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.

Adam was one month from finishing college when he decided to start a tent rental company. He maxed out credit cards, cashed in birthday bonds, bought three tents, and advertised in the Yellow Pages and the local Penny Saver. That was 22 years ago.

Today Adam runs a full party rental operation in upstate New York, tents, tables and chairs, dance floors, lighting, restroom trailers, and more, generating at least $200K per year from tents alone. His framework for the whole business: the tent is just the bread. The money is in everything under it.

This episode is packed with hard-won perspective: how to price equipment so you break even in 10 rentals, why Google Ads is the only marketing channel that makes sense for event rentals, when to say no to a revenue stream that's making your life miserable, how to use efficiency equipment to double your profit without adding a single job, and why he's made an estimated $300K in mistakes — so you don't have to.

What you'll learn

• Why Adam started with 3 tents on credit cards right out of college
• The "tent is just the bread" framework and everything under it is the real money
• Target payback: recover your equipment cost within 10 rentals
• Why he dropped $150K/year in catering revenue and doesn't regret it
• Google Ads as the only marketing that works for event rental (search-based business)
• Using Facebook Reels to reach people who don't know restroom trailers exist
• Efficiency equipment: how Adam cut tent setup time from 4–5 hours to under 2
• Profit margins: up to 30% if you run efficiently, closer to 12% if you don't
• Renting trucks seasonally instead of buying them
• The $300K in mistakes — and the credit card processor that cost him $90K over 6 years
• Why rentals are one of the few businesses where you can bootstrap to millionaire status

Timestamps

• [0:00] How Adam got started: one month before college graduation
• [2:00] First years: Yellow Pages, Penny Saver, mom's SUV
• [4:00] Why nothing went wrong early and when it started getting hard
• [5:00] The tent count question: why 30 tents isn't the right gauge
• [6:00] What he actually rents: tents, tables, chairs, dance floors, restroom trailers
• [8:00] Dropping catering equipment: $150K revenue that wasn't worth it
• [9:00] Customer acquisition: Google Ads only for tents, Reels for restroom trailers
• [12:00] Still working crew lead and the company culture advantage
• [13:00] 10-rental payback framework for pricing equipment
• [15:00] Setup equipment: from hammers to powered hand carts and stake pullers
• [19:00] Revenue: $200K/year from tents, over $1M lifetime in tents
• [20:00] Getting started revenue: $20–25K cash at age 22–23
• [22:00] Profit margins: 30% efficient, 12% inefficient
• [23:00] Weather as the biggest ongoing challenge
• [29:00] The $300K in mistakes including $90K in credit card fees over 6 years
• [31:00] "Rentals are one of the few businesses where you can bootstrap to millionaire"
• [32:00] Famous Four Questions

Find Out More

• YouTube: The Tent Guy (free — covers ~80% of the business)
• startapartyrentalcompany.com (course)
• TikTok: @realworldsidehustles

Justin had a utility trailer sitting in his backyard. He didn't want to sell it, didn't want it rotting away, so he listed it on Facebook Marketplace for $40 a day — and someone rented it three days later. That same customer still rents from him today.

Five years later, Justin runs a fleet of seven trailers out of Jacksonville, Florida, averaging $9,000 a month in gross revenue. It's his full-time income. He also built Trailer Hustle, a community and resource hub approaching 20,000 members, for people doing exactly what he does.

This episode covers the entire arc: starting with no contract, no toolbox, and a handshake in a movie theater parking lot — to building a systemized rental business with contactless pickup, a maintenance fund, local networking partnerships, and almost 40% recurring revenue from repeat commercial customers.

