25 New York Internet Pioneers – Then and Now



Is there an Inner Circle of New York tech entrepreneurs? Maybe, maybe not. Meetup co-founder Scott Heiferman spent time working behind the counter at McDonald’s – after he sold his first company for $15 million. These successful serial entrepreneurs caught the Internet bug early, and helped pave the way for a new industry. They may make it look easy, but they’ve had their ups and downs. Still, they do seem to bounce back and remember: they started at a time when many still considered the Internet a fad, and anyone who thought that they could build an actual business on it was considered to be, well, a few fries short of a Happy Meal. In no particular order:

Scott Heiferman – It was 1995 when Heiferman founded i-traffic (interactive Traffic Inc.), a direct-marketing agency whose strong suit was media planning. In 1999, i-traffic was acquired by Agency.com Ltd. for an estimated $15 million. Not long after leaving i-traffic, Heiferman was ready for his next success, but not before experiencing his first failure with Rocketboard (founded 1999), in which AOL invested, and which shut down in 2000. Heiferman then decided he needed a break – and took a job working behind the counter at McDonald’s. In 2002, he co-founded the social networking site Meetup.com, which facilitates offline group meetings in various places around the world. It allows the user to find and join a group, unified by a common interest, whether it be politics, books, games or what have you.

Today – As of April 2013, Meetup claimed to have 13.4 million members. One estimate puts Meetup’s worth at over $1 billion. There is no information available as to how much time Heiferman currently spends at McDonald’s.

David Rose – Rose has been called ‘New York’s Archangel’ by Forbes and ‘the Father of Angel Investing in New York’ by Crain’s. In 1988, Rose founded AirMedia, a wireless Internet pioneer.  He also founded Ex Machina in 1988, a computer software company. In 1999, he became managing partner at Rose Tech Ventures, which is an incubator for Internet platforms, ASP services, wireless and B2B market-making networks. In 2004, he founded the New York Angels, the leading angel capital investment consortium in New York, which provides seed and early-stage capital in the range of $100k to $1 million. Their exits were to companies including Google, Living Social, Kodak and CBS.

Today he is CEO of Gust, an Internet platform used by the majority of the world’s business angel investment groups to process their deal flow and collaborate on early-stage companies.

Brian Cohen – Cohen founded the PR firm Technology Solutions, Inc. (TSI) in 1983. In 1996, TSI was recognized as the No. 1 fastest-growing agency in the U.S., and it was awarded the Gold CIRPA award in 1998 for creating the IBM Deep Blue/Gary Kasparov Chess Match communications program.. In 1997, TSI was sold to the McCann Erickson World Group and Cohen became the vice Chairman.

Today, Cohen is Chairman of the New York Angels – the #1 most active angel group in the country – and co-founder and CEO of Launch.it, which builds launch tools for professionals and entrepreneurs.

Fred Wilson – In 1996, Wilson co-founded Flatiron Partners with Jerry Colonna. This grew into an investment fund that focused mostly on follow-on investing, pumping  money into dot-com sites such as Geocities, Kozmo, Alacra and New York Times Digital.

In 2005, Wilson co-founded Union Square Ventures with Brad Burnham.  The firm’s investments include, Meetup, Twitter, Zynga, Etsy, Tumblr, Foursquare and many others. Wilson was named the #1 Venture Capitalist by Heardable in its 2012 report on the Top 50 leading brands in venture capital.

Jerry Colonna – In 1996, along with Fred Wilson, Colonna founded Flatiron Partners, which made early investments in companies such as Geocities, PlanetOut and New York Times Digital when Silicon Alley was just a fledgling.

Today, Colonna is  a life and business coach. He also serves on the Board of Trustees at Naropa University.

Kevin Ryan – In 1996, Ryan became the president, and then later the CEO, of DoubleClick, a company he co-founded with Kevin O’Connor and one of the earliest known Application Service Providers for Internet ad-serving, primarily banner ads.

In 1997, at a cost of $1.7 billion, DoubleClick merged with Abacus Direct, a data-collection agency.  In 2005, both companies were bought, and subsequently split and run as separate entities, by Hellman & Friedman, a San Francisco-based private equity firm. In 2007, Google purchased DoubleClick for $3.1 billion. It was also in 2007 that Ryan founded Business Insider, a business and technology news site that launched in 2009, and Gilt Groupe, an online portal that offers members exclusive access to coveted fashion and luxury lifestyle sample sales, events and brands.  In 2008, Ryan founded 10gen (now known as MongoDB Inc.), a software company that develops and provides commercial support for the open source database MongoDB. In 2012, 10gen made the Wall Street Journal’s list of the 10 Next Big Things.

