Entrepreneurs gearing up for their first meeting with potential investors are sure to have a million different things on their mind that are stressing them out. Is the pitch the right length? Is it filled with jargon or ridiculous assumptions? Is the font on the slides the right size? But there is one other that’s often overlooked: Am I dressed appropriately? Sponsor This post is brought to you by Gillette. When you pitch a venture capitalist, you aren’t so much selling your product as you are selling yourself, your team and you business plan. There are thousands of variables that can influence the way VCs respond to your pitch, and dressing appropriately – while completely unrelated to your product, team or business – will have a subconscious effect on their opinions. Don’t Distract the VCs The point of dressing appropriately is to not only convey that you have the wherewithal to make the simplest of decisions, but also to keep the VCs focused on what’s important – your product and your business. If there is any question in what you’ve decided to wear to a pitch, this will ultimately distract the VCs, preventing them from being sold on your idea. New York VC Steve Brotman, co-founder of Greenhill SAVP , gave The Wall Street Journal an example of very distracting clothing worn by an entrepreneur pitching him an Internet startup during the dot-com era. According to his story, a woman dressed in a strange green outfit entered his office unannounced and offered up a business plan. “You lost me at hello,” Brotman told her. The woman was selling a product with “avocado” in the name, and was attempting to dress like an avocado. “I’m not about to do a deal with a lady dressed like an avocado,” said Brotman. The lesson here? Don’t let your product influence how you dress; VCs don’t enjoy gimmicks. Safe Bet: Business Casual A general rule of thumb for appropriate dress when speaking with VCs seems to be “business casual.” Here’s a sample outfit that fits this profile, starting from the ground up: black dress shoes or boots (no sneakers, flip-flops or Crocs), a nice pair or jeans or dress slacks (no rips, darker shades work better, in my opinion), solid color t-shirt or polo (collared shirt with no tie could work also), and a black casual sport coat. Plus or Minus 20% While your appearance should not be distracting or influenced by gimmicky product promotion, if done right you can use it to your advantage. Boulder’s Andrew Hyde of TechStars suggests entrepreneurs use the “20% rule” when deciding what to wear. “You want to look 20% better or worse than your actual position,” he says. “The key is to either look good enough to make them think you’re trendy, or bad enough to make them think you’re hungry.” I would recommend going the safe route, but more confident entrepreneurs could use this tactic to their advantage. Hyde, who also co-founded a clothing line of humorous T-shirts for venture capitalists , says whatever you do, “Don’t wear a blue shirt, or they will think you are mocking them.” Unsure? Just Ask But what does a seasoned venture capitalist think after being pitched hundreds, if not thousands of times? Silicon Valley investor Guy Kawasaki says deciding what to wear can vary from company to company, and investor to investor. While his advice is geared toward interviewing at a startup, it still applies to VCs as well. “A good rule of thumb is to dress one level above the company norm: for example, for a T-shirt-style company, wear a collared polo shirt,” he says. “If in doubt, ask what’s appropriate for the interview.” This is probably the best advice on the issue. Ask. Try finding other entrepreneurs who have pitched your potential investors first before you ask the actual VCs you are pitching about what to wear – it could convey a lack of experience. Or it could convey an attention to detail and maturity. What About Women? Ah yes, women. Seeing as I am a male, I focused this article on the male entrepreneurs out there (who are statistically more common than women, at least in Internet startups). I don’t want to leave women out completely, however, so I will offer this bit advice to the female entrepreneurs out there. It’s actually quite similar to the rules of thumb for men – business casual, don’t over think it, and don’t be distracting. What determines “business casual” and “distracting” are different for women than for men, but I defer to our female readers to provide some helpful examples in the comments below! Be Smart The truth is, there is no right answer to the question of what to wear when pitching VCs. Each situation is different, and different VCs care more or less than others about how entrepreneurs look. The best practice is not to over think it, and just rely on what is most likely to work – business casual. No suits, no ties, no problem. Most VCs are pretty laid back, at least in traditional startup cities like San Francisco, New York and Boulder. If you fail to spend your time working out the more important aspects of your pitch, what you wear will be the least of the VCs’ worries. Discuss

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In keeping with Facebook’s two-steps-forward-one-step back policy, pioneered during the Beacon and friends list debacles, the company announced it would introduce a simplified set of privacy settings soon. “Now we’ve heard from our users that we have gotten a little bit complex, I think we are going to work on that,” said Tim Sparapani, head of public policy for the company. “We are going to be providing options for users who want simplistic bands of privacy that they can choose from and I think we will see that in the next couple of weeks.” Sponsor The privacy settings, which could be called publicity settings in the wake of the company’s decisions to open up the site after the f8 conference, have been criticized as being, among other things, Byzantine. Perhaps this adjustment will provide a set of less confusing options. This still leaves new users as entering Facebook with defaults on public, sharing all of their information with the Web at large. It seems unlikely to reverse the judgment of certain segment of the user base that the forced openness is good for Facebook, but not for the user community. Sparapani made the announcement in an interview with American University radio . The portion in question starts at just over 26 minutes in. Below is a portion of the interview.

