The Side Hustle Show with Nick Loper
Episode 703: Vending Machine Q&A
Featuring: Anthony Koloje of VendingPreneurs
Original Air Date: October 20, 2025

Episode Overview

This episode features a live Q&A session with Anthony Koloje, who scaled his vending machine business from zero to over $50K in monthly revenue in under two years. Anthony, joined by guest moderators and questions from the Side Hustle Nation community, provides actionable insights on starting, scaling, and optimizing a vending machine venture. Topics include scouting locations, beating big competitors, maximizing profits, structuring your business, handling logistics, and lessons learned from the trenches.

Key Discussion Points & Insights

1. The Modern Vending Landscape

• Bulk Vending Decline; Rise of Smart, Specialty Machines: Traditional gumball and snack dispensers are being replaced by high-tech, niche-market machines (e.g., cosmetics, Pokémon, LEGOs, random 'fun bags').
  • Anthony (01:27): “The new thing now… you go to the airport and there’s a Kylie Jenner cosmetics vending machine… It’s like digital, you click it, you touch it.”
• High-margin items in vending: Apparel and specialty goods are now being sold at premium prices (e.g., hats for $35, realizing $17-20 in profit per item), making better use of limited machine space.

2. Maximizing Profits: Raw Dollar vs. Percentage Margin

• Focus on Raw Profit, Not % Margin: Opt for larger items that yield greater dollar profit even if margin percentage drops.
  • Anthony (03:04): “I would rather sacrifice margin for profit… I’m now making $2 in profit instead of 87 cents.”
• Efficiency & Staffing: Since labor costs for restocking are substantial, maximizing dollars per stop is crucial, especially as you grow a team.

3. Competing with Industry Giants

• How to Win Against Big Players: Many large operators are slow to adopt new tech and offer subpar service—independents have an edge through responsiveness and embracing smart vending.
  • Anthony (05:38): “I’ve taken over a lot of my locations from [the big guys]... They are resistant to tech.”
• Community and Buying Power: Participation in VendingPreneurs gives access to group-negotiated supplier discounts (e.g., USG partnerships for rebates and better inventory options).

4. Types of Vending Machines and Cashless Trends

• Machine Mix: Anthony’s fleet includes AI-equipped micro marts, ambient 'Stockwell' units, traditional combos, and a few beverage-only machines.
• Cashless Dominance: Most locations now prefer or require cashless solutions. Out of 77 machines, only six accept cash—and only to accommodate certain demographics.

5. Logistics: Scaling, Vehicles & Staffing

• Operational Evolution: Initially self-stocking, Anthony scaled by hiring staff and investing in a purpose-chosen van for optimal route efficiency.
  • Anthony (13:56): “I took the measurements of the totes… I literally went there with like 18 totes, empty totes, and I packed them in the van before I even bought the thing.”
• Team Structure: Full-time driver, part-time stocker, warehouse manager, and recently, an operations manager.

6. Business Structure: Entity, Insurance, and Risk

• Entity Choice: Anthony recommends an LLC taxed as an S-Corp (consult your accountant).
• Insurance: Comprehensive policies including general liability, worker's comp, and coverage for machine vandalism are critical.
  • Anthony (18:08): “Nobody needs insurance until you need it. Right?”

7. Keys to Location Selection

• The Parking Lot Test: Occupancy trumps reported size—if the lot is full, you have foot traffic.
  • Anthony (41:30): “Nothing beats the parking lot test. Nothing.”
• Optimal Locations: Focus on affluent buildings, warehouses, student housing, large medical or residential facilities. Be selective—wait for high-traffic, high-volume opportunities.
  • “Wait for the right location. Who cares if that side hustle takes you 10 months? I’d rather wait 10 months and have a $5,000 location than three $800 locations.” (23:08)

8. Profitability, Financing & Growth

• Financing Machines: Use financing rather than paying cash for machine purchases; let profits cover loan payments.
  • “Don’t pay off any of the machines cash. I would finance them all... That way, the revenue and the profits pay off the machine and that debt service.” (30:43)
• Timeline to Break Even: Most locations reach profitability by months 2-4.
• Lead Generation: VendingPreneurs provides valuable outbound lead gen; most of Anthony’s 44 locations came via the community.

9. Habits & Systems for Success

• Organization is Key: Building a simple CRM (e.g., Google Sheets for lead tracking), storing docs systematically, and setting quantifiable goals is vital.
• Consistency: Poppin’ in (cold-calling on locations) is a numbers game. Aim for a high number of pitches to secure one contract.
  • “Not to be cliche, but just try to get 1% better every single day, and eventually the floodgates will open and that's what happened for me.” (50:57)

Notable Quotes & Memorable Moments

• On betting on yourself:
  “Opportunities, they don’t disappear, they just go to the people that act on them first... I bet on myself, you know, the rest is history.” —Anthony (04:31)

• On scaling past a side hustle:
  “It’s not a side hustle anymore.” —Anthony (15:02)

• On choosing machine type:
  “I personally like micromarts... But for your business, I gotta ask you: what’s your capital situation? What’s your credit capacity? Work the numbers backwards.” —Anthony (42:56)

• On the golden rule for buying machines:
  “Do not secure a machine before you have a location.” —Anthony (44:47)

• On the power of recurring income:
  “We made $25 last night while you’re sleeping. I said that to her every single 30 days while we were getting ready in the morning, giving her an update of how much money we were making.” —Anthony (13:37)

• On market saturation:
  “Y’all would be shocked... There’s a lot of people not running these things efficiently whatsoever. If you are organized and a good person… you will get that deal.” —Anthony (48:28)

Timestamped Key Segments

| Timestamp | Segment | |------------|-----------------------------------------------------------| | 01:27-03:45 | The new world of vending: bulk decline, high-margin opportunity | | 05:23-10:49 | Beating large competitors and leveraging group buying power | | 10:51-11:43 | Types of machines; cashless trends | | 11:45-15:35 | Scaling operations: logistics, vans, hiring | | 17:36-18:57 | Entity structure and insurance | | 21:30-24:20 | Location selection, waiting for high-volume opportunities | | 26:38-30:21 | Time commitment (start phase vs. scaled phase) | | 30:43-34:06 | Journey to profitability; financing strategies | | 38:16-39:12 | ROI on machines, depreciation advantages | | 39:20-41:30 | Newbie mistakes, standing firm on location selection | | 41:30-42:48 | The parking lot test for location viability | | 44:47-45:21 | Should you buy machines before you have locations | | 45:24-46:13 | Who to contact during drop-ins (property/ops managers) | | 48:28-48:56 | Market saturation and opportunity for new entrants | | 49:08-49:37 | Addressing host location concerns (electricity, maintenance) | | 50:57-51:57 | Habits for early success: organization, CRM, goal-setting |

Final Takeaways

• Vending remains a lucrative, scalable side hustle—with a low barrier to entry but increasing sophistication via new tech and products.
• Careful location selection is the key to profitability; don’t rush to place machines anywhere just to start.
• Financing, organization, and leveraging community resources (like VendingPreneurs) can dramatically accelerate growth.
• Even in competitive or saturated markets, under-served locations abound for reliable, service-oriented operators.
• Anthony’s journey demonstrates that with persistence, systems, and strategic decision-making, vending can quickly evolve from a side hustle to a thriving business.

For more resources, book a call with the VendingPreneurs team via sidehustlenation.com/vendingcall or check the show notes for additional vendor interviews and actionable guides.