Kevin O’Leary on Marriage and Money: Why “Getting Married Once” is One of Life’s Smartest Investments

/ Kevin O'Leary
Kevin O'Leary on Marriage and Money: Why “Getting Married Once” is One of Life’s Smartest Investments

In the World of Finance: Kevin O’Leary’s Wisdom on Marriage

In the world of finance, Kevin O’Leary is known for his no-nonsense approach, razor-sharp business insights, and unapologetically practical advice. But when it comes to personal relationships, particularly marriage, O’Leary’s philosophy carries just as much wisdom. Recently, the renowned entrepreneur and Shark Tank investor sparked intrigue with a social media message that transcends typical financial commentary. His advice? “Get married once.” While seemingly simple, those three words reflect a deeper philosophy on wealth, emotional well-being, and the long-term value of life partnerships.

This article dives into the significance of O’Leary’s reflections on marriage, expanding on the interplay between love, strategic decision-making, and financial success. As we unpack his commentary, we’ll explore how marriage—when approached with the same strategic mindset applied to investments—can be one of the most prudent “financial decisions” a person can make.

Table of Contents

1. Kevin O’Leary’s Philosophy: Merging Finance with Personal Life

Kevin O’Leary, often known for dispensing blunt business advice to aspiring entrepreneurs, frequently draws parallels between professional and personal aspects of life. His recent message about marrying wisely reflects his belief that all areas of life can—and should—benefit from strategic thinking.

For O’Leary, life isn’t about compartmentalizing business from personal choices. Instead, he emphasizes integration: personal decisions have profound financial implications, and vice versa. In this light, his “get married once” advice isn’t just about romantic ideals—it’s about making informed, deliberate decisions that bolster one’s overall life trajectory.

This worldview aligns with O’Leary’s broader message: every major life decision, including one as emotionally charged as choosing a spouse, carries significant financial weight. Treating marriage lightly, or entering into it without deep thought, he argues, can lead to regrettable consequences—both emotionally and economically.

2. Relationships as Investments: The Economic Cost of Divorce

One of the central themes of O’Leary’s message is the high cost of divorce. And not just in an emotional sense—he’s specifically sounding the alarm on its financial toll.

Divorce, depending on the circumstances, can be among the most expensive life events an individual can experience. The costs include:

  • Legal and attorney fees
  • Division of property and assets
  • Potential alimony or spousal support
  • Child support and custody arrangements
  • Tax implications and lowered credit stability

According to statistics from financial analysts and family law experts, the average divorce in the U.S. costs between $15,000 and $30,000, but the larger concern is the destruction of long-term wealth. Dividing assets can severely impact net worth growth, retirement planning, and intergenerational wealth transfer.

O’Leary implies that avoiding this economic disruption starts with a conscious and thoughtful decision at the outset. In other words, don’t just fall in love—do your homework first.

3. Emotional Stability and Marital Harmony

While O’Leary is well-versed in the world of dollars and cents, he also understands the intrinsic value of emotional stability. Beyond finances, a strong, enduring marriage provides psychological and emotional support, which can ripple into improved professional performance and mental health.

Stable relationships often lead to better emotional regulation, greater life satisfaction, and generally more resilient households. Children born into secure, loving homes statistically fare better in academics, behavior, and future relationships. In O’Leary’s paradigm, a harmonious family life is not just a personal victory—it’s part of the infrastructure that supports entrepreneurial success.

By marrying right the first time, and nurturing that partnership over decades, individuals can build not just wealth, but a fulfilling and grounded life. It’s this long-view thinking that separates O’Leary’s advice from the typical romantic platitudes.

4. Choosing the Right Life Partner: The Ultimate Due Diligence

In the business world, O’Leary is relentless about “due diligence”—the thorough vetting of any opportunity before investing. He’s now applying that same rigor to romance.