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Ticketfly , a startup that helps concert promoters leverage social media and sell tickets, announced earlier this week that it has raised $3 million in Series A funding from various firms and angels. Co-founded by Dan Teree and Andrew Dreskin, Ticketfly is – in a way – the rebirth of an earlier company, TicketWeb , which sold to Ticketmaster in 2000. After years of success, TicketWeb found itself unable to grow to its full potential, leading to the birth of a new venture, Ticketfly. Teree and Dreskin’s story serves as a lesson to startups of how acquisitions by large, slow moving companies can lead to frustrated entrepreneurs. Sponsor TicketWeb launched in 1996, becoming the first online ticketing service in the market. In May of 2000, Ticketmaster acquired the company for $35 million, which was six and a half times its revenue at the time. With a solid return for its investors, TicketWeb’s sale made a lot of sense at the time, and for several years the company saw significant growth in its new home. “There is a general agreement that Facebook and Twitter are winning platforms that are growing, that are huge already, that are very important and that you can’t ignore.” – Dan Teree With the growing popularity of social media of the course of the last decade, an opportunity to expand the features of the service to fulfill the needs of venues and promoters presented itself to TicketWeb. However, Ticketmaster, a large, slow-moving company, didn’t want to see a subsidiary product of theirs undermining its main service with better features, and thus funding for new projects at TicketWeb dried up. In 2007, Teree left TicketWeb and joined forces with his former partner Dreskin, who had left the company shortly after the sale to Ticketmaster. A year later in 2008, the pair launched Ticketfly, building on the innovation they were unable to pursue while under Ticketmaster. Now the company has sniped 50 top venues from their former employers and just wrapped up a $3 million Series A round of funding to boot. Had TicketWeb been allowed to grow under Ticketmaster, it “would have been way bigger and we would have been way farther along,” Teree told ReadWriteWeb. Instead, Ticketfly is now launching on a foundation of technical skills, management skills and relationships in the music industry built by its founders over the last ten years. “It’s allowed us to come out of the starting blocks far quicker than the average bear,” added Teree. Looking back, Teree doesn’t regret the original sale to Ticketmaster because for a long time the relationship was good for TicketWeb. Since Ticketmaster has been too slow to adopt social media innovations, they are an easy target to compete with, Teree says. Ticketfly focuses on sales and marketing for venues and promoters within the music industry, and attempts to solve several problems these clients have. Tradtional online ticketing platforms, like Ticketmaster, do not make it easy for promoters to get event information online in a timely and efficient manner. Ticketfly makes the process of promoting an event easy and instantaneous through web-based tools, whereas posting an event on Ticketmaster requires that the information pass through a Ticketmaster employee before it can go live. Ticketfly also places a strong emphasis on integrating with social media networks like Facebook and Twitter, eliminating the need for clients to re-enter their information in a handful of locations. “Three years ago, you’d talk to a 45-year-old concert promoter in some city and you’d say ‘Oh, Facebook , Beebo , Myspace ,’ – it’s always gonna be something new,” Teree told ReadWriteWeb. “But now more than ever, there is a general agreement that Facebook and Twitter are winning platforms that are growing, that are huge already, that are very important and that you can’t ignore.” Ticketfly, he says, is perfectly positioned to help promoters who are now beginning to realize that social media is critical to the success of their events. With offices and employees in San Francisco, New York and Chicago, Ticketfly is able to meet face-to-face with many of their clients. But the benefits of the service aren’t only on the promoter’s end. Ticket buyers who use Ticketfly will pay 30-40% less in fees compared to Ticketmaster, and printing tickets at home comes at no added price. Investors in the company’s Series A funding include High Peaks Venture Partners and Contour Venture Partners , both based in New York. Angel investors include Roger Ehrenberg of Information Arbitrage Capital Partners , and Howard Lindzon , known for his leading investments in StockTwits and other well known startups. While the acquisition of TicketWeb by Ticketmaster was not an outright negative experience, Ticketmaster did, however, miss out on an enormous opportunity to expand their efforts in social media marketing. Instead, Ticketfly’s founders left the company, and decide to innovate all on their own. Photo by Flickr user Hamed Saber . Discuss

