#265: Jim McCann, American entrepreneur and former CEO of 1-800-Flowers – Find a way to connect

13 Nov 2025 · 1 h 18 min · 33 chapters

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In short

1-800-Flowers’ Jim McCann on building a relationship-first gift business, leading through mistakes, and using technology/AI to deepen customer connection.

Guest backgrounds

Jim McCann is an American entrepreneur and former CEO of 1-800-Flowers. He grew up in Queens/Brooklyn, learned business at his father’s painting-contractor “kitchen table” planning, worked social work at St. John’s Home for Boys in Queens, and bartended to overcome shyness. He later built 1-800-Flowers into a national brand and expanded into food gifts (Harry & David), cookies (Cheryl’s Cookies), popcorn (The Popcorn Factory), chocolate (e.g., Scharffenberger/Simply Chocolate), and personalization (Personalization Mall/Things Remembered).

Key claims

1-800-Flowers is not “in the flower business” but in the relationship business. Leaders must “find a way to connect” with individuals, not groups. Innovation is required to avoid being disrupted; “let it be by us.” AI should be embraced for capabilities (relationship follow-through), not just efficiencies, and teams should be prepared transparently for disruption.

Notable examples

Teresa’s story—sending flowers to a estranged sister (“I still love you”) restarted a seven-and-a-half-year silence. McCann’s boy-home lesson: he bonded with volatile “Joe” by customizing a greeting ritual (fixing Joe’s hair) and building trust. He describes buying the 1-800-Flowers name for $2M while assuming undisclosed $7M debt, then using bankruptcy avoidance to recover. He cites early tech moves (AOL transactions, 1992 website) and investing in mobile/social during the 2008–09 crisis.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Exploring Bankruptcy and Family Values

0:00 to 0:45

Jim shares insights from his family's perspective on bankruptcy and responsibility.

“One of my uncles suggested, well, maybe you ought to look at this bankruptcy thing where you can shed all that debt.”

The Business of Gifts: Seasons and Stories

0:45 to 3:08

Discussion on the various holiday seasons and gift categories for 1-800-Flowers.

“and make wonderful gift boxes and gift baskets and prepared foods.”

Connecting Through Flowers: A Story of Reconciliation

3:08 to 4:53

Jim recounts a touching story about a customer reconnecting with her sister through flowers.

“You know, after being in business for 50 years and helping millions of people send flowers, what's a moment with a customer that really captures what you think 1-800-Flowers really is all about?”

Jim's Childhood and Early Influences

4:53 to 6:39

Jim reflects on the leadership lessons he learned from his family's painting business.

“And I really want to dig into how you built this incredible company of yours.”

Lessons from a Social Worker

6:39 to 9:00

Jim discusses his experiences as a social worker and the lessons learned about leadership.

“But listening to my grandmother really be in charge, but subtly letting them think that they were really in charge was a great education for me in small business, business in general, and personalities.”

Building Individual Relationships in Leadership

9:00 to 14:01

Jim shares strategies for building personal connections with individuals he worked with.

“I was part of a family, a family that had a brand reputation And when she said, we don't do that, it was end of discussion.”

Building Bonds with Young Men

14:01 to 16:48

Learn how personalized connections can foster relationships with youth.

“But it was our way of bonding and me giving him our special personal hello.”

Facing Fear as a Leader

16:49 to 19:33

Discover the challenges of showing vulnerability while leading in tough situations.

“I think being genuine is critically important.”

The Journey to Social Work and Bartending

19:34 to 21:46

Explore Jim McCann's path from bartending to social work and its impact on his career.

“And after dinner, he says, come on downstairs to my office for a few minutes and said, Jim, do you think you'd like to give this work a try?”

Community Connections at the Flower Shop

21:47 to 23:45

Learn about the importance of community relationships in business.

“What did you like about working in that shop?”
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The Birth of 1-800-Flowers

23:46 to 28:00

Understand the strategic decisions behind creating the 1-800-Flowers brand.

“How good is this conversation with Jim McCann?”

The Shift to Franchising

28:00 to 29:20

Jim McCann discusses how he transitioned to a franchise model and its impact on his business.

“But so many times the worst decision turned out to be the best decision because we became a brand without any money.”

Expanding Beyond Flowers

29:20 to 30:59

McCann explains his strategic decisions to expand his business beyond just flowers.

“You're not just the flower business now.”

Innovative Product Development

30:59 to 33:31

The journey of acquiring various brands and products that align with customer preferences.

“to get us through the growing season in the melt.”

Embracing Change and Innovation

33:31 to 36:33

The importance of innovation in business and how McCann adapted to new technologies.

“And I was thinking, what's going on here?”

AI and Relationship Building

36:33 to 41:16

McCann discusses the role of AI in enhancing customer relationships and engagement.

“And now this wave that's breaking on a shore, which is being aided by everything AI, is frankly the most exciting wave in our career's history.”

Preparing for Disruption

41:16 to 42:03

McCann addresses how to prepare teams for the disruptions that AI may bring.

“So I think the capability side is the really exciting side of what's going to be efficiencies, I understand, but capabilities are where the real magic is going to happen.”

Navigating Disruption and Employee Investment

42:03 to 46:38

Learn how transparency and investment in employee skills can help navigate disruption.

“But we were talking about the fact during the courting process when I was trying to lure him here in those many months before he started, we were talking about the efficiencies and the impact it's going to have.”

The Concept of Resume as a Verb

46:38 to 48:54

Explore the idea of treating your resume as a dynamic reflection of your skills and experiences.

“And, you know, you released a book a little over a year ago or last year called Load Start.”

Lessons from Dr. George Everly

48:54 to 53:10

Discover powerful insights on potential and achievement through the story of Dr. Everly.

“plus years teaching at Johns Hopkins University, where he's emeritus on the faculty now at the School of Public Health, the Bloomberg School of Public Health and the medical school.”

Embracing Technology and Cultural Change

53:10 to 56:00

Understand how to lead teams through technological changes and foster a culture of innovation.

“And, you know, you really are a change agent and you've managed the company through so many different changes.”

Lightning Round with Jim McCann

56:00 to 58:31

Jim McCann answers rapid-fire questions about his preferences and life.

“And this celebration seems to be the key.”

Navigating Marriage and Entrepreneurship

58:31 to 59:45

Jim shares how he and his wife have balanced marriage and business challenges.

“And, you know, your wife has always been supportive.”

Inspiring Young Minds to See Opportunities

59:45 to 1:02:22

Jim discusses his experiences helping young people realize their potential.

“is work-life integration is a gift, and you should be working at it and tuning it all the time.”

Personal Reflections on Family and Legacy

1:02:22 to 1:04:37

Jim reflects on his family, legacy, and the importance of being a good grandparent.

“The closest idea to someone being in business was a young man said, I think I'd like to be a barber.”

Advice on Leadership and Deliberation

1:04:37 to 1:05:12

Jim emphasizes the importance of being deliberate in leadership.

“and have appreciation for long after we're gone.”

Understanding and Empowering Teams

1:05:12 to 1:06:15

Jim discusses balancing vision with team understanding to foster success.

“critical of me, and I really appreciated it.”

Conclusion and Show Wrap-Up

1:06:15 to 1:07:01

David and Jim conclude their discussion with reflections on the interview.

“But if you spend more time, like I expect Adolfo has and will, understanding what everyone's metric needs to be, what their particular job is, what their goal is.”

Understanding Customer Insights for Growth

1:10:02 to 1:11:18

Learn how understanding customer needs drives successful business acquisitions.

“We'd actually like to buy Harry and David so that it's the one-stop shop for people to go buy all their gifts.”

Resume as a Verb: A Philosophy for Growth

1:11:18 to 1:11:59

Explore the concept that a resume should reflect continuous growth and learning.

“And that's really a philosophy that they try to ingrain into their people at the 1-800 Flowers company.”

Embracing AI: Preparing Employees for Change

1:11:59 to 1:13:08

Discover how to prepare employees for technological changes, including AI.

“they have developed this training program and they call it Fresh University, which, by the way, I love that name because you want your flowers fresh, therefore Fresh University.”

The Power of Humor in Leadership

1:13:08 to 1:14:06

Understand how humor can be a competitive advantage in leadership roles.

“And that's part of his resume as a verb.”

Self-Deprecating Humor and Its Benefits

1:14:06 to 1:18:06

Learn how self-deprecating humor fosters connections and improves workplace morale.

“And humor is this concept that I'm honestly surprised it doesn't come up more on this podcast because you've got some jokes, David.”
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Transcript

Automatic transcript. May contain errors.