Today Ryan is Chairman of Gilt Groupe, Business Insider and 10Gen

Kevin O’Connor – O’Connor was Kevin Ryan’s co-founder in DoubleClick in 1995 but left in 2005.  In 2001, he founded O’Connor Ventures, which provides seed capital to technology companies in Southern California.

Today – In May of 2009, O’Connor co-founded, and is now CEO, of FindTheBest, a site that acts as a research hub for consumers and small businesses. He recently made news by pledging $1 million of his own money to fight the patent troll that went after his company.

Craig Kanarick – Kanarick, along with Jeffrey Dachis, helped get the ball rolling in Silicon Alley in 1995 by founding Razorfish, one of the first purely interactive ad agencies. In 1999, Razorfish went public, raising $48 million and eventually acquiring Integration International, Inc. (I-Cube) for $1.2 billion.

Today, Kanarick is the co-founder of another company—Mouth, a site dedicated to helping people find the best, most interesting artisanal/indie food products and, subsequently, helping indie makers grow their businesses. So far, Mouth has 200 vendors from 30 different states. Kanarick has stated that year-to-year sales are up over 300 percent and that Mouth is currently undergoing its second round of financing, with a goal of raising $1-2 million.

Dachis currently lives in New York City where he founded One Drop, an app for diabetes management that raised $8 million in Series A funding.

Jeff Stewart – In 1995, Stewart founded his first company, Square Earth, a consulting and development firm focused on web technology. Square Earth’s customers included Citibank, UPS, AIG, Merrill Lynch and a host of others. After posting approximately $2 million in revenue in 1997, Square Earth was acquired by Proxicom in 2008. The quintessential serial entrepreneur, in 1998, he went on to found Mimeo, an online printing and overnight delivery service.

Today, Stewart acts as the founder and CEO of Lenddo, the world’s first online community that empowers the emerging-market middle class to use online social connections to build their creditworthiness and access local financial services. Stewart is also an active angel investor in New York City, investing $25K-$100K a year in roughly six different start-ups.

JJ Rosen – Rosen jump-started his career in 1994 by co-founding, and acting as president of, N2K, a one of the first internet-based music sites, which built loyal user communities around genre-specific websites that provided music content and enabled consumers to purchase music and related merchandise.

After a successful IPO in 1997, the company was part of a $101.8 million dollar merger with CDNow. Bertelsmann eventually acquired the merged company in 2000 for $117 million. Rosen’s next startup was RUNtones, a mobile entertainment company that offered consumer and business-based wireless services including RUNtones, a ringtone service; RUNpics, a personal photo service; Mobile Media Hub services, offering private label wireless portals; and mobile media production. The company was acquired by Sony Music Entertainment in 2002, and Rosen was acqu-hired along with it.

Today – In 2011, Rosen left Sony to become CEO of Indaba Music, an integrated services platform and social media network that enables over 550,000 musicians to learn, meet collaborators, record, sell and license music.

Richard Foreman – In 1995, Foreman founded Register.com—one of the original domain registrars. In his time as president and CEO, Foreman grew the company from $900,00 to over $115 million in sales. He also successfully completed its IPO, which raised over $125 million.  Foreman was ousted as CEO in 2003, but then co-founded Vitals.com in 2007. Vitals offers online doctor ratings, as well as the ability to book appointments with some doctors online.

Today, he is an active investor. He’s Managing Partner at Health Venture Group, a privately held investment firm focused on technology and consumer-related healthcare investments, where he served as founder, investor and consultant for ExpertConsensus, LLCVitals.com, Centrihealth, Healthination, and Finpago. He is also an investor in HealthyOut, StartupHealth and Maxwell Health.

Jack Hidary – In 1995, Hidary co-founded the IT informational portal EarthWeb with his brother, Murray, and Nova Spivack. The company had its IPO in 1998 and had one of the largest first-day returns in NASDAQ history.  In 1999, EarthWeb acquired dice.com, a tech career website and in 2000, the company was renamed Dice Inc., and taken private. In 2005, Dice Inc. was sold to Quadrangle and General Atlantic Partners for approximately $200 million.

Today, Hidary is Chairman of Samba Energy, a marketplace for solar, energy efficiency and other commercial clean energy.  He is also currently a candidate for New York City Mayor, running on an independent, self-created platform.