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Last week we asked you to send us your questions for our interview with wine connoisseur and social-media expert Gary Vaynerchuk . Gary and his consulting company VaynerMedia recently ran an experiment with the NBA’s New Jersey Nets and geolocation app Gowalla (in which Gary is an investor) to see if location services could draw fans to games with free tickets. For all parties involved, the experiment was deemed a success , and the findings from it have provided a unique insight into the future possibilities for geolocationtional advertising. Sponsor As you may recall, last Friday during the ReadWriteWeb Mobile Summit , we discussed the potential road-blocks for startups looking to innovate in the localized mobile ad space. By using an existing network like Gowalla, however, the Nets experiment actually succeeded to bring in a significant amount of people to a game where thousands of seats went unsold. By using Gowalla to check-in at local gyms, parks and other locations where supposed basketball fans might frequent, 38 users found and redeemed 1 of 250 pairs of tickets made available for the game. 76 of 500 (15.2%) of the seats offered through the application were filled directly because of the mobile promotion – seats that would have otherwise been left empty. These patrons instead paid for parking, merchandise and other concessions at the arena that would have previously not been purchased. VaynerMedia Case Study from Gowalla/Nets Experiment One of the major conclusions Gary says was drawn from this experiment is that for the next few years, mobile advertisements are going to play a large role in how expiring inventory is sold. For the Nets, this inventory was tickets to the final home game of the season. For other businesses, this could mean the last batch of doughnuts that is thrown away at the end of a day, or unfilled hotel rooms and airplane seats. But why only for the next few years? As Gary pointed out in our interview, soon enough, everyone is going to be using a service like Gowalla or Foursquare , and the novelty of the app combined with the emotional attachment of discovery will fade with time. The thing that separated this experiment from other promotions is that the people offered the tickets discovered them through their own actions, creating a sense of responsibility to redeem them. In the future, however, if everyone is using applications to find deals, the novelty of the game mechanics introduced could eventually dissipate. One of the major conclusions Gary says was drawn from this experiment is that for the next few years, mobile advertisements are going to play a large role in how expiring inventory is sold. A significant hurdles for mobile advertising is when a customer attempts to redeem a coupon only to be denied by an unknowing store clerk oblivious to the business’ mobile ad efforts. Gary says while this is a problem due to the relatively new nature of geolocation apps, only medium-sized businesses have to really worry about it. Small businesses with one or two locations and a handful of employees can easily spread the word of such a promotion, but a company with a half dozen locations across a metro area may have more difficulty. Unfortunately, this represents the majority of U.S. businesses. Examples taken from Twitter showed that the promotion with Gowalla and the Nets was well received by fans and helped to create new relationships between the team and its fans. One happy father even Tweeted about how his six-year-old son called the experience “the best day of my life, ever.” Clearly the integration of social media into a mobile ad promotion has helped to uncover some fascinating results about consumers. We also took the opportunity to ask Gary some of your questions about anything and everything, including managing work and family, following your passion, selling wine and – of course – his favorite football team, the New York Jets. Here’s what Gary had to say. Pete asked, “How do you maintain your ‘Crush It’ attitude and continue on the path to success while following the rule of family comes first?” Gary: Super hard. No question, by far my biggest challenge. I think it’s understanding the players. And what I mean by that is, just paying attention to what my wife feels It’s communication and making smart choices. Always filtering. The same things that excite me about the Internet – filtering and restrictions – are the same things for life, I just have to keep filtering. Renee wanted to know, “How do you overcome the fear of leaving a routine life to follow your passion?” Gary: For me, it was the fear of living a routine life. I think about legacy a lot, I’m a very big picture kind of thinker, so not taking chances and not being happy along the way just seems so insane to me. I’m very aware that everyone is wired differently, I’m nothing special. I’m just me. What I’d like for people to do is embrace more of the “try to be me” more than somebody else. I envy people that can sit down on a project and focus on