Why We Celebrate Failed Businesses But Shame Failed Marriages: The Double Standard Nobody Talks About
From the Podcast to the Page™
This post is inspired by Episodes 34 and 35 of The Joy! A.A.C.T.™—where real conversations meet real healing.
Recently, I came across an interview with Kevin O'Leary—you might know him as "Mr. Wonderful" from Shark Tank—where he called marriage an "economic union" and declared that divorcing is "the stupidest thing you could ever do." But what really caught my attention was his statement that if you're getting married for the third time, "it's not them, it's you. There's something wrong with you."
This could easily be viewed as a "hit dog will bark" situation. Having been married four times myself, you might think I'm just reacting defensively to his comments. I prefer to see it differently: I have a dog in this fight. My experience—both personal and professional working with women through divorce—gives me a unique vantage point to examine whether O'Leary's logic actually holds up.
And when we look at the data and apply the same business principles he champions, his double standard becomes impossible to ignore.
The 80% Failure Rate We Celebrate
Here's what O'Leary openly admits about his own business ventures: eight out of ten deals go to zero. That's an 80% failure rate. He's even said, "If starting my first company hadn't worked out, I would've started my second company. And if that failed, I would've started my third company."
We celebrate this. We call him experienced, savvy, resilient. People seek him out daily for advice because of his failures.
But apply that same logic to marriage? Suddenly there's something wrong with you.
The Real Numbers Behind Marriage and Business Partnership Failures
Let's look at actual data. Business partnerships fail at a 70% rate. Marriages fail at under 50%. If we're treating marriage like a business partnership—as O'Leary suggests—marriages are actually performing better than business partnerships.
So why does O'Leary accept and celebrate failed businesses but shame people whose marriages end?
Why Marriages and Business Partnerships Actually Fail
The reasons O'Leary's businesses fail are remarkably similar to why marriages fail:
Wrong partners - Sometimes you just choose wrong
Fraud and deception - Remember his FTX situation where he lost nearly $10 million?
Market or life circumstances change - Hello, pandemic
Fundamental incompatibilities - Values don't align
One party not holding up their end - Imbalance of effort and contribution
Abuse - Financial, emotional, psychological
In business, we understand these things happen. We recognize that sometimes you partner with the wrong people, that market conditions change, that sometimes you ignore red flags and it costs you. Things happen.
But in marriage? We stigmatize people who leave relationships that aren't working.
My Own Business Divorces
I've had my share of business divorces too. I once worked for a priest running a not-for-profit where I discovered his wife's office was fully furnished while the preschool had no computers and staff had no medical insurance. When I complained about unethical practices—including lying to employees and the state—I got fired.
Was I wrong for refusing to participate in unethical behavior? For choosing my integrity over a paycheck?
In another business relationship, I experienced constant gaslighting. I was told my energy would "negatively affect the team." I was verbally insulted in meetings for expressing opinions different from the CEO's. I was told, "I wasn't attacking you, it was what you said."
A business relationship where your voice is dismissed, your perspective is punished, you're gaslit about your own experiences, others witness the toxicity and stay silent, and you're constantly walking on eggshells—that's not a partnership. That's an abusive dynamic.
Leaving that type of situation isn't failure. It's self-preservation.
Related: [Why Leaving a Toxic Relationship Is an Act of Courage, Not Failure] (internal link opportunity)
The Hidden Health Costs of Staying in an Unhappy Marriage
O'Leary wants us to focus solely on the financial cost of divorce. But what about the cost of staying?
Research reveals disturbing health impacts of remaining in unhappy marriages:
Cardiovascular health: Men in unhappy marriages nearly double their stroke risk and have a 21% higher overall mortality risk over three decades
Immune system: Chronic marital stress weakens your immune system
Physical healing: Couples stuck in negative communication patterns heal slower and have higher inflammation
Metabolic health: Unhappy marriages increase risk of type 2 diabetes and obesity due to prolonged stress hormones
Cognitive function: Marital unhappiness speeds cognitive decline, impairs memory and decision-making
Mental health: Higher risk of depression and anxiety, lower self-esteem
Sleep quality: Chronic conflict reduces sleep quality (and we know how critical sleep is to overall health)
A 12-year Penn State study found that people in unhappy marriages have lower self-esteem, worse health, and less life satisfaction than people who divorce. People who never remarry actually report higher life satisfaction than those who stay in unhappy marriages.