0:00One of my uncles suggested, well, maybe you ought to look at this bankruptcy thing where you can shed all that debt. And my grandmother looked at me and gave me the Irish finger, David. Come here. And she called me into the dining room and she just said to me, that bankruptcy thing, we don't do that. Figure it out.

0:22David Novak:I got to imagine that Valentine's Day is your biggest day. Am I right on that or? Wrong. Wrong. What is it? Well, remember, we're flowers and gifts, and we have three categories of gifts. All of our floral product are things you would find in the greatest flower shop experience. We have food gifts, and our lead brand in our food gifts category is Harry and David. So we grow pears and peaches and apples and kiwis and grapes and et cetera, et cetera, and make wonderful gift boxes and gift baskets and prepared foods. And then we have a newest division, which is called Personalization Mall, Things Remembered.

0:56So it's all gifts that you would personalize, like some of the knickknacks you see behind you there. We would manufacture those. So if there's a couple getting married, you might send them the champagne flutes with their names on it and the date of their wedding, all those kinds of things. Now we have a big push on photography. So if you and your daughter had just finished your round of tennis and someone snapped a picture of you and you just loved it, you might send it to her this afternoon, already framed or emblazoned on a mug for her to put with her collection.

1:27David Novak:That's great. That's to say that Valentine's Day is a busy holiday, particularly for the floral brands and our chocolate brands. But the biggest holiday in our calendar is the Christmas season, this fourth calendar quarter, our second fiscal quarter, because all of our food gifts, this is their quarter. Harry and David, this is their quarter. Cheryl's Cookies, the Popcorn Factory, all of those brands are biggest in the fourth quarter, the Christmas holiday season. Then for flowers, the next biggest occasion is Mother's Day, the biggest floral gift occasion. And Valentine's Day is very busy, but about half of Mother's Day because apparently there are a lot more moms than there are sweethearts.

2:06David Novak:I love it. Boy, I was eye wrong on that. But I bet you, you might have a story. What's your favorite Valentine's Day story? Well, there's ones I can tell and there's ones I choose not to tell. But it's amazing. You know, we used to encourage people to order early because it's such a crush at Valentine's Day. It comes in the last several days, whereas Mother's Day is stretched out over a two-week period of time. And, of course, the Christmas holiday starts before Thanksgiving and runs right through the month of December. But Valentine's Day is a crush. And we guys are known for not being advanced planners.

2:38I don't know if you've ever heard that. And sometimes we forget that Valentine's Day is sneaking up on us. So we'd always encourage our customers to order early. And I remember taking a call from a gentleman at a quarter of nine on February 14th saying, can I get this delivered by noon? I said, I can't do it for you. And he said, well, you said to call early and this is pretty early. So what you say, you think you understand how people interpret it, but then you find out otherwise.

3:08David Novak:You know, after being in business for 50 years and helping millions of people send flowers, what's a moment with a customer that really captures what you think 1-800-Flowers really is all about? Well, I think what we're all about and what we've learned, let's say, in a recent bunch of years, David, is that we think we're in the flower business, but we're not. We're really in the relationship business. That is, we're in the business of helping people express themselves and connect with all the important people in their lives. And I think of a story from, you mentioned my Queens roots. Well, not in Queens, but next door in Brooklyn.

3:44There was a lady, her name was Teresa, and they lived in a semi-attached home, which would be very common in Bensonhurst, Brooklyn, the neighborhood that she lived in. And she lived right next door to her adult sister. And they were each married, had their own families. And Teresa wrote to me a story after she had ordered flowers from us. And she said, my sister and I haven't spoken in seven and a half years. And she says, I'm not even sure what the argument was about anymore. But it's so bad that if we pass one another on our common stoop, so one stoop, two separate front doors to two separate homes.

4:19She said, we'd just turn our heads and walk the other way. She said, I read something you wrote recently and I took a chance and I sent my sister, I called 1-800-Flowers, sent her flowers and just signed the note saying, I still love you. And I signed it, Teresa. And a day went by, I didn't hear anything. And there we were. I was leaving the house and I was just locking the door and I turned and there's my sister. And she said she didn't say a word to me. She just came up. We hugged and we cried and we forgot what we were mad about. And it just was the icebreaker we needed.

4:50David Novak:I love that story. And I really want to dig into how you built this incredible company of yours. But let me take you back a little bit first. What's the story from your childhood that shaped the kind of leader you are today? I grew up in a household. My dad was a painting contractor. The business was started by his father, Queens, New York, and he had two brothers. My grandfather passed when my father was only, I'm going to say, 19 or 20 years old. So he just came out of, graduated high school, went to college for a year, was drafted into the military, but it was late in the war. So he was too young to have gotten into combat in World War II.

5:31So now he's home and he's playing football semi-professionally. And his mom, his dad passes, and his mom came to him and said, you know, this is pre-social security, David. So there's no safety net. And she said, look, I have to keep this business going. So I need you to return to the business that you'd worked in part-time as a kid. And I need you to be the face of the business because he was the oldest of his three brothers. And so my little five-foot-one Irish grandmother ran this business out of a home. They had shops behind the home where they kept the trucks and the paint and all the ladders and all the equipment.

6:09And so from 20 or 21 years old, my father was, quote, unquote, the boss of the business. But my grandmother's house, which was only a few blocks from where I lived, was a place we hung out all the time. It was our home, and it was also corporate headquarters. The kitchen table in the morning would be my father and his two brothers, and they'd be planning job sites, where they're going, who's going. And I learned everything I needed to know about business then and to get me started by being a fly on the wall at those kitchen tables, listening to those conversations. When they came back from all their jobs late in the afternoon, and they might stop for a drink and talk about what's going on before they each headed home.

6:45But listening to my grandmother really be in charge, but subtly letting them think that they were really in charge was a great education for me in small business, business in general, and personalities. Explain that. Talk a little bit more about that. Well, you're just sitting there and you're listening and you hear what the arguments are, what pressures of jobs and having a couple of dozen employees and all the things they had to deal with, none of which related to the business, always personal. and I remember I this is a long time ago I just bought the company that had in it the the 800 number and I was commuting back and forth to Dallas where the company was based and I had a terrific partner a local partner there who worked with me the first year or two what what happened was I'd been in business now for 10 years I'd opened up a bunch of flower shops one at a time every six months I'd open up another shop then every three months and after 10 years I had a whole lot of flower shops.

7:44So I was able to leverage that to put down$2 million borrowed against those to buy this company to get at the 1-800 number. The company had failed. And being a smart aleck kid from Queens, I figured, why would I spend money on lawyers, accountants, bankers? Why would I spend that money? Well, I now know why you would spend that money because I didn't do due diligence. I did do negligence. And I signed the purchase agreement personally and assumed all of its debts. And because it had failed, there was really no one around to tell me that they had accumulated$7 million in debt that was undisclosed to me.

8:21And I remember discussing this at my grandmother's kitchen table with my father and his brothers. And one of my uncles suggested, well, maybe you ought to look at this bankruptcy thing where you can shed all that debt. And my grandmother looked at me and gave me the Irish finger, David, come to them. And she called me into the dining room and she just said to me, that bankruptcy thing, we don't do that. Figure it out. That was it. That was the extent of our conversation. It was one way and it motivated me to go back and forget about bankruptcy and just figure out how to work out of this debt. And it was great advice.

9:00But the whole idea of I was part of something bigger, not just myself. I was part of a family, a family that had a brand reputation And when she said, we don't do that, it was end of discussion.

9:12David Novak:I love it now. And one of your first jobs, Jim, was as a social worker running a boy's home in Queens. What was the biggest lesson that taught you? Oh, so many lessons, David. In fact, I hadn't been back there in 15 or 20 years. And I was privileged this year to be asked to be the commencement speaker at St. John's University here in Queens. a wonderful institution with great people doing the great work of educating mostly first time to college and there was a lady in the audience who's the executive director of St. John's Home for Boys where I'd worked for many years and I didn't know it because I hadn't been connected to it in the last decade or so and she had a son graduating and she wrote me a note said my son's been quoting you for the last two months now since the commencement and so it gave me the nerve to sit down and write you a note and invite you to come home.

10:08So this is in Rockaway Beach, Queens, the St. John's home. So I made a trip two weeks ago down there to visit. It looks physically the same, but it's very different in terms of the population of kids they take care of. But I spent a good part of a day down there and sat down for lunch with about 14, 15 of the guys and just had wonderful conversations about future, their futures, their perception of the future. And And it was just great to go home. But the lessons I learned there over the 14 years I worked there were just tremendous. I started there as only six. I started as a living counselor, evening counselor in one of our group homes.

