One entrepreneurial type loves the cool factor associated with being known as a serial entrepreneur. The badge of honor is starting a bunch of things, even if (and this is typically unspoken) many of them never come to fruition. A serial entrepreneur gains advantage in that each new project, effort, or company is positioned separately, which allows greater clarity in how they are marketed and discussed.
The other entrepreneurial type develops an umbrella business model and puts a variety of things underneath it. While an umbrella holder entrepreneur may not be doing quite as many different things as the serial entrepreneur, the volume of activity under the single umbrella makes it seem substantial. There are administrative advantages to this (i.e., you don't have to mess around with forming all those LLCs), but the messaging isn't nearly as clear since the umbrella has to morph to accommodate what might be disparate ventures.
I don't know that either one is generally better than the other, although I have my preferences. What's more important is to know which entrepreneur type best suits you, how you work, and how you want to talk about the work you do?
This is one you definitely have to decide for yourself. - Mike Brown
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