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The key considerations for would-be serial entrepreneurs.

Serial entrepreneurs, like serial daters, come in many different stripes. Some are serial monogamists, exclusively entertaining one startup at a time. These people devote their time and attention to the one who’s caught their eye, moving on only when they’ve stopped getting anything from the investment.

Others, however, like to juggle multiple interests. These entrepreneurs have passions pulling them to Germany, Taiwan, and India; they’re intrigued by the possibilities inherent in mobile marketing, gaming, and trading. Their varied interests consume them all at once.

But does this latter group accomplish anything? They do if they court their ventures properly.

What it Takes for Serial Entrepreneurship to Work
Every entrepreneur has to remember one thing: Entrepreneurship works within limits. We have a lot of good ideas thrown at us, but we simply can’t do everything. We must carefully consider the best of the bunch, investigating and analyzing our options to ensure we’re putting our money and effort behind ventures that have true potential.

Here are key indicators that simultaneous serial entrepreneurship is worth considering:

  • Time: Can you dedicate enough time and attention to each interest? How long will these ventures take? Are you remodeling a building in a handful of weeks, or are you constructing a resort over two decades?
  • Money: Do you have enough cash to support the growth of your interests in the short and long run? Businesses can be as high-maintenance, or low-maintenance, as significant others.
  • Location: Does one require you to be in Alaska, while the other demands you be in Australia the next day?
  • People: Who’s involved in your situation? Do you have partners polluting–or supporting–your relationships? Do you have the right people to handle the workload and supply talent?
  • Sequence: Is one development already underway, or are you jumping into bed with both from day one?
  • Experience: What experience do you have as an entrepreneur? What kind of knowledge do you have in the field you’re adding?

Beyond this, of course, there’s the fact that the nature of the ventures you’re considering impacts your success. It’s much easier–on the wallet, the schedule, and the brain–to undertake two startups that work hand-in-hand with each other than to invest in two divergent businesses.

Businesses that dovetail with existing offers and services make sense on many levels. In any economy, but particularly a rough one, it’s difficult for businesses to grow or find traction in order to establish a brand that can keep pace in the marketplace. Developing complementary ventures allows entrepreneurs to cross-promote their ventures, reducing marketing expenses and increasing the sheer number of customers and opportunities for upselling.

Such a structure also lowers expenses and maximizes the bottom line. While two wildly different ventures would have their own CEOs–and, therefore, double the salaries–related businesses can be run by a single entrepreneur without difficulty and with enhanced strategy. (Of course, paying yourself double negates this savings!)

There are more entrepreneurs willing to brave the shark-infested waters of simultaneous serial entrepreneurship than ever before. Dreama Lee, for example, is the president at Efficient Enterprises, which also owns Intern Profits,,, and Each of these companies focuses on investments of some sort, whether for interns aspiring to be entrepreneurs or homeowners facing foreclosure. The common investment thread surely helps Lee.

Christina Norsig, CEO and founder of and (Norsig Enterprises LLC), is a luxury tabletop e-tailer, as well as a real estate entrepreneur who helps retailers shop for temporary stores. Her own experience as a retailer enhances her ability to help other retailers find outlets for their wares.

My company, too, has invested in multiple ventures at once. Our core eBook business,, has been established for a while; after our success with that company, we launched, an online community that assists writers composing eBooks. These sites are serving different needs for the same community, readers and would-be writers, so our experience with one feeds the other.

Sidestepping Landmines
Make no mistake: There are wrong ways to dive into serial entrepreneurship. One startup founder I knew would throw anything against a wall to see what stuck. Any venture that sounded good in basic theory earned a chunk of his time and his hard-earned cash. He met with success a few times, but he tried to take on too much, ran himself ragged, and eventually saw everything go bust. When you only have two hands, it’s hard to put them in three cookie jars at once. There is a limit, and you need to establish what that is.

As the celebrity chefs on The Food Network note, a restaurant with a limited menu of high-quality options will always be more successful than one with countless pages of unappetizing food. This rang true for my company, too: We once ran multiple websites in different niches, completely unrelated to one another. We sold a number of them, and while we run just as many today, they’re all within a single industry. We know this industry well enough that we can apply our knowledge to new ventures and duplicate success, rather than attempt to become experts in conflicting fields.

Take a hard look at the opportunities that have caught your eye thus far. Do you have a type? Do you tend to gravitate toward specific interests? Just like a serial dater who prefers blondes, you may find yourself striking gold with just your mobile marketing apps. Stick with what you know and find ways to meet the needs of new and existing audiences. By courting your ventures properly, you have a much stronger chance of remaining in a long-term relationship with them.