Please ensure Javascript is enabled for purposes of website accessibility

Billionaire developer reveals secrets to his never-be-satisfied, rags-to-riches life

John Catsimatidis says he’s never satisfied with success. "Every time I climb a mountain, I see another one I want to climb."

  • By Mark Gordon
  • | 5:00 a.m. June 22, 2023
  • | 2 Free Articles Remaining!
John Catsimatidis recently spoke at a book signing event at the St. Petersburg Museum of History.
John Catsimatidis recently spoke at a book signing event at the St. Petersburg Museum of History.
Courtesy photo
  • Leadership
  • Share

Billionaire real estate developer and grocery magnate John Catsimatidis, a fast-talking, sometimes brash and almost always colorful character — with seemingly enough stories to match his bank account — lives by, for him at least, what appears to be a counterintuitive leadership principle: he uses the two ears, one mouth approach.

“I always try to listen to both sides before I make a decision on anything,” says Catsimatidis, No. 679 on the 2023 Forbes Billionaire list, with what the magazine says is a net worth of $4.1 billion. “I try to keep an open mind.” 

Catsimatidis, with his nasal-quick New York accent and free-range answers in a 20-minute interview, doesn’t necessarily scream rational decision-making prowess. But his ability to lead like that, mixed with fearlessness and frank conversations, has led to a series of significant successes in a 50-year entrepreneurial career. That’s wrapped around Red Apple Group, parent company of the popular New York City grocery chain Gristedes, among several other entities.  

Red Apple is also the developer behind The Residences at 400 Central in downtown St. Petersburg — what’s projected to be the largest luxury condo tower on the west coast of Florida when complete, likely in early 2025. Plans call for 301 luxury condos, Class A office space, ground-level restaurants, shops and cafes. Units in the 46-story tower will have panoramic views from Tampa Bay to the Gulf of Mexico.

Catsimatidis visited 400 Central during a recent trip to St. Pete. He also spoke to college students at USF-St. Petersburg and talked up his life story and new book, “How Far Do You Want to Go? Lessons from a Common-Sense Billionaire,” at an event at the St. Petersburg Museum of History.    

Catsimatidis first started visiting St. Petersburg, where his wife’s mother lived, decades ago. The Residences at 400 Central, he says, is one of the crown jewels of his career — and he intends to buy and live in one of the top penthouse units. (Even with one recent condo, a 4,237-square-foot, 4 bedroom, 4.5 bath unit on the 43rd floor selling for $5.23 million, Catsimatidis believes The Residences at 400 Central is undervalued. Overall prices for units range from $900,000 to $8 million, a spokesperson for Red Apple says. “I keep yelling at my people, we should be charging what they get in Naples, in Sarasota,” Catsimatidis says in the phone interview. “We can charge triple.”)

Catsimatidis has lived a rags-to-riches life. Born on the Greek Island of Nisyros in 1948, his family emigrated to the States six months later. Catsimatidis grew up in the Harlem neighborhood of New York City, where his father was a busboy and his mother was a stay-at-home mom. 

The young Catsimatidis worked in a small neighborhood grocery store to help his parents pay bills. The hard work ethic he learned then became a staple of his success. By the time he was 25, he owned 10 supermarkets under the Red Apple brand. That company has since grown into a diversified conglomerate, with holdings in energy, aviation, retail and real estate.   

In the brief phone call and in his book, Catsimatidis details the themes and business/leadership principles that fueled his success: hard work always pays off; take care of customers and employees and don’t neglect either; and never stop looking for new opportunities are three that stand out.  

Simple says

Search light

Catsimatidis, 74, says success is a moving target. “Every time I climb a mountain, I see another one I want to climb,” he writes. “Here I am, half a century into adulthood, and I am still looking for new opportunities. New companies to invest in. New political causes to get behind. New forums for sharing my insights. New ways of making myself and my loved ones happy.”

Always hustling

Long before Red Apple, Catsimatidis had what he calls a job/money-making opportunity, at Sloan’s supermarket in New York City. The gig? Stand next to checkout lines, bag groceries for free then offer to walk the bags to the customer’s apartment — in the hopes of landing a tip. “What that experience taught me was how to hustle,” he writes. “You had to be friendly. You had to be energetic. You had to deal with all kinds of customers, the friendly and the grumpy ones. You had to learn their little quirks and expectations. You had to learn to smile. The tips were always better if you smiled.” 

Keep it simple

Catsimatidis says the trifecta of his success has mostly been the same since he opened his first store: focus on the product, keep customers happy and get employees to work well together. “It sounds so simple, laying it out like that. But those principles, I came to see, really are the foundation of building a successful business — any kind of business in any field. As the leader, it was my job to make sure all of those principles remained front and center every day of the week.”  

Next level

Catsimatidis had a growth mindset with the grocery business almost for the day he opened. But, he writes, he knew if he was to make it past two small stores and a dozen employees, he would have to hire people who “were smart, loyal, hardworking and dedicated to the business — people who knew more than I did, a lot more. That last point was especially important. As hard as I was working, as quick as I was to catch on, I couldn’t know everything. That was one of my leadership lessons I learned back at Brooklyn Tech (high school.) You need your people in place.”

Sweet lessons 

Catsimatidis ends his book with a list of 16 tips for success — in leadership, business and life. The list includes: 

  • You can’t win if you’re too afraid of losing 
  • Know your products, your customers and your vendors better than they know themselves — and treat them all like family. 
  • Hire people who know more than you do, and inspire them to do their jobs. 
  • People do what you inspect, not what you expect.
  • Mentors are hugely valuable — but take only the best from each of them. 
  • Always be seeking the next opportunity 
  • Own the real estate
  • Great success comes with great effort — outwork everyone. 
  • Take reasonable risks — somewhere between reasonable and risky. 
  • The right time to negotiate is when the other person needs the deal. 
  • Seek allies in unexpected places, and dream up mutually beneficial ideas. 
  • Time is the most precious commodity — use every second purposefully. 
  • Failure is not an option — ever. 
  • Help others at every opportunity. You’ll benefit as much as they do. 
  • Dedicate everything to the people you love the most
  • Have fun. 



Mark Gordon

Mark Gordon is the managing editor of the Business Observer. He has worked for the Business Observer since 2005. He previously worked for newspapers and magazines in upstate New York, suburban Philadelphia and Jacksonville.

Latest News


Special Offer: Only $1 Per Week For 1 Year!

Your free article limit has been reached this month.
Subscribe now for unlimited digital access to our award-winning business news.
Join thousands of executives who rely on us for insights spanning Tampa Bay to Naples.