Carlos Watson ’95 cofounded, led, and eventually sold a successful Silicon Valley startup. Now a regular contributor on CNN, he provides political commentary, writes a column, and occasionally hosts his own interview show.

Four years ago, Carlos Watson ’95 was at a turning point in his career. After starting and then leading a successful educational counseling company, he sold the business to a subsidiary of The Washington Post Company. At 32, with an undergraduate degree from Harvard College, a law degree from Stanford University, a stint at McKinsey & Company, and now a successful venture under his belt, Watson had plenty of opportunities before him.

Instead of launching another startup, as so many Silicon Valley entrepreneurs are wont to do, or working as an attorney, venture capitalist, or business executive, Watson once again took a risk and set his sights on television. He decided to pursue a wide-ranging interview show, one that would match his eclectic interests with his love of biographies, conversation, and people. It would be similar to The Charlie Rose Show.

Fat chance, one might say. After all, what were the odds of being able to land your own national interview show? A million to one? Ten million to one? Most people wouldn’t even attempt it.

But Watson isn’t easily dissuaded. After all, what were the odds of the son of a Jamaican immigrant—a kid who was kicked out of school while still in kindergarten—graduating with honors from Harvard and Stanford? What were the odds of turning one’s passion for working with teens into a successful business that sells for millions of dollars to one of America’s premier companies?

But with his usual determination and a healthy dose of optimism, Watson decided he wanted to be on television, and that was that. “I started pitching the show in late 2002. People would say, “Hey. You’re great. But you’ve never done this before.” After getting turned down by a number of networks, both Fox and Court TV suggested that he start off as a guest on their existing shows. “So I was a guest. And if you do well the first time they invite you back.” Which they did.

Prime-time Breakthrough

His big break came in the summer of 2003 when CNBC gave him the opportunity to host a prime-time national interview special on Labor Day, a day when there isn’t much business news to report because the stock market is closed. “They said, ‘If you think you can do a younger, hip-per, fresher version of Charlie Rose, come on.” Watson put together a show that featured presidential candidate Howard Dean, quarterback Joe Montana, and future Desperate Housewives star Eva Longoria.

The show did remarkably well in the ratings, so Watson was invited back to do a second one, which also went well. That prompted CNBC to offer Watson his own interview show. But CNN was also interested, and offered Watson the chance to be a regular contributor on its newscasts. “It was a very tough decision, because I really wanted to do the inter-view show, but I loved CNN.”

Watson went with CNN. It proved to be a wise choice. During the last two years, Watson has appeared regularly as a political commentator on CNN, often five times a week or more. He helped cover the presidential debates and was co-anchor of the network’s 2004 election night coverage along-side veterans Wolf Blitzer, Larry King, and Jeff Greenfield.

From Silicon valley to CNN
(Left to right) Cable News Network anchor Wolf Blitzer, senior analyst Jeff Greenfield, and political analyst Carlos Watson discussing the 2004 presidential debates during CNN’s coverage of the second presidential debate held at Washington University in St. Louis. Photo by Cable News Network (CNN)










He also has a widely read column on that gives him the opportunity to write about a broad range of issues. (See p. 20 for excerpts from his column “The Inside Edge with Carlos Watson.”) Because he lives in California and regularly travels around the country, Watson often picks subjects unfamiliar to Washington insiders. “I was one of the first to write about the role political blogs would play in the presidential election; I was also the first national columnist to write about Barack Obama,” Watson said. His columns often draw nearly a million readers.

On CNN, Watson has also hosted two airings of his own prime-time interview show, Off Topic with Carlos Watson, featuring a diverse lineup of stars including basketball great Shaquille O’Neal, U.S. Senator Barrack Obama (D-Ill.), California Governor Arnold Schwarzenegger, and super-model Heidi Klum. Watson’s goal is to offer viewers the unexpected. “Everyone knows that Heidi Klum is sexy. But what they don’t know is that she runs a $100 million business with operations around the globe. She’s a serious entrepreneur.” “A lot of people get a shot at TV. But it doesn’t work out. They are boring, inarticulate, or haven’t done their homework,” said CNN anchor Wolf Blitzer. “Carlos was a natural. He always does his homework. He’s easy to work with and has a good sense of humor. He has a great smile, and he comes across well on TV.”

“Carlos is destined to be a television star, if that is what he wants,” said Princell Hair, a senior executive at CNN. “He is telegenic, charismatic, smart as heck, and a natural in the business. I have rarely seen someone with such ease in front of the camera and the ability to connect with people in the way he does.”

