How To Grow Your Investment 1,000 Times

This issue features America’s richest persons, and no surprise, Jeff Bezos is the richest in the U.S.—and the world. Amazon has gone orbital since first raising capital in 1994. Founder Bezos had asked 22 friends and family members to put in $50,000 each, for a total of $1.1 million, giving Amazon a valuation of $6 million. An investor and later board member, Tom Alberg, was alarmed at the audacity of Bezos keeping 80% of his startup. But Alberg later said he invested anyway because he liked Bezos’s laser focus. Good thing. Today Amazon is worth $1.65 trillion. Bezos has multiplied Amazon’s value by 275,000 times since that first investment.

Bezos is surely the modern world’s champion wealth creator. But even CEOs who’ve grown value by 1,000 times are exceptionally rare. I recently interviewed one of them—Coupa CEO Rob Bernshteyn—for my new Forbes video series “Scaling Up.” 

Coupa was founded in 2006 by two entrepreneurs who had an idea of using cloud-hosted software and artificial intelligence to automate business spending. But Coupa struggled and by early 2009 the founders were out. The new CEO, Bernshteyn, was 34 years old and had never held the top job. This unlikely CEO had a rough start. The world economy was at the depths of the financial crisis and recession. Coupa was rapidly running out of cash. After dozens of calls, and with days to spare, Bernshteyn was able to raise $7 million that left Coupa valued at a very humbling $15 million. Today, Coupa is publicly traded and worth $18 billion. Over 11 ½ years, Bernshteyn has multiplied Coupa’s value by almost 1,500 times. How did he do it?

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I believe Bernshteyn has a mastery of three essential tech CEOs skills: One is a vision of where technology is taking the world. Bernshteyn doesn’t hide his vision; rather, he writes books about it. In September he released his latest—Smarter Together: How Communities Are Shaping the Next Revolution in Business. Now, I’m always on guard when I hear the word “communities” because it is often a pretext for well-intended, but anti-business, ideas about social engineering. Bernshteyn means something else. The “community” is the sum of your customers, suppliers and partners—your ecosystem, in other words. And the more data that is shared within your ecosystem, the smarter everyone within that ecosystem becomes.

Bernshteyn uses Waze to illustrate what he means. Waze is a map and traffic app that shows a driver the best route to a destination, including the location and time-delay estimates of traffic jams. Waze gathers its data from two sources: Waze customers who actively report on traffic conditions (i.e. “a tree fell on the road, blocking the left lane; expect delays”) and from the GPS data generated from Waze customers who are simply driving.

For business procurement and expenses, the same principle applies. Real-time pricing, shipping times, areas of potential delay and other problems can be seen by all in a shared ecosystem. Bernshteyn is convinced that most companies will come to see that sharing their data to create the benefits of larger ecosystem data sets will lead to better predictive analysis and thus will in most cases outweigh privacy concerns. “Figure out what is truly proprietary to your business,” he advises. “Keep that private, but share the rest. You’ll benefit.”

Bernshteyn’s other two CEO superpowers are toughness and empathy, two qualities that rarely exist within the same individual. That Bernshteyn has both traces to his background. He was born in Leningrad (now St. Petersburg) in the former Soviet Union. His Jewish parents applied to emigrate to the U.S. but had to wait five years. They landed in a poorer New York City suburb with $1,000 in their pockets. Bernshteyn remembers raiding garbage bins for used furniture. Vision, toughness and empathy. Combine all three, and you might have that rare 1,000x CEO.

Rich Karlgaard is editor at large at Forbes. As an author and global futurist, he has published several books, the latest of which is Late Bloomers, a groundbreaking exploration of what it means to be a late bloomer in a culture obsessed with SAT scores and early success. For his past columns and blogs visit our website at www.forbes.com/sites/richkarlgaard.