They say you should never work with your spouse. There is an old adage, repeated quietly among investors, echoed in HR manuals, and whispered over drinks at startup conferences, that love and business are oil and water. “You’ll get tired of one another,” they say. “You’ll bring it home, you’ll never escape work, it’ll end in heartbreak or, worse, a slow bleed of resentment that ruins both your life and your company.” They say it with such certainty that you can almost believe them, especially if you’ve watched a partnership collapse from up close. And I have.
At thirty-eight, I stand at the beginning of what most would call a second act, hoping it's my prime. My first act, if I’m honest, was a collection of sharp pivots and deep studies, preparation for my prime, an apprenticeship in the real world and, in many ways, a study of power and partnership.
I have never been married. I have no children. I’ve built, managed, mentored, lost, and begun again. My friends would say I am ambitious; my family might call me stubborn; I call myself a craftsman, someone building something too big to be done alone. Yet here I am, a bachelor, approaching the crossroads where my own story and the “rules” of business are set to collide.
I grew up among men who were, in a sense, penguins: monogamous, dutiful, never straying from their chosen mate. My father and four of his five brothers have all been married for over twenty years, some more than thirty, and my uncle Dennis for over forty. My father, albeit married twice, has been married for nearly 45 years, altogether. Each of his marriages came with its lessons: about love, about risk, about the unpredictable way life rewrites its own rules. Growing up, he was very much the measure of a man for me. My parents tell the story of how they planned to have me when he was 32 years old so I would be turning 18 when he turned 50. They were married for 15 years and divorced when I was 5 years old. The hardest part is that I never want to get divorced. Now I'm older than I thought I'd be when making this decision and I'm still not exactly where I thought I'd be at this point in my life. Nevertheless, been feeling a slight sense of urgency lately.
I recently made a career pivot and it feels like I'm starting from scratch. I even moved back in with my mother while I get things in order. From the outside looking in, I may have no business looking for a girlfriend, at this point. On one hand, there is the voice of tradition: build your castle, make your fortune, become the provider, and when your coffers are full, choose a wife. On the other hand, there is the raw honesty of my own nature, the part that says, “You will need a teammate for this journey, not just a celebrant when you arrive.” What complicates things further is that, as much as I’ve admired the idea of a stay-at-home wife, making our family our true work, I have also been drawn to the vision of partnership. Not just in life, but in my work, as well.
There is a woman out there, at least I choose to believe there is, who could walk any of these paths with me. Sometimes, when I look at what’s next, I think it would be easier to find her after I have everything exactly how I want it to be. At the same time, there’s another voice, quieter but insistent, asking whether that’s the truth or just another fear wearing the mask of pragmatism. Couldn't we do it together?
If you say aloud that you want your romantic partner to be your business partner, most people flinch or cringe. Sometimes it’s subtle, a raised eyebrow, a “Good luck with that.” Sometimes it’s direct. I have seen it all, both in the corporate world and on the startup frontier. In the circles where money moves fastest, the skepticism is baked into the system. Venture capitalists call married cofounders “key-man risk, squared.” HR professionals, governance experts, and even seasoned entrepreneurs will warn you that the odds are stacked, that the marriage and the company form a single point of failure.
These are not idle fears. The data tells its own cautionary tale. Divorce rates among entrepreneurs are several points higher than the general population. The stresses of launch, scale, and survival multiply under the roof you share. There are stories, too many to count, of marital conflict becoming company conflict, of boardrooms deadlocked by a couple’s personal grievances, of founders hiding their relationship until the check clears.
In my own professional orbit, I watched Rhubarb Studios, a promising venture studio, implode when its married cofounders unraveled their partnership not just in the office, but at home, over inter-office infidelity. The business could not survive the aftershocks. And it is the reason why so many business mentors advise drawing clear, cold boundaries between your heart and your ledger. I don't necessarily disagree.
I do believe it's become stigmatized and the stigma is not just practical; it is deeply emotional. There is a lurking suspicion that romance is somehow less serious, less rational, less scalable than pure business partnership. To work with your spouse is to put both of your reputations at risk in a way that feels, to outsiders, almost reckless.
I have felt this anxiety myself, the fear that if I bet on love, and it fails, I lose not just my partner but my standing, my future, my hard-won identity as a builder. I have seen what happens when partners mix business and pleasure, only to end up the subject of office gossip, or worse, a case study in “what not to do.”
But honesty compels me to go deeper. In all my years watching, learning, and occasionally failing, I’ve never been convinced by the cynics. Because there is a flip side, often ignored by the risk-averse. There are couples who not only survive but thrive in the crucible of business. There are marriages forged in the fire of co-creation, unions where trust and ambition do not compete, but compound.
To give the skeptics their due, their case is well documented and, frankly, intimidating. Investors, for example, often pass on companies founded by couples, fearing that when the partnership falters, so too will the enterprise. They point to research showing that entrepreneur marriages dissolve at a higher rate than others, that work stress seeps into the home, and that the inability to leave work at the office accelerates both professional and personal burnout. Some studies reveal that married founders are more risk-averse, taking fewer big swings for fear of putting both the marriage and the business on the line.
Then there is the specter of governance failure. What happens if you and your spouse disagree on strategy? What happens if a marital dispute becomes a boardroom brawl? I have heard more than one investor describe married cofounders as a “voting bloc with a built-in civil war.” Employees, too, may hesitate to raise issues, fearing that any conflict will be interpreted as a slight against “the family.” In some cases, founders hide their relationship, not just from investors, but from their own teams, waiting until the company is too big to fail before going public with the truth.
Underlying all of this is a fundamental discomfort with blurred boundaries. In a world obsessed with specialization, the idea that someone could be both your romantic partner and your professional equal seems to violate an unwritten code. Even the language betrays our suspicion: “Don’t mix business and pleasure.” “Don’t fish off the company pier.” These are not just old wives’ tales; they are reflections of a culture that prizes compartmentalization, that fears the messiness of overlapping roles.
But here’s the part I can’t let go of: so much of the logic behind this stigma is rooted in fear: fear of failure, fear of judgment, fear of what might happen if we try to have it all and fall short. As someone who has lived long enough to see both the cost of caution and the price of regret, I am not convinced that fear is the best guide.
It’s easy to find cautionary tales about lovers who went into business and left with nothing but broken hearts and empty bank accounts. What’s less discussed, but infinitely more inspiring, is the quiet army of married couples who have built some of the world’s most successful companies, defying the prevailing wisdom that love and business are fundamentally incompatible. I don’t just mean small family stores or side hustles. I mean empires.