10:44Ten teenage boys, myself. And I'd be the only one on at night from, I'd started four when the other staff had leave by 6, 6.30. And then I'd go to bed around midnight, get up in the morning, make sure I got them off to school. And then I was off during the day. School or work or whatever was going on. And I learned so much from being very bad at that work to then getting counseled. The fellow who was executive director was a member of a religious order of brothers and priests. And again, I just reconnected with him in the last couple of weeks. He reached out out of the blue to say, you know, it's been too long.

11:19We had a wonderful conversation. But he taught me so much about people, motivation, skills. And when I told him I was going to be leaving, he said, no, you're not leaving. You have a passion for this work. and let's look at what you're doing and what other people in other group homes or our main home where we had 170 boys, what the good leaders are doing and what you're not doing. And one of the first things I learned is the people who were really good, the men and women who were really good at running their group homes, they came to work with a plan every day of what they wanted to accomplish.

11:51And I didn't. At first, I'd go and I'd just react. There was an incident with the police. I'd take care of that. There was a problem in school. I'd deal with that. So I was bouncing around with no influence or control over the environment other than reacting to what happened. But the really good people had a plan. Whether or not they stuck to the plan or were able to was immaterial. They had a plan. They were going to affect what was happening that day, that evening, that week, that month, that school year. And that was one of the first lessons I learned. And the other one was something I've heard you talk about a lot.

12:25I tried to have a relationship with a group of 10 guys. You don't have relationships with groups. You have relationships with individuals. And I had to find a way with good counseling and coaching from my boss, my immediate boss, and from Brother Tom, the executive director of the home, about finding your way to connect. And with 10 different boys, I had to find 10 different ways to connect. I had one young man, his name was Joe, and he had a beautiful head of black hair, straight, and he'd comb it, and he was meticulous about it, and he put this gel in it. But Joe had some issues based on his background.

13:07His issues were you couldn't touch him. I mean, if you brushed up against him, it could be a holy war going on. And I had to find my way to build a relationship with him because he was volatile, and he could really set the whole house off. and get quite physical too. Well, I invested so much in my relationship with him. What happened between us, I'd get him to work. I started four o 'clock, get there by 3.15 or so. If I didn't find my way to go find Joe in the house and mess up his hair. Now, if anyone else had done it, they might've died. But the bond we built, the relationship we built, the trust, the caring that was evidenced, it got so that if I didn't go and find him, there'd be trouble.

13:50Because he complained, he did it again. This is ridiculous. He'd be in the mirror, combing his hair back. And he loved it. He loved the attention. He loved that it was our thing and that he complained about it. But it was our way of bonding and me giving him our special personal hello. And you had to find a different way with each of the young men to build that bond. Was I successful every time? No. But eight out of 10 for sure, we developed a special relationship. They knew I cared, and they knew it was individual and customized and personalized between he and I.

14:25David Novak:That's great. You know, and I've heard you say that if the boys saw fear in you, they'd take advantage of it. Let's have an example of a situation where you were terrified inside, but you couldn't show it. I had my second group home in a neighborhood only 10 blocks from where I grew up, but a million miles away in Attitude. and I had a young man who was, I'm sure he was developmentally disabled, although not properly diagnosed, but he was unbelievably well-built and he had a scowl. He looked like one tough hombre, and he was, but he was very limited and he'd get into trouble a lot in the street.

15:08And he got into an incident with a gang and it wasn't very far from the group. I could see it brewing a block away. So I go running up there to try and intercede. And he got into a fight with this one guy. And I pulled Tony up off of this guy. And this guy had a knife and he didn't know it. And he cut Tony across the abdomen. The good news, it wasn't terribly deep. So he wasn't terribly hurt by it, but a lot of blood. And then I had to try and stand down this gang who wanted to finish the job. and I'm telling you, I was shook. I had not seen anything like this. I felt responsible for having pulled Tony off this guy down on the ground.

15:55But I had to stand this gang down so nothing else happened to Tony and I can get him away and get him to the hospital. And just in a moment, I didn't realize how frightened I was until I was walking away from the situation that had de-escalated and they were moving in another direction. And all of a sudden, the magnitude of what just happened, and here I am, 21 years old. I have this young man, I'm hobbling, carrying him, dragging him back to the house so I can get an ambulance or get him into our station wagon back then and get him to the nearby hospital. And all of a sudden, the magnitude of it hit me.

16:27And I said, I'm playing in a different league now.

16:31David Novak:You know, in this age where today it seems like everybody's talking about vulnerability being the big thing you need to show as a leader. Do you believe that leaders need to mask the fear that they have? How do you think about it? I don't know. It's not something I've thought a lot about. I think being genuine is critically important. But I think having a temper on your highs and your lows is appropriate too. I don't think you need to have everything out on your sleeve. And so I think having a good, sober, genuine behavioral pattern is what I'm comfortable with. You know, I understand you also worked nights as a bartender.

17:24David Novak:What did that experience teach you? Well, it was deliberate on my part to this extent, David. You've been in the hospitality industry your whole life. If you're a shy person, and I was, I'm still in recovery. One of the things that I did to help me overcome my shyness is I worked in a retail store. I worked in a men and boys clothing store. And you worked for a commission. Well, if you're shy and you can't interact with customers, you're going to starve. But you had a role. And it was easy to get into character to play your role to service people. And that helped me to be comfortable working with people.

18:06And so we had a lot of older guys on this staff. When I say older guys, I'm in my teens and then 20s working this job. They taught me the value of using humor. So these guys I worked with, they were salesmen for their brand, Levi's, the shirt manufacturers, Arnold Palmer, all these salesmen. And because we were a big account, my boss would say to them, okay, you're not busy for Father's Day because you're done selling. Part of the deal is all places order with you, but I expect you to come work here the week of Mother's Day because I can never get enough talent to help. And you're a professional salesperson.

18:42So these were older guys and salesmen. And so they all had these crazy personalities. And I learned from them. There's something I do all the time that I learned at 16 years old from one of these crazy sales guys who'd be in once or twice or three times a year to work with us. and he said to me one time, I don't care what everyone here says about you. I don't think you're that bad. I still use that line. I learned it from Irv back 100 years ago and I learned the benefit of using humor to break the ice, to get quicker into a relationship, to disarm people, to give you an atmosphere of genuine interaction.

19:26David Novak:How did you end up social working, bartending you know how'd you end up in the flower business well it goes back to bartending so uh i got my job in the in the group home my first job because i'm working being an irish catholic kid from south queens i had a genetic requirement to be a bartender and i'm working in a neighborhood pub and one of my customers a friend uh ran this particular group home and i'd ask him about it all the time and finally he said you know you seem interested why don't you come have dinner with me next Wednesday night at the group home. So I said, great. And I did that.

20:02And after dinner, he says, come on downstairs to my office for a few minutes and said, Jim, do you think you'd like to give this work a try? And I said, yeah, Bob, I think I'd like to give it a try. He said, good. He flipped me his key ring and said, can you do me a favor? I have no one to work tonight. And I've worked like six nights in a row besides my day shifts. Can you do me a solid work tonight? And that's how my career started there. Well, fast forward, I'm now the administrator of the home. So we had group homes and we had a main campus with a bunch of services and all there and a few hundred people working there.

20:34And as a very young man, I'm the administrator. And I had married young. And fortunately, I won the lottery there. And we had kids right away. And it's very rewarding to work in the not-for-profit social services field, except financially. It's not very rewarding at all. So back to bartending to supplement my income. I'm not 24-7 anymore. I'm Monday or Friday. So I'm working Friday and Saturday nights at a pub on the Upper East Side, you know, flipping bottles, you know, the place where they filmed the movie Cocktail with Tom Cruise. And one of my customers, again, stayed late on Saturday nights and we'd chat as we were wrapping up to close up for the evening.

21:13And he owned a flower shop across the street. And I'm thinking of flower shop. There's a, back in Queens, there are a couple of flower shops that seem to be pretty successful and seem to be making a good living. And it's working with the public. I've worked in retail. This seems pretty easy. So I said, Nick, do you mind if I come work a couple of Saturday afternoons in your flower shop before I come into the bar? Because he told me he was thinking of selling. So he said, sure, but why? I said, well, maybe I'm a buyer. So I did that for a couple of few Saturdays, and I really, really liked it. And so I said to him, Nick, I'm a buyer.

21:45So bartending led to my two career kinds of jobs. 1-800-Flowers and St. John's Home. What did you like about working in that shop? Well, here it is, the Upper East Side of Manhattan. I'm from Queens. I think I know everything. I don't. And I think Manhattan's just this big, one big neighborhood. And it's not. It's all these little micro neighborhoods. And our little flower shop, and when I say little, it was little, was the centerpiece of our little community of maybe four square blocks. And I got to meet people I didn't even know existed before, you know, all different kinds of characters. I found out what a walker was.