Staying isn't protecting you. It may be causing you harm.
Free Resource: [Download the "Is It Time to Leave?" Self-Assessment Checklist] (lead magnet opportunity)
What About the Children? The Real Impact of High-Conflict Homes
Many parents justify staying in unhealthy marriages "for the kids." But research shows something different. Children living in high-conflict homes suffer more mental health struggles, sleep disruptions, and difficulties with healthy relationships later in life.
Children don't just hear what you're saying—they observe and absorb what you're modeling. If they see coldness, constant conflict, or deafening silence, they learn that:
Love equals conflict
Marriage means unhappiness
Money is more important than wellbeing
I'll never forget sitting in therapy when my ex said he'd never seen his parents argue. The therapist tilted her head and said, "That means you never saw them resolve one either." That insight has stayed with me. Children don't just need to see conflicts being avoided—they need to see them resolved in healthy ways.
Research shows children do better with two separated parents than with two miserable parents trying to parent together.
Choosing yourself isn't selfish. It's teaching your children what self-respect looks like.
Questions Kevin O'Leary Won't Answer
If I could sit down with Kevin O'Leary, here are the questions I'd ask:
If you would leave a business partner for embezzling, why should someone stay with a spouse who's committing financial infidelity or abuse?
If we celebrate entrepreneurs who try over and over again because they want to make their business work, why do we stigmatize a person who does the same thing in marriage?
If you view cutting your losses in business as smart, but walking away from a soul-sucking marriage is wrong—what's that about?
If pivoting in business is honorable, isn't divorce often the smartest pivot a person can make?
What's the ROI on doubled stroke risk, therapy for traumatized kids, and years of lost productivity at home and at work?
Who O'Leary Would Have Told to Stay
Based on what O'Leary said, he would have told Tina Turner, Mary J. Blige, Halle Berry, Kelly Clarkson, Sheila Johnson, and Gayle King to stay. How about my mom, my aunts, me? We should have all stayed. What about you?
The price tag for maintaining that dysfunctional marriage economy was way too high. You can always make more money—and many of the women I listed did—but you can't buy back your freedom. You can't buy back your health.
And even for the women who didn't end up becoming wealthy or millionaires or wildly successful, their peace of mind was the most important thing. Their safety and their peace of mind.
Marriage Is More Than a Balance Sheet
Yes, marriage has economic components. I know people whose emotional relationship is over but can't afford to physically separate. But marriage is so much more than an economic union.
Marriage, at its best, is about emotional intimacy and support, physical connection, shared life experiences, mutual growth and evolution, companionship, and building a legacy together. When a marriage is healthy, it enhances every aspect of your life. But when it's unhealthy, it erodes everything. And staying doesn't automatically preserve anything—it could just be prolonging the damage.
The Real Question You Should Be Asking
O'Leary is right about one thing: divorce does have costs. But the data shows the greater cost often lies in staying.
The real question isn't "Can you afford the divorce?"
The more important question is: "What will it cost me if I stay? Can I afford that?"
When entrepreneurs fail repeatedly, we call them resilient. When people divorce more than once, O'Leary says something is wrong with them. That double standard has to go.
Choosing yourself is not stupidity. It's wisdom. It's courage. It's survival. And if you've left a marriage that was harming you—whether it was your first, second, or third—there's nothing wrong with you.
Walking away from something that's harmful isn't failure. It's self-respect in action.
Ready to Move Beyond Divorce With Confidence and Joy?
If you're navigating divorce or still healing from one, you don't have to do it alone. My book Divorce Is Not a Destination is your roadmap to:
Healing from heartache without getting stuck in bitterness
Rebuilding your confidence and sense of self
Creating a life filled with purpose and joy
Understanding why accountability (not shame) is your path to empowerment
Winner of two book awards, this is the guide professional women turn to when they're ready to reclaim their lives.
Continue the Conversation
This article is based on my two-part podcast series examining why I don't agree with Kevin O'Leary's views on marriage and divorce:
