I founded 1-800-Flowers.com 50 years ago. This is the secret to business success

Fifty years is a long time for any company to stay in business. About 20% fail in their first year. By year five, roughly half are gone. By the end of a decade, nearly 70% don’t make it. Reaching a golden anniversary raises a question about what allows some businesses to last.

The answers are often framed in terms of Herculean efforts, access to capital, and brilliant strategy. All those matter. But in my experience, the gift of longevity is the result of something less visible and harder to measure: the quality of the relationships built along the way.

This factor was apparent to me when I opened my first flower shop on April 1, 1976, and it only grew stronger as that little business blossomed into 1-800-Flowers.com. When we stayed focused on our relationships, we moved forward. When we lost sight of them, we stumbled.

Those relationships, of course, begin with customers who trust you with moments that matter in their lives. They extend to the florists, growers, makers, and partners who bring care and craftsmanship to the work every day. And they include the people inside the company, whose pride, judgment, and commitment ultimately shape what the business becomes.

Relationships, up close

Fifty years ago, I was working full-time as a social worker and part-time as a bartender. Both jobs showed me how our lives are shaped by relationships and how difficult it can be to express what we feel when the stakes are high.

When the opportunity arose to buy the small flower shop across the street from the bar where I worked, I took it. In both jobs, I had seen people searching for ways to connect. If words sometimes fell short—and alcohol helped loosen them—why couldn’t flowers do their own kind of work?

That tiny shop on Manhattan’s Upper East Side became a place where people brought moments they cared about: a birthday, a reconciliation, a loss, to name a few.

In those early days, orders rarely came without context. A customer might explain that her daughter had just moved into her first apartment and felt lonely. Someone else would describe a gathering they hoped would feel warm rather than formal. People shared intimate details of their lives—it was the 1970s!—and many stopped by simply to say hello, swap gossip, or ask for a restaurant recommendation.

Funeral work made that lesson unmistakable. Families came in for flowers, but what they really wanted was a way to express what words couldn’t reach. Over time, we became known for deeply personal tributes—arrangements shaped like garbage trucks for a sanitation worker, or gates left intentionally open because, as one family put it, “you never lock the gates to heaven.”

Those moments stayed with me. They made it clear, early on, that carelessness had consequences—and that trust, once given, had to be earned again every single day.

Scaling trust

Built on strong relationships, that single flower shop grew into a small chain. Business was good, but I could see opportunities to grow further. The challenge then—as it remains today—was how to expand without losing the trust that had been built one customer at a time.

We learned early on that convenience plays a role in trust, and technology became a powerful way to deliver it. In 1984, while listening to the radio one morning as I shaved in the bathroom, I heard about the growing impact of toll-free phone numbers.

The company that owned the 1-800-Flowers number hadn’t figured out how to turn it into a national floral business. I thought we could with the right investment in telemarketing—this has always been a relationship business, after all. It worked so well that the phone number eventually became the name of the company.

That was just the first of several technology waves we’ve navigated. We moved online when plenty of people doubted anyone would buy something so personal over the internet. We embraced mobile early. And today, we’re exploring how artificial intelligence can help people choose, personalize, and communicate more thoughtfully.

Each shift mattered only to the extent that it made human connection easier. Technology earned its place when it helped people act on intentions they already had. It succeeded when it reduced friction in relationships—and failed whenever it distracted from them.

Stewardship is a choice

The trust required to build and sustain relationships is neither automatic nor permanent. It has to be earned again and again. I saw it up close as 1-800-Flowers.com expanded beyond flowers into gourmet food and gift baskets, and we began evaluating businesses to bring into the family.

I remember my first visit to Harry & David after we acquired the company in 2014. Years of ownership changes and aggressive cost-cutting had taken a toll. Trust between leadership and employees had been badly damaged, and customers had noticed.

When I arrived, the leadership team braced for a familiar conversation. They had grown used to owners focused on extracting value by cutting costs, narrowing ambition, and shrinking the future. People were understandably guarded, uncertain about what came next.

But the conversation took a different turn. Instead of talking about what could be stripped away, we talked about planting more fruit trees and protecting what made the brand distinctive for the long term. The focus was stewardship rather than short-term returns.

Previous owners had talked about harvesting value. We were talking about cultivating it. One longtime employee told me afterward that he had never heard an owner speak that way.

Staying connected in a crisis

The shift toward digital commerce brought challenges, especially when it came to maintaining relationships with customers who now encountered us through screens rather than storefronts. Technology created reach and convenience, but it couldn’t replace the power of being together.

The pandemic brought that reality into sharp focus. In a moment of urgency, we closed all but one of our remaining Harry & David retail stores.

As the crisis unfolded, I asked a simple question of my executive team: How do we stay close to our customers now? How do we check in, not as a business, but as people? A young woman in my office suggested writing a newsletter. That idea became the Celebrations Pulse.

The first subject line captured the intent: “Just checking in.” In those early weeks, I shared thoughts on staying connected and maintaining perspective during a period of isolation and uncertainty.

The response surprised me. Readers were struck that a brand wasn’t trying to sell them anything. As weeks turned into months, the focus naturally widened from COVID to loneliness, from crisis to connection, from coping to the deeper reasons we celebrate in the first place. We eventually invited readers to share their own stories, many of which became the foundation for future letters.

What began as a simple outreach grew into an ongoing weekly conversation. Circulation steadily expanded, from six million to 10 million readers. Today, it’s approaching 20 million—proof that even in a digital world, people still value being seen, heard, and remembered.

Another turning point

Technology continues to evolve, and customer expectations evolve with it. The tools change, the pace increases, and leadership requires a willingness to keep learning. What matters most is staying attentive to the people you serve and the promises you’ve made to them.

It’s easy to rely on approaches that worked well in earlier chapters. Over time, though, the work asks for new skills and fresh perspective. Relationships don’t stay strong by standing still; they grow when you meet people where they are.

We were reminded of that in late 2024, when our food brands introduced a new order-management system ahead of the holiday season. The rollout didn’t meet our expectations, and some customers were left waiting during moments that mattered to them. It was a difficult experience, and a revealing one.

As the company approached its 50th anniversary, that moment prompted reflection. Longevity brings responsibility—not only to honor what has worked, but to make thoughtful decisions that support the relationships the business depends on today and in the future.

In the spring of 2025, I stepped aside as CEO of 1-800-Flowers.com and continued as chairman. I’m now partnering with our new CEO, Adolfo Villagomez. His experience at Home Depot and strength in operations and team culture balance my own perspective. He’s the yin to my yang as we move into the next chapter.

After fifty years, the lesson is a simple one. As title and tools change, what endures is the work of earning trust—by listening closely, acting responsibly, and making decisions that keep relationships at the center.

50 years of gratitude

Rather than protecting a legacy, the work ahead is about continuing to earn trust one decision, one interaction, and one relationship at a time. Gratitude keeps that responsibility front and center.

Businesses don’t last because they declare success. They last because enough people decide, again and again, that they’re worth believing in. For that belief—and for the people who continue to extend it—I remain deeply grateful.