Over a cup of tea at the Flatiron District's cozy Subtletea, I recently caught up with consummate tech matchmaker Bobby Orbach. In the Go-Go '90s, Orbach was best known for hosting "schmooze fests" -- cocktail parties where entrepreneurs, investors and reporters mingled to make connections, view gadgets and forge deals. These days, Orbach may be keeping a lower profile, but he's still focused on brokering deals and investing in startups, and like many other PC industry pioneers, he spends a significant chunk of time and money on charity.

Orbach grew up alongside the PC industry. He got his start in the 1980s when he was director of business development and marketing at 47th Street Photo, a Midtown Manhattan store synonymous with getting a good deal on electronics. Orbach is credited with being one of the first people to figure out how to sell PCs to the masses. Orbach left 47th Street Photo in April of 1990, and eventually the company ran into trouble, filing for bankruptcy protection in 1992. Contrary to industry myth, Orbach is not related to the owners, and he never owned a piece of the company. "I wish I did," he quips.

Today, Orbach's bread and butter is helping companies find value in assets they may have overlooked, especially intellectual property, or IP. For example, last year, the CEO of a backup software company came to him for help raising $1 million to $3 million. Orbach realized quickly that the company had valuable IP. In December, he sold three of its patents for a total of $1 million. Orbach says he did roughly 10 similar deals last year.

On the buying end of the patent deals is often Intellectual Ventures LLC. While other firms, known as patent trolls, acquire IP solely to leverage fees from other companies, Intellectual Ventures sees itself as an invention incubator intent on bringing innovations to market. It boasts an impressive brain trust, including Nathan Myhrvold, Microsoft Corp.'s respected retired chief strategist and chief technology officer, who co-founded Intellectual Ventures in 2000.

"Bobby is one of the legends in our industry," says Myhrvold. "His background and knowledge about technology is unusually broad and deep, spanning nearly every industry sector in fact. The reputation he's built over the years is no doubt based upon his track record for thinking like an innovator but approaching new ventures with the experience of a seasoned business executive."

When asked to explain how he chooses the new ventures he invests in, Orbach says he goes with his gut. "I always think, is this something exciting to me? Is this something I can get my friends excited about?"

One recent example is Enquisite Software Inc., a company that measures and analyzes traffic coming to Web sites through paid Internet searches. His favorite part of Enquisite is that it gives Web sites a way of auditing the bills they get from Google Inc. and other search engine companies. 

"Enquisite keeps Google honest," says Orbach. 

What's the biggest home run Orbach ever hit? "Like Ace Greenberg, the former chairman of Bear Stearns, likes to say, the best investment I ever made is in charity."

One of the charities he contributes to currently is Chai Lifeline, which provides services for children with life-threatening illnesses. "Chai Lifeline provides laptops and video conferencing for children who are in hospitals undergoing treatments (or homebound chidren post-treatment) so that they can communicate with teachers and friends."

In other words, so they can schmooze.  - Mary Kathleen Flynn

Listen to David Coursey's January 2006 interview with Bobby Orbach on Gearlog Radio
See January 1992 story on 47th Street Photo from The New York Times