What you'll learn

• Why the best trailer to start with is the one you already have
• How Justin went from $40/day to ~$100/trailer/day average
• Four customer acquisition channels: Marketplace, Google Reviews, local networking, rental platforms
• The donut-and-pizza strategy for building referral relationships with U-Haul locations
• Why 39.5% of his revenue comes from recurring commercial customers (HVAC, roofing, landscapers)
• How to set up a maintenance fund: $100/trailer/month, covers almost everything
• The $20 flat-rate minor damage fee that adds up and trains customers fairly
• 24-hour minimum rentals and why he never does hourly
• Contactless rental setup and when to go hands-on first
• How to handle discounts: pick one percentage (his is 20%) and never deviate

Timestamps

• [0:00] How Justin got started: trailer in the backyard, $40/night
• [2:00] First rental: no contract, movie theater parking lot, handshake
• [4:00] Adding a toolbox, raising to $50, the iterative improvement approach
• [5:00] Current operation: 7 trailers, full-time income, founded Trailer Hustle
• [6:00] Four ways to find customers
• [7:00] The donut strategy for U-Haul partnerships
• [9:00] Networking with commercial businesses; HVAC, roofing, landscapers
• [13:00] Pricing philosophy: be selfish, train your customers
• [18:00] Contactless rentals: pros, cons, when to start
• [24:00] Revenue: $9K/month average, slow $7K, great $11–12K
• [25:00] The maintenance fund and tire warranty strategy
• [29:00] The $20 minor damage flat rate
• [32:00] What he got wrong: not taking it seriously early enough
• [35:00] Biggest challenges: market saturation perception and spouse support
• [41:00] Famous Four Questions

Find Out More.

• TrailerHustle.com
• Trailer Hustle Facebook group
• Trailer Hustle Podcast

Jamie Schluckebier was making $300 a week as a youth pastor when he spotted an opportunity at a church fundraiser: someone was getting paid just to set up and pick up bounce houses. He sold a car someone had given him, bought his first inflatable, and started building — treating those two units like they were a hundred. Thirteen years later, he runs a fleet of nearly 100 inflatables in rural South Georgia, bringing in over $500K a year while working about 30 minutes to an hour a day.

Jamie talks through the full journey: starting from zero with no budget, learning SEO and Google Ads from scratch, pricing himself out of the race-to-the-bottom trap, building a team he trusts, and eventually stepping back from the day-to-day entirely. This is an honest conversation about what it actually takes. The dopamine hits when things click, and the big learning curves that wipe people out if they're not ready for them.

What you'll learn

• Why Jamie treated 2 bounce houses like they were 100 from day one
• The $79 bounce house that made him furious and what he learned from it
• How to get customers without Facebook Marketplace (and why he quit it 8 years ago)
• Pricing strategy: why being the cheapest kills your business
• The weekend delivery model that protects his team and his family time
• Average ticket order of $445 and which units make the most money (water slides)
• What 20% profit margin looks like at scale with employees and trucks
• How he automated almost everything with Event Rental Systems software
• What first-year operators can realistically expect: $75K–$100K if they hustle

Timestamps

• [0:00] Jamie's origin story, from six figures to $300/week
• [3:00] Buying his first bounce house with a donated car
• [5:00] The pride of that first delivery on a beat-up 4x6 trailer
• [8:00] What his operation looks like today: ~100 inflatables, 4 trucks, 2 FT employees
• [13:00] How he gets customers: SEO, Google Ads, no Facebook Marketplace
• [16:00] Pricing strategy and the $79 bounce house story
• [22:00] Revenue: $500K+/year in rural South Georgia
• [24:00] Best units: wet/dry combos and 20-ft dual lane water slides
• [29:00] The weekend delivery model
• [30:00] Profit margins: ~20% after salaries, insurance, trucks
• [33:00] Biggest challenge: keeping up with AI and marketing
• [35:00] Famous Four Questions

Found out More

• kosocialsoftware.com
• TikTok: @jamiepartyrentalmarketing

What if the stuff you already own could pay you every week?

Rent It Out is the podcast for anyone who's ever looked at a trailer, a bounce house, a flower wall, or a washing machine and wondered — could that make me money?

Every Thursday, host Cal Hardage sits down with real people who've built rental side hustles one item at a time. No real estate. No landlord headaches. Just creative entrepreneurs who looked at what the market needed and figured out how to put it to work.

These aren't overnight success stories. They're real businesses built by real people who started with one thing and figured out the rest.

Cal runs his own trailer rental operation out of rural Oklahoma — three trailers, real numbers, and a genuine obsession with what's possible in the rental economy.

New episodes every Thursday. Subscribe on Apple Podcasts, Spotify, or wherever you listen.

Got a rental side hustle? Cal wants to hear from you at rentitoutpodcast.com.

List it. Rent it. Repeat.