Michele Romanow has a disarming presence: modest, decisive and quick with a self-deprecating joke. That blend of humility, conviction and humour makes her easy to trust—even when she’s delivering tough advice. It’s also why she is so compelling on CBC’s Dragons’ Den and on her podcast, The Revisionaries 2: 70 Percent Factor, available on audible.ca. We also spoke with her for a My MoneySense profile. For this piece I reviewed season two of her podcast, in which Romanow interviews entrepreneurs and leaders about lessons learned the hard way. I then asked her how those lessons translate to personal finance. She agreed to the exercise. Here’s her advice for managing your money as if it were your own business.
“You only need to be 70% there before you jump in.”
How it applies to business: Many entrepreneurs delay launching until everything seems perfect. Romanow argues that being about 70% ready is often enough to begin.
How it applies to your money: “Being 70 percent ready means accepting some risk before you feel fully prepared. With personal finance, you will rarely feel completely ready for big moves—buying your first home, for example, often feels out of reach and intimidating. Markets are uncertain, timing is imperfect, but if real estate belongs in your plan you have to be willing to take that step.
“The same goes for betting on yourself. Investing in your own education or experience—taking a lower-paying role to learn a craft, or putting your savings into starting a business—can be the best form of self-care. You’ll rarely feel perfectly equipped; you take informed risks and learn along the way.”
“You don’t need to be perfect—sometimes you have to trust your gut.”
How it applies to business: Founders often must make rapid decisions based on instinct to maintain momentum.
How it applies to your money: “Diversification will solve many problems with money. As a founder you bet heavily on one outcome; after you’ve made money, you tend to manage it more conservatively. Early in my career, when we launched Buytopia, we used the last $13,000 of our savings on advertising because it was the clearest path to sales. If that spend hadn’t worked, we would have been in trouble—but it was a calculated, necessary risk.
“Today I balance my investments: a small portion—perhaps 10 to 20 percent—may go into venture bets, while the rest is more conservative. Trusting your judgement matters, but balance and diversification are critical.”
“I can deal with this.”
How it applies to business: When PayPal’s lawyers told Romanow she might be personally liable for $1 million due to unfulfilled orders, she felt panic but committed to daily action and problem-solving instead of avoidance.
How it applies to your money: “That episode taught me about the danger of personal guarantees. If you personally guarantee business obligations and things go wrong, lenders can come after your home and savings. In our case, we were simply using a payment processor and didn’t realize a personal guarantee was attached. For weeks I woke up in cold sweats, but we kept showing up, managing refunds, supporting the team and searching for solutions.
“You can get through severe financial stress one day at a time. Learn from the experience and don’t repeat the same mistake—avoid personal guarantees if possible, and structure your business so it can access capital without putting your personal assets at risk.”
“You need to fail.”
How it applies to business: The only way to know whether an idea works is to try it. Failure teaches vital lessons that inform future decisions.
How it applies to your money: “I once started a company without buying health insurance. Six months in, I needed a root canal that cost $5,000—about half my savings. That was a hard lesson in preparing for predictable risks. Plan ahead for foreseeable expenses rather than reacting after the fact.”
“You have to laugh at black swans.”
How it applies to business: Black swans—rare, unpredictable shocks—can upend markets and plans.
How it applies to your money: “Any asset you buy can theoretically go to zero. People often forget that. Housing markets can fall dramatically; physical problems with a property or life events like health issues or divorce can impose huge costs. That’s why you save for emergencies and diversify income streams. Be creative about supplementing income and protect yourself against low-probability but high-impact events.”
“Don’t let people put you in a box.”strong>
How it applies to business: Others may underestimate you, but lowering your standards isn’t the answer. Use underestimation as fuel rather than a constraint.
How it applies to your money: “I’ve been underestimated my whole life, and it motivates me. When investing, there are straightforward choices—GICs at attractive interest rates, diversified portfolios—that don’t require heroics. Compared with entrepreneurship, investing is often simpler: investors write a cheque and wait, while founders do most of the heavy lifting.”
“No one just gives you money.”strong>
How it applies to business: Money requires work. Even gifts usually come with expectations or some form of value exchange, and creating lasting value typically takes years.
How it applies to your money: “You have to earn or create value to receive money. If an opportunity promises cash without effort or a clear exchange, be skeptical. High-risk deals require far more diligence—check references and seek reviews. When private investments are involved, the potential for things to go wrong is higher, so do thorough homework.”
“Relationships are part of business.”strong>
How it applies to business: Romanow was married to and later divorced her business partner, Andrew D’Souza. She speaks candidly about navigating that overlap.
How it applies to your money: “Breakups can be constructive if you approach them with the right mindset. Labels like ‘ex’ carry negative connotations; I prefer to view these as chapters. When separating a partnership, aim for fair and reasonable outcomes. Consider mediation or therapy to manage emotions and preserve goodwill. Financial splits don’t always require perfectly equal division; seek solutions that acknowledge what matters to both parties.
“Also, maintain some assets that are solely yours. Having a financial safety net—especially for women—makes it easier to handle difficult transitions.”
“Your business plan should be able to fit on a Post-it.”strong>
How it applies to business: Clarity and focus are essential. If you can’t summarize your plan succinctly, it may be too complex.
How it applies to your money: “Keep your financial objectives simple and actionable. Protect enough of your portfolio for safety while taking targeted risks to reach your goals. I set an unconventional, personal target—to be able to step back from work early to start a family—and I structured my career and risks around that objective. Your timeline and ambitions will be different; the key is to define what matters and act deliberately.”
“It’s OK to be scared.”strong>
How it applies to business: Fear often comes from lack of understanding; learning reduces anxiety.
How it applies to your money: “Feeling scared about money or investing is normal. The remedy is education and curiosity. Break concepts into small pieces, read reliable sources and ask questions. Do basic math to understand interest rates and expected returns. Ultimately, you are responsible for your finances—no one else will care for your money the way you do.”
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