8 Important Business (And Life) Lessons A Billionaire Taught Me ( POWERFUL)


8 Important Business (And Life) Lessons A Billionaire Taught Me ( POWERFUL)

And how I became a second-degree connection to Warren Buffett

Two down. 2666 to go.


That was my initial thought when I received a message from Bill Cummings. Cummings had read an article I had written on him for a news website and had reached out.

Oh yeah, Cummings is one of just 2,668 billionaires in the world.

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Last month I was fortunate enough to interview Bob Clark, a member of this elusive club. And it appeared lightning had struck twice as I now had the opportunity to pick the brains of another successful entrepreneur, billionaire, and — as I was about to find out — a very generous man.


Cummings put a lot of thought into his answers, deliberating on them and wanting to give value to this article and to readers.

His answers were long and considered — exactly what a writer wants. And from them, I could draw out some great lessons applicable to entrepreneurs, leaders, managers, and…well, anyone.

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A quick bio

Cummings had worked a few jobs before acquiring a fruit juice manufacturing business, Old Medford Foods, in 1964. He built it up and sold it in 1970 and moved to a new industry — real estate

Cummings started a real estate company, Cummings Properties. The company started with a small building in Boston and has grown its property portfolio to “include 11 million square feet across 11 suburban-Boston communities.”

This business has made Cummings a billionaire, but as he tells me, “there are very few things more enjoyable than giving away large sums of money to worthy organizations. When Joyce [his wife] and I determined that we would have far too much wealth for our own needs, we formed Cummings Foundation to begin giving most of it away.”

He has kept true to that word; so far, the Cummings Foundation has awarded more than $375 million in grants to non-profits in Greater Boston.

And not only does he give away grants, but he also gives away something more important — information.

#1. It starts early

I keep telling my teenage boys to get off their computers and get a job — so far, without success. Unfortunately, many of their friends are similar.

Cummings, however, was different. As a high school student, he washed windows and sold ice cream from the back of his bicycle, providing him with valuable experience.

“Any kind of childhood work experience can provide an enormous advantage to people just entering the workforce. The self-confidence, work ethic, and sense of fiscal responsibility young people often develop during early professional experiences…will serve them throughout their careers.”

I hope my sons read this. You, too, can become a billionaire — go get a job!

2. The art of the deal

The art of the deal — a terrible name for a book but a great subheading for an article.

Cummings entrepreneurial journey kicked off thanks to the deal he negotiated to buy Old Medford Foods — a 100-year-old enterprise. He knows how to negotiate a deal, and I wanted to understand his strategy.

Requesting an “asking” price conveys that you expect the seller to negotiate an actual price that is something less than the figure that was initially requested. Each individual will negotiate differently, but practice, practice, and more practice will steadily improve anyone’s negotiating capabilities.

#3. Don’t be afraid to pivot

I would guess that very few people have pivoted from fruit juice to real estate. But then again, very few people have had the success Cummings enjoyed.

Before age 30, I built a very profitable business, manufacturing and selling concentrated fruit juice drinks in a niche market consisting of several hundred college and university dining halls from Boston through the Carolinas. Soon after I built my first commercial building to lease to other businesses, however, I realized that the professional opportunities in real estate yielded far more lucrative rewards. I knew almost immediately that commercial real estate development would provide a very strong career path. Before age 35, I could have comfortably retired with the income from our first three buildings.

If you see a better business opportunity, don’t be afraid to take it. First, however, make sure you…

#4. Know your limitations

It’s easy to see the zeros after his net worth and assume that Cummings hasn’t put a foot wrong. But one of his business ventures proved to be a failure.

My biggest mistake was owning and operating Beacon Grille, a 300-seat steakhouse-type restaurant we built directly off Interstate 95 in Woburn, Massachusetts. Using sheer willpower, I forced the restaurant to be successful, and it was lots of fun to operate (most of the time).

Unfortunately, operating a popular restaurant required distinctly greater management involvement than any of us had anticipated. It required a major time commitment — for me as well as many Cummings Properties colleagues

Although an undeniably valuable experience, owning and operating a restaurant did teach me something about the pitfalls of overextending myself. It became clear that the restaurant was consuming far too much of my professional and personal life. Lesson learned: Mind your knitting, and don’t let side operations detract from the central role of running a major enterprise.

This is a good reminder for those reading this who may be trying to take on too many side hustles.

#5. Even the successful get mentored

In 2011, Cummings and his wife Joyce signed the Giving Pledge. This was created by Warren Buffett, Melinda French Gates, and Bill Gates to build a tradition of philanthropy amongst the ultra-wealthy.

I had to ask Cummings what his interactions with this trio were like? And if he tried to pick their brains in the same way, I was with Cummings.

There were especially pleasant interactions and welcomes from all founders when we first joined, and certainly all three are typically present during annual meetings. One time, Warren Buffet specifically taught us all about how things operated in the Republic of Rwanda, where Joyce and I were at the time just starting to become philanthropically active.

Joining The Giving Pledge has afforded Joyce and me the easy opportunity to connect with and learn from dozens of other philanthropically minded individuals who share many of our ideals. The organization is not any kind of social club or networking group. Our personal interactions with its founders might average about five or six minutes per year — although one other significant contact with Melinda Gates resulted in her graciously providing a very nice book cover quote for “Starting Small.”

I guess I’m now just one connection from Melinda; I’ll have to get her to write a cover quote for my next book.

#6. Being a billionaire doesn’t open every door

Cummings has written a book, Starting Small and Making it Big, which outlines his journey.

As a writer who recently published his first book — yes, a small plug for me — I wanted to know how the writing and publishing process was for him. Surely he had publishers banging down the door, for there are few more powerful words in marketing than a billionaire.

Yet Cummings, like me, was forced to self-publish.

I wrote “Starting Small” by myself, and mostly by hand on yellow legal pads over a period of more than two years. I quickly gave up on finding a publisher or getting into local bookstores except in my hometown of Winchester, Massachusetts. Instead, I made arrangements to do traditional author talks in more than 100 locations, especially colleges. We never directly sold any books at these talks, but I was happy to appear for no speaking fee if the school, convention, or financial organization first purchased at least 200 copies to provide to those who attended the event.

It was a good lesson in leveraging his business knowledge and the marketing power of Cummings speaking to students and parlaying that into book sales.

And more.

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#7. Rejections are temporary

One of the colleges Cummings regularly spoke at was Harvard Business School, which led to an interesting outcome.

At least a half dozen talks at Harvard Business School resulted in the School deciding to write its own case study. “Bill Cummings: The Cummings Way” is now taught not only at Harvard but at other schools, far and wide, that use its case studies.

The ironic twist is that Harvard was the only business school to which Cummings applied after graduating from Tufts University, which didn’t accept him.

#8. Keep them wanting more

I’ve been fortunate to interview several very successful entrepreneurs, and I always end with the same question — ‘what’s the one tip you would give an aspiring entrepreneur.’

This is where Cummings leaves me hanging, offering to give me a list of bullet points at a later time.

I think, like me, he wants a follow-up interview.


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