When Will We Learn to Stop
Doubting Kobe?


On Wednesday, May 12th, Game 5 of the Western Conference Semifinals, Lakers rookie Kobe Bryant had his most memorable day of 1997. The Los Angeles Lakers were facing elimination down three games to one to the Utah Jazz. His first 70 games gave the world a glimpse at an emerging Hollywood star and in the waning minutes of his 71st game he had a chance to solidify the impression. After being down by 13 in the 3rd quarter, the Lakers gained then lost a lead that sent the game into overtime.

In overtime, Bryant, eager to prove that the 12 teams that passed on him in the previous year’s draft made a grave error, would go on to shoot four consecutive air balls, costing the Lakers the series and eliminating them from the postseason. To be fair, the Jazz overmatched the Lakers in experience and chemistry. The duo of Stockton and Malone was a deadly combination of strength and what seemed to be an almost robotic programing of how to successfully run a pick-and-roll. Add to that an occasional sneaky three-pointer from Jeff Hornacek and even the inept coaching of Jerry Sloan couldn’t slow down the Jazz on their trek through the West.

As for Bryant, the public jumped at the chance to criticize the teenage rookie. By now the story is legendary, but while the rest of his teammates headed home from the airport, Kobe went directly to nearby Palisades High School, found his way into the gym and shot baskets until the sun rose over the smoggy California sky. Kobe, it seemed, was determined to never again allow himself to be so unprepared for such a big moment.

New challenge. New critics.

A few weeks ago, news of Kobe's latest pursuit started to spread. And not unlike that night in May, people began to speculate whether or not he was ready to enter into the big world of venture capital. Others took it a step further and outright categorized Bryant's $100 million venture fund, co-run by LA-based VC Jeff Stibel as “dumb money.”

Dumb money is nomenclature that bounces around Silicon Valley distinguishing who is in the elusive savvy-investor club and who is out. Noah Kulwin of Vice News put it this way: "[Bryant Stibel Investments is] the latest 'dumb money' initiative from wealthy celebrities who want to hitch their wallets to the rocket-ship trajectory of Silicon Valley." He also wrote, "Dumb money investors are the people that an entrepreneur goes to when they can't find funding from anyone else." In other words, unless you're from the Valley, it’s best if you stay out of Valley business. It is true that celebrities don’t have a great track record when it comes to investments, but while Kulwin claims to be making a case about all celebrities, he goes on to name only two other individuals, both black athletes: Kevin Durant and Carmelo Anthony. No mention of Curt Schilling’s video game company disaster, Bono’s big bet on Palm or Burt Reynolds thinking that a restaurant named Po’Folks was a good idea.

The problem with dumb money as a categorical distinction has less to do with distinguishing between rookie and veteran investors and more to do with painting athletes, particularly those of color, with a broad brush.

The problem with dumb money as a categorical distinction has less to do with distinguishing between rookie and veteran investors and more to do with painting athletes, particularly those of color, with a broad brush.

The term is passive aggressive and deeply misguided. For Bryant, who is African American, married to a Mexican American and who spent part of his childhood in both Italy and America, his experiential complexity could benefit the often homogenous world of venture capital. As the creative visionary and TED talk legend Cindy Gallop told AdAge about the advertising industry, “We have not even begun to see what this industry could be with the creativity and the talent and skills of women and people of color.” This is certainly also true for the industry that’s fueling the ideas of the future in tech and media.

Photo: ©2016 Andrew D. Bernstein / bryantstibel.com

The Naturally Gifted Myth

Another problem with grouping the likes of Anthony, Durant and Bryant as dumb money is the not-so-subtle stereotype it reinforces. The idea that black athletes are more naturally athletic than their white counterparts is a common go-to. In order to make up for this perceived gap in natural talent, words are ascribed to white players that speak to their intelligence and effort on the court, while black players are thought to "get by" on account of their physical gifts. It’s a covert attempt to assign the label “hard worker” to a person based exclusively on the color of their skin over another.

According to Bryant, the idea to launch the firm didn’t come on a whim. Like his 20-year career built on intense methodical preparation should infer, Kobe dedicated much time and effort to learning everything he could to conquer his next challenge. When the often insufferable Jim Cramer asked Bryant about his involvement on CNBC’s Squawk on the Street, Bryant said, “Jeff and I have been quietly building this for four years and getting a chance to learn each other but also learn the business and see if I actually love it.”

Kobe is obviously gifted, but that’s no reason to overlook his dedication to excelling at his craft. Implying that the white men that saturate the world of venture capital are “"hard workers,"” but a newcomer with Bryant’s well-earned reputation is not, says nothing about his character and everything about his detractors.

There is room to argue that while Bryant was in his prime he never quite learned his limits. He’ll likely be remembered as a top-10 player, but no one will forget his forced shots and steely withdrawal from the usual rituals of NBA camaraderie. Even still, adjusting to injuries and age the last four years of his career forced him to confront those limits. And maybe all that effort helped Bryant develop an understanding of where his true strengths lie. When asked by Carl Quintanilla whether he’s getting good at reading balance sheets, Bryant admitted it wasn’t his strength, stressing his reliance on Stibel to run the operations of the firm.

Speaking of Stibel, the fact that Kulwin overlooked his accomplishments as an entrepreneur is also odd. He was 32 years old when he became one of the youngest CEOs of the publicly traded company, Web.com. Before that, he was CEO of a search engine company called Simpli which was eventually sold to NetZero and ultimately informed what we now know as Google Adsense. Even if Kobe couldn’t find a way to always get along with his teammates on the basketball court, he seems to value the importance of team chemistry.

