Why 1-800-Flowers Continues To Bloom Through Decades Of Change

Forbes

12-05-2025

Almost 40 years ago when 800 phone numbers that spelled something were all the rage, Jim McCann transformed his chain of New York flower shops into what became the national chain 1-800-Flowers. It's stayed relevant through the years by adopting new technology, making acquisitions in the gift-giving and delivery space, and staying true to an always-desired product. Today, the day after one of the busiest in the flower delivery business, Adolfo Villagomez takes over from McCann as 1-800-Flowers's new CEO. McCann will remain the company's executive chairman.
I talked to McCann last month about his time in the flower business, the risks he's taken, and the reasons business has persevered. This interview has been edited for length, clarity and continuity. It was excerpted in the Forbes CEO newsletter.
How did you get started in the floral business?
McCann: It was an accident. I grew up in Queens, New York, and looking around at the potential role models around me, there were some bad people and there were lots of good people: civil servants, shopkeepers, tradesmen. I decided to be a policeman, so I went to John Jay College of Criminal Justice.
While I was in school, I started working in a group home for teenage boys. I was a live-in night counselor, and that caused me to accidentally have a career in the social services because I really came to like the work and did it for quite a while. Over the years, I went from living in a group home to running a group home to running all the group homes. That's where I grew up. It really changed me as a person, matured me, so I kept postponing going into the police department.
But working in a not-for-profit social work world, you don't make very much money. I married young, we started a family young, and so money was always an issue. I worked part-time in other jobs. And being an Irish Catholic kid from South Queens, the prevalent job was bartending.
1-800-Flowers founder and Executive Chairman Jim McCann.
I was working Friday and Saturday nights on the Upper East Side of Manhattan. One of my customers who would stay late on Saturday nights owned the flower shop across the street and chatted a bunch. He told me he was going to be selling that flower shop. I thought, that's interesting, retail. I've worked in retail all of my working years. I understood it. I asked him how much he was asking for the flower shop. He said $10,000. I thought it was a sign from God because I just sold a building that I had bought in Brooklyn and fixed up. I had a $10,000 profit. So, I said, this is a sign.
I wound up buying that flower shop. I kept my job at St. John's Home with the intent of not just becoming a florist, which of course I did, but to build a business. Six months after I bought the first shop, I opened the second shop, and every six months I'd open a shop. Then every three months. Eight years later, I was full-time in the flower business.
How did you go from flower shops in New York City to the nationwide company 1-800-Flowers?
Ten years in, I had 40 or so flower shops, and I decided to buy the company that had the telephone number that became 1-800 Flowers. Then I changed how we went to market. I changed the name of the shops to 1-800-Flowers. Everyone thought that was crazy: To buy the telephone number, to change the name of the retail stores to a telephone number. But so far it's worked.
I sold those shops because I needed money to build this idea, to market it. I didn't know anything about venture capital or private equity. I didn't have any of those skills or knowledge. So I became a franchisor because I needed to sell the shops to get money to build this brand. The good news is, five years later, we were a national brand because we didn't have any money, so we couldn't make any big financial mistakes. And we caught the wave of interest in people using 800 numbers. We got a lot of free press and promotional opportunities that really helped us become a brand.
At that point, my younger brother, 10 years my junior, joined us in business. We said, 'If we could become a national brand with no money and no knowledge, what's going to replace us?' So we were always on the lookout for what's next.
What happened next?
Of course, what's next was the internet. We were early to it. That was our third wave.
The fourth wave was just at the beginning of the 2008 financial crisis. We were impacted by it and we said, 'Geez, we can't afford to do all these development ideas we had in mind.' We went from 16 to three that we continue to fund. One was our technology platform and the other two were social and mobile. And boy oh boy, they were the right guesses, because social and mobile changed everything for us.
The fourth wave was just at the beginning of the 2008 financial crisis. We were impacted by it and we said, 'Geez, we can't afford to do all these development ideas we had in mind.' We went from 16 to three that we continue to fund. One was our technology platform and the other two were social and mobile. And boy oh boy, they were the right guesses, because social and mobile changed everything for us.
How have you decided which business gambles to bet on? You've done well with all of them.
Not really. When we got on the internet, we were tracking how many other things we tried, and it was over 50 other tech changes. We put our catalogs on a CD-ROM when that was in vogue back in the early '90s. It was a bomb. There were 50 of those bombs.
The one we kept coming back to and iterating on was this online world, which was dominated at that time by CompuServe, Prodigy and this little outfit called AOL. My brother and I are very curious and we're not afraid to ask a lot of people what's going on. In my case, you don't have to be the smartest person in the world, but you have to ask a lot of questions, and you have to get to the right people to get their insights so you can make your judgment about what's coming through the pipe.
Throughout your time in the flower business, what has been your philosophy?
A wise fellow who I stay in touch with is Bob Pittman. [He] was running AOL with Steve Case and Ted Leonsis back in the early '90s when we chose them to partner with. We try to do all of our judgments based on genuine relationships, and Bob convinced us then that we should go public. That was a wise recommendation.
He also espoused the theory of convenience. He said convenience trumps everything. We've been on our path as a company looking for how can we be more convenient for our customers. Basically, what we want to do is be convenient enough to help them to easily act on their thoughtfulness. What would be more convenient than coming to the store? My friends in the flower business told me, no one wants to use a credit card. They all want a house account. And no one wants to call you 24 hours a day, seven days a week. All of which is wrong; Bob's prediction was ignore them. How can you be more convenient for your customers to enable them to act on their thoughtfulness? That's been our driving mantra: How can we be more convenient, which is why we adopted mobile so early, why we adopted the internet, and why we're using AI now.