Choosing a spouse, after all, is arguably the biggest “investment” of one’s life. It’s not just about love, but about:

  • Aligning life goals and values
  • Understanding communication styles
  • Clarifying financial philosophies
  • Evaluating emotional intelligence and behavioral patterns

This isn’t to say that love should be robotic or transactional. Rather, O’Leary’s point is that entering marriage blindly or impulsively—because of social pressure or infatuation—can lead to devastating outcomes. Instead, he encourages people to assess compatibility with the same clarity and seriousness as they would a seven-figure business venture.

5. The Compounding Value of Long-Term Commitment

Long-term marriages offer the same benefit as long-term investments: compounding. Just as invested money grows over time, so too does emotional intimacy, trust, and shared history within a committed relationship.

Couples who commit to growth, navigate obstacles together, and continuously reinvest in their relationship often enjoy rewards that become more valuable with each passing year:

  • Deeper companionship and understanding
  • Shared milestones and family traditions
  • Increased resilience through hardship
  • A sense of legacy and continuity

From O’Leary’s perspective, avoiding divorce isn’t just about costs—it’s about protecting and nurturing an emotional and economic enterprise that grows in value over time.

6. Lessons from the Boardroom: Applying Business Strategy to Love

As a seasoned investor, O’Leary often returns to a simple principle: make fewer, smarter bets with long-term upside. This logic easily applies to personal relationships.

Building a strong marriage involves:

  • Clear goal-setting (family vs. career balance)
  • Ongoing communication (like regular “board meetings”)
  • Crisis management (navigating conflicts with grace and compromise)
  • Growth mindset (continuously learning and evolving as partners)

Just as businesses need plans, milestones, and teamwork to succeed, so too do marriages. O’Leary’s view beckons couples to approach their unions with intention, responsibility, and—most importantly—a shared vision.

7. Prioritizing the Marriage “Asset”

Once formed, a marriage must be maintained as an asset—something you check in on, invest in, and protect.

  • Emotional reinvestment: spending quality time, expressing appreciation, and nurturing intimacy.
  • Financial transparency: open conversations about spending, saving, and financial priorities.
  • Collaborative decision-making: treating each other as equals in shaping life’s direction.

In this context, love and connection aren’t assumed constants. They are active forces, continually built and preserved through choices, just like business assets.

8. Financial Security and Family Legacies

For entrepreneurs like O’Leary, family legacies and generational wealth are top-of-mind concerns. Strong marriages often act as the pillar supporting such aspirations.

When spouses work in harmony, they can better:

  • Build and preserve estates
  • Raise financially literate children
  • Model healthy relationship behaviors
  • Make coordinated long-term investments

Fragmented families, by contrast, frequently experience legal battles, split inheritances, and diminished household net worth. O’Leary’s advice echoes the principle: keep the foundation strong if you want the house to prosper.

9. Critics and Counterpoints: Is Love Really That Strategic?

Of course, not everyone sees relationships through such a pragmatic lens. Critics argue that love is messy, unpredictable, and fundamentally different from business. They caution against approaching romance too analytically, as it might strip away the emotional spontaneity and warmth that make love meaningful in the first place.

While these concerns are valid, O’Leary isn’t suggesting that love become purely transactional. His main point is balance. Just as reckless financial decisions often bring ruin, so too can reckless emotional choices. Applying a little strategy doesn’t diminish love—it protects it.

Ultimately, his philosophy invites individuals to elevate the way they choose and maintain romantic partnerships—to combine heart and mind in an intentional, long-view approach.

10. Final Thoughts: Balancing Heart and Mind in Love

Kevin O’Leary’s candid advice to “get married once” challenges conventional thinking about relationships. While many associate love with passion, fate, or emotion, O’Leary introduces an important counterbalance: strategy, intention, and discipline. He’s not arguing against love—he’s arguing for treating it as the significant life decision that it is.

Choosing a life partner should be done as thoughtfully as any other long-term commitment. Once in it, the relationship should be nurtured like a valuable enterprise. With the potential for financial stability, emotional fulfillment, and generational success on the table, marriage deserves all the seriousness we give to ventures, investments, and career planning.

So whether you’re already married, considering marriage, or reflecting on past relationships, Kevin O’Leary’s perspective provides something worth pondering: Are you managing your heart like your most valuable asset?