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Jim McCann 1800 Flowers Dave Kerpen

Jim McCann On How To Future Proof Your Business

Dave Kerpen, serial entrepreneur, author and speaker, hosted Jim McCann of 1800-Flowers on Clubhouse, in the Likeable Business Club.

Jim McCann went from being a social worker having a home for boys to building the world’s largest flower company. We learned his story and so much more wisdom and insight in the Likeable Business Clubhouse room.


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Here’s a summary of the discussion and questions that Jim answered from Dave and the room moderators, such as Ramon Ray of SmartHustle.com, and the guests.

Jim McCann 1800 Flowers Dave Kerpen

Decisions we make in our life impact other decisions.

Jim McCann was running a home for boys in NYC and he was a bartender on Friday nights and was into reel estate investing.

One of his customers owned a flower shop and wanted to sell it. Jim offered to work at the flower shop for a few hours to get a feel for what it was like. He then bought the flower shop for $10,000.

Every 6 months for 5 years he opened a new shop.

He realized there was no economy of scale in doing it this way and he realized had to change things.

How was Jim McCann able to make key pivots?

Jim realized that the best thing they could do was to be convenient. In those days companies relied on gimmicks to get people to remember their 1800 number.

It turns out Jim’s biggest mistake was a good mistake.

He bought a company with a great number, the 1800-Flowers number, but it was a failed company.

He was a young man who didn’t know about buying companies and he signed for liabilities the company had, personally. Soon he learned the company he bought was $7 million in debt, that Jim owed personally.

However, even with this mistake, it was a success as he got the 1800-Flowers number.

Why was it important for 1800 Flowers Be on Facebook early on?

Jim McCann has been through 5 major waves

  1. Stores
  2. 1800 number
  3. Online world – the internet
  4. Social and mobile
  5. Social commerce

1800 Flowers was created with no money and a lot of debt. In 5 or 6 years they turned the company into the largest company in the flower business.

Andy Grove’s book and motto, “only paranoid survive” is part of Jim and Chris’s corporate DNA to be looking to be better and be more accessible to their customers.

Yes being online, “all over Facebook” was one thing that did work, but they did other “50 things” that didn’t work.

CURIOSITY and a WILLINGNESS to fail is a key part of their success!

Working with family members

Jim’s dad was a painting contractor and had family working with him in his business. So being in a family business was natural for Jim.

Who else is going to work as hard as your family? Who’s gonna “deliver flowers during Thanksgiving”.

Family rule? While in school you have to work. After college, you must work for someone else for 5 years or get an advanced degree or some other professional advancement.

Future Proof the Business

A lot of things keep the company alert – such as supply chain and keeping up with demand.

Covid, gave an opportunity to accelerate the company’s thinking. From thinking about customers as people who buy stuff from us, TO members of a community!

Their thinking has morphed into thinking how we can better engage with our customers to how we serve them. Such as even working with an acclaimed psychologist how do we help our community 

Jim writes a letter to about 7 million people weekly. The responses are almost “overtaking” Jim’s life – but in such a positive way

Jim McCann Message to young people? (Question asked by Ramon Ray)

Young people have so many opportunities to learn that were not available many years ago. During the day Jim listens to podcasts and presentations. He educates himself.

Next exciting way to lead the future?

Jim and Chris have known about new technologies but have not invested much in them. They started a family office, Clarim – to invest in new technologies.

Has Jim thought about Impact?

  • Beyond flowers and gifts but into more and better relationships
  • Think differently about how they connect and express to customers
  • Jim wants to find a way to help people reach the first rung of success via entry-level jobs. Today their new hires are doing online and via recruitment systems. He wants to find a way to get back to how they used to be able to be more involved in directly impacting people’s lives as they were hired.

How does 1800 Flowers seem to always make the right investments in their future?

  • We’re wrong a lot, Jim says.
  • Trying new things is all a part of our corporate culture
  • We reward people for taking chances to do things first
  • We celebrate that you can make mistakes
  • We keep a list of what didn’t work
  • For example, many years ago we tried to do delivery via robots. It didn’t work out BUT we got great PR for it.
  • Reward people for taking the chance – not just the success

Investing criteria

  • People who have a dream
  • Investing in a team that has a vision of where they’re going
  • Are they crazy enough to get there
  • Curiosity
  • Driven people
  • Move mountains type people

Future proof. What are things that Jim and the team think about?

  • Is our customer service good enough?
  • How are we using AI
  • Who should we work with to help us understand what will the future look like
  • Roadmap to train out leadership

Jim shared about a relatively new project. Instead of buying radio advertisements, he worked with a radio host to have a conversation about how to handle death, across cultures. Not buying an advertisement but a CONVERSATION about dealing with loss.

Jim closed by saying he relies on smart, younger friends, who are smart, daring and want to try new things.


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