Grief Didn’t Just Break My Heart—It Tanked My Business

Why Grief and Entrepreneurship Aren’t Opposites—They’re Inseparable

I’ve never said this publicly before: grief tanked my first venture. Because as I’ve come to learn, grief and entrepreneurship go together more often than we’d like to admit.

At the height of growing my first consulting firm, I stepped away. Not because the business was failing. The business was actually taking off. Clients were coming in. Momentum built quickly. Confidence followed.

It wasn’t a question of whether I’d be there for my mom.
Stepping in felt automatic. I’m my mother’s son, after all.

Like she did for her own parents, I felt pulled to do the same—to walk with her to the end.
To make her laugh.
To help her die with as much dignity and humanity as possible.
To soak up every story, every ounce of wisdom this three-dimensional person had left to offer.

That decision? A no-brainer.

What came after?
That’s what I wasn’t wired for.

The Quiet Unraveling Beneath the Surface

At first, it was about presence. Showing up. Offering joy and stability in her final chapter. But the longer I sat with her—witnessing her clarity, her humor, her surrender—the more something in me began to fracture. Not just from the pain of letting her go, but from the way her death cracked open a vault I’d long kept sealed.

What came rushing out was more than grief. It was trauma from my time living in Israel. A divorce I had never fully mourned. It was every unresolved feeling I had pressed down in order to function. All of it came flooding forward—uninvited, unrelenting.

The Mental Health Reckoning That Followed

It stopped being about caregiving. It became an all-out emotional reckoning. I looked put together on the outside, but inside I was unraveling. That unraveling, I now believe, was the start of becoming something more whole.

There wasn’t a real choice. But there were consequences.

And here’s what I want to say out loud, for anyone who’s been here or will be: grief and entrepreneurship are not separate paths.

If you’re building something meaningful, life will find a way to interrupt it. Sometimes at the worst possible time. And it doesn’t make you less of a founder.

It makes you human.

When Grief and Entrepreneurship Collide

I’ve had time to reflect on this. To ask myself what I could’ve done differently—not in choosing her, but in how I prepared.

And here’s what I know now: wanting to put something more important first may cost you your business. That doesn’t make it a mistake. That doesn’t make it weak. But we owe it to ourselves—and to the people in our orbit—to stop pretending it’s not a possibility.

It’s strange that something as universal and predictable as death still sits outside the frameworks of most professional roadmaps. We don’t talk about it in MBA programs. It doesn’t appear in pitch decks. It’s not built into startup accelerators or boardroom agendas. But it should be.

What I Didn’t Build For—and Why It Matters

I didn’t build my first business to withstand what life would eventually ask of me. So when the time came, I stepped away. And the business didn’t survive. I pretended it did, mostly to save face and maintain the illusion I’m still a force to reckon with. I’m not ashamed of that.

But I think we could do better—for ourselves and the people who come next—if we start talking about it.

Why We Need a Strategy for Grief in Entrepreneurship

Writers like Anne Helen Petersen have been naming these gaps in how we treat burnout, tradeoffs, and the human cost of ambition. Because grief will come. Loss will come. Disruption will come. And we act like founders shouldn’t have to make those tradeoffs—as if acknowledging mortality would weaken the hustle.

What if we taught people to expect it? What if we taught people to build for it?

Grief and entrepreneurship aren’t opposing forces. They’re eventual companions. And yet, we’ve inherited a culture—especially in male-dominated leadership spaces—that treats pain like a liability. As if inviting it into our work makes us less credible, when the truth is: it makes us more sophisticated.

When Founders Crumble Under Grief and Entrepreneurship

Because I’ve worked with founders who were flying high—on the edge of Series B funding, speaking center stage at South by Southwest, on everyone’s radar—when grief struck. And what I’ve seen is this: when loss comes knocking, and you’re being pressed to carry on, it can unravel everything.

A friend and colleague of mine once said, “We don’t fear change. We fear loss.” And when loss is coming, founders can crumble. Not because they’re weak, but because we’ve built no structure around them for that moment.

Everyone around them—with dollar signs in their eyes—pretends that the person who pitched them last week is still the same person leading the all-hands this week. But they’re not. And when we ignore that, we fail them—and everyone they lead.

We don’t need more tolerance for grief and entrepreneurship in the same breath—we need a strategy for it.

We need to wrap our arms around our key players—not just to protect their humanity but to keep the company solvent. It’s not a tradeoff. We can take care of people and the business in one fail-safe move: by making sure our founders don’t make decisions they’ll regret 20 years from now.

