One of the best ways to overcome the chicken-or-the-egg problem the guy is hung up on, is by using the classic bowling pin strategy. You don't need to have huge advantages in your favor to make use of that.
eBay had a severe chicken or the egg problem when it started out. So did Craigslist. Almost anything that needs buyers and sellers simultaneously has that problem (or content suppliers and content consumers). Most people overcome it by knocking down one local pin to start with, and then knocking down more pins and more pins and more pins. Groupon is another more recent example, they didn't start out in 250 cities. Amazon.com didn't start out trying to sell everything, they sold a tiny selection of books. Facebook didn't try to conquer the world on day one, they started as an extraordinarily tiny 'app' for Harvard, and once they knocked over that bowling pin....
My favorite example: Plenty of Fish, the dating site. Started by a complete nobody, with almost no money, never took venture capital, and had no famous backers. He knocked down a pin in Canada and around his general area of Canada, to get started. Then it spread across the border to America and went international. He did all of that while stacked up against extreme competition in the dating scene, with monsters like Match & eHarmony that were a million times larger - he managed to find a space he could exist in (free), and focused locally with a product that could later spread globally.
SkyChalk perhaps should have just been for San Francisco, or insert market here, but had the ability to scale once they conquered that first market and proved their product.
eBay had a severe chicken or the egg problem when it started out. So did Craigslist. Almost anything that needs buyers and sellers simultaneously has that problem (or content suppliers and content consumers). Most people overcome it by knocking down one local pin to start with, and then knocking down more pins and more pins and more pins. Groupon is another more recent example, they didn't start out in 250 cities. Amazon.com didn't start out trying to sell everything, they sold a tiny selection of books. Facebook didn't try to conquer the world on day one, they started as an extraordinarily tiny 'app' for Harvard, and once they knocked over that bowling pin....
My favorite example: Plenty of Fish, the dating site. Started by a complete nobody, with almost no money, never took venture capital, and had no famous backers. He knocked down a pin in Canada and around his general area of Canada, to get started. Then it spread across the border to America and went international. He did all of that while stacked up against extreme competition in the dating scene, with monsters like Match & eHarmony that were a million times larger - he managed to find a space he could exist in (free), and focused locally with a product that could later spread globally.
SkyChalk perhaps should have just been for San Francisco, or insert market here, but had the ability to scale once they conquered that first market and proved their product.
The creators of SkyChalk have a lot to learn yet.