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Eric Jackson: Behind the Eight Ball


Upon our arrival to interview Eric Jackson, we found ourselves relaxing on comfy couches in a popular ad agency, which has a variety of clientele including

Konami, Sony, NBC and Zico. We pass by buildings like this all the time without having the slightest idea of what it is like on the inside. These modern day advertising agencies feel a bit like a trip to the future with their elegant simplicity and high-tech feel.

As we navigated our way through this spacious corporate paradise, we arrived at Eric Jackson’s office, which you could tell was systematically organized to be minimalistic. It had a certain tranquil charm to it, and aside from a couple of photos of his wife and a plaque with the words “It CAN be done”, the office was virtually devoid of personal memorabilia. This was no accident; he explained that he wanted to keep the focus of his office on his current project, which is CapLinked.

Eric Jackson has the demeanor of a philosopher with the humility of a monk, and his accomplishments leave you with a genuine admiration for his work. Having graduated from Stanford in 1998 with honors and holding a bachelor’s degree in economics, Jackson went on to become a part of the PayPal Mafia, which is a label given to those who were a part of the PayPal alumni that went on to start new ventures after eBay acquired the online payment firm.

Jackson has tackled the online payment and publishing industries, and his most recent venture—CapLinked—takes on online project management. Beyond his accomplishments in business, Jackson has also used his publishing prestige to dip into American politics via his publication company as well as public commentary.

Despite his illustrious career, Jackson never had any intention of becoming an entrepreneur. He described himself as a person who was “responsible, took studies very seriously, was analytical and wanted to go to a good college.” Jackson saw himself as a future-oriented high school student to which he added, “or a nerd if you wanna use that term.” Afterwards, Jackson’s plan was to do some consulting for a couple of years, then go back to school and get a business degree. With a conventional education, he expected to have a conventional, stable and successful lifestyle.

However, his life took an unexpected turn when he decided to join a small startup known as PayPal. Jackson emphasized the lessons learned and the incredible experience he had during his time with PayPal. He considers the journey of going from a small startup to being acquired by eBay as an invaluable experience; he also explained his deep appreciation for the mentorship he received from major names in entrepreneurship such as Peter Thiel (Former CEO and Co-founder of PayPal) and David Sacks (Former COO at PayPal). His philosophy on mentorship is that it is a blessing, and he says, “when you get a blessing, do something with it.”

Jackson describes Peter Thiel as the equivalent of a chess master in business, claiming that Thiel is the type of guy who can think “eight moves ahead” as opposed to someone who’s “decent at chess and can think two or three moves ahead.” Jackson credits Sacks with teaching him a great deal about how to handle technology product management.

Living in the Present

When we asked him directly, “Who is Eric Jackson?” he replied, “Eric Jackson is a person who realizes that you can’t write your own script, and I truly believe that. I believe that you will find yourself in some place at some time with certain circumstances that are beyond your control, and from there it’s up to you to make the choices that can best affect the outcome.”

His sentiment echoed the experience of playing a billiards game. You start a game of pool without even knowing for certain whether you’ll be solids or stripes. Once that is established, you continue to make the best choices possible in each given situation. Each time your turn comes around, the composition of the balls on the table have been changed by forces outside of your control. Even though the 8 ball is the ultimate goal, it’s never kept at the center of attention; the only way to win is to take it one step at a time. This ties into his belief that “it’s naïve to think you can predict the future, which is why it’s best to think in the present.”

Choosing Entrepreneurship

On a personal level, the thing that attracted Jackson to entrepreneurship the most was, as he put it, “the possibility of success.” He stressed that it can’t be merely about financial success because there are “so many other avenues through which you can achieve financial success.” When speaking of entrepreneurship, he admits “There’s a certain randomness about it. The guy on Facebook doing graffiti can make more money than 90 percent of successful entrepreneurs, and I’m not even counting the entrepreneurs that failed…but the idea that you can build something and lead some sort of an effort in hopes that the organization will achieve what it had set out to achieve…That’s very exciting!”

Jackson also spoke of the potential to “benefit and bless a lot of people. Entrepreneurial success does this by creating jobs, which means helping people provide for themselves and their families, providing a good service or product to customers or clients and not to mention—making investors happy.” When emphasizing the reward that comes as a result of entrepreneurial success, Jackson explained, “It’s about making something out of nothing, and you take that something to a place where it’s doing some good for people.”

The Ups and Downs of Entrepreneurship

Jackson had a lot to say about the emotional and psychological “tension” that goes along with the entrepreneurial lifestyle. He began by saying “If you really like entrepreneurship and the kind of creative destruction that it brings, then it’s a chance to bring something brand new to the world. If you find it exhilarating and can deal with the lack of structure which goes along with making that happen, meaning there are no set rules and no set roles, then there are very few avenues to do that other than entrepreneurship.”

However, Jackson warns startups and entrepreneurs about the difficulties that lie ahead. He said that his biggest frustration with startups is that “They always underestimate how hard it will be.” He advises that startups should be prepared for the fact that they will experience a lot of ups and downs before reaching any real success. Commenting on the ups and downs of entrepreneurship, Jackson stated, “There’s good news and bad news. The bad news is that it doesn’t go away! There’s always something that you’ll be wrestling with. The good news is that you learn how to regulate them a little better and gain some healthy perspective. When experiencing the inevitable ups and downs of entrepreneurship, do you find yourself flying up and dropping down constantly, or are you able to keep level headed and realize that you neither achieve success in a day nor do you normally obtain utter defeat in one day? There’s always another day that comes.”

We wanted to know what Jackson would like to achieve that he hasn’t already. In a subtle and serious demeanor, he replied “Good and wise.” He described this “wisdom” as “the ability to see patterns in life.” He spoke of ancient proverbs and their tendency to be about human behavior as well as patterns that can still be applied today; “And to be good for me just means making good choices, morality, being fair and humane. And there’s no easy answer to that, because nobody is completely good.” Concerning his ambitions to reach the bar he has set for himself, he admits, “It will not be something for me to say…that I’ve accomplished these things. It’s just something that I think I’d like to strive for over the course of my life.”

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About the Author

Alejandro

Alejandro is a writer/editor based in Orange County, CA. He holds a bachelor's degree in Communication Studies from Cal State University, Long Beach, which he combines with an excellent command of the English language to produce genuine quality content. Besides his passion for writing and editing, he is also a big fan of soccer, video games, music, and film.


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