NEW YORK (TheStreet) -- In September of 1999, I moved to San Francisco and, for about two years, worked for a company that sells sports hospitality packages to corporations. In the shell of a nut, my job was to cold call Presidents, CEOs and VPs of Sales at companies -- from the Fortune 500 to recent IPOs -- and pitch them on ticket and hospitality packages for themselves and their clients to events ranging from the Masters to the Super Bowl. The size of a typical deal -- anywhere from $10,000 to more than $100,000.
And, in large enough numbers to register, these guys spent money like drunken sailors. Usually their company's money, but, on occasion, their own fresh IPO proceeds.
For example, there was a guy named Woody Shackleton, VP of Sales at Foundry Networks, established in 1996, public in 1999 and sold to Brocade Communications (BRCD) in 2008. Shackleton, now on the Michael J. Fox Foundation board, cashed in on what was, at the time, the biggest IPO debut ever. Not only did he spend money with me to send his clients to events, he took about 15 seconds to decide on a $30,000 purchase to attend the Major League Baseball All-Star Game in Seattle with his kid.
Looking back, that $30,000 splurge seems like nothing when you consider I witnessed it as a 25-year old. Plus, so many stock option-fueled and tech-related obscenities were happening at the time and have happened since. For goodness sake, just a few days ago we had an app that says "Yo" receive more than a million dollars in funding. Not only did it receive funding, but a gaggle of obnoxious venture capitalists and "entrepreneurs" defended the insanity.
The defenses of "Yo" triggered an uneasy feeling inside of me. And it's a sense similar to the one I had back in 1999-2000 when it didn't take a whole ton of persuasion -- just a little persistent aggressiveness -- to get IPO millionaires to spend their new-found riches on over-priced hospitality. That willingness to spend came crashing down with the stock market, particularly the tech sector.
After the implosion, you couldn't get companies who routinely dropped six figures on sporting events to spend a dime. Closing a $10,000-$15,000 deal was like pulling teeth. And I'm talking about from IPOs such as Foundry Networks to huge divisions within companies such as Nokia (NOK) (Nokia was still a pretty big deal in 2000).
While I have been reluctant to say we're about to see a tech bubble 2.0 burst, the "Yo" thing got me thinking a lot about 1999-2000 and what we might be on the verge of. Specifically, I wondered why guys such as noted venture capitalist Marc Andreessen feel the need to make lofty defenses of Yo. I came to the preliminary conclusion that it's not necessarily "Yo" he was defending; rather, even if he doesn't know it, he's attempting to keep the party live. Attaching some form of legitimacy to "Yo" helps prop up the larger tech scene, which is largely comprised of venture capitalists like Andreessen and founders moving money from one place to another and executives getting rich off of stock options regardless of how well their companies do or do not do.
If a voice such as Andreessen follows the pessimistic crowd on "Yo," he naturally adds fuel to the argument that the "Yo" funding is a sign of things really getting out of hand again. But if he comes up with some cockamamie notion that "Yo" is something we should not blow off -- that it is and might even remain somehow significant -- than he, even if subconsciously, perpetuates the sentiment that all is well in the broad tech sector.
One of "Yo's" investors argued that the app is worth his cash simply because it has a massive user base and engagement. That defense keeps alive the idea that you don't need to build a businesses anymore. Your ideas -- even if they never turn into companies that turn profits -- are good enough. Sort of like Twitter (TWTR) -- Jack Dorsey's great idea that Dick Costolo runs around acting like he can monetize when, in reality, he's as clueless as the rest of us.
Lots of columnists like to point to charts to prove the bubble's about to burst. Or that there's even a bubble in the first place. Many misguidedly use Amazon.com (AMZN) -- one of the actual survivors from the 1999-2000 crash -- as their main support. All I'm telling you is things don't feel right. We've gotten ahead of ourselves. And today's millionaires and billionaires seem, at least to me, more arrogant than the ones I dealt with 15 years ago. That's a recipe for something scary.
--Written by Rocco Pendola in Santa Monica, Calif.