Kyle Shannon & Chan Suh – Starting with an $80 investment, in 1995 these two founded Agency.com, a pioneer in interactive marketing. In 1996, Omnicom Group purchased a significant minority investment, which provided Agency.com with the capital needed for rapid expansion.  In 1998, Agency merged with Eagle River Interactive to form what was, at the time, the world’s largest interactive marketing agency. Then came the acquisitions: New York-based Spiral Media and Boston-based Interactive Solutions. In 1999 the company acquired Scott Heiferman’s iTraffic to bolster its online marketing services offering, and went public in December of that year. When the dot-com crash hit, the company suffered and eventually transitioned back to being a private company in 2001. Shannon left. Agency.com was eventually sold to Omnicom in 2003.

Today, Suh is a senior partner at Prophet, a strategic brand and marketing consultancy with clients such as BMW and McDonald’s. Shannon founded and is CEO of Storyvine, a platform for people and businesses to create professionally produced, user-generated video at scale

Andrew Weinreich – Having launched SixDegrees.com in 1997, Weinreich may well be considered a founding father of social media. SixDegrees was the first site to combine personal profiles, instant messaging, friend lists and the ability to search other members’ friend lists. The site was bought by YouthStream Media in 2000 for $120 million. He next founded Joltage, the first company to provide operational support system to wireless networks, but he might have been too early in the game. Then he became Founder and CEO of I Stand For, Inc., a full service technology ASP for political campaigns and non-profits, which he sold in March 2006. In 2007, Weinreich founded MeetMoi, the first location-based mobile dating service available across all major carriers in the US. Then, in 2008, he founded Xtify, which offers a location-based services that allows any web site to location-enable their service.

Today, he serves as Chairman of both Meetmoi and Xtify.

Esther Dyson – After being a journalist for a number of years, rising up quickly at Forbes, in 1983, Dyson bought Rosen Research from her employer, Ben Rosen, and renamed it EDventure Holdings. Since then, she has been a board member or made early investments in companies such as Flickr, TrustedED, Eventful, Del.icio.us, Netbeans and Meetup, while admitting to having passed on such companies as Google and YouTube.

Today, she is Chairman at HICCup (Health Intervention Coordinating Council), an initiative to set up citywide health intervention programs in several cities, and is a founding member of Space Angels Network.  She is also an active angel investor.

Owen Davis – Davis was always a bit ahead of his time. In 1995, he founded ThinkingMedia, an online advertising and marketing agency that pioneered sophisticated tracking of online media and marketing and counted Proctor & Gamble, IBM, Honda, Panasonic, Condé Nast, Excite/atHome, Deutsch, Young and Rubicam among its clients. In 1999, he launched Sonata, providing software and services to wireless carriers to enable them to offer location-based services. Unfortunately, a basically negligible percentage of the population had smartphones at the time. In 2001, he founded Petal Computing, which was basically a cloud provider, long before the term had entered the lexicon.

Today – Davis is Managing Director of New York Seed, providing funding, mentoring and support to create the next generation of companies in New York City.

Benjamin Sun – Sun burst onto the scene in 1996 when he co-founded Community Connect, a social network/digital media business, which grew to be a leading online publisher which, targeting various niche markets. In 2008, Community Connect was acquired by Radio One, Inc. for $38 million.

Today – Since then, Sun has moved on to become a partner at both LaunchTime LLC, an early-stage investor and incubator focused on digital media and e-commerce, and High Peaks Venture Partners, an early-stage venture capital fund.

Lewis Gersh – Gersh began his Internet career in 1998 as Chairman of Worldly Information Network, Inc., a financial information site that provided unique, objective and independent advice, commentary and investment ideas on issues ranging from investment management to wealth maintenance strategies.

Worldly was eventually acquired by Advisor Software in 2003.

Today, Gersh acts as a managing partner at Metamorphic Ventures, LLC, a New York-based venture fund that invests in start-up and early stage technology businesses focused on digital media and digital commerce.

Gerald Levin – In 1972, Levin began with Time, Inc. He eventually worked his way up and became CEO of Time Warner in 1992.  In 2000, at the height of the dot-com bubble, Levin brokered the merger between Time Warner and AOL.  When the dot-com bubble burst, Levin was left with egg on his face. He eventually stepped down as CEO of AOL Time Warner in 2002 and was named one of the worst CEOs of all time by CNBC.

