Why Some of the Best Entrepreneurs Start as Accountants – Lessons From Ali Gillani

When people picture entrepreneurs, accountants are rarely the first professionals who come to mind. Entrepreneurs are often portrayed as bold risk-takers driven by vision and creativity. Accountants, on the other hand, are usually associated with financial statements, compliance, and attention to detail.

Yet some of the world's most successful business leaders have accounting backgrounds. A report from the Association of Chartered Certified Accountants (ACCA) found that finance professionals often possess many of the same skills that strong entrepreneurs rely on, including strategic thinking, risk management, problem-solving, and long-term planning.

For Toronto entrepreneur and accountant Ali Gillani, accounting became more than a profession. It became a framework for understanding how businesses operate, where opportunities exist, and what separates sustainable growth from short-term success.

Today, Gillani's work spans accounting, hospitality, healthcare, international real estate, and philanthropy. While the industries may seem unrelated, he credits much of his entrepreneurial perspective to lessons learned through accounting.

“In accounting and entrepreneurship, trust is everything,” Gillani says. “Clients and partners must know that your word is solid.”

Why accounting provides a different view of business

Many entrepreneurs enter business through a single product, service, or idea. Accountants often see something different.

They gain exposure to how organizations function behind the scenes. They see operational strengths, financial challenges, growth patterns, and decision-making processes across multiple industries.

Before founding Soberman Goldstein & Associates, Gillani earned an honours degree in Accounting and Business Law from Ryerson University and later obtained his accounting license. That experience gave him technical expertise, but it also helped him understand how successful businesses are built over time.

“My academic experience focused on developing strong expertise alongside an ethical foundation,” he says.

Rather than viewing accounting solely as a numbers profession, Gillani saw it as a way to better understand organizations and the people who run them.

That perspective would later influence how he evaluated opportunities beyond the accounting industry.

The transition from advisor to entrepreneur

Many accounting professionals spend their careers advising businesses. Gillani became interested in building them.

Over time, his entrepreneurial interests expanded into hospitality, healthcare, and real estate. Today, his portfolio includes multiple restaurant ventures, including Osmow’s locations in Toronto, THG’s Hot Chicken, Crema, and Shahs of Kabob in Miami. He also owns Healthy Heart Clinic and remains active in real estate development projects.

“One of the biggest challenges was learning to balance rapid business growth with personal discipline and long-term planning,” Gillani says. “Entrepreneurship can move faster than your systems if you are not careful.”

That observation reflects a challenge many founders face. According to research from CB Insights, one of the most common reasons businesses struggle is not a lack of ideas, but operational issues that prevent sustainable growth.

Gillani learned early that scaling requires more than ambition.

“I underestimated the operational complexity of scaling multiple businesses at once,” he says. “That experience taught me the importance of systems, delegation, and patience.”

Why successful entrepreneurs think long term

One advantage accountants often bring to entrepreneurship is a focus on long-term outcomes.

While trends, markets, and technologies constantly change, sustainable businesses are usually built on consistent principles. For Gillani, those principles include integrity, adaptability, and discipline.

“Markets change, regulations evolve, and industries shift,” he says. “Success belongs to those who can adapt without compromising their principles.”

That mindset was influenced long before his professional career began.

Raised in Toronto by immigrant parents, Gillani watched firsthand as his family worked to build stability and opportunity. Those experiences shaped his views on responsibility, perseverance, and long-term planning.

Today, he applies those same values to both business and leadership.

“Growth requires humility,” he says. “No matter how much you achieve, there is always more to learn.”

Why business success should create more responsibility

While accounting helped Gillani understand how organizations grow, his philosophy extends beyond financial performance.

Through the Truman Foundation, he supports initiatives focused on humanitarian aid, poverty reduction, and sustainable development. The organization's work reflects a broader belief that success should create opportunities for others.

“The foundation prioritizes dignity, opportunity, and self-sufficiency,” Gillani says.

This perspective has become increasingly important throughout his career.

“Success is freedom with responsibility,” he explains. “It’s about supporting the people you love and using your resources to make a positive impact beyond yourself.”

For Gillani, entrepreneurship is not simply about building profitable ventures. It is also about creating organizations that contribute to the communities they serve.

The bigger lesson from accounting

The biggest lesson from Gillani's career may not be about accounting at all. It is about perspective.

Accounting taught him how businesses function. Entrepreneurship taught him how to grow. Philanthropy reinforced why they matter.

Together, those experiences shaped a leadership philosophy centered on responsibility, trust, and long-term impact.

“Financial performance matters, but so does reputation, team development, and the positive influence a project has on others,” Gillani says.

At a time when entrepreneurship is often associated with rapid growth and short-term wins, Gillani offers a different viewpoint. The strongest businesses are not necessarily the ones that grow the fastest. They are the ones that create lasting value.

As he puts it, “True success leaves a legacy beyond numbers.”