22:23Now, you would know, David, of course, but I didn't know what a walker was. A walker was this very tall, very distinguished looking gentleman who looked great with his salt and pepper hair. And I'm told he's a walker, which means a rather wealthy lady is going to the fundraising dinner and she wants an appropriate date with her and she's no longer married or her husband's deceased. And the walker be called upon and that was his career and he was very good at it the the the original plus one what i learned was we were so this is 50 years ago soon to be 50 years ago and we had 50 customers who made that business work we had more than that in terms of customers but it was 50 who would come in all the time and they'd make themselves a cup of coffee and they'd comment on the work we were doing.

23:11They ask about when the restaurant around the corner is going to be reopening and any good shows. I got some friends coming in town. What are you hearing about? What the best shows are? So we were like the little focal point of our community. The irony is fast forward. We now have 50 million customers. It's 50 years later. And the only way we can try and mimic that relationship we had with our customers back when it was one store and 50 who made it go is to use technology to get personal and to serve those customers better and better. So the lesson learned back then, we're still trying to apply today.

23:46David Novak:Hi friends. How good is this conversation with Jim McCann? I love his energy. I love that he's from Queens and I love that he loves flowers so much and just making people happy. Be sure you stay tuned to the very end of this conversation between David and Jim McCann because he and I, David and I, are going to debrief this conversation and give you some really practical ways that you can take the key learnings from their interview and apply them to your own leadership, to your own life and to your own work. And we get to talk about flowers, which is just really fun. I hope you enjoy the rest of this conversation with David and Jim McCann and be sure you stay tuned for the debrief.

Read the full transcript

24:23David Novak:You know, you mentioned earlier that you acquired the 1-800 flower name for$2 million and then you had the due negligence story. But how did you get hooked up with that 1-800-Flowers name to begin with? Well, I realized after 10 years of building up a chain of flower shops that it wasn't working. What I mean by that is there was no economy of scale. There's a reason why we florists are oftentimes, very oftentimes, family businesses. And you touched on it early on, David. That is, we have these peaks and valleys, Christmas, Valentine's Day, Easter, Secretary's Week, Mother's Day, Father's Day. We have these spikes.

25:09Well, those are terribly, you know, we'll go 10x, normal week to holiday week, 10x. How do you stare for that? Well, traditionally, how we stare for that was Uncle Barry works for IBM, but he takes his personal day, the Wednesday before Thanksgiving, to deliver flowers for us because he wants to be invited for Thanksgiving dinner. And that doesn't happen when you work for the XYZ company. And so what happened was we got up to 30 or 40 flower shops, and I ran out of family. And we didn't have that economy of scale any longer. So I was looking around, how else can we do this? I wanted to build something bigger.

25:45And 800 numbers were very new at that time. And everybody was spending money on TV campaigns to get people to remember their 800 number and toll-free numbers. By the way, a long-distance call was very expensive then. People were very reluctant to make a long-distance call if they didn't have to. Remember, hurry up. It's long distance. That's right. So this was a new concept that the company you're dealing with would pay your bill. And in the flower business, I went around and I said, you know, I think people would like to use their credit cards. I'd like them to be able to call 24 hours a day.

26:20And everybody who was smart and knowledgeable about the flower business said, that's crazy. People want to come into the shop. People, if they're going to call, they want to put it on their house account. They don't want to put it on a credit card. And they certainly don't need 24-hour-a-day service, all of which we now know is wrong. But common wisdom was none of those things are necessary. But I just felt that convenience was the key factor there. And if we could be easier and more accessible to our customers to enable them to act on their thoughtfulness, that would be a winning proposition for us.

26:57So you had Sheridan hotels out there with singing, dancing girls and chorus lines on their commercials trying to get you to remember 800-325-3535. There's only one person who remembers that, and that's me. And it's not even Mr. Sheridan. But I thought, is it a better way? If you could just remember the corresponding numbers, flowers is 356-9277. That would be an easy way to remember. But lo and behold, this company had already gotten a hold of their telephone number. And they launched this business. I called out to them and said, I'd like to be your fulfilling partner for the New York City area.

27:36They said, great. We started that. And for about a month, it was good. And then, boom, it just went to zero. And I called. They said, you know, we only had so much money. And we had some marketing ideas. And they didn't work. So we're closing down. So I got on a plane, flew to Dallas, became best friends with American Airlines. and wound up buying a company for the aforementioned$2 million down and an assumption of debt. And while it was a terrible business decision, it was something I was embarrassed about for a long time, having put my family and everything we'd worked seven days a week, 24 hours a day for and had good luck in the pursuit, was now in jeopardy.

28:15But so many times the worst decision turned out to be the best decision because we became a brand without any money. And that was in 1986. By 1992, we were the leading player in our category. And then we had some really good fortune come our way that helped us to become a national brand without having the money to cause it to happen.

28:35David Novak:And you really went after the franchise model. How did you get excited and learn about the franchise model? By accident and default. I didn't have capital. I didn't know how to raise capital. I didn't know what private equity was. I didn't know about financing and all. I was on educationally I was on my way to be a New York City policeman when I started working in social work and and then just putting off going to the police to bomb until it was too late so I didn't have a business education other than sitting around grandmother and grandmother's kitchen table what I did was I had all these stores and I needed capital and I knew that they were better run by families than by a company so I started selling those stores off to raise capital to franchisees.

29:16And that's how we got into the franchise business. How'd you make a decision that you talked about a little bit earlier?

29:23David Novak:You're not just the flower business now. You've really expanded. How did you make that decision to expand beyond flowers? So many times businesses get in trouble because they aren't focused and they go too broad, but you really found the right way to do it. What do you think made it work for you? Well, if you think of what we as a florist would do, we merchandise our store in different ways seasonally. So Christmas, it's going to have one look and a different mix of merchandise. You get the Valentine's Day, it skews to chocolate and flowers heavily. And then Mother's Day, it skews to different color flowers, different gifts.

30:03A lot of gift baskets come into play for Christmas and gift baskets for Mother's Day. And then Father's Day is a very different mix. It's chocolate, it's gift baskets, it's hobbyist baskets, very little in terms of flowers. So we were used to changing our mix for the appropriate season and the holiday that was next to come. And then we started, especially when we had online data and we could see where did our customers go after they shopped with us. And where did they go? Well, 16 % of the time they were going to this place called Harry and David. That was their next stop to finish their shopping list.

30:38And so we yearned to buy Harry and David for a decade. And then finally, it was purchased by a private equity firm. They took it through a bankruptcy and we had the opportunity and we seized it. And it's just a great brand. And that got us into agriculture. Who knew that this kid from Queens would be concerned about snowcap in southwest Oregon to get us through the growing season in the melt. But we have 5 ,000 acres of agricultural production there. And we've owned that company now for 10 years. And it's just a terrific company with a really wonderful product and good people. But that's what we did.

31:13We followed our customers while they wanted to buy chocolate. So we bought a couple of different chocolate companies. I was flying to Dallas on that aforementioned American Airlines. And in the little food box they gave you, there was a cookie. And I'm not a big cookie eater, but I opened the clear wrap on the cookie and I tasted the cookie. And it was delicious. This buttercream cookie with this icing on top. And I took the label after I finished the cookie, it stuck in my pocket, and I called Cheryl's Cookies in Columbus, Ohio and said, these cookies are delicious. I think our customers will like them.

31:44We begin selling their cookies. And several years later, Cheryl came to me that she had some health issues and she wanted to sell the business. And we were by far her biggest customer would be interested. So that's how it happened. And it happened with the Popcorn Factory and Cheryl's and Schaffenberger Chocolates and Simply Chocolate. So we either started them, bought them, or certainly tried to grow all of them. But it's all giftable. So our products are primarily used as gifts. You know, about 20 % self-consumption, but mostly gifting. And then finally, a few years later, a few years ago, my brother Chris, who succeeded me as CEO at the time, thought we should be in a personalization business because so many people wanted us to do other things for them.

32:27So he bought the personalization mall, and then we bought the Things Remembered brand just a couple of years ago. So personalized gifts, all these different kinds of food gifts and wine, and our flower gift baskets.

32:38David Novak:I love that phrase, followed your customers. You followed your customers that took you into these different categories. Was there ever a time that you realized that if you didn't innovate, you'd get left behind? Or has just innovation and expansion always been something you've naturally done? Well, if you go back to the point I was just on, which was 1986, I got a hold of that telephone number. I started selling off stores to raise capital to invest in this idea to get it to become a brand. And we had success at that. And at some point I thought, you know, geez, we could sell pretty much everything if it had flowers on it.

