How a Basketball Star, a Garage Landlord, and a Relentless Investor Got in on Google’s $2 Trillion Ride

In Part 1, we covered how Google’s first investors (tech founders, a professor, and an angel investor) spotted an opportunity before the rest of the world caught on.

But what about the outsiders?

Not every early Google investor was a Silicon Valley insider. Some stumbled into the deal by pure luck, proximity, or by simply being helpful.

Here’s how a basketball legend, a garage landlord, and a relentless investor got their slice of what became one of the most valuable companies in history, and what physicians can learn from them.

Lesson 4: Be Relentless. Founders Don’t Always Want Your Money

Ron Conway, one of Silicon Valley’s most successful angel investors, did not get an easy "yes" from Google’s founders.

By the time he met Larry Page and Sergey Brin, they already had enough angel investors lined up. They wanted to work with a big venture capital firm, not more individuals.

But Ron knew a good deal when he saw one.

He refused to take "no" for an answer. Instead of just writing a check and hoping, he made himself indispensable, helping Google orchestrate their next VC round, making key introductions, and proving his value.

Eventually, Google gave him a slice of the deal, and that investment turned into hundreds of millions of dollars.

✅ Takeaway for Physicians:

• The best founders don’t always need your money. They need your help.

• If you offer value beyond cash, whether it’s connections, domain expertise, or strategic insight, you can get into deals that others miss.

Lesson 5: The Power of Being in the Right Place at the Right Time

🏀 Shaquille O’Neal – Shaq accidentally made one of the best investments of his life. He was in a hotel lobby when a VC walked in with his grandkids, who instantly recognized Shaq. He entertained them while that VC was in a meeting. That VC just happened to be Ron Conway. The conversation turned into an invitation to invest in the Series A of a cool new tech company. Google. His investment would be worth hundreds of millions of dollars today if he held on.

🏠 Susan Wojcicki – She wasn’t a tech mogul or investor. She was a marketing manager renting out her garage for extra cash. Google’s first "office" was in her garage. By pure proximity, she got to know the founders, joined as employee #16, and later became CEO of YouTube.

✍️ Jeff Bezos – Before Amazon became a trillion-dollar empire, Bezos personally invested $250,000 into Google’s seed round. No official reason was ever disclosed, but it’s rumored he recognized how much traffic Google was already sending to Amazon. His stake today would be worth over $6 billion.

✅ Takeaway for Physicians:

• You never know where your next great investment will come from.

• Be in the room where things happen. That might mean attending AI and tech conferences, joining founder meetups, or connecting with health tech accelerators.

Bonus Story: The Persian Rug Salesman Who Became an Angel Investing Legend

🛋 In the late ‘90s, Iranian immigrant rug shop owners sold luxury carpets in downtown Palo Alto. They began to notice a lot of their customers were tech millionaires and billionaires.

Despite not knowing anything about tech, they decided to invest in the people they met, sizing up their brilliance when they would come to buy rugs.

Instead of just selling rugs, they started writing small angel investment checks.

Another Iranian immigrant, who was working at a car wash in the area and still had very poor English, applied for a job with them. Despite no sales experience, they gave him a chance. He proved to be a great salesman and an even better judge of people in the investment game.

Although the rug salesmen didn’t invest in Google, whose first real office was 2 blocks away, they ended up becoming some of the most successful early investors in Silicon Valley. They backed some of the biggest companies, including Paypal and Android.

The shop owner ended up creating Plug and Play Center, a popular startup accelerator and network hub, and his star employee created Pear VC, one of the top early-stage VC firms.

✅ Takeaway for Physicians:

• Startup investing doesn’t require being a tech genius. It requires access to builders.

• If a rug salesman can turn casual conversations into life-changing investments, imagine what physicians, with deep industry knowledge, can do.

Why This Matters Now

Google’s early investors weren’t hedge fund billionaires.

They were professors, engineers, and entrepreneurs who recognized an emerging wave before others did.

Right now, the next big wave is AI in healthcare.

Physicians have a rare window to invest in the tools that will reshape medicine.

Most of these startups will fail. But we may get the next Google of healthcare.

Final Takeaway: How to Start Seeing the Best Deals Before Everyone Else

✅ Get in the right rooms – Join tech-physician groups, AI accelerators, and startup events.
✅ Invest in founders, not just ideas – Bet on people with grit, speed, and agency.
✅ Start small but diversify – A $10K investment in the right startup can return 100x.
✅ Offer value beyond money – Helping founders navigate healthcare can get you into top deals.

And most importantly, don’t wait until everyone else sees the opportunity. By then, it’s too late.