The Cost My Wife Paid: The Unseen Partner Who Made It Possible
Every founder has a shadow stories. The following is one of mine. The first paragraph on this page is quoted directly from Chapter 5 of my book: I Join the Startup, Army of 3
“The employment onboarding process was not a pleasant experience at my home with my wife, the mother of our five children. She was very upset with me (there are more colorful words for this) that I left a Fortune 100 company with a $43 billion market cap, $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, 401(k), family 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 401(k) match, and no paychecks.
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 the founder, and the difficult decisions that can drive a wedge between a founder and their loved ones.
At the time I joined Digital Island, my office was four miles from our home, and I was readily available, both practically and logistically, to help raise our five children, ages 2–10. A month later, and for the next three years, I started traveling around the world, and my wife was left to raise those children by herself until my return. This was not something she agreed to in advance or signed up for.
It was compounded by the fact that she was never shown any gratitude from the company. It was simply expected that she would deal with it because I had to be in Moscow, São Paulo, Beijing, Hong Kong, Tokyo, Seoul, Paris, London, Frankfurt, Taipei, Honolulu, Singapore, Kuala Lumpur, New York, and elsewhere, repeatedly, to acquire the initial infrastructure and then the expansion facilities for our network services.
Believe me when I tell you: no potential future stock options that may be recommended by the board, or may someday have value, are going to satisfy a mom who has to get five children to and from school, activities, medical, dental, and optical visits, keep up with their nutrition, laundry, and do all the house cleaning by herself. She was entitled to feel pressured and contemptuous. She did not endorse this entrepreneurial decision that I made.
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, E*Trade, Charles Schwab, and many 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, and the absence, often more acutely than you do. The long hours and constant travel mean you are not there for the everyday moments.
The financial insecurity means they live 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 conflict in ways that are hard to repair.
The startup world celebrates the founder’s hustle, but we rarely talk about the emotional cost to the people who support them, the ones left navigating the fallout of a dream they did not 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 sagely so.
But entrepreneurialism often demands a different mindset, one willing to take unilateral risks, even when it means going against the wishes of the people 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 is 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, the customers and investment 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 of speculative venture capital, 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.