33:15And so we launched a catalog of giftable products. And one of the lessons I've learned from you on leadership is the importance of letting people know that you make mistakes and it's okay to make mistakes. And I was taught that lesson by a lady who was our chief merchant at the time. And I walked into the office and people were giggling. And I was thinking, what's going on here? And finally they took me over. She had taken a couple of bookcases, three of them, and put them together. And she made a sign, Jim's Wall of Shame. I have a few of those. Not one, it's many. These were all my product ideas that didn't work.

33:51And in the center of those three bookcases was a Chinese satin jacket that I had that had a big, beautiful embroidered rose on the back of it. And I thought, this is going to be a killer item. David, if you're interested, there's probably a warehouse someplace that still has a few boxes of them left if the moths haven't finished them by now. But the lesson I learned from Ho was it was funny and it was making fun of me. but what the lesson she was teaching us was everyone in the company now knows of course you're going to make mistakes and you shouldn't be embarrassed about them you should celebrate them and may turn it into a joke and there's a lesson there and i think that contributed to our culture of being early and being risk takers so to the to the evolution you talked about when we had found this so we had the chain of stores retail was our first wave second wave was the 800 number But then 1992, three, four, I'm working with my friend Steve Case and Bob Pittman and Ted Leonsis at AOL.

34:55And we think this online, my brother Chris had joined the company by then at a university. And he's doing all these new tech things. And we're saying, wait a minute. If these guys from Queens with no money and no business experience created a national brand by embracing a new technology, an 800 number, what was going to be the next technology wave that would push us aside. So if we're going to be disrupted, let it be by us was his motto. And so when the internet, the online world, then the internet came along, we were early to it, very early. We had a website in 1992. Nobody cared. We were the first transaction of any kind you could do on AOL.

35:36That was important to us. So the relationship with Bob Pittman and Steve Case and Ted was extremely important. And then, frankly, the next wave was during the financial crisis in 2008 and 2009, which was damaging to us. It really hit us like it did everybody. But we didn't stop investing. We maybe had 15, 16, 17 developmental projects. We said we can only afford to do two or three. What should they be? And we said mobile is going to be huge and social is going to be aided and abetted by mobile. So let's invest in those two things and let's invest in our new tech stack. The other 14 projects we're going to put aside, we can't afford to do them now.

36:22And that was a good decision on our collective parts because everything social mobile is our fourth wave. And then I think my brother might be the first person I ever heard use the term conversational commerce, which he coined about 10 years ago. And now this wave that's breaking on a shore, which is being aided by everything AI, is frankly the most exciting wave in our career's history. And I think it'll be the most transformative in terms of how we relate with our customers, the tools we can bring to them to help them in their relationship development. Our marketing has already changed from buy my stuff to, hey, let me engage with you.

37:00I started writing a newsletter every Sunday in the first months of COVID. We now have 14 million subscribers to that. I get to do our podcast and talk to unbelievably interesting people like you. And what we write about in that newsletter is not buy our stuff or here's our product, but we write about relationships. And we have a group of experts we turn to on a regular basis. And we use the calendar as an excuse for our community to think about using their power to express and connect. So if it's Grandparents Day, which it was last month, and I write for a couple of weeks about Grandparents Day, and as a grandparent, I remind my other grandparents, don't just sit back and wait for the call or the note or the card or the gift or the attaboy.

37:52What are you doing? What's your responsibility as a grandparent to do something for your grandkids? How do you choose to give them a gift of your time with them one-on-one? And so we talk a lot about that and the engagement. David, I know you won't be surprised because you were the king of engagement. It's just magical for me now because I'm no longer the CEO. I was smart enough to fire myself back in May and hire a real CEO. And now I get to spend my time on engagement and content and community building. And I've just never had more fun.

38:23David Novak:You know, imagine you're leading a CEO roundtable on AI, which you probably may have done. What would be the top one or two insights you'd want everyone to take away? I think, number one, we don't have an excuse. We don't have any choices. You have to embrace it. It's going to change everything. And the second thing that I think about is I think about AI in two clusters. One is efficiencies. That I can understand. It's going to make everything more efficient. If you have 12 people in legal, if you build a small language model in there, you could probably get by with nine or six people in legal a couple of few months from now because contract reading, smart contracts, auto paying is just going to be built into the system and it's already happening and we're already using.

39:10So efficiencies, I can understand that. Then the other thing is capabilities. What kind of things did we not imagine being able to do that AI will allow us to do? and I'm not a super smart technologist, but I do understand from our business point of view that for the last four or five years at New Year's time, I write to our community about resolutions. And I encourage our people not just to do a resolution about I'm going to exercise more, I'm going to read a book every month, I'm going to do this. I ask them to build a relationship resolution and I ask them to make three groups on their relationship resolution.

39:48This is a group of people I have relationships with, and I want to continue and invest in those. Here's a group of people who I have, maybe the relationship has waned. I haven't seen them in a year or so, but they used to be important to me. I'm going to reinvest in those relationships. And then there's a group of, the third column is people you don't have a relationship with, family, workplace, community, that you're going to be deliberate about building bridges to them to try and develop a relationship. But now our team in the AI and our AI development team has written an app for me that automates that.

40:24So it asks you the proper questions about those relationships and it prompts you to think about them. And now he says, would you like me to help you to follow through on your resolution? So he said you wanted to get to know David Novak better. Well, David Novak was just honored by the institute he created on leadership for all the work that he's done over the last couple of years. And here's the article that was in the Louisville Gazette about that. You might want to drop David a note congratulating him on that. And then it comes back a few months later. He said, you know, you said you wanted to invest in your relationship with David, but I haven't seen any correspondence, either text or phone calls or messages to him.

41:02Here's something else that just happened in his life. You might want to take note of that. So it prompts you to do follow through on the things you said you were going to do in areas that are a little esoteric, a little bit more esoteric than diet or exercise regimens. So I think the capability side is the really exciting side of what's going to be efficiencies, I understand, but capabilities are where the real magic is going to happen. You know, you're such a people person and, you know, you're highly regarded for that and building a culture where people are valued. How do you prepare your team about the efficiency side of AI?

41:42It's a tough question. One that we've been deliberate about. I mentioned I hired a, my board and I hired a new CEO. We started in May. His name is Adolfo Villagomez. as a terrific guy, just extremely qualified. And boy, if there's one good choice I've made in the last bunch of years, it seems like Adolfo is it. But we were talking about the fact during the courting process when I was trying to lure him here in those many months before he started, we were talking about the efficiencies and the impact it's going to have. And what we decided as a team internally with Adolfo's input long before he even came to work with us is we have to be very honest with our team and say, we can't say, hey, don't worry, we're going to protect you.

42:27Everyone's job is, we can't do that. It's not realistic. So we're very honest and we say disruption is going to happen. We'll be as transparent as we can with you about that disruption, but there will clearly be disruption. And now Chip Cutler in the Wall Street Journal back in June wrote a piece where he talked about all of the Fortune 500 companies are now collectively have lost 3.5 % of their headcount in the last three years. And they're all projecting to have smaller headcounts in the years ahead. And the mantra in business has gone from, David, I can't keep up with business. It's growing so much.

43:03I can't hire enough people to being proud of being able to say, we can do more with less. So the attitude has changed. So we're honest with our team. And what we did was we said, let's reinvest in something we created a few years ago called Fresh University. So what we say to our team is there will be disruption. AI is going to disrupt us in ways we can guess at now, in ways we can't imagine, but it will happen. And our investment is going to be in you. We're going to give you all the tools, give you all the opportunity to learn these new capabilities and tools. We'll have coursework online. We'll have trainers in person.

43:41We'll give you the opportunity to develop as best you can personally, and professionally. And so that's our commitment to you. So even if you do get disrupted here, if you've learned these skills, you're going to feel that you have options. You can certainly go to work for someone else because you're very employable. You can hang out your own shingle and create your own business. You can become a consultant, or you can just use these tools in your own life. And a new board member of ours, Shelly Palmer, did some research at the Palmer group about people who really do embrace and learn these AI tools, they feel very confident.

44:19They're not worried about losing a job because they know they have superpowers now. And so that was the evolution of our thinking here. We can't protect you from the disruption, but we'll be transparent about it and the timing will be obvious to you. Secondly, we're going to invest in you so you have all the capabilities you need to be successful personally and professionally going forward. And that was our decision. That's how we communicate. The third element of that, David, is we said resume is not a noun. Resume you should think of as a verb. And you should be thinking about resumeing all the time.

