Thank you to our sponsor SteadyMD. Find out more about them here: steadymd.com/venturevoice

If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

For show notes, past guests and transcripts, visit venturevoice.com

Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome

Follow and connect on social:

On Twitter: https://twitter.com/gregory

On Instagram: https://instagram.com/gregory

On YouTube: https://www.youtube.com/c/GregoryGalant?sub_confirmation=1 

On LinkedIn: https://www.linkedin.com/in/galant/ 

Today’s media executives plotting to charge for their content would do well to hear how Larry Kramer beat Jim Cramer’s TheStreet.com by resisting pressure to put most content behind a pay wall while not relying entirely on advertising. To the average consumer, MarketWatch.com

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.

“Dial 1 for sales, dial 2 for support…” Ten years ago it cost over $10,000 to get a phone system with the advanced options we’re used to hearing when we call big companies. Having a professional-sounding phone system was a surprisingly big challenge for small businesses short on cash.

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.

Joel Spolsky first came on Venture Voice over three years ago to discuss his company which he launched in a very different way from most entrepreneurs. Rather than start with the big idea and pay lip service to building a great team, Joel focused on getting great programmers first.

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.

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.

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.

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.

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.

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.

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

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.

The name Tom Perkins is now almost synonymous with venture capital, but it’s clear that he cut his teeth as an entrepreneur. Educated at MIT and Harvard, Perkins first made his mark by managing the initial growth of Hewlett-Packard’s computer business while simultaneously inventing the first cheap and reliable laser.

Jeremy Stoppelman is the co-founder and CEO of Yelp, a site where users can write and share reviews of local businesses. Everyone’s now a restaurant critic. However, local reviews were not the original focus, but just one of several features in the earlier versions of the site.

Not many entrepreneurs have a motor like Kevin Ryan’s. Kevin is best known for his work as CEO at the on-line advertising firm DoubleClick, which he grew from a 20 person start-up to the largest Internet company in New York at the height of the dot-com boom.

Marketing a startup is tricky business. Every entrepreneur faces the dilemma between allocating time to improving the product and marketing the product. If the two can be mixed just right, then perhaps sterile marketing can go viral. We tackle that issue in part 2 of 3 of our very own Venture Voice Startup Workshop coverage in New York City.

Before the rise of the Internet, cable TV was the new form of distribution remaking the entertainment business. Life-long entrepreneur and former jazz producer Fred Seibert pioneered that field, and is known in the industry for branding MTV (remember their ever-changing animated logo) and Nickelodeon (remember Nick-at-Nite).

The battery is an afterthought for most inventors. All the fun seems to be in developing a device, not in powering it. But when was the last time you cursed your phone, camera or podcast player because it ran out of batteries?

Premal Shah believes your last name doesn’t need to be Gates or Rockefeller in order to make a real dent in global poverty. After leaving his job as a Principal Product Manager at PayPal, it has taken Premal less then a year to make good on Kiva’s pledge that all it takes to become a micro lender is a credit card and access to a computer.

Real business networking takes place in the country club, at the chamber of commerce and on the golf course. After all, the Internet is just for friending strangers on MySpace and poking friends on Facebook. If you said all that to Reid Hoffman, he might think twice about adding you as a contact in LinkedIn, the business networking site he started that connects over seven million professionals.

If technology entrepreneurs have a guru, it surely must be Guy Kawasaki. For about two decades, Guy’s been advising entrepreneurs in one way or another. First as an evangelist for Apple, he courted software entrepreneurs and developers to write code for the Macintosh.

There are not many entrepreneurs who have spent their entire 10-year careers starting new ventures in online media, but Jason Calacanis just can’t help himself. Jason rode the dot com wave in New York by starting Silicon Alley Reporter. His publishing company Rising Tide Media grew to $12 million in sales.

Digg, the news website that uses its own readers rather than editors to decide what stories are most important, has been growing with a fury. While founder Kevin Rose has gotten a lot of attention including a recent cover of BusinessWeek, CEO Jay Adelson has been guiding Digg toward business success.

If there are best practices in entrepreneurship, you’ll hear the secrets to them in this coverage of the first half of the recent Venture Voice Startup Workshop in New York City. If there are in fact no best practices for entrepreneurs, then you’ll at least enjoy the heated discussion about how entrepreneurs should navigate the startup seas.

