{"id":3089,"date":"2026-07-09T16:42:58","date_gmt":"2026-07-09T16:42:58","guid":{"rendered":"https:\/\/crosscountrymovingteams.com\/?p=3089"},"modified":"2026-07-09T16:42:58","modified_gmt":"2026-07-09T16:42:58","slug":"my-microsoft-exit-with-no-business-plan-led-to-a-40-billion-internet-company-and-a-debate-over-risk-vs-timing","status":"publish","type":"post","link":"https:\/\/crosscountrymovingteams.com\/?p=3089","title":{"rendered":"My Microsoft exit with no business plan led to a $40 billion internet company\u2014and a debate over risk vs. timing"},"content":{"rendered":"
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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\u2019s founder Bill Gates, I was meant to be an entrepreneur.<\/p>\n

Read more Current price of Bitcoin for July 9, 2026<\/a><\/p>\n

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.<\/p>\n

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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.<\/p>\n

So, one day I went into my boss\u2019s office and gave my notice. Just like that, I left my cushy Microsoft job. And then, I went home to tell my wife.<\/p>\n

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.<\/p>\n

I found Anu standing at the kitchen counter. She turned to look at me, her brow furrowing in confusion. \u201cWhat are you doing home so early?\u201d she asked.<\/p>\n

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I took a deep breath. \u201cI quit,\u201d I said, letting the words hang in the air.<\/p>\n

Anu\u2019s eyes widened. \u201cYou did what<\/em>?\u201d<\/p>\n

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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\u2014to chase an idea I didn\u2019t have yet. She stared at me, her eyes eventually narrowing. \u201cHave you completely lost your mind?\u201d she asked. \u201cYou don\u2019t even know what you\u2019re going to do next?\u201d<\/p>\n

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The truth was, I didn\u2019t. 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\u2014a 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.<\/p>\n

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Still, the weight of her doubt and visceral fear hit me hard. I couldn\u2019t 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: \u201cIf I need a job in six months, will you hire me?\u201d<\/p>\n

His response was immediate and almost amused. \u201cOf course.\u201d<\/p>\n

I hung up and turned to Anu. \u201cGive me six months,\u201d I said. A hint of a smile tugged at her lips. And just like that, I had her reluctant approval.<\/p>\n

Looking back, this might have been the first time I was truly thinking clearly. Ideas don\u2019t become reality on their own\u2014you have to act on them. Taking action, even in the face of uncertainty, is what sets those who succeed apart from those who don\u2019t.<\/p>\n

Read more Companies still don\u2019t know how to incorporate AI in a holistic way, says Wharton expert<\/a><\/p>\n

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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\u2019t just a business; it became part of our family. Within a few years, it was worth over $40 billion.<\/p>\n

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.<\/p>\n

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\u2019t working to realize someone else\u2019s 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.<\/p>\n

The experience taught me that success isn\u2019t defined by job titles or wealth; it\u2019s 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 intra<\/em>preneur\u2014taking initiative, driving results, and creating impact rather than waiting for instructions. That\u2019s what true success looks like.<\/p>\n

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You don\u2019t have to be perfect or wait for the ideal situation\u2014what matters most is becoming a doer<\/em>. The best entrepreneurs aren\u2019t the ones with the greatest ideas; they\u2019re the ones who execute. Without action, there are no results. There\u2019s 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.<\/p>\n

As I\u2019ve learned over the years, it\u2019s the fear of taking action\u2014especially being the first to do so\u2014that 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\u2019t about a single action; it requires hundreds of them. You must remain steadfast, even when your situation feels hopeless.<\/p>\n

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Pursuing massive dreams will always present countless opportunities to stop and quit. The bigger question then becomes: how do you keep going?<\/p>\n

The answer lies in having the right mindset\u2014a counterintuitive one at that.<\/p>\n

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I won\u2019t spend much time on the basic day-to-day essentials\u2014how to identify key metrics, or hire the right people. These foundational skills, often referred to as the \u2018blocking and tackling\u2019 of business, are relatively easy to learn.<\/p>\n

One thing that isn\u2019t 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\u2014the mindset of someone who takes initiative and makes things happen rather than waiting for others to act.<\/p>\n

Read more Christina Qi left behind a hedge fund trading $7 billion a day for a farm in Utah. Her new startup just raised $97 million to rival Bloomberg<\/a><\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

In my new book Counterintuitive, I talk about how one thing that isn\u2019t taught enough is the mindset needed to keep going when times get tough.<\/p>\n","protected":false},"author":1,"featured_media":3088,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[282],"tags":[],"class_list":["post-3089","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-book-excerpt"],"yoast_head":"\nMy Microsoft exit with no business plan led to a $40 billion internet company\u2014and a debate over risk vs. timing - Cross Country Moving Team<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/crosscountrymovingteams.com\/?p=3089\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"My Microsoft exit with no business plan led to a $40 billion internet company\u2014and a debate over risk vs. timing - 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