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If You Want to Be a Big Deal, Never Stop Learning Jason Calacanis sold Weblogs Inc. to AOL in 2005 for a reported $30 million, was an early investor in ride-sharing company Uber and is a co-founder of the online news blog, Inside. The secret to success with Internet technology-based companies is always bettering your skillset, he says.

By Catherine Clifford

Opinions expressed by Entrepreneur contributors are their own.

To be a successful entrepreneur, particularly in tech, there is one thing you must accept: You need to always be learning.

If you ease up on learning new skills, you are going to get lapped. "The industry keeps moving. What you have to fall in love with is the process of learning and iterating and getting better," Jason Calacanis told an audience of entrepreneurs last week at AlleyNYC, a startup co-working space in New York City. (Entrepreneur Media, the parent of this website, is a strategic partner with AlleyNYC.) The event was organized by The Phat Startup, a company that works to bridge the gap between entrepreneurship and Hip Hop culture.

With enough patience, perseverance and dedication, anybody can have a shot at greatness, he said. "For anybody who is an entrepreneur, this is a magical time."

Calacanis would know. He's lived it.

Related: Success Secrets From the Entrepreneur Behind a Billion-Dollar Business Who Started Out as a Dishwasher

Calacanis grew up in working class Brooklyn, N.Y. His family struggled financially. When his dad fell behind on the tax bill at his bar, U.S. Marshals shut the place down. Calacanis was on his own to pay his way through Fordham University.

While Calacanis was never much of a student, he took to the Internet. In the '80, the idea of the Internet was still a futuristic concept relegated to a forward-thinking few.

After college, Calacanis got a job working in the IT department of Sony in Manhattan. His knowledge of the Internet pushed him quickly through the ranks at Sony. Meanwhile, he started a magazine – a term he claims was a stretch -- on the burgeoning industry and talent surrounding the Internet. "I was delusional. But if you are delusional, sometimes the reality catches up with your delusion and then all of a sudden you are a genius." He called it the Silicon Valley Reporter.

The publication began printing a Silicon Valley Top 100 list that ranked the most important innovators in the industry, which sent Calacanis to the top of the popularity charts in the emerging tech space. Executives, publicists and entrepreneurs all wanted to be on Calacanis's list. He was wielding the sort of power he'd always wanted, living high in his dream New York City apartment, taking cabs to and fro, and often enjoying basketball games court-side at Madison Square Garden.

And then 9/11 happened. And then the tech bubble burst. Calacanis was forced to sell his magazine for two years' salary and a $100,000 bonus. A year prior, Calacanis received an offer for $20 million for the Silicon Valley Reporter. He had passed on it.

While initially resistant to the idea of unedited blogs, Calacanis warmed to the idea when he saw a few of his best employees leave his magazine to start blogging. He launched Weblogs, Inc. with his former employee, Brian Alvey, in 2003. Within 18 months, the duo had 500 bloggers running through their content management system, no office, no phone system and only two additional employees beyond themselves. In 2005, Calacanis and Alvey sold Weblogs to AOL for a reported $30 million.

Related: Airbnb Co-Founder: If Rejection Slows You Down, Entrepreneurship Isn't For You

Watching his bank balance jump into the millions was a milestone. Talking about it today even brings the hard-charging, fast-talking Calacanis to tears. "My mom doesn't need to work ever again. I can pay their house off," Calacanis said through wet eyes. "It was a great moment for me, because I realized anybody could do this."

When Calacanis launched the very first version of The Silicon Alley Reporter, he didn't have any idea what he was doing. He remembers going to the Barnes and Noble in New York City's Union Square, buying a book on pagemaker and teaching himself how to lay out a story with the correct formatting. "If you just keep iterating, if you just keep working on your skill, you will get lucky and you will make your own luck and things will happen for you," he said. "You can't be ever embarrassed about hustling."

Calacanis has since become an angel investor, taking stakes in early-stage companies such as ride-sharing app Uber. He is also the co-founder of the news blog Inside, which launched in January.

Calacanis can afford to not work, but he's constantly learning new skills so he can build better products. One example is his radio podcast called "This Week In Startups." To improve his interviewing skills, Calacanis studied Oprah's interview techniques. He learned to really listen to the people he was interviewing and to make direct eye contact.

In Calacanis's eyes, skills are "the great equalizer."

"We are on the same, level playing field. Either your shit is beautiful and crisp and deserves to exist, or not."

Related: SBA Chief: The Secret to Being a Good Boss Is Being a Good Cheerleader

Catherine Clifford

Senior Entrepreneurship Writer at CNBC

Catherine Clifford is senior entrepreneurship writer at CNBC. She was formerly a senior writer at, the small business reporter at CNNMoney and an assistant in the New York bureau for CNN. Clifford attended Columbia University where she earned a bachelor's degree. She lives in Brooklyn, N.Y. You can follow her on Twitter at @CatClifford.

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