While many restaurants offer dozens of wines, beers and mixed drinks, there are few non-alcoholic options on the menu. Former dot-com entrepreneur and self-described foodie Sharelle Klaus was fed up with her lack of beverage options during the time she was pregnant with her four children.

What do you do after building and selling a business for $1.5 billion in the course of only a few years? That’s the question David O. Sacks, one of the co-founders of PayPal, faced after eBay bought his company. It didn’t take him long to find the answer: Go to Hollywood and make movies.

Venture Voice has been illuminating entrepreneurship through the podcast for just short of a year. Now, at the Venture Voice Startup Workshop on June 26 in New York, you can interact with top entrepreneurs and venture capitalists to find out how to start and grow innovative businesses.

Starting a service aimed at the blogging community is like jumping into a pressure cooker – all of the users are critics and have bullhorns. Good thing David Sifry, the founder of Technorati, has a thick skin he’s built after founding four businesses.

Being robbed at gun point and being threatened by the mob are not problems the average entrepreneur encounters. Steve Hindy faced these problems and more, but what concerned him most was the fate of his brewery. Steve started the Brooklyn Brewery with Tom Potter.

Scott Johnson is a long-time entrepreneur on the bleeding edge of technology. He started his first business in 1987 and successfully sold it. Then he rode the dot com wave up and down with Mascot Network, a company that was trying to do what Facebook does now by providing online communities for college students.

Shoba Purushothaman’s career has shifted dramatically since she started her first job as a business journalist in Malaysia. After spending several years working for the Wall Street Journal and Dow Jones Newswires, she grew restless just covering how the world was changing.

If you’re making lots of money in a fat industry for doing relatively little, then the last thing you want is a competitor like John C. Bogle. He founded The Vanguard Group in 1975 and revolutionized the mutual fund industry by slashing management fees.

When a startup launches its first product, should it expect a lot of fanfare? It should if it launches at DEMO before an audience of hundreds that includes some of the nation’s top journalists and venture capitalists (not to mention Venture Voice).

Kelly Perdew may have won The Apprentice 2, but the listeners of Venture Voice have given him a new recognition for his entrepreneurial work since then. Kelly got the most votes for the Venture Voice 2005 Entrepreneur of the Year Award.

The listeners have spoken. Jason Fried of 37signals and Joel Spolsky of Fog Creek Software have won Venture Voice Entrepreneurial Achievement Awards. They came in second and third place out of a pack of over 20 world-class entrepreneurs we’ve interviewed on the show (we’ll announce the Venture Voice Entrepreneur of the Year Award winner next week).

“Stock lockup” is a term remembered with horror by many entrepreneurs who weren’t allowed to sell their dot com shares before the bubble burst. Bo Peabody founded Tripod, which was sold to Lycos for $58 million in stock. The terms of the sale forced him to hold onto his stock for two years — while its value happened to increase ten-fold.

It’s not easy to stand out at Kleiner Perkins, one of the most prestigious venture capital shops in Silicon Valley that counts Google in its portfolio. Though Randy Komisar joined the firm just this year, it’s clear he’s not a typical venture capitalist.

We’ve interviewed some of the most accomplished and most hungry entrepreneurs on this show, but now the year’s almost over and it’s time to choose the Entrepreneur of the Year. We have no distinguished panel of judges or wise editorial board to make this decision.

If you think the ringtone business is for kids, then Fabrice Grinda has a $130 million lesson to teach you. After starting the eBays of Europe and Latin America, Fabrice brought the ringtone business concept to America by starting Zingy. We caught up with Fabrice, now 31 and a millionaire several times over, just a couple of hours before he finished his last day at the helm of Zingy.

While some entrepreneurs fret over new business ideas, Joel Spolsky of Fog Creek Software focuses on hiring the best and brightest for his New York City-based software company, and then figures out how to make a profit with the products they create.

Many would-be tech titans dream day and night about how their hot new idea will change the world. Derek Sivers just wanted to have his independent band’s CDs sold over the Web. No one would do it, so he built his own music store.

At age 28, Mena Trott is a veteran blogger and an accomplished company founder. Six Apart, the business she started four years ago with her husband Ben, now has over 100 employees. Its stable of popular blogging products (including Movable Type, TypePad and LiveJournal) are used by writers of all types — from the most influential bloggers to children who communicate after school.