Watson was a novice when it came to television, but he had already worked in both politics and media, as a campaign manager and as a newspaper reporter. He published more than 70 articles in The Miami Herald and the Detroit Free Press during summer breaks from college. While studying politics at Harvard, Watson also worked for former Miami mayor Xavier Suarez, retired U.S. senator Bob Graham, and former Democratic National Committee chairman Ronald Brown. After Harvard, he served as chief of staff and campaign manager to Florida Representative Daryl Jones, managed Bill Clinton’s 1992 election day effort in crucial Miami-Dade County, and wrote political policy papers.

“He’s not only incredibly smart and motivated, but he’s an extremely nice person who is genuinely interested in other people,” said classmate Phoebe Yang ’95, vice president for business strategy and digital media at Discovery Communications Inc. “He has the ability to ask tough and substantive questions of people without them feeling attacked. It’s why he is able to get interviews that even seasoned reporters can’t get.”

Inauspicious Beginnings

For all of Watson’s current success, it wasn’t always obvious that he would do so well. Quite the opposite. “My mom always likes to joke that anyone who saw my first 10 years would not have predicted my last 10—except for a mother,” said Watson. His problems started the first day of kindergarten. “The teacher would ask a question like, ‘What’s 2 plus 2?’ And I would answer, ‘Yellow.’” He knew that the answer was 4. Thanks to his older sister, he could add when he was 3, which was one of the reasons he didn’t like to give a straight answer to what he thought was a dumb question. He was bored. So bored and disruptive that he got kicked out of kindergarten a dozen or more times. “Eventually my parents had that conversation with the principal that went some-thing like, ‘Guess what. We need your kid to go elsewhere.’”

So Rose and Carlos Watson senior had to find another school for their youngster. “It’s to my parents’ credit that they didn’t completely give up and lose confidence in me,” Watson said. But the Watsons believed strongly in education. Both had earned graduate degrees, and Watson’s maternal grandmother and grandfather both graduated from college. So did all six of his grandmother’s siblings—quite an accomplishment for any family, and certainly noteworthy for African Americans raised in Mississippi in the early 1900s.

Rose Watson worked first as a teacher and then as an administrator in charge of international students and services at Florida International University. Watson’s Jamaica-born father came to the United States as a teenager in the 1950s. He became a sociology professor at Florida International University in Miami. These were good jobs, but they didn’t pay enough to support a family, so both often worked second and even third jobs teaching in community colleges and evening high school programs.

In an Academic Groove

Around fifth grade Watson’s academic career began to turn around. And in seventh grade he received a scholarship to attend one of Miami’s oldest and most elite private schools, Ransom Everglades School. He was a top student academically, elected class president three years running and student body president his senior year. Watson excelled in athletics as well, quarterbacking the varsity football team, starting on the basketball team, and competing in track. He was an editor of the school newspaper, and worked summer jobs at grocery stores and law firms to help pay for his schooling.

Still, when it came time to think about college, Watson was not sure where he should apply. “There was no doubt I was going to college because that was expected in my family,” Watson said. But he credits Ransom’s college counselor with convincing him that he could be admitted to any college in the country. “Even though I knew that other kids at Ransom had gotten into these colleges and that I was one of the top students in my class, to hear her say it was significant, and it gave me confidence.”

That’s how the kid who had gotten kicked out of kindergarten and had been labeled by one teacher as possibly developmentally delayed found himself applying and being admitted to Harvard, Princeton, Stanford, and Brown. Watson chose Harvard.

At Harvard, Watson was like a kid in a candy store. “I remember looking at the course catalog and thinking, ‘I get to choose only 32 classes over my four years!’ There were 32 classes I wanted to take that first semester.” He took graduate-level courses at Harvard Business School, Harvard Graduate School of Education, and the John F. Kennedy School of Government. Watson eventually focused his interest to major in government, which allowed him to study with noted political scholar Martin Kilson. “He made me an intellectual optimist,” said Watson. “He made me not only believe that things could be better, but he actually showed us how things had already gotten better and how they could keep getting better.”

After graduating from Harvard with honors, Watson worked for a year and a half as chief of staff for Florida representative Daryl Jones. “It was an opportunity for me to learn a lot about the legislative process and about campaigns,” said Watson. As much as he enjoyed politics, Watson decided to apply to law school after being strongly encouraged to by his father. “My dad was worried that I wasn’t going to attend graduate school,” Watson said. “After a lot of soul searching, because it wasn’t obvious to me that it was the right thing to do, I ended up applying to law school.”

