A space where I share the hard-earned insights from my journey navigating the realities of entrepreneurialism. 

The Emotional Impact of Startups on Loved Ones and the Decisions That Divide Us

Precursor from my book regarding my joining the startup:
“The employment onboarding process was not a pleasant experience at my home with my wife and mother of our five children. She was very upset (there are more colorful words for this) with me that I left a Fortune 100 company with a $43 billion dollar cap value, $14 billion in annual revenue, an 18% ten-year annual rate of return to investors, millions of customers, uncountable products, global operations, paychecks, commission bonuses, 401k, medical, dental, optical, disability, etc. for a start-up with no products, no customers, no revenue, no network, no website, no employees, no business registration, no premises, no bank account, no payroll, no medical benefits, no 401k match, no paychecks for the first 45 days, and I had not met the individual in-person who offered the position that I accepted. My wife was so mad at me that she did not speak to me for thirty days—and I mean, she did not speak one word to me for thirty days.”

We often hear about the startup founder’s journey—the late nights, the big risks, the triumphant wins. But there’s a side to the story that rarely gets told: the emotional impact on the people closest to them, and the difficult decisions that can drive a wedge between a founder and their loved ones. When I co-founded Digital Island in 1996 to globalize the internet, I was chasing a dream that would eventually connect 95% of the world’s ISPs and enable eCommerce with Visa, MasterCard, and others, scaling the internet to 5.3 billion users and $5T in eCommerce. But that dream came with a cost—not just for me, but for my family.

When you leave a stable job for a startup with no revenue, no products, and no guarantees, it’s not just your life that gets turned upside down—it’s the lives of your family too. They feel the uncertainty, the stress, the absence, often more acutely than you do. The long hours and constant travel mean you’re not there for the everyday moments. The financial insecurity means they’re living with the same fear of failure, but without the passion for the vision that keeps you going. And the emotional toll of watching someone they care about take such a massive risk can create distance, tension, and even conflict, in ways that are hard to repair.

I saw this firsthand with my own family. The startup world celebrates the founder’s hustle, but we rarely talk about the emotional cost to the people who support them—the ones who are left navigating the fallout of a dream they didn’t choose. But the impact starts even earlier—with the decision itself. If I had made the choice to join Digital Island a “decision by committee” with my wife, I’m certain she would have voted no. The risk was too great: leaving a secure job for a startup with no safety net and no guarantees. She would have prioritized stability, security, and the well-being of our family—and rightfully so.

But entrepreneurialism often demands a different mindset, one that’s willing to take unilateral risks, even when it means going against the wishes of those you love most. If I had listened to that “no” vote, the work we did at Digital Island—work that fundamentally changed how the world communicates and transacts—would not have happened the way it did.

That’s the paradox of startups: the very decisions that lead to world-changing outcomes can also create the deepest rifts with the people who matter most. My choice to move forward with Digital Island wasn’t just my risk—it was a risk my family bore, too. They felt the weight of that decision in ways that left lasting impacts on our relationships. We rarely talk about this side of the startup journey, but it’s a reality every entrepreneur needs to face.

I don’t regret doing it—the success of Digital Island speaks for itself, connecting the world in ways that were unimaginable at the time—but now that I’m older and more mature, I can see other points of view much more clearly. Today, I understand better why my wife was so upset with me. I took an enormous risk that I saw as a once-in-a-lifetime entrepreneurial opportunity, but it was undeniably risky to our family’s financial security.

Looking back, I often ask myself, “Why did I do it?” At the time, I felt we had a decent chance to succeed. I was convinced that if we could establish the necessary infrastructure to globalize the internet, customers and investments would follow. My co-founders Ron, Sanne, and I really thought that with some good luck and the right people, we could do it. As it turned out, we needed a ton of good luck, nearly a billion dollars, and the combined efforts of thousands of exceptionally talented people.

To aspiring entrepreneurs: your dream matters, but so do the people in your life. Before you take the leap, have the hard conversations. Acknowledge the impact your choice might have on them, and be prepared for the possibility that they might not support your decision. If you’re already in the thick of it, take a moment to check in with the ones who matter most—they’re on this journey with you, whether they signed up for it or not.