Hello, I’m Richard – son of immigrants, husband, father of two adult sons and a teenage daughter, wealth planner, wealth advisor, business owner, writer, teacher, and avid cyclist. I’m the founder of Dri Financial Group, where we offer investment advice with a special focus on the needs of entrepreneurs and business owners.
For business owners, building a successful enterprise is only part of the journey. To live well and become the best version of yourself, it is essential to achieve financial independence. During 30 years of building a thriving practice and advising hundreds of business owners, I have seen firsthand what it takes to achieve financial independence. And I have developed the “Live Well, Stay Rich, Never Retire“ philosophy that inspires business owners to ignore conventional thinking about the end of their career so they can pursue their passion for working as much as they want for as long as possible.
This is my story.
In the mid-1950s, my parents were among the thousands of Italian immigrants who sailed to Canada and eventually arrived in Toronto. They were both young, uneducated, spoke no English and had almost no money. My brother and I were raised primarily by my non-English speaking Nonna while both my parents worked at multiple jobs to get by.
Because we had so little money, my parents also did everything around the house themselves. They made their own wine and cured cold cuts. And like many Italian families in our neighbourhood, they had a vegetable garden in the yard. (To this day, I feel like I’m committing a sin if I buy tomato sauce from the grocery store!) They also handled all of the repairs and chores themselves or with the help of friends and family.
My parents take great pride in the life they made here in Canada. But once I was old enough to understand, I began to see their struggle. They were always exhausted and there was often tension in the home. Could they cover the bills each month? What if one of them were laid off? What if the car broke down or the furnace exploded? What if something happened to my brother or me?
As soon as I was old enough to work, I promised myself that I would not live paycheque to paycheque as my parents did. I didn’t know it at the time, but I was making a commitment to achieve financial independence. I also didn’t know the struggles I would face – or the enormity of the pride I would feel – on the path to getting there.
When I was in high school in the 70s, I started my own landscaping company and worked part time at a Dominion grocery store. With this income, I was able to fund my university education and even afford an occasional night out, complete with the platform shoes I needed to fit in at the discos!
During my undergraduate education, I studied accounting because it seemed like a profession that would offer a stable source of income and career advancement. Looking back, I know I was never passionate about it, and that lack of drive meant I didn’t excel, eventually failing the accountants’ qualifying exam twice.
What I did have a passion for was achieving financial independence and starting my own business, so I kept searching.
After leaving the accounting profession, I spent several years as a real estate investor, where I once again found that I didn’t really fit with the job. When a deep recession hit in 1990, I gave up on my real estate endeavour and starting looking elsewhere.
Around that time, I was having breakfast in a local diner and saw an ad for a Chartered Financial Planner (CFP) certification program. I was immediately fascinated by the possibilities of this new career track, which fit nicely with many things that interested me. That was the inflection point of my life and career.
I read dozens of books about total wealth planning and investing en route to acquiring my CFP designation. At first, I worked for another firm, but as my passion and experience grew, I made plans to break away on my own. At age 31, I opened my own wealth planning practice and became a mutual fund dealer.
As I built my business, I was shocked by the number of people I met who failed to engage in deliberate wealth planning – either because they didn’t know how or didn’t think it mattered. They weren’t saving, had no will, had inadequate insurance and were, most shocking of all to me, not maximizing readily available opportunities to defer or reduce taxes.
It was at this early stage of building my own practice that I settled on what would become the driving passion of my career: helping people achieve their Live Well, Stay Rich, Never Retire strategy.
Guided by a deep belief in the power of financial education and coaching, I began to give seminars at schools and corporations, eventually teaching wealth planning courses for about 10 years. As I did, with my client base growing, my passion evolved.
I loved working with business owners just like me. I could relate to so much of what they were going through.
They worked harder than anyone else. They lived with no income guarantee, no pension, and no playbook. They took chances and had no safety net. And they were motivated by their drive to build a successful enterprise and deep desire to achieve the goal that got me started in the first place: financial independence.
Through these experiences, my practice shifted to providing total wealth planning and investment advice tailored to the unique needs of entrepreneurs and business owners.
As my business grew, it came to revolve around two philosophies for living, planning and investing.
The first is my belief that financial independence is the key to living well and being the best version of yourself. Anyone living like my parents did all those years – constantly scraping by and worrying about how to pay the bills or dreading the possibility of impending financial doom – won’t be at their best.
When we have the financial resources we need to achieve financial freedom, we are able to be the best possible spouse, child, sibling, friend, colleague, philanthropist, and community member. Why? Because financial independence allows us to focus our attention on what matters.
To provide business owners with a step-by-step plan for achieving financial freedom, I wrote a book called The Ladder to Financial Independence. It guides business owners through the stages of turning their passion for building a business into establishing the financial resources they need to have the flexibility to take their career and their life in whatever direction they choose.
My second philosophy of living, planning and investing was inspired by my work with business owners.
Over and over again, I saw that business owners don’t retire well. They are driven individuals who thrive when they can jump out of bed every morning ready to face the challenges of building a business. Most I have met like what they built and would have – or have had – a hard time walking away.
Informed by this experience, I developed the Never Retire philosophy.
A business owner already has a passion and is good at it, so why retire? Slow down? Sure. Delegate a range of duties to other members of your team? Absolutely. Focus your attention on the elements of your business you love and are good at? Definitely. But why retire completely and be idle the rest of your life?
All the things you might want to do in retirement – travel, culture, time with family, education, hobbies, and so on – can be pursued while continuing to run your business. You don’t need to retire to live your life fully. And if you have achieved financial independence, you won’t need to.
There are so many examples of people who have worked long past the age when conventional wisdom said they should retire. Look at Warren Buffett. He is 89 and still working. Or actor Betty White, who is still working at 98. Or Queen Elizabeth, who continues her duties at age 93. Or Robert Redford, who is 83 and continues to manage a range of business interests.
The Live Well, Stay Rich, Never Retire philosophy grew out of what I was seeing my clients go through, but in the last few years, it has become an increasingly personal mission.
As I have approached the age people typically associate with retirement, friends, colleagues and family members have increasingly asked me about my plans for life after work. It’s a question that never really made sense to me. I love what I do – why would I stop doing it?
I set out to achieve financial independence so that I would never have to live with the stress and strain that was so detrimental to my parents. Along the way, I discovered a passion for helping other business owners achieve their own financial independence and make plans so they Stay Rich and Never Retire.
Today, I have the ability to pursue what matters to me.
I worry about how to teach my children about money, and support them without making them too soft. I worry about my aging parents, and whether they have enough money to cover their daily needs and mounting health care costs. And I worry that the drive to make money leaves many entrepreneurs missing the point: money is a tool we can use to become the best version of ourselves.
These are my passions. And that’s my story.
Did this article resonate with you? What did I miss? Send me a note and let’s start the conversation.
The process of finding a financial planner can be overwhelming. Our proprietary financial planning process is designed with you in mind. Its simple framework helps you make an informed decision about hiring the appropriate advisor.
Call me if you want to map out how you can Never Retire. You can also subscribe to our Never Retire newsletter, contact us to Order a complimentary book, register for one of our events, and call us to meet with a Certified Financial Planner. We offer you a range of services from a wealth plan to investment advice or help you take advantage of our investment models. Call me at 416-355-6370 or email me at richard.dri@scotiawealth.com.
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