Two good articles in recent editions of The New York Times point to just how unpredictable and exciting a time we’re living in when it comes to the intersection of technology and commerce. First up is the tale of Pebble, the latest Kickstarter poster child to turn an entrepreneurial dream into millions of dollars of pre-production capital upon which to launch a business.

Pebble is a smartwatch conceived by some folks familiar with the watch industry and its nascent smarwatch offshoots. Eric Migicovsky, a 25-year-old engineer central to the Pebble team, said they tried to raise money via venture capitalists but none would bite on a hardware project. So Pebble turned to Kickstarter in hopes of raising $100,000 via pre-orders of a $99 version of the watch. As of my writing this, they’re up to $7.3 million raised with 18 days before funding closes.

Jenna Wortham details Pebble’s story as well as that of Kickstarter, which she says, “began as a way for people to raise money for quirky projects like pop-up wedding chapels,” but “quickly expanded to include video game production, feature films and innovative new gadgets.” We’ve written about more than one Kickstarter-started gadget on these pages, including LunaTik’s iPod nano watchbands and the Brydge iPad keyboard case. LunaTik set a then-Kickstarter record by raising just shy of one million dollars, while Brydge has already more than tripled its goal of $90,000, racking up $340,000 in pre-sales with more than a month of funding still to go.

Second is Nick Bilton – one of my favorite tech writers – writing about the insanity that is Silicon Valley circa 2012. Get this: Start-ups are reporting on investors telling them to avoid earning money at all costs, or at least to hide any sales they might be making. Why? Actual revenues could endanger made-up valuations of the sort that make enormous acquisitions possible:

“It serves the interest of the investors who can come up with whatever valuation they want when there are no revenues,” explained Paul Kedrosky, a venture investor and entrepreneur. “Once there is no revenue, there is no science, and it all just becomes finger in the wind valuations.”

On the one hand, I get it. As Bilton’s article deftly explains, the Internet economy is (as it was in the pre-2000 bubble) all about creating and selling perceived value; it’s all just a global game of high-stakes poker. On the other hand, if that’s not a sure sign that some people have no place to live while others get to pay for their dinner checks with Monopoly money, I don’t know what is.

Taken as a pair, these two tales tell an interesting story about the Internet’s continued impact on business, investments and dreams of entrepreneurship. On the one hand, the “old guard” of Silicon Valley continues to rule the world of big business online, finding billion dollar exits for companies yet to have earned a single dollar in revenue. On the other hand, the new darling on the scene is crowdfunding, which looks more and more like centralized pre-ordering for trendy gadgets all the time. The former is all about the eternal quest to find new ways to monetize online eyeballs, while the latter instead flashes quirky and innovative new gadget ideas in front of those eyeballs in hopes of making a good old fashioned (pre) sale. Either way you look at it though, one thing’s for certain: There’s still plenty of money to be made and lost in the Wild West of the Web.

[Source: NYT (1), (2)]