The business world seems to keep getting more complicated, but Jason Fried is all about keeping things simple. When founding 37signals, Jason and his two partners staked their careers on simplicity. They wrote a manifesto to convince others of their philosophy of keeping design on the Web simple.

Dropping out of college to start a technology company is almost a cliché. But is technology the only industry that can seduce an ambitious student into entrepreneurship? Tom Szaky dropped out of Princeton because he saw an opportunity in trash. At 19, he started developing an alternative to Miracle-Gro by using the excrement of worms that eat compost.

You might expect that if you launched your pride and joy — your startup company — at a conference, it would automatically be the center of attention. At DEMO, the leading technology product launch conference, you’re hatching your business alongside 64 other companies with cool new technologies.

New businesses usually start small and work slowly and steadily to build their reputation. But that’s not true of startups that choose to launch their product at DEMO, the most prestigious conference dedicated to launching new technologies. Presenters have to agree to be radio silent about the cool technology they’ve been working on night and day for the past several months, if not years, of their lives.

Entrepreneurs who were doing business in the eighties might still remember IBM for its suits and corporate ways. Now Drew Clark, the co-founder of the IBM Venture Capital Group, has shed his tie and is changing that image. His group is opening up IBM’s vast resources to startups.

Statistically speaking, Starvest Partners shouldn’t be in business: Few venture capital funds raised in 1998 survived the dot com bust, first-time partners are a huge bet, and no other venture capital firms are run by women. But don’t tell that to Deborah Farrington, the founder and co-chairman of Starvest.

If you thought you’re an entrepreneur just because you started a software company in Silicon Valley, you’re dead wrong, according to Scott Rafer. It’s just too easy. Scott’s the CEO of San Francisco-based Feedster, an RSS search engine and ad network that allows people to find blogs, jobs and more.

Some venture capitalists keep a low profile, preciously guard their e-mail addresses from needy entrepreneurs and put on a jacket for publicity photos. Not Brad Feld. Brad started his career building his own technology consulting company with nothing but $10 and a 19-year-old’s ambition.

While some people still wonder if the fax machine has been rendered obsolete, Jeremy Hague is ready to write e-mail’s obituary. Jeremy’s brand new company, Netralia, recently released a product to rave reviews called Skylook. Many people use Microsoft Outlook to manage their contacts and send e-mail.

If someone told us to listen to business insights from a former game show contestant back in the day when The Price is Right was the closest thing to a televised business competition, we would have laughed in their face. Since then The Apprentice has attracted many ambitious young professionals to do battle for a spot in the Trump Organization.

A quick glance at Evan’s bio might make it seem as though he just stumbles into all the newest, hottest trends. However, the only thing Ev stumbled into was traffic (the kind you get on the non-information highway — where he discovered the value of listening to podcasts) on his commute.

Entrepreneurs need community. This entrepreneur makes communities. An Illinois native, Scott Heiferman came to New York while working for Sony in 1994. He quickly joined the avant-garde of the Silicon Alley community while growing his new media ad agency, i-traffic.

We covered the past with Joe in our previous show, but it’s clear he spends a lot of time thinking about the future. Many people muse about how they would do things differently if they had only the chance to do it all over again.

Conventional wisdom tells us to go get a job out of college to learn the ropes, not to take on friends as business partners, and to accept defeat gracefully. Joe Kraus’s business war stories are anything but conventional. Before graduating college, he convinced five of his friends to pass on blue chip job offers to start a business of their own.

This Internet bad boy doesn’t think he’s so bad, and one of the top venture capital firms agrees to the tune of $4 million. Don’t know who Philip Kaplan of AdBrite is? Well if you were doing anything remotely dot com related in the late 90’s you probably know who Philip Kaplan of F___edCompany.com

Sick of potential investors not taking your phone calls? Pitch a venture capitalist on his iPod. Dick Costolo of FeedBurner tells us how his CTO did just that in the second and final part of our conversation. (Be sure to check out the first half too if you haven’t already).

Dick Costolo of FeedBurner joins us for our first show. FeedBurner provides services for publishers of RSS (Really Simple Syndication). RSS is an interface that allows users to access data from blogs, traditional media, podcasts and other sources in the way they want to view it.