44:56And toward that, we put in a transcript system here, like a college transcript, only now we record not only everything you did in college and everything you did before you got here, But we ask you to record, and we record for you, any of the courses and certificates that you earn here. We even ask you to fill in things like, what do you do with your volunteer time? What do you do with your vacation time? So if you have two people, one goes to the Caribbean and sits on the beach drinking Coronas in the afternoon and snoozes a lot, great, wonderful, you're entitled to it, it's your decision. But then you have someone else that takes that same week vacation and they go down to Honduras and they work with the round hut people building three round huts for communities that have been devastated by the most recent hurricane.

45:44And you immersed yourself in Spanish and tried to sharpen your Spanish skills and you get this wonderful letter of thanks from the charity you worked with. And that should be on your transcript too, part of your resume, because it indicates to you and to anyone else who'd be interested, future employers at all, what your makeup is. What's important to you? What are you doing to invest and sharpen your own skills? What are you doing to give back to the community? What are you doing to be the best fully rounded individual you can be? So that's our program. Be honest. It's going to impact us. You should be, if you're not working on AI tools to solve the things that you shouldn't have to spend your time on, that gives you the capacity to do the things that only humans can do, be assured your boss is thinking about it.

46:29And then finally, we're going to invest in you and give you all the tools while you're here to help you to be the best person and the best professional you can be.

46:37David Novak:I love the idea of making your resume a verb. I think that's fantastic. And, you know, you released a book a little over a year ago or last year called Load Start. tapping into the 10 timeless pillars of success. What's a pillar every leader should know more about? Well, the book I did was with a partner. His name is Dr. George Everly. George is a gift to the world. He's a wonderful guy. And I met him because at the beginning of COVID, he wrote an article in Psychology Today about what he thought the impact of the lockdown was going to be on relationships. Major relationships, familial relationships, and casual relationships, waving to your regular friend at Pizza Hut when you visit there on Friday evenings with your family and just waving to them.

47:25It's a social contact, even if it's just a familiar way. And I wrote him a fan letter and I said, George, this is really good work. This is terrific. This is how I became familiar with you. It was an accident, but I just hope we have occasion to chat someday. So he wrote back to me and said, well, I'd love to talk to you. Why don't we make it happen? And we became friends. Now, for the first couple of years, We were COVID buddies. We never met in person. But I was getting all these questions to our newsletter, which is called the Celebrations Pulse that I do every Sunday. People asking about what do I do with my kid?

47:53He's not in school. He's not participating in sports. I think he's deteriorating socially. I'm concerned. I wasn't qualified to answer these questions, but I was qualified to collect a panel of people who were. And George was the first to join our Celebrations advisory panel. And so he called me one day. I was traveling in Florida, my wife and I on vacation. And he called and I answered it on the phone in the car. So my wife could hear and he said, Jim, I'm loving the work we're doing together. It's really exciting stuff. I love the other people you've assembled. This is a really amazing panel and I just enjoy the interaction.

48:32I have a suggestion. I said, what's that, George? He goes, why don't we write a book together? Now, my wife perhaps thinks I'm a little overcommitted and maybe I don't balance my time properly. She was about to hit me when I said, George, I'd love to. And that was a two and a half year project of working together, writing together. And for me, David, an opportunity to learn from a really brilliant man. But in answer to your question, so George has taught at Harvard and spent the last 20 plus years teaching at Johns Hopkins University, where he's emeritus on the faculty now at the School of Public Health, the Bloomberg School of Public Health and the medical school.

49:09And he's a psychologist and he's wonderful. But he tells a story that I think is a lesson for all of us, both as individuals and as leaders thinking about your organization. And that was he was undiagnosed ADHD and dyslexia. He's a junior in high school, and the great advisor to guidance counselor calls George's father, who's a very successful CPA in a small town in rural Maryland outside of Baltimore. and he said, look, George is an okay kid, but he's not very bright and he's certainly not going to college and he's probably not going to graduate from high school. So why don't you take him out of school and see if you can get him a job in a filling station or a factory or in a warehouse someplace because then he'll beat his graduating buddies to the place where maybe he'll already have a job.

50:03George's father told George that story. Not then. but many years later at the lunch to celebrate George's first of several PhDs. And George said to him, dad, why did you never tell me that story? And his father said to him, I didn't want it to become self-fulfilling. And that's when you asked me, I learned so many things working with George, but that one sticks in my head. So whether you're an individual or a person, what you imagine and what you realistically think you can achieve is likely to be what you do achieve. But if you're told that you're good for nothing, and you'll never amount to anything, whether it was the 10 boys I lived in a group home with for years or it's the people I get to work with today.

50:47My job is to help them achieve the most that they can achieve, to form groups that give them the benefit, to be conscious of the social construct in our companies so that it gives people the opportunity to perform at their best. Working at St. John's Home back then, I remember I promoted a lady who had just returned to work to run our services. So that would be maintenance, housekeeping, dietary, purchasing. And her experience was she had just raised nine children. And the youngest of which was off to college so she could return to work. And everyone said to me, you're out of your mind. She was terrific.

51:27Absolutely terrific. And she'd walk through the maintenance department and there'd be all these grizzled guys there and they're mumbling under their breath about this woman thinks she can tell us what to do. And she taught me the lesson of selective hearing. She says, you don't need to hear everything. Just smile and whistle and go about your work. So my job today, like your job was for so long, is to create an environment where everyone can achieve their best possible development self.

51:57David Novak:That's great. And you also say that leaders are cultural engineers, but they can't control it. They can influence, but can't control it. Say more. Well, when you were building Yum! Brands, you couldn't control every environment. And certainly a culture in one restaurant would be different than it would be in this region, than different it is in this country, than different it is in this hemisphere. It's going to be different every place. So you had a few dials as a cultural engineer of Yum! Brands that you could turn that would influence that culture. What you choose to reward, what you choose to ignore, what you choose to punish, who you choose to hire, what standards you set for behavior, how you compensate people, what you celebrate.

52:41And those are your dials. So you have to be careful with those dials because that's signaling to this enormous organization you built what our values are, what our core principles are, what you value, what you celebrate. And that's going to dictate and influence the behavior, but you cannot control. There'd be a rogue store every once in a while. There'd be a rogue employee every once in a while. Overall, as a cultural engineer, you have to be conscious of what your limits are and what your dials are.

53:09David Novak:Great, great points. And, you know, you really are a change agent and you've managed the company through so many different changes. And you seem to be a huge lover of technology. You know, how have you led your teams through these changes without overwhelming them? You embrace it. You know, this is something that you love, you know, but people don't like change. So how have you brought your people along with you as you've visioned the success and the direction for this company? Well, I would blame my brother Chris for a lot of that. We worked together for 40 years. He had to retire a couple of years ago for a health issue.

53:55And he always pressed us to be early to new technologies. He thought it should be part of our culture. And he always encouraged people to be early and first. And when we had those victories of recognition, he'd really celebrate it. For example, I remember we had no idea, but Mr. Zuckerberg at Facebook then, I don't think it was meta yet, was introducing a voice bot. So was that seven or eight years ago? And the first thing that he did that he ordered online through this voice bot was he called and placed an order with 1-800-Flowers on stage with a worldwide audience. We had no idea it was coming.

54:40It was news to us. But we had someone on my brother's team who'd been working with them. And what we said to the technology companies, we're a good poster child for you. We'll try your new technologies. We like to be early. We like to be first. And then when we have a victory, we like to really celebrate the heck out of it. And so he had someone on his team who had been working with the Facebook team and convinced them that we'd be a good partner to try that with. And he did that over and over again, whether it was with AT &T in the early days, whether it was Facebook or Amazon, whoever had the new technology.

55:13We'd like to be early. will be a great proving ground for you. And when we have a victory, we'll celebrate it. And so he helped knit that into our culture that encouraged everyone and everyone that had any exposure to a new technology to be first, to be early, make some mistakes. I remember we had an appearance on 60 Minutes one time when someone's robot that we were working with delivered flowers in some community in California. And of course, the robot crapped out in the middle of the demonstration. But we sure celebrated that. We had that robot in the office. We had pictures of the robot everywhere.

55:50So I'd lay that blame on him for us culturally being people who embrace technology, be early, be first, make mistakes, and celebrate every step of the process.

56:02David Novak:And this celebration seems to be the key. Indeed. You know, this has been so much fun. And I want to have some more with my lightning round of questions. Are you ready for this? We'll see. The three words that best describe you? Curious, improving, passionate. If you could be one person for a day besides yourself, who would it be? I like the new Pope. Your biggest pet peeve? Risk-taking drivers on the road. Who would play you in a movie? Somebody with a better hairline. What's your favorite flower to have on your kitchen table? There's so many. When I started in this business, the amount of flowers we had, the range and variety, but it was really embarrassing.