Today, Levin is back. He is currently Chairman at Startup Health, which provides health and wellness innovators with a structured curriculum designed to help navigate the challenged of building a sustainable growth business.

Dawn Barber – In 1998, Barber took a job as Director of Conferences and Events for the New York New Media Association, New York’s premier, if not seminal, industry association back in the mid to late 90s.

Today – With the contacts she met through her work there, she co-founded (with Scott Heiferman) the New York Tech Meetup, an influential platform for tech start-ups, in 2004. Current household names such as Tumblr and Foursquare made their debuts on stage at a New York Tech Meetup.

Andrew Rasiej – in 1997, Rasiej founded MOUSE (Making Opportunities for Upgrading Schools and Education), an educational non-profit, focused on connecting public schools to the Internet. Currently, MOUSE trains students in public schools to provide technology support for their schools, teachers and fellow students. Rasiej also co-founded the now-defunct Digital Club Network, the first live music streaming and archiving channel on the Internet.

Today, Rasiej is Chairman of NY Tech Meetup, which was founded in 2004 by Scott Heiferman.

Mark Ghuneim – Mark Ghuneim was a corporate online guy, running online and emerging technology for Sony Music Entertainment back in the mid to late 90s. In 2004, he left to found Wiredset, a real-time digital agency and technology incubator specializing in online engagement marketing for Fortune 500 brands, networks, studios and the like.  In 2006, Wiredset developed Trendrr, which allows users to identify volume, sentiment, location, demographics and influences around their product and brand, as well as the velocity around the media and links being shared on the social web.

Today – In August 2013, Trendrr was acquired by Twitter (financial terms were not disclosed).

Jason Calacanis – Calacanis founded Silicon Alley Reporter in 1996. It was at first a small, photocopied newsletter but grew into a 300-page magazine. When the dot-com bubble burst, SAR went under.  VentureReporter.net, which Calacanis also founded, was sold to Dow Jones. In 2003, Calacanis co-founded and became CEO of Weblogs, Inc., a network of about 90 blogs (including Engadget) on various subjects such as computers, gaming and food. Calacanis sold Weblogs, Inc., to Time Warner for $25 million. In 2007, he founded Mahalo.com, a human-powered search engine. He has raised over $20 million for the project with notable investors such as Elon Musk, Mark Cuban and CBS.

Today – Since 2009, Calacanis has been involved in angel investing, founding Open Angel Forum, an event that connects early-stage startups with angel investors. His investments include Gowalla, Blippy, Uber and Backupify.

Scott Kurnit – In 1983, Kurnit founded Viewer’s Choice, which eventually became iN Demand and is now jointly owned by Comcast, Cox Communications, Time Warner cable and Bright House Networks. iN Demand provides pay-per-view services, as well as video-on-demand. In 1996, Kurnit founded About.com and became its CEO. During his tenure there, About’s public market value surged all the way up to $1.5 billion. About was acquired by PRIMEDIA in 2001 in a deal that valued About for $690 million, then sold to the New York Times Company in 2010 for $410 million, who sold it to IAC in 2012 for $300 million.

Today – In 2010, Kurnit founded AdKeeper.com, an online advertising platform that allows consumers to keep online ads for future use, of which he owns the parent company, Keep Holdings, where he is CEO and Chairman.

Kaleil Isaza Tuzman – Tuzman got his start in 1998, co-founding govWorks, Inc. with childhood friend Tom Herman. govWorks produced software to help government clients track contracts and purchasing functions.  After raising $60 million in venture capital, govWorks was hit hard by the burst of the dot-come bubble. The company eventually had to file for bankruptcy and was sold to First Data Corporation for $12 million. govWorks’s rise-and-fall was memorialized in the 2001 documentary film, Startup.com. In late 2007, Isaza Tuzman purchased a controlling interest in ROO, an Internet video technologies company, which became one of the leading end-to-end IP video providers under the new name of KIT Digital. Tuzman left the company in April 2012.

Today, Tuzman is Managing Partner at KIT Capital, an entrepreneur-led investment and advisory group focused on digital media and emerging markets in real estate, where he is once again working with Tom Herman.

Image credit: CC by Christian Schuster

About the author: Alexander Maykowski

Alexander Maykowski is a recent graduate of Marquette University, where he studied journalism and political science. He has an ardent interest in cryptocurrencies (such as Bitcoin) and how they will shape the financial and global landscape in the future.

You are seconds away from signing up for the hottest list in New York Tech!

Join the millions and keep up with the stories shaping entrepreneurship. Sign up today.