Building Multiple Ventures Successfully: Challenges of the Parallel Entrepreneur

Two startups are better than one?

Launching one startup is hard enough. Imagine juggling multiple early-stage companies at the same time. Certainly this would not be possible right? Well yes and no. There’s no written rule anywhere saying that it is not impossible — it really all depends on the founder and their approach towards entrepreneurship. These entrepreneurs are not called serial entrepreneurs per se but parallel entrepreneurs! According to the Oxford dictionary, the word ‘parallel’ refers to: “very similar or taking place at the same time”. In terms of entrepreneurship, launching different ventures at the same time and running them alongside each other is called parallel entrepreneurship or “side-hustling” as it is commonly referred to. For most, this already sounds like a very difficult endeavour and it is! Building multiple ventures at the same time is very time consuming and energy intensive. So why would anyone want to be a parallel entrepreneur?

Launching one startup is hard enough. Imagine juggling multiple early-stage companies at the same time. Certainly this would not be possible right? Well yes and no. There’s no written rule anywhere saying that it is not impossible — it really all depends on the founder and their approach towards entrepreneurship. These entrepreneurs are not called serial entrepreneurs per se but parallel entrepreneurs! According to the Oxford dictionary, the word ‘parallel’ refers to: “very similar or taking place at the same time”. In terms of entrepreneurship, launching different ventures at the same time and running them alongside each other is called parallel entrepreneurship or “side-hustling” as it is commonly referred to. For most, this already sounds like a very difficult endeavour and it is! Building multiple ventures at the same time is very time consuming and energy intensive. So why would anyone want to be a parallel entrepreneur?

Why do the impossible?

It’s hugely rewarding! For some, it is the drive and passion they have for entrepreneurship and wanting to do more in less time. Building a handful of successful businesses in five years au lieu of doing so in fifteen long years might seem more appealing. Some founders also feel more secure having multiple streams of income instead of just having one (e.g. a business or day job), which can be prone to changes due to the economy or (as we’ve just seen) a new pandemic for example. Others have an investor mindset from the start of their careers and want to build a portfolio of ventures which they can leverage to invest and/or build new ventures with. This means having strong entrepreneurship skills, experience and knowledge on how to build a venture, scale it and grow it successfully. In essence, this strategy follows investment portfolio theory as you are not investing all your time and resources into one venture but into multiple companies at the same time. This helps to spread risk and increase the chances of success. Angel investors that invest in a portfolio of startups and/or venture capital funds are often-times not impressed when a startup fails as it’s essentially “part of the game”.


All images in this article were sourced from Unsplash unless otherwise stated. This is an excerpt of a medium article. To stay in touch and receive our blog updates, please follow us on twitter.