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Any shareholder in a startup can tell you there's a big difference between paper wealth and cash. Short of an IPO or outright acquisition, there are few options to cash out for the shareholders of even the most thriving private companies. Barry Silbert is determined to change that with his company SecondMarket -- an exchange like the NASDAQ for private stock and other illiquid assets. He founded the company in 2004 focused on restricted stock, and quickly reached profitability with only $350,000 in angel funding. The road to this point was not without challenges; Barry's business partner was diagnosed with cancer and passed away as they were establishing the company. In 2008, SecondMarket made $20 million in revenue. Barry's success has not tempered his ambition as he's spent 2009 aggressively moving into new asset classes such as private companies (Facebook stock is already being traded on his platform), limited partner interest in venture capital firms and even California IOUs. Hear how this former bankruptcy banker did it and why he believes "The sky's the limit" for his business.

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Craigslist seems unbeatable. It’s often blamed (or celebrated) for destroying the classifieds business that helped keep American newspapers afloat. Now second-time Venture Voice guest Fabrice Grinda is seeking to dominate online classifieds with OLX, his latest venture. Unlike Craigslist, OLX is translated into many languages and has a global focus. OLX is completely ad supported so there are no fees for job or real estate listings as there are on Craigslist. Still, it sounds crazy to compete with Craigslist. If anyone can do it, it may be Fabrice. When we interviewed him in December, 2005, it was on his last day working as CEO at Zingy, a ring tone provider that he founded and sold for $80 million against all odds. OLX already has 125 employees and 60 million unique visitors per month, but with $28.5 million is venture capital it has a lot of growth ahead of it before it’s a success. Hear how Fabrice plans on getting there.

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Graham Hill started the blog TreeHugger to cover green issues in 2003. After a steady climb in traffic and advertising, Graham sold the company to Discovery Communications in 2007 for $10 million. Since launch and even after the acquisition, Graham ran his business virtually. Graham lived in different cities from New York to Barcelona while working many hours to grow his company. His team of writers, ad sales people and developers chatted over Skype, got paid through PayPal and used Google documents to collaborate. Simultaneously, Graham launched a ceramic version of the iconic New York paper coffee cup (video below). Listen to how Graham built his businesses without an office or home town.

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It takes only a few seconds to customize a radio station on Pandora. Its founder Tim Westergren has been struggling for almost a decade to make it that way. Pandora was five years in the making before it streamed a single song to a user. For over two of those years the company was completely broke. While Tim convinced employees to defer over $1 million in salaries, Pandora underwent several changes in name, product and revenue models. Now Pandora is a leading online radio destination that’s starting to bring in sizable ad revenue. Tim is still battling with the record industry for its survival.

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The title financier conjures images of mahogany desks and million dollar checks for most. But for anyone pitching to David Cohen’s TechStars, the outcome is getting accepted to what’s essentially a summer camp for entrepreneurs in Colorado and being offered a check of $18,000 or less in exchange for 6% of the startup. This two year old program is part of a new trend in structured angel investing and mentoring that was started by Paul Graham’s Y Combinator. Two companies founded at TechStars have already been acquired: socialthing! was sold to AOL and Intense Debate was sold to Automattic (the makers of WordPress). David tells his own stories of success and failure as an entrepreneur, and his transiton to becoming an angel investor.

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Not to be called a one trick pony, Sam Wyly’s turned himself into a billionaire by starting and growing companies in technology, oil, retail and even in the restaurant industry. Coming from a modest upbringing, Sam worked in sales at IBM and Honeywell before founding University Computing in 1963 at age 29 with just “$1,000 and an idea” as he puts it in his book of that title. The company IPOed and grew to over 5,000 people. Sam hired CEOs and stayed an entrepreneur. He’s founded and acquired numerous companies including Bonanza Steakhouse (grew to 600 restaurants), Earth Resources Company, Sterling Software (sold for $3.3 billion), Sterling Commerce (sold for $4 billion), arts-and-crafts chain Michaels (sold for $6 billion), Maverick Capital (a hedge fund with over $10 billion under management) and clean-energy producer Green Mountain Energy. Despite being soft-spoken, Sam’s fought and won several high profile proxy fights. Sam’s been undeterred as several of his ventures have had visible failures over the years and he’s lost audacious bids to take over Western Union and Computer Associates. On the whole, Sam’s created a huge amount of value that’s put him on the Forbes list of the 400 richest people. Hear how he does it.

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Jeff Stewart needed that done yesterday. Jeff became an entrepreneur when he founded the web consultancy Square Earth in 1995. Only three years later he became a serial entrepreneur by starting Mimeo, a service that lets you send a file directly from your computer to be printed, bound and shipped overnight. Mimeo struggled in the dot com crash of 2000-2001 just as it was getting off the ground. Jeff was able to pull Mimeo though the downturn despite almost running out of cash, which has allowed the company to flourish and make $55.4 million in 2007 revenues. Ironically, Jeff didn’t have the same success in good economic times with ample cash after he raised $20 million for Monitor110. He discusses the company’s shutdown and lessons learned. Now Jeff’s focused on allowing businesses to hire good salespeople faster with Urgent Career. He announces on this show for the first time that he’s just raised a six-figure angel round to speed up Urgent Career’s success.

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Last time Derek Sivers was on Venture Voice three years ago he told us he had to “whack ‘em [investors] off with a stick”. Now we know why. Derek announces on our show for the first time the amount he sold his company for this past summer: $22 million. Derek owned 100% of the equity. Though he might have made more money than most of his fellow music entrepreneurs, Derek’s no Gordon Gekko. In this interview, Derek tells us how he put all of his money from the sale into a charitable trust, that he didn’t even visit CD Baby’s office once during the last year he owned it, and what he’s up to next.

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Attention entrepreneurs dealing with the current economic downturn: This interview is for you. After working as a journalist for Jason Calacanis at Silicon Alley Reporter, Rafat Ali ended up broke in a market with a dearth of employment opportunities. To try to find a new job, Rafat created paidContent.org as an “interactive resume.” Luckily, no one hired him. From these humble beginnings, Rafat bootstrapped his blog holding company, ContentNext Media, for four years before taking a small investment from famed media investor Alan Patricof in June 2006. From its inception paidContent has doubled revenues each year and was recently acquired by UK-based Guardian Media Group for a rumored $30 million. Listen in as Rafat outlines the past, present, and future of online media, while sharing his war stories from another uncertain economic time.

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Whether working with market trends or against them, Frank Addante has found entrepreneurial success. Before he was 29 years old, one of Frank’s companies went public and two were acquired. At his worse, he returned capital to investors. Suffering from serial entrepreneurship, Frank left the Illinois Institute of Technology just four classes shy of his degree. His companies range from an early search engine to a Sequoia Capital-backed enterprise email solution. Now Frank aspires to be a web publisher’s best friend with his new ad network optimization service that he says is boosting their clients’ revenues by 30-300%. Listen in as Frank details his ongoing entrepreneurial journey.