Ideas Taking Shape at SLS

Watson saw a legal education and a law degree as a path to other careers. “Daryl, my boss at the time, was a lawyer, Bob Graham was a lawyer, and Ron Brown was a lawyer,” said Watson. “That deepened my hunger for a law school that wasn’t overly traditional.” That was one of the reasons he chose Stanford.

“I liked the fact that Stanford didn’t feel predictable and straitlaced,” Watson explained. Law students were counseling clients at community clinics, working for public interest organizations, and interning with venture capitalists. “The students seemed like they were making things happen. I liked Stanford’s entrepreneurialism.”

It could almost be said that Stanford helped bring out Watson’s inner entrepreneur. “I started several businesses while I was at law school,” Watson said. At the time Snapple was becoming a popular drink, so Watson rented five vending machines, struck a deal with a Snapple distributor, and installed Snapple beverage vending machines at Stanford and at nearby Menlo College. “I was a rookie, but it was a good experience. I made just enough money to buy dessert for my girlfriend and me at Max’s Opera Café,” he joked.

A second venture was a student calendar business that Watson created with Ira Ehrenpreis JD/MBA ’95. The two created a poster-like calendar with paid advertising around the perimeter and gave them to Stanford students. “It was a way to get entrenched in the Stanford community, meet interesting people, and have fun doing something together,” said Ehrenpreis, now a partner at the venture capital firm Technology Partners in Palo Alto.

A Passion Turns into a Business

Watson is the kind of person who enjoys whatever he hap-pens to be doing at the time. But even for him, some kinds of work are more rewarding than others. That was certainly true at Achieva, the company he co-founded to provide college counseling to high school students. “I think this was a way of giving back to the community while pursuing his dream of creating a business,” said Ehrenpreis.

Watson’s passion for working with teens began at Harvard. For two and a half years Watson volunteered as a counselor in the Inner City Outreach Program tutoring elementary school children in Dorchester, Massachusetts. During his sophomore year, Watson also became a student teacher at Boston English High School. “The very first day I was at Boston English I couldn’t get control of the kids,” Watson remembered. “So like any new teacher I desperately looked to find something that would captivate them. I realized that most of them came from families where no one had gone to college, so I started talking to them about college and working with them on their applications.”

“I wasn’t just helping kids go from 12th grade to fresh-man year, but in some ways I was helping them go from childhood to adulthood. They had to think about questions like, What do I want to become? Where do I want to live? What do I want to study? What kind of friends do I want to make? There is something really powerful about being there when the kids are going through this process. It was a wonderful thing to see.”

Watson underwent a similar life-changing experience years later. In the summer of 1996, Watson was on vacation in Brazil with two of his sisters. At the time Watson was working at the management consulting firm McKinsey & Company. He was having a good time at McKinsey—advising CEOs of major banks and technology companies, traveling to Europe, and making lots of money. But when talk turned to what each of them wanted to do with their lives, Watson realized his passion lay elsewhere. That’s when he hit on the idea of starting a business that provided college counseling to teens.

So without much hesitation, Watson set about doing just that. He enlisted his sister, Carolyn Watson, who at the time was a manager for an academic-enrichment pro-gram in Washington, D.C., and one of his best friends from Harvard, Jeff Livingston, who was an investment banker in New York City for Merrill Lynch. All three of them quit their jobs to start Achieva.

“My dad was understandably a bit panicked. Not only had I left a high-paying job at a top firm, but I had talked my sister into quitting her job as well,” Watson said.

Achieva began by selling college counseling services to individual parents and schools. The company’s tutors worked with students one-on-one or in small groups. Achieva’s growth took off after it expanded its market to provide academic and testing counseling to students in grades 6 through 12; began supplementing its own tutors with online counseling tools, books, and teacher workshops; and began selling its services to entire school districts. “Instead of selling contract deals one kid at a time, we could sign six- and seven-figure deals, which is what we did,” said Watson.

“One of the things he did effectively as CEO was that he sought out the advice of lots of people. He was commit-ted to learning,” said Issac J. Vaughn, a partner at Wilson Sonsini Goodrich & Rosati in Palo Alto. Vaughn served as outside counsel for Achieva. “You have to be able to bring in people around you that could execute. And he did that.”

By 2001, just five years after Achieva was founded, the company was counseling nearly 100,000 students in 20 states. It had contracts with school districts in San Francisco; Washington, D.C.; Chicago; Miami; and New York. At the end of 2001, an agreement had been reached to sell Achieva to Kaplan, Inc., one of the nation’s leading providers of educational and career services. Watson spent the first part of 2002 helping Achieva make the transition from an independent company to being a part of Kaplan. Once that was done he took time off to travel and reflect before embarking on his latest career as a television commentator and host.

