In 1995, I was working at Microsoft, one of the most powerful and influential companies in the world. Yet, I felt incomplete. I questioned whether I wanted to be an employee for the rest of my life or if, like the company’s founder Bill Gates, I was meant to be an entrepreneur.
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The internet was on the verge of transforming the world, and we were seeing the birth of companies like Netscape, Yahoo, Amazon, Lycos, Infoseek, and Excite. It was an era ripe for bold moves and innovative ideas. I realized that now was the time to start a groundbreaking company and that I needed to take bold actions of my own.
I had moments of doubt. Could I create my own company, or should I stay at Microsoft? I was no longer satisfied with working for someone else. I dreamed of running my own business. I wanted to see what I was truly capable of, even if it meant risking it all. Could I do it on my own? I had to find out.
So, one day I went into my boss’s office and gave my notice. Just like that, I left my cushy Microsoft job. And then, I went home to tell my wife.
The house was unusually quiet, the rare kind of stillness that only occurred before my kids came back from school. My heart was pounding, not from what I had just done, but from what I was about to do.
I found Anu standing at the kitchen counter. She turned to look at me, her brow furrowing in confusion. “What are you doing home so early?” she asked.
I took a deep breath. “I quit,” I said, letting the words hang in the air.
Anu’s eyes widened. “You did what?”
I told her I had walked away from a nice salary, the millions in stock options, and the security of a job I excelled at—to chase an idea I didn’t have yet. She stared at me, her eyes eventually narrowing. “Have you completely lost your mind?” she asked. “You don’t even know what you’re going to do next?”
The truth was, I didn’t. I had no plan, no business model, and no clear timeline for how this wild leap would lead to a safe landing. All I had was a gut feeling—a belief that the internet was about to change everything and that I needed to be part of it. I told her we had enough money to survive for six months, maybe a year. It was enough for me to try.
Still, the weight of her doubt and visceral fear hit me hard. I couldn’t let this decision drive a wedge between us. So, right then and there, I made a call. I dialed a friend I had made through Microsoft, put him on speakerphone, and asked a question I already knew the answer to: “If I need a job in six months, will you hire me?”
His response was immediate and almost amused. “Of course.”
I hung up and turned to Anu. “Give me six months,” I said. A hint of a smile tugged at her lips. And just like that, I had her reluctant approval.
Looking back, this might have been the first time I was truly thinking clearly. Ideas don’t become reality on their own—you have to act on them. Taking action, even in the face of uncertainty, is what sets those who succeed apart from those who don’t.
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In the days that followed, doubts crept in, but that leap of faith was what led to my first major success: InfoSpace. It wasn’t just a business; it became part of our family. Within a few years, it was worth over $40 billion.
Even if InfoSpace had failed, I still would have succeeded because I took action to pursue a dream. I also would have grown and learned in ways my job at Microsoft could never have offered. Failure would have brought me closer to my next business success. This is the value of acting on our wildest ideas and dreams.
By jumping in and taking full responsibility, I discovered a sense of purpose and self-worth I had never felt before. For the first time, I wasn’t working to realize someone else’s vision. I was building something of my own. I had shifted my perspective in life and I now had a purpose. I was dreaming, acting on those dreams, and proving to myself that I could shape my reality and influence the world around me. It was a monumental time because I learned that pursuing dreams, even when they feel uncertain or irrational, is incredibly liberating. Every day as an entrepreneur, I felt more alive and empowered, knowing I was fully accountable for everything that happened, whether good or bad.
The experience taught me that success isn’t defined by job titles or wealth; it’s about having the courage to act, the resilience to persevere, and the satisfaction of bringing something new into the world. Even if you work within a company, you can be an intrapreneur—taking initiative, driving results, and creating impact rather than waiting for instructions. That’s what true success looks like.
You don’t have to be perfect or wait for the ideal situation—what matters most is becoming a doer. The best entrepreneurs aren’t the ones with the greatest ideas; they’re the ones who execute. Without action, there are no results. There’s also no substitute for the sense of control, purpose, and fulfillment that comes from creating and executing a vision. This is why those who take action ultimately win.
As I’ve learned over the years, it’s the fear of taking action—especially being the first to do so—that holds most people back. Self-doubt often accompanies that initial leap. And even after you take action, staying the course on your mission can be incredibly challenging. Success isn’t about a single action; it requires hundreds of them. You must remain steadfast, even when your situation feels hopeless.
Pursuing massive dreams will always present countless opportunities to stop and quit. The bigger question then becomes: how do you keep going?
The answer lies in having the right mindset—a counterintuitive one at that.
I won’t spend much time on the basic day-to-day essentials—how to identify key metrics, or hire the right people. These foundational skills, often referred to as the ‘blocking and tackling’ of business, are relatively easy to learn.
One thing that isn’t taught enough is the mindset needed to keep going when times get tough. To stay the course and reap the rewards, you need a specific kind of resilience—the mindset of someone who takes initiative and makes things happen rather than waiting for others to act.
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