

If the idea of owner financing appeals to you, Hannah Ingram did exactly that in Episode 571, buying an entire self-service car wash with the seller footing part of the bill.

Andrea also passed on another deal where clients paid three months late and visits were priced at $25, far below their $60 minimum.

In her own company, clients are billed on the first of the month, before any work is done. She warns that raising prices and changing terms after an acquisition will usually cost you those customers.

Tech/Tools

Here are the main tools Andrea mentioned:

Make – automation platform for connecting apps and building workflows
Jobber – CRM built for landscaping and cleaning services
Claude Code – tool she uses daily to build automations
VAPI and Retell AI – platforms for building AI phone receptionists
Upwork – where she hired freelancers to help build automations

Where the Business Is Now

Today the company is leaner and steadier. Andrea’s husband goes into the office about one day a week for sales, and they promoted their longest-tenured worker to organize the crews each morning. Last month the business did $75,000 with 7 employees.

What’s Next for Andrea?

These wins freed Andrea to build her own venture at AndreaPalacio.ai, where she helps other owners run an “AI-first company.”

She launched a program, Crewless, for business owners making that shift — mainly local services plus coaching and consulting.

You can find her on Instagram and YouTube. DM her the word “sidehustle” on Instagram for a personalized plan.

Andrea’s #1 Tip for Side Hustle Nation

“Don’t quit on your goals and dreams.”

Episode Links

Looking for More Side Hustle Help?

Start Your Free $500 Challenge. My free 5-day email course shows you how to add $500 to your bottom line.
Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.