Podcast Summary: The My Wife Quit Her Job Podcast With Steve Chou

Episode 617: Charles Chakkalo Makes 8 Figures On Amazon Doing Something Everyone Said Was Dead
Release Date: December 6, 2025
Host: Steve Chou
Guest: Charles Chakkalo

Episode Overview

This episode spotlights Charles Chakkalo, a student of Steve’s “Create a Profitable Online Store” course, who has defied conventional wisdom by scaling “dead” retail arbitrage and wholesale reselling into a thriving eight-figure Amazon business with multiple warehouses. Steve and Charles dive deep into the realities, challenges, and technical nuances of arbitrage and warehouse operations, providing exceptionally detailed, tactical advice for ambitious e-commerce entrepreneurs.

Main Discussion Points & Insights

Charles’s Origin Story & Business Model Evolution

• Charles started reselling as a high school freshman, buying tech on sale at Best Buy and flipping it on eBay and Amazon (03:32).
• He almost pursued law, but decided to give business a real try with his brother during college, using their combined “life savings” (03:41).
• The venture turned into a family business with two brothers, each having distinct but complementary skills (04:57).
• Emphasizes importance and complexity of working with family—keeping business and personal life separate is key (05:21).

The State of Retail Arbitrage in 2025

• Retail arbitrage (RA)—buying products from retail stores and reselling on Amazon—has become much harder due to strict Amazon policy enforcement, particularly around product authenticity and UPC codes (06:31).
• “If you have relationships, not necessarily directly with companies, but with at least distributors that distribute authentic product… it’s worth trying.” – Charles (07:07)
• Warns against starting with just retail receipts: Amazon increasingly rejects ordinary store receipts as proof due to authenticity crackdowns (07:05).

Navigating Amazon’s Policy Shifts

• Amazon now suppresses ASINs that don’t have a valid GS1 UPC; sellers sometimes stranded with large volumes of unsellable inventory (07:50).
• Proving authenticity is critical. Distributors and proper paperwork help, but even then, Amazon’s algorithms and support are “vague” and difficult (11:04).
• “I have a VA employed full time putting together invoices, paper trails, bills of lading…” – Charles (11:24)

Gating, Receipts, and the Realities of Scaling RA

• Pre-purchase, Charles checks if he’s “ungated”—able to sell certain brands/categories—since ungating is now complex and highly dependent on account history, health, and size (13:15).
• “The ungating process is hell and a half… but is largely algorithmic based on your history, age of account, sales volume, and also account health rating.” – Charles (13:15)
• He experiences frequent demands for proof, but can usually keep selling unless certain serious warnings kick in (12:26).

Starting Today: Retail Arbitrage vs. Private Label

• Charles does not recommend the classic “Walmart clearance” retail arbitrage model for beginners—it’s essentially dead due to administrative overhead and risks (14:32).
• The real opportunity lies in forming relationships with distributors and wholesalers—the modern take on RA (15:02).
• “The secret sauce behind all this, right?” – Steve (15:04)

How to Find Distributors (15:12–16:28)

• “Go to trade shows, wholesale shows like ASD in Vegas, and engage with sales reps.” – Charles
• Most distributors are wary of ‘online-only’ sellers; persistence and demonstrating real order volume can turn them around.
• Sometimes, sellers misrepresent themselves as having retail locations to get approved.

Fighting for the Amazon Buy Box & The Logistics Edge

• Competing for the Buy Box comes down to price and logistics.
• Key: You must own your logistics (warehouse, fulfillment prep) to survive razor-thin margins (19:33).
• “Owning your own logistics is a big unlock as far as maximizing your margins.” – Charles (19:33)
• Repricers are must-haves—set rules for how aggressive you want to be and always account for your true costs (21:27).

The Real Costs and Benefits of Warehousing

• Charles runs two warehouses (Brooklyn & Westchester)—owns them rather than relying on 3PLs for cost control, reliability, and flexibility (25:06).
• “I can go downstairs and touch my goods. I don’t have to wait at the mercy of some 3PL...” – Charles (25:46)
• Upfront costs are significant, but the competitive margin and operational control is invaluable.
• Funny and humble story about sitting on the sidewalk overnight guarding pallets after a logistical mishap—illustrating “hands-on” approach to growth (28:50).

