This episode is different.

Instead of another success story, I’m sharing my own journey into the trailer rental business. And it’s still a work in progress.

From buying my first trailers to dealing with damage on day one, chasing “passive income,” and realizing I wasn’t marketing nearly enough… I break down what actually happened.

If you’ve ever thought about starting a rental side hustle, this is the honest version, not the highlight reel.

I cover:

• Why I got into trailer rentals in the first place
• The biggest mistake that cost me money
• What I misunderstood about “hands-off” income
• Why my business grew… then slowed down
• Marketing efforts that worked (and didn’t)
• Lessons from buying the wrong equipment
• What I would do differently if starting today
• The decision I’m facing: go all-in or get out

This isn’t a polished success story. It’s a real look at building something that hasn’t fully clicked yet and figuring out what comes next.

If you're in the middle of your own journey, this one’s for you.

What started as a single idea and about $3,000, turned into a fully booked rental business.

In this episode, you’ll hear how Amberlyn Richie built a photo booth side hustle from scratch while working a full-time job and raising a family.
After spotting a gap in her small-town market, she took action, landed her first event, and quickly found herself booked nearly every weekend.

We talk through how the business actually works—from 360 booths to selfie booths, digital vs print, and what it takes to run events without burning out. Amberlyn also shares what she’s learned about pricing, managing multiple bookings, and why staying in smaller markets can be a major advantage.

If you’re looking for a rental idea that works in real life—not just online—this episode will give you a clear starting point.

In This Episode:

• How she started with one 360 photo booth
• Getting fully booked through word of mouth
• 360 booths vs selfie booths (what’s the difference)
• Digital vs print rentals (and what customers actually want)
• Pricing, time minimums, and event structure
• Managing multiple rentals with a small team
• Lessons from early mistakes and upgrades
• Why small towns can be better than big cities

🛠️ Resources & Mentions:

• Canva (for templates and overlays)
• Photo booth event software platforms
• TikTok (for learning and marketing ideas)
• YouTube (learning setup and operations)

👤 Connect with Amberlyn:

• Website: Richie 360 Photo Booth Rentals | https://www.richie360photoboothrentals.com/
• Social: Richie Photo Booth Rentals (Facebook, Instagram, TikTok)

David Stillson hated cardboard boxes and that frustration turned into a business.

When David and his wife Nikki needed to move, he went looking for a cheaper alternative to buying boxes and stumbled onto tote rental. For about $2,000, he bought a pallet of commercial logistics totes and dollies, used them for his own move, and started renting the rest. Their first customer needed totes to transport live coral from a 180-gallon fish tank. Their fourth rental was a 150-tote corporate order they didn't have the inventory to fill...yet.

Now they're running 380 totes out of their garage, hitting 61% utilization, and booked out weeks in advance with residential movers, real estate agents, and corporate clients.

In this episode, David covers:
→ How he researched and validated the idea using ChatGPT and competitor scraping
→ Why he chose commercial logistics totes over $7 Home Depot bins
→ The bundle pricing structure that makes it easy for customers to say yes
→ How in-person networking (and premium cookies) outperformed paid ads
→ Logistics of delivering, cleaning, and storing hundreds of totes from home
→ His advice for anyone who wants to start a rental side hustle this year

If you've been looking for a physical rental idea that's low drama, low loss risk, and easy to scale from your own driveway, this episode is for you.