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Gen Y: Here's Why You Should Never Get a Real Job

A frightening number of young entrepreneurs are writing books these days, and many of them are heavy on cheer leading ("if I can do it, so can you!") and far too light on reality checks.

Not so with Scott Gerber's Never Get a Real Job: How to Dump Your Boss, Build a Business and Not Go Broke (Wiley, Dec. 7, 2010). Full disclosure: Scott and I share The Entrepreneurial Generation blog on, a partnership I suggested after getting to know him and his work. He's started several companies, including a video production firm called Sizzle It, and he's a finger-wagging skeptic with attitude. It's occurred to me more than once that Scott is far less sanguine about his own generation than I am. I don't always agree with him, but he makes some pretty compelling, and often controversial, arguments. Here are some highlights from a recent conversation we had:

DF: The title of your book is "Never Get a Real Job," but I'd argue that there are plenty of young people out there who really should get a real job. Are you suggesting that there's an entrepreneur in everyone?
SG: And where do you suggest many of these young people get a "real" job in the first place? The Mall? Wal-Mart? Reality check: Millennials are no longer beneficiaries of the hand-out, resume-driven society of old. Boomers and Gen Xers need to stop training Gen Y to believe that the mantra of 'work hard, get good grades, go to school and get a job' that they were told to buy into, is alive and well. It's not -- it's dead -- and now it needs to be buried for good.

Fact: there are over 81 million young people unemployed worldwide. And this number does not account for the tens -- if not hundreds -- of millions more that are underemployed. It's becoming more and more apparent that in today's world, young people will need to create a job to keep a job. Millennials need to re-train themselves to become self-sufficiency experts capable of generating their own incomes. I truly believe everyone can become entrepreneurial and partner with individuals whose strengths fill in gaps and weaknesses. The key is for us to stop thinking "Facebook" and start thinking about practical, nuts-and-bolts, income-generating, on-the-ground businesses. When we finally turn that corner, Gen Y will truly become the most entrepreneurial generation in history.

DF: You took some heat on our blog when you suggested that "Be Passionate" is terrible advice for a young entrepreneur. How do you feel about optimism, a trait that's common among entrepreneurs?
SG: Much like passion can blind young, amateur entrepreneurs into thinking they have a business model when they don't, the same can be said for optimism. Optimism leads to phrases such as "it will all work out somehow" rather than realistic mindsets such as "how can we make this work at all costs." In many cases, the "the glass is half full" mentality blinds an entrepreneur from seeing all of the true challenges and issues that surround his business and decisions. In business, as in life, things don't always work out -- and almost never work out as planned. This is why I strongly believe that looking at every problem and business decision from a pessimistic point of view (e.g. asking yourself "why isn't this going to work?" versus thinking "this isn't going to fail") makes for a stronger, more effective business owner. This doesn't mean that your attitude needs to be that of Droopy Dog with a rain cloud following you around everywhere you go, but from a decision-making perspective, be a cautious pessimist instead of an eternal optimist and your business will be better as a result.

DF: How should young entrepreneurs go about determining if their "passion" can become a scalable business?
SG: The Hollywood-esque scene for most young entrepreneurs, where two guys are sitting at a bar, write their idea on a napkin and then proceed to build a gazillion dollar business is fiction -- at least for 99.9999% of us. In truth, every entrepreneur needs to have a gut-check moment. They shouldn't simply "believe" their idea will work as a business and get started. Rather, they need to prove it to themselves, poke holes in it, determine if it can generate real revenues -- as well as how fast those revenues will start rolling in -- and be able to defend their assumptions to their harshest critic. I know my detractors will mention "revolutionary" and "game-changing" companies such as Facebook and other Silicon Valley darlings that went on to raise millions, get acquired for billions, or go public. However, I would never advocate to young entrepreneurs, especially in our current economy, that jumping right into a business on passion alone is an advisable way to start a business.

DF: You've started several businesses. What's the worst mistake you ever made?
SG: I would have to say that it was not simplifying my business idea. My first venture (which I refer to in Never Get a "Real" Job as "the company that shalt not be named") became a total unmanageable mess because I tried to do too much in too many places too fast -- mostly without knowing exactly what I was doing at all. My original concept was simple and straightforward: To combine marketing and creative media to produce exciting and targeted solutions that generate results for our clients across all mediums.
Yet through egotism, irrational decision-making, and a lack of focus, my partners and I managed to turn that simple and profitable business into this nonsensical gobbledygook: Company X is the premier one-stop-shop venture management company, with a primary concentration on media-based startup enterprises. Our mission is to combine multichannel marketing, creative media, and innovative technology to offer startup enterprises exciting, inventive, and consumer-speci�c solutions that generate or enhance topline revenue growth. After conducting comprehensive due diligence, our Company will select clients with minimal �nancial resources and...
Blah. Blah. Blah. You get the idea. Absolute crap. My key to success now: Do what you know, know what you do and keep it simple, stupid. If you don't keep it simple, you're stupid.

DF: Have you ever had a "real" job?
Never. And I will always tell Gen Y to steer clear.

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