Dine & Grind: Canter's Deli: How Alex Canter Is Reinventing a 90-Year-Old LA Restaurant

What does a fourth-generation deli owner, multi-million-dollar tech CEO, and "high-end gas station" founder have in common? Relentless hustle, fearless reinvention, and an unshakeable love for food and people.

That's the thread woven through our latest Dine & Grind, featuring Alex Canter—one of LA's most quietly influential restaurant-tech disruptors.

If you've ever waited hungrily for a Cantor's pastrami on Fairfax or juggled tablet hell as an operator, you're living in the world Alex Canter helped transform. But his journey—from washing bakery pans at age 12 to closing $100 million deals with SoftBank—is packed with lessons for anyone obsessed with hospitality, entrepreneurship, and reinvention on-the-fly.

Let's dig into the key takeaways.

Growing Up Cantor's: Business, Grit, and Sandwiches

"My cousins and I played hide-and-seek in the kitchen. At 12, I was waiting tables. Thanksgiving debates weren't about politics—they were about firing bartenders."

Sound familiar? For Alex Canter, being raised in a family business was equal parts playground and bootcamp. Over decades, he watched his dad, Mark, and grandpa pour blood, sweat, and literal tears into keeping Cantor's Deli bustling—often at the cost of vacations, sleep, and personal comfort.

But even as a kid, Alex Canter looked for ways to experiment and adapt. The menu? "Why does this come with these sides? Why not change it?" His dad handed him a Sharpie and said, "Fix it!"—and together, they trimmed, expanded, and modernized a menu that had barely changed in half a century.

Lesson: Legacy isn't an anchor—if you're willing to challenge, edit, and experiment, you can create new momentum from old roots.

Kitchen Tech Pioneer—From Tablets to SoftBank Millions

As delivery apps exploded ("Millions a year on DoorDash, Uber Eats, Grubhub—over 30% of revenue!"), Alex Canter saw the chaos: nine tablets, two laptops, random faxes, and staff on the brink. The solution? Build Ordermark to aggregate every online order in one painless spot—the back counter at Cantor's was his first testing ground.

Soon, Ordermark was signing 200–1,100 new restaurants monthly, powering thousands of locations through the pandemic. Investors—and eventually SoftBank—came calling. Masayoshi Son's advice on their now-legendary $100 million round: "You need a thousand salespeople. Go faster. Think bigger." For a 24-year-old CEO, it was a rocket ride through the highs and lows of scaling, layoffs, pivots, exits, and gut-wrenching uncertainty.

Lesson: Entrepreneurship thrives on urgency, kindness, and fun—but it also demands resilience when nothing goes as planned.

Next Big Thing: Maggie's—Reinventing the Gas Station Experience

After the tech rollercoaster, Alex Canter is heading back to his roots, armed with hard-won lessons and fresh vision. His next venture? Maggie’s—a hospitality-forward, "high-end gas station" launching in LA.

Imagine espresso bars, fresh-baked pastries, sparkling clean spaces, local wines, and innovative tech for mobile orders—all in places we barely stop long enough to grab mediocre coffee. Inspired by food-forward convenience concepts in Japan and Italy, Maggie's is out to make refueling a pleasure, not a pitstop.

Lesson: The future of hospitality is everywhere—if you're bold enough to rethink what people crave on the go.

What Makes Alex Canter Tick?

"Urgency, kindness, and fun." That's his recipe for success, no matter the industry. Whether battling legacy inertia or scaling new markets, his story is proof that you can respect tradition and still break the mold—if you approach every challenge with grit, humility, and the drive to keep learning.

Final Bite: The Best Is Yet to Come

If you're hungry for inspiration—and new ideas about where hospitality can live—look to Alex Canter: Embrace legacy, challenge the status quo, and never stop making things better for those you serve. 

🎧 Listen now on Spotify, Apple Podcasts, or visit Dine & Grind for show notes and more inspiring chef interviews.