56:41And there's so many more available today. But at the end of the day, David, and I love to play with flowers at home. You know, I usually take one variety at a time. I don't like a mixed bouquet. And I like to see how long I can stretch the shelf life. And an astromaria, I can get two, three plus weeks out of them at home. But at the end of the day, a rose is a rose is a rose.

57:04David Novak:What's the best part about being a co-owner of the New York Mets for a decade? The best part was family. I worked with some wonderful people, Fred Wilpon, the principal owner, good friend. But for that 10 years, we were owners and on the board there. My three children are local here on Long Island, seven grandchildren. We had a box there. The fact that my grandkids are such avid Met fans and we'd go to spring training, spend a weekend down there. They'd get to meet players and wander around the training fields. The fact that my 13-year-old son had to call me this year to ask my forgiveness because he wasn't going to play baseball this year.

57:44Because all his buddies were on the lacrosse team and he wanted to play lacrosse and it conflicted. The best part was family get-togethers. We'd get my broader family, I'm the oldest of five, get my brothers and sisters. their kids, their grandkids together at a Met game was just magic. And we still do it, but not as often.

58:00David Novak:What's the one thing you do just for you? Exercise. Besides your family, what's your most prized possession? Friends. If I turned on the radio in your car, what would I hear? A podcast. What's something about you few people would know? Well, we're going to keep it that way. What's one of your daily rituals, something that you'd never miss? I start with a list for the day. What I need to get done that day. Yeah, you took that planning mode right with you. All right, you were out of the lightning round. Great job there, Jim. You know, you've been married for 50 years. You said you hit the lottery.

58:35David Novak:And, you know, your wife has always been supportive. How have you two navigated all the ups and downs that come with entrepreneurship? Well, I'll take it back to my friend George Everly. And he gave me the vocabulary to develop some comprehension there. First of all, I married a woman who's completely understanding and has been terrific. We saw it at the very beginning. She'd work with me. We'd go into the store on Saturdays and Sundays, and I quickly learned that I'd rather stay married than work together. And so I tried, you know, the whole idea of you can't work with family. Well, that's obviously silly because we did and we do.

59:12George said to me a few years ago, we were talking about work-life balance. He said, work-life balance is a joke. He said, what you want is good work-life integration. And I think the gift that we discovered that my wife gives to me is she knows I'm in business and she knows I have passions and she gives me lots of rope and I earn it more and more every day, the rope she gives me. And she knows I want to expose my kids to all different kinds of people and businesses. So I think understanding that I'm in business and it's part of my life and it's never going to be different. And to come to that understanding, which George helped me to come to just in the last few years, is work-life integration is a gift, and you should be working at it and tuning it all the time.

59:55David Novak:You know, you've grown up believing, and you obviously continue to believe that everything is possible. You know, how do you help your teams, your kids, see the world with that same lens of possibility, particularly in an environment where there seems to be so much negativity and divisiveness? You know, I mentioned to you that I returned to St. John's home a couple of weeks ago and spent several hours there and had lunch with a group of guys. And I was reminded of my first couple of weeks working in that group home, which was just, as I say, 10 blocks from where I grew up. And I said it was a million miles away.

1:00:35speaking with those young men about what their futures might be was frankly depressing because their perception of opportunities is so different than mine. I remember one of the most important, when I was running a group home, summers, my main job was to make sure I got each of my kids a job for the summer because A, they'd be tired. B, they'd have a couple of bucks in their pocket and they wouldn't be out all night because I had to get up to go to work the next day. And they learned things. They saw things. So I remember one young man, I got him a job in the hardware store that was nearby in Far Rockaway, Queens called the Empire Hardware Store.

1:01:16And Norman worked there, and he's a black kid. And there's a vendor who would call on them, a tool vendor, also African-American. And Norman struck up a relationship with his tool salesman. and he had this big truck and he was a nice guy and he took a liking to Norman. And Norman discovered that you could have these jobs. He would never have thought of selling tools, going around to different mechanics and hardware stores and selling specialized tools. And one of the great success stories of my social services career was running into Norman 10 years later. And after he finished high school and he did two years of community college, he wound up buying that route from that guy he met in that summer job in a hardware store.

1:02:01And he had a home in Queens and in Cambria Heights. And he had two kids and he was happy and healthy and he was a big active member of his church. And I said to myself, wow, what a success. Yeah, that's great. But it wouldn't have been if he didn't have that exposure. Because those 15 kids I spoke to two weeks ago had no clue. The closest idea to someone being in business was a young man said, I think I'd like to be a barber. I said, oh, yeah, why? He goes, because if you have a barber shop, that's where everybody hangs out. You can have a whole bunch of friends around. But no one else had a perception of a real opportunity.

1:02:38School, career, no. Their role models were very different.

1:02:43David Novak:How do you tackle that? Well, I think St. John's Home is trying to do that. They've been doing that for 100 years now where they give them exposures and expose them to other people and other opportunities with job programs, with education programs. They used to have a singing group that would tour around and go to different events. And they'd meet people and someone would take a liking to them. And, hey, you know, if you're looking for a job, I got something for you. So it's taking them out of a really bad environment, even if it's just for a short period of time, getting them righted, show them a path where they can increase their exposures and change their perception because their perception is handcuffs.

1:03:23David Novak:What do you see as your unfinished business now, both for your company and personally? Well, from the company point of view, this is very exciting for us. This is a foundational year for us. We have to do a lot of, we have to change a lot of things. We have to embrace these new technologies. But I think we have a chance of becoming a company I've always wanted it to be and didn't have the wherewithal to get there. But now we do. So we're changing how we relate to our customers, how we serve our customers, how we communicate with our customers, how we message them. So this is an unbelievably exciting opportunity for us.

1:03:55And for me now to step aside to do what only I can do and allow real managers and professionals to re-engineer our company and to get it ready for this exciting growth era in front of us is terribly exciting. On a personal point of view, the things I think about most are, what I'm proudest of is my kids and my in-laws are, three of them are all good parents. I think about, Mary Lou and I want our grandkids to remember us. And so we want to be deliberate about giving them exposures. I think grandparents can and do play an important role in kids' lives. and I want that to be something they remember fondly and have appreciation for long after we're gone.

1:04:40David Novak:And I'm sure they will. Last question here. What's one piece of advice you'd give to anyone who wants to be a better leader? To be deliberate. Read about other people. You've had great leaders on your show. Steve Case you had on your show. I listened to him back in August. I think you had him on. He's very different than me, but a great leader. You've had Jamie Dimon on. And Jamie's a friend, as is Steve. And I've learned so much from him. I'm a couple of years older than Jamie, but I still have learned so much from him. I remember one time my brother Chris and I were having lunch with Jamie, and he got very critical of me, and I really appreciated it.

1:05:18He told me, I spend way too much time evangelizing. What do you mean, Jamie? He said, you want everyone around you to get it. They don't need to get it. They're not all capable of getting it. But if you get it, all they need to do is understand that you have a dream, a passion, and a plan. And if you're in pursuit of that, they know if they move their needle from here to here, and everybody around them moves their needle appropriately, it'll crescendo into this beautiful new idea. But if you spend all your time evangelizing, you're going to frustrate yourself, and you're going to weigh yourself out, and you're going to spend your energy in the wrong direction.

1:05:51And that was such good advice, and I'm still guilty of it. But I try and corral myself because—

1:05:57David Novak:Yeah, but doesn't that evangelization, doesn't that evangelizing get that person to want to move their needle from point A to B? I'm not sure I agree with Jamie. It's to a degree. If you spend all your time and energy evangelizing and expecting that everyone will get it, you're wasting your time and you're wasting your resources. But if you spend more time, like I expect Adolfo has and will, understanding what everyone's metric needs to be, what their particular job is, what their goal is. and here's your goals, here's your metrics, everyone's watching. And if you deliver, we'll all deliver and we'll all get, I think the balance is the point he was making.

1:06:33So it was great advice 10 years ago, 20 years ago. And it's, I think, still good advice today. And every once in a while, I have to say to myself, I'm doing it again.

1:06:43David Novak:And I tell you what, in the role that you're in, you doing it is a pretty good idea. I would be more balanced in that than the other side of the equation. You're awesome. I really appreciate it. And thanks for being on the show. Really was fun. It's a treat to talk to you, David. Thanks so much.

1:07:08This 1-800-Flowers interview touched my soul in a very, very special way.

1:07:15David Novak:Why is that? Tell me about this. Why? Because when you think about the last time you got flowers or the last time someone sent you flowers, It just makes you feel good, like deep on the inside, because people are thinking about you and you didn't know they were thinking about you until you got flowers, probably from 1-800-Flowers. Well, what happens if you're dating somebody and you don't get flowers on Valentine's Day? Aren't you expecting that day? Yeah. Well, hopefully they would call up Jim McCann and say, I forgot to get flowers. Can you please help a brother out? And they do everything they can because they know how important it is for you to save that relationship.

