Ryan Kugler on building three layered companies and moving inventory

Executive overview

Most entrepreneurs rely on one revenue stream until a crisis exposes the risk. Ryan Kugler runs three businesses simultaneously — wholesale liquidation, events, and marketing — with the same team serving all three. When COVID collapsed two of them, the third kept the operation alive.

The core model is layered companies: shared staff, diversified income, no single point of failure.

Resilience comes from building multiple revenue streams before you need them — not after.

From family video business to liquidation at scale

• Started at 17 in the family business supplying video stores (Blockbuster, Hollywood Video, Movie Gallery)
• Pivotal break: an odd call about 50,000 McDonald's Happy Meal VHS tapes led to a bulk sale to Target
• That deal prompted a shift from small-lot buying to large-lot thinking — 20,000, 100,000+ units
• Rebranded the family business from DVA (Distribution Video and Audio) to Plan B as entertainment inventory shrank
• Today moves everything from luggage to plywood to candles; entertainment is now ~20% of volume
• Has helped move roughly 500 million units over his career, keeping product out of landfill

How the layered company model works

• Three businesses run simultaneously: Plan B (liquidation wholesale), Five Events (event production), Ideal Content (video marketing)
• All employees work across all three companies — no siloed headcount
• Built the structure after 2008 recession made him unwilling to rely on a single income source
• COVID proved the model: events shut down, marketing slowed, but wholesale pivoted to PPE and kept cash flowing
• When one company has a bad day, the others absorb it — no single failure sends everyone home

The wholesale liquidation business

• Buys excess, returned, or unsold inventory in bulk — minimum tens of thousands of units
• Primary customers: TJ Maxx, Ross, Dollar General, and smaller discount chains (5–20 store regional players)
• Deliberately focuses on smaller retailers who get overlooked when manufacturers go to big chains first
• Does not drop-ship or sell in small quantities — bulk only
• Overstock.com has shifted away from closeouts entirely; now competes with Wayfair on furniture
• Has declined categories like pig ears and human hair — every day brings novel inbound offers

Navigating retailer complexity

• Every major retailer runs its own EDI system; onboarding a new account means new software, new carrier, new monthly fees
• Routing guides (thick books of packaging and labelling rules) generate chargebacks for minor infractions
• Policy: if a deal takes too long to approve, walk away — friction in the courtship predicts worse friction later
• Walked away from a major deal mid-call when the buyer was repeatedly harsh; avoided years of charge-back headaches
• COVID briefly suspended all routing and charge-back rules — retailers just wanted PPE shipped any way possible

Events and marketing businesses

• Five Events produces charity runs and walks (thousands of participants); was at 30 events per year pre-COVID
• All events paused March 2020; declined to pivot to virtual because physical production is a different skill set
• Goal: re-book 30 events in the next six months, grow to ~90 (roughly two per week)
• Ideal Content makes video brochures — physical printed brochures that open to play a video on a small screen
• Also produces presentation boxes with branded merchandise plus video; grew during COVID as a remote gifting tool
• Positioning: not the cheapest option; competes on quality and customer service

Leadership and operating instincts

• Core skill: decisive action under pressure — when 1,000 runners hit a blocked road, you act immediately
• Does not freeze when things go wrong; treats on-the-spot problem solving as a learnable, practicable skill
• Hardest moment in COVID: telling part-time event staff there was no work for a year
• Biggest re-entry challenge: muscle memory — running a large event after 18 months off will feel unfamiliar
• Banking constraints surfaced during COVID (24-hour wire limits); solved by routing through a second account

Advice for younger founders

• Make decisions fast — the longer you sit on a deal, the more likely it disappears
• Start saving and investing as early as possible; the compounding gap between 17 and 30 is significant
• Cash gives peace of mind and the ability to move on opportunities when others are panicked