Kevin O’Leary, or Mr. Wonderful, as most of the world knows him, is well known for his tough love, sharp instincts, and unapologetic financial wisdom. So when he shares advice on the softer things, like love and marriage, people take notice. Recently, Kevin dropped a truth bomb on what he calls his most important piece of marriage advice. Here’s what he had to say:
“Marry once. That’s the key to success. Choose wisely. And then stick it out. Because the worst thing you can do is get married and then get divorced—it wipes out half of your financial assets. Ugh. Nightmare. How stupid is that?”
As someone who had the honor of pitching to Kevin on Shark Tank and gaining his investment in my company, HelloPrenup, I’ve had a front-row seat to how he thinks about money, decision-making, and risk. And I can tell you: this advice is 100% in line with his real-world philosophy—and with the financial reality most couples face. Let’s unpack why “marry once” isn’t just old-school advice. It’s a strategy. Plus, where prenups play their part in Kevin’s no-nonsense approach to protecting your future.
Marriage is a business
We romanticize weddings, marriage, and happily-ever-afters—and rightfully so. Love is truly a beautiful thing. But the fact of the matter is we tend to overlook what marriage actually is from a practical standpoint: It’s both a contract you sign that comes with government-granted rights, risks, and responsibilities. It’s also the merging of two financial lives into one legal and economic unit, which some may view as a pseudo-business. From taxes to debt to property, marriage functions like a business partnership. So, it should be treated with the same level of legal protections, planning, and clarity.
Unlike most real businesses in life, you don’t need a business plan to make decisions within the marriage—yet the stakes can be just as high, if not higher. Things like purchasing property, taking on loans, contributing to retirement accounts, etc. are all ways your marriage can function like a business and can result in either growth or decline in wealth.
Enter: The prenuptial agreement. A prenup acts as your marriage’s financial and business blueprint—a tool for defining roles, setting expectations, and protecting what you build together (or separately) during the marriage. Just like you would get legal documents in place before entering into any serious business arrangement, you should do the same for a marriage.
Kevin’s warning about divorce “wiping out half of your financial assets” is not hyperbole—it’s an accurate depiction of what happens when couples go into marriage without a plan, especially in community property states like California or Texas.
Marrying once is the goal. Planning is the tool that gets you there.
Kevin’s point isn’t just about treating marriage as a business. It is also about entering into marriage with the same care and foresight you might also apply to making a major business decision. Think about it this way: You wouldn’t invest $100,000 of your own money into your budding business idea without due diligence. You wouldn’t bring on a business partner without an operating agreement. So why would you enter into one of the most financially significant partnerships of your life (i.e., marriage) without discussing expectations and protections through a prenuptial agreement?
That’s exactly why I founded HelloPrenup—to give modern couples an accessible, affordable, and empowering way to create prenuptial agreements together. Kevin immediately saw the value in this approach because he understands what’s at stake—a lot of money.
As Kevin puts it, “Choosing wisely” for your future spouse doesn’t stop at choosing the right person. It also extends to choosing to have the tough conversations early, things like talking about money, debt, retirement, divorce, and death through the process of a prenup. This helps you and your future spouse build a plan that supports both love and financial security.
Wealth isn’t all about the dollars—It’s also about the peace of mind
One of the most overlooked benefits of a prenuptial agreement is the peace of mind it offers. While we always hope we “choose wisely,” as Kevin says, the future is uncertain, and knowing you and your partner are aligned not only emotionally but financially can actually strengthen your relationship. In fact, 83% of HelloPrenup users agree that the prenup process brought them closer together. Why? It sets the stage for healthier communication, clearer expectations, and less stress around money, which we all know is a major cause of conflict in many marriages.
Kevin’s “marry once” mantra may sound blunt, but at its core, it’s deeply optimistic and underscores the importance and benefits of marriage. He’s telling us that the best path to wealth, stability, and long-term success is choosing a partner who complements your values—and then building a life together with intention.
Remember, you wouldn’t think getting travel insurance means your vacation is going to go bad. Same goes for prenups–they aren’t about anticipating failure. They’re about protecting the life and the “business” you’re building together through marriage. It’s about ensuring that, should things ever go off-course, you’re not forced into emotional and financial chaos. They’re about giving your relationship the tools it needs to thrive.
Final thoughts: Marry once, but plan always
Kevin O’Leary nailed it. Marry once. Choose wisely. Stick it out. And from where I sit—as a former divorce attorney turned legal tech founder—I’d only add one thing: Have hard conversations upfront through the prenup process. Put some legal guardrails in place. Plan ahead. Because the couples who plan ahead are the couples who stay ahead.
At HelloPrenup, we’re proud to support couples in building that plan—whether you’re high-net-worth, a startup founder, or simply someone who believes love and logic can go hand-in-hand. So yes—marry once. But plan like the intelligent, values-driven business team you are. That’s the real key to a lasting, loving, and financially sound marriage.
Julia Rodgers is HelloPrenup’s CEO and Co-Founder. She is a Massachusetts family law attorney and true believer in the value of prenuptial agreements. HelloPrenup was created with the goal of automating the prenup process, making it more collaborative, time efficient and cost effective. Julia believes that a healthy marriage is one in which couples can openly communicate about finances and life goals. You can read more about us here Questions? Reach out to Julia directly at Hello@Helloprenup.com.
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