We realized a long time ago that we're not really in the flower and fruit and chocolate gift businesses. We're really in the relationship business because when people come to us, they want to express themselves and their emotions to somebody.
Tell me about some of the options you have; the company is more than flowers.
We just developed a small company last year and broadened its capability to help people to be able to send a greeting card. Now you can come to any of our sites, and you order a greeting card. You can choose from our library. You can write what you want in it, or you can take what we suggest. You can use our AI tools. My wife, who knows that I'm not at all creative, got a little emotional [earlier this year] on her birthday. I told our AI tool that my wife likes to garden, she loves spending time with her grandchildren, she's a baker and she loves teaching her grandkids how to bake, and once in a while, she likes a glass of good wine. The tool asked me: Would you like a poem, a limerick, a sonnet? When my wife opened that card last month in front of the whole family and read this message from me and got emotional, I was thrilled because she at least knew I was thoughtful enough to remember what things to tell the tool. She knows I couldn't compose that poem, but she knew I was thoughtful enough to get help to do it. I handed her the card, but we'll mail it for you for $5.99.
People even within our company say, we can't give people a $5.99 alternative. They won't buy our $100 dollar gift baskets. I think they're wrong. More people come to us more frequently now because we have that capability. We have free recommendations. If you ask us to remind you about your mom's birthday, we'll remind you. You'll tell us you want to be reminded two weeks before or a week before or the day of. We use reminders more and more to help our customers to stay connected with the people that matter to them.
[We also give] suggestions: gift suggestions, and we always say, here's something you can tell her. Here's something you can text to her. You could send a free digital greeting card. The first set of recommendations we always put forth are free, and then we give you [more options]. You want to send a $5.99 card with postage included? If we give you more reasons to come to us more frequently and you feel like you're having better, and deeper relationships, then it'll be good for our business.
What are some other things you've been doing?
At Celebrations.com, we've introduced a relationship management tool.
In the beginning of Covid, I started writing a newsletter every Sunday to our customers. I didn't know what else to do. We didn't know if our business was going to go away, and the young lady who was my chief of staff at the time suggested, 'Why don't you just write what you're thinking and feeling and how we're managing through this to our customers? Don't try and sell anything.'
I said, 'That's a good idea.' The good news is it worked. The bad news is it's a lot of work. I write about relationships, and I used the calendar a lot: Yesterday was National Siblings Day, so last night I gave everyone else the advice they should connect to their sibling. We use things like that to [remind you of] National Siblings Day, or National School Nurses Day and National Teachers Day. That's our newsletter. We have over 10 million subscribers now. It's taken off and become a podcast that we do exploring relationships and great stories.
The community was starting to ask me questions at the beginning of Covid especially: What do I do if my kids are out of school? I created a panel of a half a dozen of the most prominent and thoughtful professionals, psychologists, mostly. Dr. George Everly was the first one that I asked to be on that panel. He called me one day and said, 'Jim, you love this work. I do too. We've been doing some really neat things together. Why don't we write a book?' He convinced me we should do it. It came out in the fall. It's called Lodestar.
That resulted in us developing a relationship management tool at George's suggestion. I always remind people at the beginning of the year about their resolutions in my newsletter. And two years ago I started reminding them: You're going to change your diet. You're going to exercise. You should be cognizant of your relationships. Make a list of relationships you have that are going fine. Make a list of relationships that you had, but have waned over the years. Which of those do you want to reinvest in? Give me a list of three, four, five relationships you don't have that you want to be deliberate about: at work in your career, socially, in your community. What's your plan to ignite a relationship there?
We use an AI tool to remind you what you tell us that you want to do. You said you wanted to get to know Megan better, but I don't see any correspondence between you, and Megan just got an award. I saw this clipping on it. You might want to drop her a note to say congratulations.
We're building those tools into our every day using AI, which is the only effective way to do it, to help people be deliberate about relationship building.
There are some founders that stay with their company for a long time, and there are others that don't. You've been in it for the duration. Why have you stayed in the business?
I'm not a business person. I'm a person who's in pursuit of success, of feeling accomplishment and purpose. What I am going to do is fire myself again. Nine years ago, I stepped down as CEO. My younger brother Chris took over. Unfortunately, he has some health issues, so he had to step away. I'm only back in it for a temporary period, but I'll always be working and I'll always be around the company, my passion. I'll do the things that I can do: the podcast, the newsletter, thematically working with the management team.
What do you see in the future for 1-800-Flowers?
I'm very excited about the future, frankly, more excited than I've ever been. This celebratory ecosystem that we're developing has been an idea of mine for a dozen years. But now, finally, the tools are there for us to do that. Like the relationship management tool. We couldn't have done that a year ago.
I'm very excited about fleshing out the celebratory ecosystem, helping our customers have better, bigger, deeper relationships, and giving them all the different ways they can connect, whether there's a transaction involved or not. We're starting now to track our customers' engagement with us, not just their transactions.
What advice do you have for other CEOs?
The advice I give myself is don't think that you have all the answers, and develop a support system of people that you can turn to get a different point of view. Get people who tell you things that you should hear, that you're not going to hear from the people who work for you.
I turned to a friend this week and said, 'Bob, these are the three things that I'm wrestling with.' He gave me very unvarnished advice about where I should be spending my time and my energy, and he was very candid with me. So it's good to have people you can turn to who you trust and who will give you the unvarnished truth.