it for ten years, but now that I’ve built that cushion, and that base, nothing wants me to do that. I want to scratch all of my itches – advise, consult, speak, author, do a show. Jason, a wine entrepreneur looking to use social media to be disruptive in the Scandinavian market, asked what Gary thinks of the idea and if he had any tips. Gary: I love the idea. My biggest tip is to keep your mind open to not just the wines you like. Don’t control it, let the pieces fall where they are, and make sure you hit as many demographics as possible. Don’t make it polarizing. Think about as many different niche markets as possible and don’t just talk at social media events, go to wine clubs and wine bars. Try to get as many people to embrace it as you can. And finally, Andrew asked Gary, “What do you think of the New York Jets’ Fight Song?” Gary: I bleed green. If I can like Jason Taylor, who was a former Dolphin and now he’s a Jet that I hated every day of my life for the last decade plus, then I love everything about the Jets. Disclosure: The author of this post is a Patriots fan, but that in no way affected his interview with Gary, a diehard Jets fan. Discuss

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Today we are announcing our third event and our first on the East Coast: the ReadWriteWeb Real-Time Web Summit , on June 11th at the Metropolitan Pavilion in New York City. As you all know, last Friday we held the ReadWriteWeb Mobile Summit , in Mountain View, California. The Real-Time Web Summit in NYC will follow the same unconference format, which we have gotten a lot of great feedback on. To see the power of the unconference format, check out the video below showing the session pitching at the Mobile Summit: Sponsor Watch live video from ReadWriteWeb Mobile Summit 2010 on Justin.tv Register for the Real-Time Web Summit The ReadWriteWeb Real-Time Web Summit on June 11th in NYC will be an exploration of the latest Real-Time Web trends. This is our second Summit on Real-Time Web, following on from our successful debut event in Mountain View last October. We invite you to register now at the early bird rate of just $295.00 . This rate is valid until May 17th, at which point it will increase. What is the Real-Time Web? We were one of the first publications to analyze the Real-Time Web and we’ve since written extensively about it . We also published a premium report on the subject last year, which featured interviews with 50 companies, developers and executives building or leveraging real-time Web technology. So what is the Real-Time Web? In a primer last year , we defined it as “a new form of communication, it creates a new body of content, it’s immediate, it’s public and has an explicit social graph associated with it, and it carries an implicit model of federation.” The most widely known application of the Real-Time Web is Twitter . However, it’s much more than Twitter or Facebook. The Real-Time Web is a set of technologies that impacts almost every service, activity and application on the Web. Come to the Summit to understand how it impacts you, your business and your next development. The Benefits of the Unconference Format An unconference is a free flowing, organically generated series of group discussions agreed on and led by attendees. “Hats off to ReadWriteWeb for one of the most inspiring conferences!” Taly Weiss, TrendsSpotting This is our third ‘unconference’ event and we think it fits our brand perfectly. Firstly, much like the current era of the Web, unconferences encourage two-way communication . This generates new, actionable ideas and means that you typically learn much more than you would at a traditional conference. Secondly, due to the high quality of our reader base, ReadWriteWeb’s unconference events attract an intelligent, influential group of people . Two-way dialog on a big Internet trend happening under one roof with the industry’s smartest people? What’s not to like I explained a bit more about how the format works in this interview with Renee Blodgett last Friday: And to get a feel for how thoughtful discussion happens at these events, check out the comments by Ted Morgan, Chris Saad and Ben Metcalfe in this video by Evelyn Rusli from TechCrunch : In short,  the unconference format makes for a creative, energized environment. We’e had some wonderful feedback on our previous two unconference events. You can listen to feedback from various attendees, via recordings by Marshall Kirkpatrick on Cinch Audio . Register Now for RWW Real-Time Summit NYC We invite you to register now at the early bird rate of just $295.00 . This rate runs until May 17th. See also banners and logos for this event , if you’d like to link to us. If you’re a company in the Real-Time Web market, you may be interested in helping to sponsor this event. Please contact our COO Sean Ammirati for more information. The ReadWriteWeb team is excited about our first New York event on June 11th, so we look forward to seeing you there! Discuss

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