The Sacca Connection

If Kobe’s work ethic, honesty, and relational growth isn’t enough to clear his “dumb money” label, perhaps the most famous new-money investor since Mark Cuban, Chris Sacca, can lend a hand. Sacca’s fame outside the venture world grew in 2014 when he invested in Alex Blumberg’s podcast company, Gimlet Media, and was prominently featured in a few episodes of the podcast StartUp. His early investments in companies like Twitter, Uber and Instagram, along with his keen attention to his personal brand (see: cowboy shirt) quickly positioned him as one of the most influential VC’s in the world.

According to Sacca a few years ago Bryant reached out to him through a mutual connection and asked if they could meet. Not being much of an NBA fan, he frantically studied Kobe’s Wikipedia page on the way to meet with him. Bryant’s message was simple: He told him he wanted in. He wanted to know what it took to operate in the startup world and how to make good investments. While describing Bryant’s qualifications on The Bill Simmons Podcast, Sacca told Simmons this:

“Look. Honestly, I see a lot of celebrities as tourists who come through this industry and think they can just cherry pick a couple of things and just tweet about it, and it'll just work out. If you're serious about this, then prove it to me. I'm going to send you a bunch of stuff that you should read...And if you do your homework, then I'll talk to you about investing. I didn't think he was going to do it. I thought it was kind of a nice way to let him down easy.”

Cramming for a test via a Wikipedia page was not Sacca’s best idea. He had no idea how much of an obsessive Kobe could be.

“So, sure enough for the next few months my phone never stops buzzing in the middle of the night. It is Kobe reading this article, checking out this tweet, following this guy, diving into this TED talk, diving into the Y Combinatory demo day stuff. And I'm getting these texts at literally two or three in the morning, and my wife is like "Are you having an affair with Kobe Bryant?” ... The guy was serious –– he was bringing the same obsessive work ethic to learning about startups that he does to training, to rehab, to his thousand makes a day to everything. I was fascinated by him. So I ended up actually becoming really enthralled by him because this is a very unique personality type that I only really see in our very best entrepreneurs — like Travis Kalnick at Uber.”

Even if you believe Kobe’s experience has little bearing on his ability to succeed as an investor, it’s obvious that Kobe hasn’t been brewing this without counsel from others that know the rigors of the job. He’s also not the only one who’s thought his particular experience might uniquely benefit the world.

Final Tip

Bryant is considered by many as either the first or second greatest Laker of all time. Most often the other nominee for this distinction is Magic Johnson, a successful businessman in his own right. Johnson famously advised Starbucks CEO Howard Schultz that his coffee empire was missing out on reaching a couple underserved demographics, telling Schultz: “Look Howard, Latinos and black folks. We like coffee too…” At the time Starbucks stores were largely absent from urban, inner-city communities. Johnson had a plan to change that. After making changes to the menu and using performance data from his theater chain, Johnson spearheaded the creation of over 100 new Starbucks stores. Eventually, Schultz purchased Johnson’s shares in the company for an estimated $27 million.

Johnson found an incredible opportunity that Schultz didn’t, because he was able to draw from a life experience largely foreign to Starbucks. Yet Johnson too initially found resistance when he approached the co-founder of Creative Artists Agency, Michael Ovitz, for advice. In James Andrew Miller’s new book, Powerhouse: The Untold Story of Hollywood’s Creative Artists Agency, Johnson recalls the meeting:

Johnson found an incredible opportunity that Schultz didn’t, because he was able to draw from a life experience largely foreign to Starbucks.

"He (Ovitz) said, “'I have all the biggest actors, producers, directors, and writers in the world. Why should I represent you? Most athletes blow all the money they make and go broke. I don’t have the patience or the time to represent somebody who won’t listen.'” I said, 'I’m different, I’ve a always wanted to be a businessman.'” He talked for two or three or five minutes, and then threw me out. So I went into his office six foot nine and walked out about five foot nine."

Johnson eventually passed a series of tests that proved to Ovitz, much like Bryant proved himself to Sacca, that he was serious about becoming a businessman. The rest is history in the form of a deal with Pepsi. His 25% stake in a Pepsi distribution plant in Maryland was not only his first official business venture but would also serve as the backbone to Johnson’s financial success for years to come.

So Magic, ruled from the top in both basketball and business. And Bryant is nothing if not competitive.

Through the course of his career he accomplished numerous All-Star appearances, earned a league MVP and either lead or co-lead LA to 5 NBA championships. Still going into his last game, it was fair to assume the magic of his career was gone. He shot a career-low 35% from the field and led a team of inexperienced Lakers to a franchise-worst 65 losses. Kobe played awful. Retirement loomed. A few weeks before the game, former teammate and frenemy Shaquille O’Neal asked him to score 50 points to which Kobe responded simply, “Uh, no. No. Absolutely not.” But only as if to cloak his determination to prove the world wrong, at least for one more night.


Even still, when the world counted him out, Kobe was determined to put on a show for the thousands of people in the Staples Center and the millions more watching at home. So, much like the rest of his career, he shot the ball. A lot.

He took a staggering 50 shots during the game and eventually brought the Lakers within a point. If you squinted, the last three minutes were like a scene from your favorite sports movie. The down on his luck sports hero rose to the occasion and capped a 60 point game with a late long jumper that put the Lakers ahead by one. His final two points were free throws that sealed the game against that same team he lost to in his first playoff series.

That night, the Jazz were the ones who were sent home. Maybe it wasn’t at the end of a hard-fought playoff series, but it was with the understanding that this time Kobe was not unprepared. These days, he almost never is.