From Silicon valley to CNN 1
Carlos Watson interviews California Governor Arnold Schwarzenegger in January 2005 for his show Off Topic with Carlos Watson. Photo courtesy of CNN.

So what’s next for the multitalented Watson? “These first three years in TV have been an incredible learning experience for me, and I feel like I have gotten my feet wet. I am having the time of my life, and I love my work. I plan to stay in this industry for some time.” And when he is not in a CNN studio or researching his next piece, he is always up for a good pickup game of basketball. Even in the course of his travels he usually finds a local game to join. “I play at YMCAs all over the country. I play overseas, in Iceland, Zimbabwe, France, Brazil—you name it. I love to play.”

What does Watson plan to do after television? He isn’t talking, but don’t be surprised if his next act is on the political stage. After all, he has the sort of biography, smarts, and personality that voters love and political parties drool over. “It’s a career that is well suited to his talents,” said Laurene Powell Jobs, one of the initial investors in Achieva. “He has a great policy mind, and he’s very charismatic. Honestly, I hope he does go into politics. We need people like him.”




Carlos Watson pens an occasional column for, titled “The Inside Edge with Carlos Watson.” From his perch in Silicon Valley, Watson weighs in on everything from California Governor Arnold Schwarzenegger’s political future to the impact of Hurricane Katrina on American politics. Below are excerpts from several of his columns.

“The Rise of the Online Citizen”

March 22, 2004

For years, conservatives have successfully used talk radio to excite their base, raise new issues, target opponents and raise money. After years in the wilderness, liberals may have finally found an answer. Not the new liberal talk radio network, but blogs—formally known as web logs. The online discussion groups have become the liberal version of conservative talk radio.

The Democratic presidential primary took Internet blogs from a politico-techie niche to powerful political status. Today, liberals are regularly using blogs like Daily Kos, Talking Points Memo and others to motivate their base, raise political issues and, ultimately, help determine races.

“Feel Lucky? Google IPO Could Be a Boon for Bush”

April 28, 2004

It may sound strange, but a company in the bluest of blue states may play a big role in helping to return President Bush to office this fall.

Google, the highly successful Internet company in California, is planning an initial public offering (IPO) of its shares on the stock market soon. If successful, Google is expected to raise billions of dollars and make its founders, officers and investors Internet-boom rich.

From a political perspective, a successful Google IPO is likely to signal the return to prosperity for the Silicon Valley after four hard years of recession.

And the revival of the Silicon Valley would likely lead to a resurgence in the California economy as a whole.

For President Bush, greater job growth and consumer confidence in the nation’s most populous state (where the unemployment numbers have been worse than national averages) could transform national employment rates and form an optimistic consensus around his argument that the economy is strong and growing.

So while much attention is being focused on the April job growth report, this spring keep your political eye on Google’s IPO.

“Nuclear Blackberry?”

June 19, 2005

A truly profound debate about American safety and security is flying far below the public radar.

At issue is whether the United States should change its decades-old nuclear policy and pursue a new class of “small nuclear weapons” that could be the size of Blackberries.

Congress has taken up the debate this spring in response to the Bush administration’s request for $4 mil-lion dollars to research a new kind of nuclear weapon that would be both smaller in size and explosiveness.

In a $2.6 trillion dollar annual federal budget, the proposed $4 million is not a lot of money. But the concept is a big one.

Indeed, despite some efforts to downplay its import, the debate over whether to research small nuclear weapons (some of which are called “bunker busters”) could be a tipping point in U.S. nuclear policy.

“Supreme Surprises?”

July 22, 2005

In an era in which wealthy people ([Justice John] Roberts, by the way, has a net worth of $3.8 million) with access to better health care, better nutrition and an overall higher standard of living, are increasing their life expectancies, what may one day be most memorable about Roberts, if he is confirmed [to the Supreme Court], is that he may be the first 50-year term justice.

Potentially, he could serve twice as long as retiring Justice Sandra Day O’Connor [’52]. Roberts is 50 years old, and if fate, luck and his health allow it, it is conceivable that he could serve on the bench for a half century.

Significantly, if Americans grasped that reality, would they look at him (or any candidate) differently? And would the example of Roberts and other long-serving justices one day lead to a constitutional amendment to limit the life tenures of federal judges?

This baby boomer’s tenure may one day raise some fundamental questions about the judiciary.