Self-made billionaire reveals secrets to his success and staying rich

EXCLUSIVE: I’m a self-made billionaire – here are the secrets behind my wealth AND my top tips for staying rich

  • Self-made billionaire Bill Cummings, 86, shares his tips for success 
  • He still flies coach and cuts coupons – touting frugality as an important practice
  • He encourages spending time in an office and being thorough with work 

The secret to success is hard work, dedication and being resourceful, according to billionaire Bill Cummings. 

The 86-year-old entrepreneur started a now billion-dollar company more than 50 years ago by building one of the largest commercial real estate empires in the Boston area.

From humble beginnings, living in a ‘one bedroom apartment with my sister and my two parents,’ Bill grew his business over decades of hard work.

Through making smart investments and working hard, the Tufts University graduate was able to build and self-finance his company. 

Bill Cummings is a self-made millionaire who shares his tips on how to develop habits that can help your career

However, he says the experience he gained in his youth – such as working ‘lots and lots of small jobs’ – gave him the resilience and skills he needed to become a successful entrepreneur. 

Despite his wealth, the businessman and wife Joyce still fly coach and shop with coupons, claiming his frugality is part of what helped him achieve success in the first place. 

‘We always fly coach and never first or business class,’ Bill told ‘I grew up with very modest means and was taught frugality, you don’t throw money at things.’

Bill, who also launched a nonprofit foundation called the Cummings Foundation in the 1980s and has given away $500 million so far, says thriftiness is just one habit he deems vital to success.

The philanthropist speaks about the habits of successful people and tips to a lucrative career in his book, Starting Small And Making It Big: Hands-on Lessons In Entrepreneurship And Philanthropy.

Don’t be afraid of hard work: Bill works a full day in the office

At 86, Bill still rides his bike into his office everyday and works a full day – in person.

‘I usually arrive at the office at 8am or 8:15am,’ he explained, saying he immediately dives into work upon his arrival.

‘I have lunch at my desk most of the time,’ he said. ‘And I usually leave here about about six.’

Bill also speaks of the importance of not shying away from a long day in the office.

‘Nothing is as important as hard work, desire, persistence, and dedication,’ he writes in his book. ‘What idle pleasure(s) are we willing to give up to achieve what we truly want?’

Bill talks more about his journey to building a successful business and non-profit organization in his book

Being in office makes a difference: It’s key to learn from coworkers

While a post pandemic world may have embraced a hybrid working schedule, Bill believes in being in an office to learn from your coworkers and mentors.

He thinks working from home results in fewer opportunities to learning from others, persistence, and company culture. 

‘I think people need to show their drive and their persistence and their dedication,’ he explained. ‘You can’t do that from home.’

‘They lose so much [working from home],’ he explained. ‘They’ll never have any opportunity to learn from their peers.’

Be a good writer: Bill gets every employee to take an editing test

Bill says they ask everyone who works for the company to take an editing test when they apply for a role.

‘We want them to show us that they know how to write, and we do that with a one-page letter, is there any 35 or 36 errors in it?’ he explained. 

‘The people we find that know how to write and put their thoughts together [will] find 30 of those errors.’

Bill says the test shows they know how to articulate their thoughts into writing and are meticulous about looking through their work for mistakes. 

‘[It shows] they care about it enough to learn what the what the rules are,’ he said. 

He stressed that being able to problem solve is an essential skill to have

Know how to solve problems: Vital for leadership

A vital skill to have for anyone seeking a leadership role or wishing to run their own business is to problem solving. 

‘When I have opportunities to coach people about the joys and perils of entrepreneurship, the concept of needing to be a resourceful problem solver is near the top of my list,’ he explained.

‘It is also totally foolish, it seems to me, for anyone to own or operate a business if the work itself and the sense of accomplishment are not always a major part of the reward,’ he added.

Look for opportunities everywhere: Be proactive

According to Bill, life is not about waiting for something to land in your lap, but more about making opportunities for yourself.

‘One of the most important things to remember about good luck is that we must train ourselves and our colleagues to recognize it when it comes along,’ he explains in his book.

He added entrepreneurs were always on the look out for their next opportunity.

‘Though perhaps they do so unconsciously at times,’ he continued. ‘Because of this predilection, most will probably never truly retire.’

Learn to work well with others: Be a team player 

Bill doesn’t look for lone wolves when he’s hiring, telling he seeks out people ‘that that work well with others.’

He added when his company received a resume, they liked to make sure the person would be a good fit for the team.  

‘It’s the person who presents here that we’re more concerned about than the resume most of the time,’ he explained.

‘We say that we hire for nice,’ he added. ‘The biggest reason that people tell me why they stay with this firm as long as they do it, because they like the people.’

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