From Family Startup to Multi-Million Exit: Jeff Leider’s Tri R Coffee Journey

On a candid video chat with Neil Swindale and Orrin Huebner, Jeff Leider traced the arc of Tri R Coffee — from a family startup in 1980s San Diego to a successful multimillion-dollar sale in 2024. What emerged wasn’t just a business highlight reel; it was a playbook for operators chasing growth and planning an exit.

From Family Start to Full-Time Grind

Tri R Coffee launched in 1984 when Jeff’s father pivoted from vending in Chicago to coffee service in San Diego. Jeff and his brother Scott grew up in the grind — loading boxes, working routes, and eventually taking the reins.

By the early 1990s, Jeff was full-time, and like many entrepreneurs, the early years meant no paycheck and all reinvestment. Growth came first, profit later.

Scaling, Stumbling, and Rebuilding

By 2019, Tri R was approaching $4M in revenue with major office pantry contracts lined up. Then COVID hit — and revenue dropped to $1M overnight.

But Jeff and his team bounced back, landing marquee accounts like Amazon through USConnect. They rebuilt fast, but the turbulence exposed cracks. A consultant helped overhaul operations — adding accountability, structure, and metrics. Suddenly, Tri R was running like a big company.

When the Buyer Calls… and Keeps Calling

Funny enough, all that structure wasn’t about selling — it was about doubling, then doubling again. But after years of persistent interest from a buyer, the offer became too good to pass up.

Once Jeff understood the tax implications and adjusted the ask, the buyer agreed. Six months later, the deal closed, allowing an independent player to stay alive in San Diego, and Jeff got his clean exit.

Lessons from the Sale

Jeff’s takeaways are pure gold for anyone eyeing growth or an exit:

• Hire sooner – don’t wait to bring on route drivers, techs, or sales pros.
• Measure everything – metrics drive accountability.
• Act like a big company early – contracts, reviews, structure pay off later.
• Say no when needed – unprofitable requests cost more than they’re worth.
• Plan for the exit – taxes, loans, deal structures matter. Don’t cram it into five months.

What’s Next

Since the sale, Jeff has explored the stock market and is building a commercial kitchen in San Diego with food delivery and retail products on the horizon. Still, he admits he misses the buzz of daily operations:

“Operating a business is fun, challenging, and addictive. The vending business does everything — shipping, logistics, customer service. That’s why we get hooked.”

The Bottom Line

Tri R Coffee’s journey is about resilience, reinvention, and reward. From a $100 bill found on a golf course to a multimillion-dollar exit, Jeff’s story is proof that with grit, process, and vision, your family business can grow, thrive, and sell on their terms.

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Orrin Huebner is the CEO of Orrin Huebner LLC. After many years of being an owner/operator, he now consults and is an intermediary to the industry. His experience as a very successful operator and then leading OCS for a Canteen provides great value.