Because when they alienate the people who matter most, when they abandon themselves to keep up appearances, they become a shell of who they once were. All that talent, all that heart—lost. Not because they weren’t capable, but because no one had the courage to say:

This moment matters more than your burn rate.

The Grief and Entrepreneurship We’re All Carrying

And if you’re reading this and thinking it doesn’t apply to you, don’t kid yourself: you’re grieving right now. We all are.

Because America is in turmoil. Because no matter your politics, the ground beneath us feels unsteady. We’re grieving the loss of identity, of normalcy, of how things used to be. We’re grieving portfolios, institutions, relationships that no longer feel as safe as they once did. We’re grieving quietly, collectively, and without a strategy.

No one prepared us for this—not in business school, not in pitch prep, not in startup culture. We never talked about what it would look like to lead in the fog of loss. And yet, this moment is showing us in real time how closely grief and entrepreneurship are intertwined.

What if we approached grief the way athletes approach setbacks? In locker rooms, in the training room, in timeouts—they don’t pretend the loss isn’t real. They huddle up, lean in, and prepare to come back.

Why isn’t there a fucking business strategy for grief?

Grief Isn’t the Enemy—It’s the Intervention

Now, we often talk about strategy in the context of solving a problem. But I would be remiss if I didn’t stress this: grief isn’t a problem. It’s not the competition and it’s certainly not the enemy.

Just because we need a strategy doesn’t mean grief is something to solve, to overcome, or exploit. It’s something to understand. Something to integrate. The problem isn’t the emotion—it’s our unwillingness to account for it. 

We can prepare for grief and still honor it. We can make room for its wisdom without letting it derail everything—something writers like Maggie Smith remind us of through personal stories of rebuilding after loss. And if we do, we may discover it has more to offer than we ever imagined.

The Gifts of Grief in Business and Life

Grief didn’t just cost me momentum. It gave me a new mission.

Grief has become the DNA of my humanity, the thing that broke me open. It gave me the ability to sit with discomfort—mine and others’—without rushing to fix or explain it away. My listening grew deeper. So did my presence. And my discernment.

And while none of this showed up in pitch decks or investor meetings the second time around, it’s what people remember. Not what I built, but how I made them feel. That’s not fluff. That’s foundation.

We don’t need to downgrade talk of mental health and emotional regulation anymore to justify their value. We can make the business case. Emotional literacy is leadership. Presence is strategy. And grief—when metabolized—can sharpen your edge in ways no performance review ever could.

Because the quiet work of metabolizing grief isn’t always visible—but it’s real. And the kind of reflection found in spaces like Suleika Jaouad’s Isolation Journals shows just how powerfully grief and creativity are intertwined.

The truth is, very few people will remember the product you launched or the quarter you crushed. But the people you love? The people who shaped you? They’ll live in the choices you make when no one’s watching. In the quieter moments.

Even now, when I grieve—whether it’s over the loss of my mother or the emotional cost of my sacrifices in Israel—it’s no longer a kind of despair. It’s a connection. It’s a reminder that I’m still in relationship with the people and places that shaped me. That grief isn’t cognitive dissonance. It’s clarity.

And that clarity is what informs my work now.

The Leadership Parallel

The idea that we should separate personal life from leadership is outdated. Founders, executives, future-makers—we bring our humanity with us. We don’t get to time grief around quarterly earnings. And we shouldn’t have to.

Grief and entrepreneurship go hand in hand. What matters is whether we build with enough foresight to withstand it—and whether we let those experiences deepen our leadership, not derail it.

Here’s the practical part. Don’t wait for a crisis to ask: How much of myself am I willing to give to the things that really matter—especially when my business is thriving? Not because you’ll always have to choose. But because you might. And being ready doesn’t mean knowing the answers. It means knowing what questions to ask.

Ask yourself: What happens to this thing I’m building if I get hit by life tomorrow? It’s not a morbid question. It’s a generous one. And it’s a strategic one.

It’s the kind of question that honors both the living and the leaving.

Final Words

If you’ve made the choice to step away from the thing you built to care for someone you love, I see you. And if you’ve come back to build again, I really see you. Because helping leaders navigate the moments that can’t be solved with a spreadsheet, is how I make myself useful these days.

Here’s a plug: If you’ve never considered how grief might shape your company, your style, your habits—start there. It’s not just a disruption. It can be the beginning of something more aligned. This one’s for the ones who chose presence over performance.

You didn’t fail. You grew.