1:07:51David Novak:And it's a relationship business. I love that. Didn't you love the fact that, you know, he sees them not in the flower business, not in the gift-giving business, but in the relationship business. Yeah. You know, the best leaders always define their business in a broader way. It's also is compelling and gives people a noble cause of why you go to work. We're out there every day. We're trying to build relationships, make the world happier, bring people together. I love that. I thought that was great. And he's a great guy. I mean, you know, he's a guy who you can see him, the fact that he loves making people happy.

1:08:28David Novak:Absolutely. And him talking about being in the relationship business reminded me a lot of your interview with Whitney Wolf heard when she says that at Bumble, they're in the business of love. They're in the business of connecting people and promoting love. And obviously, that's not the functional thing that they offer. But I just love that it allows everybody who's part of that company to buy into something that is deeply meaningful and that actually moves you. You make a very good point. That's not the functional thing that they offer. And see, the best marketers in the world, they understand what functionally they do, but then they connect with their customers by putting it in an emotional context.

1:09:10David Novak:They create love. They're in the love business, okay? And I think that's fantastic. I do too. it's such a fun way to kind of reposition your business, especially, I think, you know, for your people. And as you try to recruit people and retain people, that's much more compelling than, you know, hey, we have something that you can access on your phone. I love also an interview with Jim David when he talks about how they have, how they expanded over time from flowers into other gift items like chocolate and cookies. He uses this great phrase, David, he said, follow your customers. And he tells a story about how, you know, when they first launched 1-800 Flowers, all of his customers were buying flowers and then going to Harry and David to complete their gift buying for the holiday season.

1:09:58David Novak:So he calls up Harry and David and says, hey, all my customers are coming to you. We'd actually like to buy Harry and David so that it's the one-stop shop for people to go buy all their gifts. And he would have never known that if he didn't follow his customers. What's the real insight there? I think the real insight is understand your customers, know what they do. And then if you can buy adjacent businesses that are similar in terms of what they offer in the end, they have that emotional benefit that you're really trying to deliver, you're going to really be successful. If you try to do something for your customers that's outside of what they want, it's really difficult.

1:10:37David Novak:You're swimming upstream. But what he's doing is that he's diving off that diving board because he's going to have a perfect 10 because he understands what his customers are buying and why. And he goes out and, you know, figures out how to take advantage of that. He also did it with this cookie brand somewhere in the Midwest, like Cheryl's Cookies, I think it was. Delicious. Delicious. Jim's career is an interesting one. He was in social work and, you know, thought he was going to be in the New York City Police Department and then ends up at 1-800 Flowers. And in the interview, when you asked him about it, he says, resume is not a noun, it's a verb.

1:11:18David Novak:And that's really a philosophy that they try to ingrain into their people at the 1-800 Flowers company. And I love that resume is a verb. It's one of his, you know, more quotable phrases. How do you balance pursuing those sort of resume building growth opportunities while also doing your current job really well? Oh, I think you're growing. You know, it's just like the flowers, you know, you got to grow. And, you know, while you're doing your job, the only way you're going to really do your job well is to grow by learning how to do it better each and every day. So I don't think they're two separate things.

1:11:55David Novak:It's intrinsically linked together. At Lighting Hunter Flowers, they have developed this training program and they call it Fresh University, which, by the way, I love that name because you want your flowers fresh, therefore Fresh University. Anyways, he talks about the importance of offering skills training and development opportunities to his people, especially as all these new AI tools come into play. He wants his people to feel confident in them so that, you know, when all these companies lay people off because AI is replacing their job, at least he's offering folks a way to get really good and comfortable using all these tools.

1:12:32David Novak:So I just love how their commitment to developing their people is a real guiding force. Yeah, he's been a head of technology for a long time. You know, from the 1-800-Flowers buying that brand to now AI. And, you know, he really makes some great points in this interview about how to deal with AI. Be totally 100 % upfront with your employees. Yes, there could be some productivity gains that could mean some people lose their job. But we're going to develop you while you're here. And so that if there's a reason that your job goes away, you know, we're going to prepare you for the next job. And that's part of his resume as a verb.

1:13:21David Novak:We're just going to keep building your capabilities, building your skills so you can be the best you can possibly be at our company. but if for some reason, you know, your job is eliminated, you can go out and be a consultant, you can go work somewhere else, but we're going to prepare you to win. And I love that because, you know, when you lose your job, a lot of times, you know, it's not because of any fault of your own. You are a winner and you can win. You're not a loser, okay? And I think that it's his belief in people and their capability that really is the impressive thing here. Jim is also really funny.

1:13:59David Novak:And he talks about humor in the episode as being kind of a competitive advantage in the leadership space, especially if you aren't necessarily super extroverted or really social. And humor is this concept that I'm honestly surprised it doesn't come up more on this podcast because you've got some jokes, David. But it is a powerful leadership tool. And I'm curious, like, number one, do you think you're funny? Number two, has humor helped you in your career get things that you might have not otherwise got? I don't know. I don't always ever ask me if I thought I was funny before. I think I have a good sense of humor, okay?

1:14:41David Novak:And I love to laugh and I love to have a good time. And I think that when your humor is self-deprecating, you know, and not at the expense of others, I think it can be very powerful because it makes you very relatable. But when your humor digs in at other people and makes them feel less about themselves, that's when you have a problem. And, you know, I have to tell you, you know, I've done both. When you think you're funny or you think you have a good sense of humor, you can do it in ways where it really does release the tension and it makes people feel better and everybody laughs and it gets you through the tough times.

1:15:25But then I've used my humor in a way that at times hasn't lifted a person up.

1:15:35David Novak:And when I do that, I'm at my worst. So I think humor can be very powerful, provided it's generic. It's not personal to other people. And it's more, if you're going to make fun of anybody, make sure you make fun of yourself so that you're more approachable and people feel good about it. But I just think it's great to laugh in the marketplace. I just think it's great to go to work with a smile on your face. I think it's great. I think it's great to have fun. And it's hard to do that without having some laughter out there. And it's kind of interesting. You know, I mean, this is nothing really that revolutionary, but, you know, if you smile, it's kind of tough to feel bad.

1:16:25David Novak:It's so true. I mean, try it. I mean, just smile. Now, when you smile, I mean, come on. It's kind of hard. You're almost laughing at yourself, even if you're not feeling good about it. But just try it. You know, try to smile and see what happens. I definitely don't feel bad. And by the way, when you do that, you connect with other people because people want to be around positive people. I would say positive energy lifts you up, negative energy brings you down. So when you can have a smile, you can have some humor, you know, I think it allows you to connect. And I think if you listen to the podcast carefully with Jim, he uses self-deprecating humor.

1:17:06David Novak:You know, sometimes it's funny, sometimes it's not. But you know he's got his heart in the right place. Absolutely. Absolutely. And I think it also helps him connect in a more meaningful way with the people that he surrounds himself, with his family, with his friends, and certainly with the people that he leads. Now, great example there. I said, sometimes he's funny, sometimes he's not. Now, when he hears that, he's going to go, when am I not funny? Did I really need to say not? No, I didn't. And he's really funny. Yeah, he is really funny. I thought it was hilarious. I didn't just need to say sometimes you're not, but that was just me just like trying to be funny and not being funny because that wouldn't have lifted him up.

1:17:51David Novak:I love that as a filter. And I would say that you're funny. So you can say that I asked you and I think the answer is yes. Again, I think it's very important for others to be the judge of that. All right, David. Well, that does it for our episode of How Leaders Lead today. Hey, if you're feeling down, call 1-800-Flowers and just send somebody some flowers to say you're thinking about them. And thank Jim McCann for his great leadership and for how easy it is to do that. Absolutely, let's do it.

From the publisher

Jim McCann didn’t set out to become an entrepreneur. He was a social worker and bartender before finding his way into the floral business. But no matter what he did, he always found a way to connect with people.

That instinct eventually led him to build 1-800-Flowers, where he expanded the business strategically, turned it into a household brand, and tapped into the power of customer relationships long before it became a buzzword.

In this episode, he shares the lessons that have carried him through decades of reinvention – and why, no matter what technology disruptions may come, smart leadership always comes down to connection.

You’ll also learn:

A simple philosophy for a smart product expansion strategy

What it means to be an “engineer” of culture (and why it matters)

Why working with teenagers gave him a crash course in leadership

The #1 thing you need to do now to prepare your team for the disruption of AI

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