Buffett Watch

• Berkshire Hathaway Portfolio Tracker

Amazon and Apple were the first and second publicly listed U.S. companies to reach a $1 trillion market cap. Apple hit that milestone in August, and then Amazon did in early September.

If you invested in either 10 years ago, that decision would have certainly paid off. But which would have made you richer?

The winner is Amazon.

According to CNBC calculations, a $1,000 investment in Amazon in September 2008 would be worth more than $23,890 as of Friday morning, or more than 22 times as much, including price appreciation and dividends reinvested.

If you put $1,000 in Apple at the same time, your investment would be worth $12,299 now, or more than 11 times as much. While impressive, that's $11,591 less than Amazon.

CNBC: Amazon vs. Apple Stock, September 2008 to September 2018.

While Amazon and Apple's stock have performed well over the last decade, any individual stock can over- or underperform and past returns do not predict future results. That's perhaps why Warren Buffett, chief executive officer of Berkshire Hathaway, opted not to invest in Amazon when he had the chance, saying didn't fully appreciate the value of tech stocks.

These days, expert investors are generally bullish about both companies, which continue to innovate at a rapid pace. Amazon recently announced 15 new Alexa-enabled products, including a microwave that can operate on voice commands and a wall clock that can set timers and other time-based tasks. And Apple recently unveiled new versions of the iPhone and Apple Watch.

Marques Colston is a former NFL wide receiver with the New Orleans Saints whose team took home a Super Bowl trophy in 2010. He's also an investor and entrepreneur who has turned his experiences into an executive education course at Columbia Business School. While aimed at professional athletes, the advice he gives could help all leaders trying to make their mark.

Irrational confidence, says Colston, fueled any success he's had on or off the field. It's a mindset he teaches students in his course that blends risk-taking with old-fashioned consistency and hard work. This approach is one he says can help anyone focus despite nearly impossible odds.

As a player, Colston wasn't a sure bet. He was the 252nd pick in the 2006 draft. For non-football fans, that means he barely made the cut to play at the elite level. "As a seventh-round pick, there was a zero percent chance, maybe a .1 percent chance that I would play ten years in the NFL and have the kind of success that I had," Colston says.

Colston earned the nickname "The Quiet Storm," according to ESPN. Coaches for the New Orleans Saints told stories about how "unimpressive" he was during training, writes ESPN's Mike Triplett. But he improved, and when Colston retired after the 2015 season, New Orleans Saints coach Sean Payton said his contributions were key for the team's Super Bowl win.

"His production, consistency, toughness and work ethic were second to none," Payton said. "You always knew what you were going to get from Marques, and that was everything that he had."

For leaders or investors, irrational confidence is a way to play the long-game. "Statistics ultimately become motivation," Colston says.

Key to irrational confidence is putting in the work and research to take informed risks. Leaders and innovators who do this truly understand their odds. It's "putting yourself in a position that you're going to be the one person, the one percent, and everyone else is going to fall by the wayside," he says.

When evaluating companies, Colston looks for leaders who can see opportunities and beat the odds. He looks for founders who can take coaching, knowing they'll best weather the storms ahead. "If you don't have the ability to take an objective look in the mirror or take constructive criticism with your company, you're not going to go too far," he says.

Unsurprisingly, the Super Bowl winner is a firm believer in teamwork, and the adage: "The best teams win championships." He teaches investors to look for entrepreneurs who have built a solid team supporting them and recognize they can't do everything themselves.

Playing the long game — smartly — is advice echoed by top investors. Warren Buffett has said the only risk comes from "not knowing what you're doing." In fact, during the 2008 financial crisis, Warren Buffett kept buying stock in American companies because he knew the economy would recover eventually.

"What investors then need...is an ability to both disregard mob fears or enthusiasms and to focus on a few simple fundamentals," Buffett says.

Reign Ventures co-founder Erica Duignan Minnihan founded the course with Colston and is its program director. She has worked with professional athletes for six years. She says the students evaluate deals with the same focus they use to play their sport. "They're already extremely disciplined people," she says.

"They just get natural deal flow," she says. "As people that are in the public eye, they generally have investment opportunities coming out of the woodwork. So we're helping them understand how to take that amazing asset, which is the deal flow, and refine it and focus in on the companies that have the best potential for financial return."

Like athletes, no entrepreneur is guaranteed a shot at making it big. But those who understand their risks and the building blocks of success will win in the long term.

"It's not about dreaming big," Colston says. "It's more about being able to set goals and putting in the work to attain those goals."

Don't miss: NFL players' surprising performance hack: going vegan

Like this story? Subscribe to CNBC Make It on YouTube!

Legendary investors Warren Buffett, 88, and John C. "Jack" Bogle, 89, agree on the key to successful investing: Buy and hold the stock market for the long term.

"If you hold the stock market, you will grow with America," Bogle, founder of The Vanguard Group, said on CNBC's "Power Lunch."

In the long run, there is a high correlation between the stock market and U.S. economic growth, he said, so, regardless the economic climate, "Stay the course. Don't let these changes in the market, even the big one [like the financial crisis] … change your mind and never, never, never be in or out of the market. Always be in at a certain level."

If you try to trade in and out of the market, "your emotions will defeat you totally," Bogle added. "Short-term betting is not a good way to go."

India is a country renowned for its bustling tech start-up scene. But it's the hospitality industry that's making waves with workers, according to LinkedIn's list of top start-ups in India to work for in 2018.

Five-year-old hospitality company OYO Rooms stole pole position in the rankings this year after building a team of loyal staff in India and beyond. Dubbed "OYOpreneurs," employees are encouraged from day one to embrace a sense of ownership in the business and help shape the firm as it rapidly expands.