Amazon AWD and Fulfillment Philosophy

• Charles rejected Amazon’s AWD (Amazon Warehousing & Distribution) service, seeing it as “strong-arming” by Amazon to control more of the supply chain (32:04).
• Believes that having your own operational capacity, even just for emergencies, is essential for serious sellers (36:11).

Business Mix & Risk Management

• Charles’s business is roughly 60% private label, 40% resale, sometimes 50/50—within resale, 25% is “retail arbitrage” (physical store finds), 75% is distributor/wholesale (43:31).
• Relationships with distributors are extremely valuable—but fragile; listings can be lost overnight due to Amazon policy changes (40:07, 42:12).
• “The relationships… could be really, really fragile.” – Charles (42:12)
• Authorization letters from brands are the "holy grail," but even then, Amazon may not always honor them.

Personal Development & Community Building

• Charles is deeply involved in the seller community—attending 20-30 tradeshow events/year, continuously learning, and maintaining high visibility (41:41, 44:46).
• He authors a newsletter, Just a Seller (justasellernewsletter.com), with practical knowledge—distinct from agency or “guru” advice (38:08).

Notable Quotes & Moments

• “It’s an emotional journey that got me to a place where, you know, I’m amazed myself that I got here.” – Charles (02:58)
• “If you’re going into stores and will be providing receipts as your proof of purchase, do not.” – Charles (07:07)
• “The only way you can actually engage in retail arbitrage or wholesale or whatever you want to call it… is you have to have a repricer and it cannot be the Amazon repricer.” – Charles (19:05)
• “Owning your own logistics is a big unlock as far as maximizing your margins… Are you paying placement fees? Which is a totally separate conversation we didn’t touch on.” – Charles (19:33)
• “The only adjustment I would make...is if you have those relationships to begin with. If you do, go ahead, by all means, God bless you. But it won’t be easy.” – Charles (34:02)
• “I’m very hands on. I mean I’m nothing like the conventional Amazon seller… I am really hands-on to the point where I was at a conference last two weeks ago and people mocked me for driving that forklift.” – Charles (30:19)
• “I decided to put together that Just a Seller newsletter and...the number one thing that I learned I have to do is deliver value.” – Charles (38:08)
• “I have a VA employed full time putting together invoices, paper trails, bills of lading, showing the authenticity...Amazon almost instantly replies by saying not enough information was provided—vague, vague, vague.” – Charles (11:24)
• “It’s possible, it’s possible.” – Charles, closing encouragement to listeners (46:56)

Key Takeaways for Aspiring E-Commerce Sellers

• Classic retail arbitrage is nearly obsolete due to mounting Amazon restrictions and margin pressure. Success now requires sophisticated operations and wholesale/distributor relationships.
• Own your logistics: Real control and profit margins come only when you control your prep and warehouse operations (or at least a portion of it).
• Relationships matter: Building rapport with distributors or brands is the modern ‘edge’—fragile but powerful.
• Constantly adapt and learn: Charles attributes much of his success to relentless learning, frequenting conferences, and networking.
• Transparency and true costing: Sellers must thoroughly understand and incorporate all their costs (labor, prep, freight) into pricing to survive.
• Private label is now the recommended starting point: Unless you have distributor connections, channel resources toward private label brand-building.

Timestamps for Important Segments

• Charles’s Background & Origin Story: 03:32–04:47
• Retail Arbitrage Today & Warnings: 06:31–14:42
• Distributor Sourcing & Trade Shows: 15:02–16:28
• Fighting for the Buy Box, Repricers: 19:01–24:24
• Owning Warehousing, Cost/Benefit: 25:06–27:30
• Scaling Evolution: Pallet Story: 28:50–30:15
• AWD and In-house vs 3PL: 32:01–33:19, 36:11
• Business Model Breakdown & Current Mix: 43:31
• Newsletter and Community Engagement: 38:08, 44:46

Closing

This episode delivers a reality check on arbitrage and a masterclass in the operational grind of high-volume Amazon reselling. Charles’s unconventional success underscores that while the old playbook is dead, extreme persistence, logistics control, and relationship building can still lead to outsized results—if you’re willing to get your hands dirty.

Charles’s resources:
Just a Seller Newsletter

For further learning and tactical strategies, check out Steve Chou’s course and events at mywifequitterjob.com and Seller Summit.