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How Leaders Lead with David Novak

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

How Leaders Lead with David Novak

David Novak Leadership

Entrepreneurship, Business, Management

4.8596 Ratings

🗓️ 13 November 2025

⏱️ 79 minutes

🧾️ Download transcript

Summary

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 Take your learning further. Get proven leadership advice from these (free!) resources: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The How Leaders Lead App⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: A vast library of 90-second leadership lessons to stay sharp on the go  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Daily Insight Emails⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: One small (but powerful!) leadership principle to focus on each day Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.

Transcript

Click on a timestamp to play from that location

0:00.0

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

0:06.5

And my grandmother looked at me and gave me the Irish finger, David, come to that.

0:11.2

And she called me into the dining room and she just said to me, that bankruptcy thing, we don't do that.

0:16.4

Figure it out.

0:22.4

I got to imagine that Valentine's Day is your biggest day. Am I right on that?

0:27.6

Wrong.

0:28.4

Wrong. What is it?

0:30.3

Remember, we have flowers and gifts, and we have three categories of gifts, all of our floral

0:34.2

product or things we find in the greatest flower shop experience.

0:38.7

We have food gifts, and we are lead brand in our food gifts category is Harry and David.

0:42.9

So we grow pears and peaches and apples and kiwis and grapes and et cetera, et cetera, and make

0:48.4

wonderful gift boxes and gift baskets and prepared foods.

0:52.2

And then we have a newest division which is called personalization mall, things remembered. So 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.

1:13.0

Now we have a big push on photography.

1:19.2

So if you would, 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,

1:22.6

already framed or emblazoned on a mug for her to put with her collection.

1:27.4

That's great.

1:28.7

So that's to say that Valentine's Day is a busy holiday, particularly for the floral

1:32.9

brands and our chocolate brands.

1:34.4

But the biggest holiday in our calendar is the Christmas season, this fourth calendar

1:38.4

quarter, our second fiscal quarter, because all of our food gifts, this is their quarter.

1:43.3

Harry and David, this is their quarter. Cheryl's cookies, the popcorn factory, all of our food gifts, this is their quarter. Harry and David, this is their quarter.

...

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