Elsewhere, transportation, fitness and insurance proved they were among the industries ripe for disruption in the fast-evolving country. CNBC Make It takes a look at the full list of the 25 most attractive start-ups in India right now.

Fintech may be one of the few industries looking back fondly at what happened to Wall Street after 2008.

The chaos and disruption of the credit crisis instilled lack of trust in existing banks and brought on new regulations and the rise of technologies that would allow scrappy Silicon Valley start-ups to reshape consumer finance.

These new financial technology companies have made serious competitive inroads in areas banks have backed away from, and billions of dollars in venture capital money has followed.

A key reason fintech companies have flourished, analysts say, is a lingering distrust in banks.

Ten years ago the first wave of the millennial generation was settling into early adulthood just as the economy dipped into the Great Recession. Memories of foreclosed homes and savings lost in a Wall Street-fueled crisis continue to influence where they put their money.

"What that underscored for people is that banks can't be trusted, and your money is only as safe as the government allows you to believe," said Fundstrat founder and managing partner Tom Lee, who worked at J.P. Morgan in 2008. "That's why millennials today have so little trust in banks, because of what their parents went through."

More than half the world's population is under 30 right now, according to the World Economic Forum, and 10 years after the crisis, they're still wary of banks. Last year, 45.3 percent of respondents to WEF's Global Shapers Survey said they "disagree" with the statement that they trust banks to be fair and honest. Only 28 percent of the more than 30,000 millennials surveyed said they agree.

The skepticism isn't reserved for young people. Shareholders and regulators still want to see that the banks are in check, and questions of solvency and compliance come up consistently on bank earnings conference calls.

"Every quarter, every year for a decade banks have to earn back the trust that was lost from the financial crisis," said Mike Mayo, Wells Fargo's head of U.S. large-cap bank research, who worked at Deutsche Bank when Lehman Brothers went under. "The financial crisis was terrible for the industry's reputation of trust."

In a world swimming in debt, the next crisis is likely to bear at least a passing resemblance to the last one. The good news is that day seems to be a ways off.

Not that anyone's in a hurry, but there are few obvious signs of a situation akin to the 2008 meltdown on the horizon. The financial system is well-capitalized and operating with lower leverage and risk-taking than in at least a generation or two. Economic pillars remain strong, the health of corporate America has rarely been better and new buffers put in place have been effective at absorbing shocks.

In fact, if anything it's too quiet. That almost always has been the recipe for a good crisis.

"There was abundant liquidity in the system in 2006, too," said Danielle DiMartino Booth, CEO and director of intelligence for Quill Intelligence, a research and analytics firm. She also served as advisor to former Dallas Federal Reserve President Richard Fisher during the financial crisis, so she had a front-row seat to how it unfolded.

In the fall of 2008, global markets were failing. Lehman Brothers, an investment bank with $600 billion in assets, filed for bankruptcy protection on Sept. 15 of that year, an inflection point in the economic slowdown that brought unemployment rates as high as 10 percent.

Two weeks later, during a single day on Sept. 29, the U.S. stock market lost $1.2 trillion in value as the Dow dropped 778 points, nearly 7 percent.

"You just felt like the world was unraveling," a senior equity trader named Ryan Larson told The New York Times that day. "People started to sell and they sold hard. It didn't matter what you had — you sold."

But there was one big investor who had a different outlook: Berkshire Hathaway CEO Warren Buffett.

In fact, Buffett was buying.

"I've been buying American stocks," Buffett wrote in a an opinion piece for The New York Times on Oct. 16, 2008. Berkshire Hathaway also made big investments during the crisis, backing General Electric and Goldman Sachs.

Buffett understood the severity of the crisis; he told CNBC that year it was like an "economic Pearl Harbor." So why was he buying stocks that were rapidly falling in price when everyone else was socking cash under their pillow?

"A simple rule dictates my buying: Be fearful when others are greedy, and be greedy when others are fearful," Buffett wrote in the Times.

This week marks the 10th anniversary of the collapse of Lehman Brothers and the start of the Great Recession. And some experts say that another financial crisis is inevitable.

As legendary investor Jack Bogle told CNBC's "Power Lunch" on Wednesday, "There are always blind spots or, as I have said, the fog of the stock market: Nobody really knows what's going on."

Thanks to the 2008 crisis, "there are risks that we know," the founder of The Vanguard Group added, "but there are risks that we don't know even exist. And that's the problem. Every crisis is different. Every bear market is different."

Warren Buffett warns that another financial crisis is inevitable.

Buffett was asked by CNBC's Andrew Ross Sorkin if he is worried another crisis will happen again.

"Well there will be one sometime," Buffett said in an interview for CNBC's "Crisis on Wall Street: The Week That Shook the World" documentary. The documentary airs Wednesday night at 10 p.m. ET/PT.

This week marks the 10th anniversary of Lehman Brothers' bankruptcy, which many investors regard as the seminal event of the financial crisis.

The Oracle of Omaha explained another bubble is unavoidable due to human nature, jealously and greed.

Berkshire Hathaway continues to unload its stake in Phillips 66, disclosing Monday the sale of another 36 percent of its holdings in the stock since the end of the second quarter.

In a filing with the Securities and Exchange Commission, Warren Buffett's conglomerate said it held 22.186 million shares, down around 12.5 million from holdings reported as of the end of June. In the second quarter, Berkshire unloaded 24 percent of its stake. It cut more than 40 percent of its shares in the energy company in the first quarter, when it sold 35 million shares back to Phillips 66 to bring its holding below 10 percent.

At the time, Berkshire said it would continue to be a long-term holder of Phillips 66.

The most recent move reduces Berkshire's stake to 4.8 percent of Phillips 66, from 7.5 percent.