Dude, Where’s My Startup?

Travis Siflinger, now 25, was a first-year college student when he decided on a change of plan: Instead of learning about business, he’d skip that step and start his own business. To Siflinger, it made perfect sense. After all, he’d grown up being told that anything is possible — by his parents, his teachers, his friends … by just about everybody.

“You watch MTV and all you see are guys rapping about cars and money,” he says. “You go online and you see Internet companies started by people my age getting sold for hundreds of millions of dollars. It’s hard to watch that and not be inspired, not believe that you can do it too.”

Siflinger learned otherwise. After four years, Dirt Alliance, his promotions company focused on the off-road motorsports market, ran into the economic downturn and sputtered to a halt. In his mid-twenties Siflinger was broke, living with his parents, and figuring out his next move.

He is also now rethinking what it means to be part of what many are calling the most entrepreneurial generation of all time — a generation that exudes optimism and confidence, a generation of independent thinkers who embrace multiple forms of self-expression, including tattoos, piercings, and social media. Siflinger’s peers believe their natural affinity for technology makes them distinct and gives them a unique ability to think in new ways and develop breakthrough ideas.

If this all sounds too good to true, it is, says Jean Twenge, a psychology professor at San Diego State University and author of Generation Me and The Narcissism Epidemic.

Many of the factors that have made Millennials so self-assured (or spoiled, if you wish) may not serve them so well when it comes to starting an actual business, says Twenge. Growing up, they have been overscheduled with activities and escorted from practice to practice. Not only have they been told they’re great at what they do, they have been told exactly what to do.

“There’s lots of anecdotal evidence that if you leave them on their own, they don’t know what to do,” says Twenge. “I’ve seen it myself over the last 15 years of teaching. But when you start your own business, there is no road map. That’s something that works against this generation.”

Scott Gerber, author of Never Get a Real Job, a new book that chronicles the highs and lows of young entrepreneurs, agrees. “The reason our generation is doomed to fail if it doesn’t shape up is because we are getting into entrepreneurship for the wrong reasons,” says the 26-year-old author. “We think it’s a sexy and glamorous way to gain the spotlight and pay the bills. In fact, nothing could be further from the truth. But nobody removed the wool from our eyes and said, ‘OK, here’s how the world really works.'”

Another serious obstacle to Millennials is their tech-driven attention-deficit disorder and the way this affects their approach to daily tasks and objectives, says Kevin Melgaard, the 29-year-old founder of Beyond Credentials, a job site that focuses exclusively on Millennials. “We can get online to check our e-mail and favorite blog but end up two hours later reading about something completely unrelated and not even remembering how we got there,” he says. “It’s the same with ideas and executing them.”

Not only does this generation have unrealistic goals, critics say, they’re unwilling to work hard to accomplish their objectives. In fact, Millennials are the only generation that doesn’t cite “work ethic” as one of their principal claims to distinctiveness, according to a new Pew Research report titled “Millennials: A Portrait of Generation Next.” 

Yet it’s also true that members of Gen-Y have worked hard, very hard, and been responsible for some impressive successes. “Our generation is responsible for starting some of the most innovative companies around today,” says Dan Sartin, the 26-year-old cofounder of The Engine Is Red, a marketing and advertising agency. “Companies like Google, YouTube, Twitter, Facebook, and WordPress were started and staffed by mostly Gen Y-ers.”

But this oft-cited handful of ultrasuccessful Internet entrepreneurs only fuels the delusional optimism, argues Scott Gerber. “Our generation assumes that all we have to do is build a website, traffic will come and we’ll be sitting on the beach by 30,” he says. “That’s the way the media has portrayed it. But people like Mark Zuckerberg of Facebook are one in a billion.”

Beyond the differing viewpoints of those like Sartin and Gerber, the inarguable reality is that this generation has no choice but to be more entrepreneurial. Entry level jobs are being shipped overseas, companies have dramatically altered their hiring practices, and gold watches are a thing of the past. “We do need to be more self-sufficient or we’ll find ourselves in this never-ending cycle of just sitting at home and sending out résumés,” Gerber says.

His solution: Forget about creating the next Facebook, forget about being famous, forget about making the Forbes billionaire list. Simply start a real business with a proven revenue model that can earn you real money, even if it doesn’t make you a household name.

Siflinger, for his part, is taking that advice to heart. He just raised $10,000 to launch a new underwear company called Br4ss (pronounced “Brass”). “I guess I could go out and get a regular job, but that’s just not the way my brain is wired,” he says. “Besides, everybody needs underwear.”