What Do the 5 Richest Men in America Know That We Don’t?

Amy Osmond Cook

After the announcement of the 35th Annual Forbes 400 Ranking of the Richest Americans, what business lessons can we learn from America’s richest entrepreneurs?

The strength of the team is each individual member; the strength of each member is the team.” Phil Jackson.

There are successful CEOs. And then there are serial disruptors—CEOs who lead their teams to produce repeated success, time after time. These CEOs produce the “dream teams” of entrepreneurship and provide the environment in which investors, marketplaces, and employees flourish.

Forbes recently released its 35th Annual Forbes 400 Ranking of the Richest Americans. At the top of the list was Bill Gates, Microsoft’s founder, who retained the top spot for the 23rd consecutive year. Next was Amazon’s Jeff Bezos, then Berkshire Hathaway’s Warren Buffet, Facebook’s Mark Zuckerberg, and Oracle’s Larry Ellison. These entrepreneurs are now enjoying the fruits of their labors as they achieve success in the billions, year after year. How have they and others accomplished this kind of winning streak? According to serial CEO Joe Wang and Dave R Taylor, a key executive in multiple successful tech ventures, the secrets to longstanding success include investing in your own product, employing a winning team, setting high goals, and following a clear strategy. 

1. They invest their own capital. 

As many of the Forbes 400 have experienced, going “all in” is often a prerequisite to entrepreneurial success. Successful business owners invest heavily in their own business ventures. This is advantageous in two ways: first, owners capitalize on their own success; and second, their investors know they are dead set on winning. 

“When outside investors see that the company founders have already invested significant time into the business, that’s well-received. But sweat-equity alone is not enough to persuade investors to fund the deal,” wrote Entrepreneur contributor David Newton. He added that in addition to plenty of hours invested working in the business, the owners must also be equity investors with money at risk. Otherwise, capital providers view the level of commitment as being less than desirable.

2. They keep winning, so they can cherry pick talent. 

Everyone wants to be on a winning team. Wang’s serial successes in LANDesk, WatchGuard Technologies, and now Impartner PRM have given him the ability to recognize and then cherry pick great talent from day one. In addition, because of this track record, talented people want to move with him from company to company. “You can see so much in an interview,” Joe said. “When you already know the strengths and weaknesses and how you work together, you can cherry pick and mix and match and move more quickly.” Currently, 29 percent of Impartner’s all-star team has worked together at one of Joe’s previous companies. 

The ability to assemble awesome talent has its in-house advantages, and it also bodes well in building confidence for business ventures. Whether you exit multiple companies or stay committed to one, a solid team with a proven track record minimizes risk in the minds of investors.

3. They set high expectations.

Amazon’s motto, “It’s Still Day One,” exemplifies the high expectations and lofty goals that winning CEOs set for their employees. But employees don’t mind—because they’re winning. 

This “winning team” mindset, made popular in part by Netflix CEO Reed Hasting’s famous presentation on his company’s culture, is useful to motivate employees’ competitive nature. It drives them to compete, promotes team spirit and collaboration, and stimulates energy and productivity. It also allows companies to “combine a realistic view of the often-temporary nature of the employment relationship with a focus on shared goals and long-term personal relationships,” states Harvard Business Review contributors Reid Hoffman, Ben Casnocha, and Chris Yeh. 

As Wang stated: “We wake up markets. We get inside competitors’ heads, and we cause a ruckus in the market and wake up segments.” And, as a team, they meet those high expectations with confidence and optimism.

4. They are simple, clear, and repetitive. 

Simplicity, clarity, and repetition are the key factors to making entrepreneurial vision stick. This applies to organizations large and small. In fact, the larger the team, the more simple the message needs to be.

Scott Belsky, founder of Behance, stated in a recent Entrepreneur article: “Effective leaders (and brands) repeat themselves to the point where they can barely stand to hear themselves anymore. When it comes to setting strategy, they make a few simple points multiple times. And they compromise on ‘new messaging’ to reiterate what is most important.” 

I may not ever be one of the richest people in America, but I aim to follow Joe Wang and Dave Taylor’s sound analysis of success and propel my own business forward. Whether we’re Elon Musk or the food truck guy down the street, by investing in our own company, surrounding ourselves with a competitive team, setting ambitious goals, and keeping things simple, clear and repetitive, we can achieve our own winning results.

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