Running a business isn’t a job—it’s a full-time, all-consuming way of life. The late nights, early mornings, and constant decision-making aren’t something you can fully grasp unless you’ve lived it yourself. That’s why working with a financial or insurance advisor who’s also a business owner can make all the difference.
When you partner with an advisor who understands firsthand what it takes to build, grow, and protect a business, you gain more than just technical expertise—you gain an ally who sees things from your side of the desk.
Here’s why it matters.
1. They Understand the Pressure You’re Under
Business owners live with a level of pressure that’s hard to describe. There’s no guaranteed paycheque, no “off switch,” and no clear boundary between professional and personal life.
An advisor who’s also a business owner knows this reality. They understand the mental load you carry—from payroll to expansion plans to protecting your family’s financial future. They know financial planning isn’t just about spreadsheets; it’s about reducing that constant pressure so you can focus on what matters most.
2. They’ve Experienced the Cash Flow Rollercoaster
Cash flow isn’t always predictable. A business-owning advisor knows how fast things can shift—how a big invoice delay can throw your whole month off track or how one unexpected expense can wipe out your buffer.
They’ll help you build cash flow strategies that keep your business stable, whether you’re riding a growth wave or facing an unexpected dip. They know timing matters, and they’ll recommend financial moves that reflect the ups and downs you know all too well.
3. They Know How Growth Creates New Challenges
Scaling a business sounds exciting—and it is. But the reality? Growth creates pressure points. New hires need training. Bigger clients expect more. Overhead swells.
Advisors who run their own businesses have faced these challenges too. They know how to manage the financial strain that comes with expansion—whether that means building cash reserves, timing equipment purchases, or ensuring payroll scales with your revenue.
4. They Know Taxes Hit Business Owners Differently
Taxes aren’t straightforward for small business owners. Advisors who’ve structured their own business finances know this better than anyone. They understand how to manage taxable income, plan corporate withdrawals, and reduce tax burdens through smart planning.
A Toronto financial advisor with business experience, for example, may recommend tax strategies that protect your wealth while supporting the unpredictable cash flow patterns that small businesses in Canada’s biggest city often experience.
5. They Know How to Separate Personal and Business Finances
For many small business owners, personal and business wealth can blur. It’s easy for business expenses to spill into personal cash flow, and vice versa.
An advisor who’s also a business owner knows how dangerous this can be—and how to fix it. They’ll guide you on separating accounts, protecting personal savings from business risks, and ensuring your long-term financial security doesn’t depend entirely on your business’s success.
6. They Understand the Value of Insurance for Business Owners
Insurance isn’t just a box to tick—it’s a critical piece of your business protection plan. Advisors who’ve built their own businesses know this because they’ve structured their own protection.
From key person insurance that safeguards your company’s leadership to critical illness coverage that protects your income during recovery, they know what it takes to build a strategy that keeps your business and family secure.
For business owners in Quebec, a Montreal group insurance specialist with real-world business experience understands how to structure benefits packages that reduce costs while maximizing value for employees.
7. They Value Efficiency—Because They’re Busy Too
Business owners don’t have time to waste. A business-owning advisor won’t drag you into endless meetings or drown you in jargon—they know you need fast, effective strategies.
They’ll focus on what moves the needle: actionable advice, clear steps, and efficient solutions that work in the real world.
8. They’re Invested in Your Long-Term Success
An advisor who’s also a business owner knows that trust isn’t given—it’s earned. They understand that if they deliver results today, they’ll earn your loyalty for years to come.
Because they’ve built their own business through referrals, relationships, and repeat clients, they’re motivated to help you succeed—not just now, but for the long haul.
The Bottom Line: Find an Advisor Who Knows What It’s Like to Build Something
Financial advisors and insurance advisors are everywhere. But finding one who’s faced the same struggles you have? That’s a different story.
Whether you’re seeking a financial advisor who understands the demands of running a business or an employee benefits advisor who knows what it takes to attract talent in a competitive landscape, working with someone who’s been in your shoes can change everything.
Look for an advisor who’s done more than studied wealth—they’ve built it, protected it, and fought to keep it secure. Because when you work with someone who’s walked the entrepreneurial path themselves, you gain more than advice—you gain a partner who’s committed to your success.
Lynn Martelli is an editor at Readability. She received her MFA in Creative Writing from Antioch University and has worked as an editor for over 10 years. Lynn has edited a wide variety of books, including fiction, non-fiction, memoirs, and more. In her free time, Lynn enjoys reading, writing, and spending time with her family and friends.
