Serial Entrepreneurship 101

September 13, 2018

Entrepreneurship comes in many different forms.
Some entrepreneurs seek to start one business, with a primary goal of growing that business to the point of global expansion and ever-higher profits. Other entrepreneurs seek social businesses, with a goal to change the world while generating a profit for themselves. Then there is another type of entrepreneurship, one that may not be as well known as the options above, but which can offer a different kind of business life: serial entrepreneurship.
What is serial entrepreneurship?
Serial entrepreneurship involves a person starting a business, growing it to a point where it is successful, and then starting another business. This pattern can repeat over and over again, with many serial entrepreneurs starting a number of businesses throughout their professional careers.
What type of businesses do serial entrepreneurs begin?
Anything and everything; some serial entrepreneurs focus on an individual niche, some prefer to branch out and explore other areas. The same variance is found in the types of business models serial entrepreneurs engage with: some may choose to grow businesses in and of themselves; others will work with franchise consultants to create an opportunity they can sell to others; while some will opt for sociopreneurship and non-profit organizations – the options genuinely are endless. There’s no specific route that a serial entrepreneur will follow and, in fact, this is part of the attraction: serial entrepreneurs like to do things differently, mix things up, so they may explore a variety of different business types and niches over the course of their career.
Is serial entrepreneurship beneficial?
Serial entrepreneurship is a great choice if you like the excitement of starting businesses, but are less enthralled by the day-to-day running of an established business. Some people are natural visionaries; they love to start a new venture, but cannot settle into that venture being their full-time career – serial entrepreneurship is a great way to keep life interesting for you, while still allowing you to explore the reaches of your entrepreneurial spirit.
Is serial entrepreneurship risky?
In some ways, yes: there is never a guarantee that a serial entrepreneur’s next business will be a successful one. It’s all-too-easy to be tempted to borrow money from one business to keep another afloat, which can lead to a “house of cards” being created, with each business depending on another rather than being financially independent entities.
However, serial entrepreneurship is no more risky than standard entrepreneurship. You’ll likely be far busier if you are involved with multiple businesses, which may have an impact on your work/life balance, but provided each company has its own financial and legal identity, the risks are no more substantial than with a single business.
How do serial entrepreneurs manage multiple businesses?
Serial entrepreneurs have a number of options for managing their responsibilities to different businesses. Some serial entrepreneurs prefer to keep an eye on each business, though they will appoint a management team to take care of the day-to-day running of the company. Others won’t remain involved in a business for long; they will sell and move onto their next venture as soon as they can find a willing buyer. Again, there’s no right or wrong way to approach serial entrepreneurship; it’s very much a path that involves charting your own course through your business dealings.
What are the signs serial entrepreneurship might work for you?

  • You find the idea of starting a business exciting, but find actually running a business rather tiresome.
  • You have a number of business ideas you believe to be viable and would like to explore.
  • The ideas, as mentioned above, span a number of different niches, so it would be difficult to combine them into a single company. For example, you want to start a video production company, but you also like the idea of starting a medical supplies company – these niches are so different, it would be next-to-impossible to integrate them into a single enterprise.
  • You like the idea of exploring different business models, such as franchising and sociopreneurship, which is very difficult – if not impossible – to achieve with a single company.

In conclusion
Serial entrepreneurship is an unusual course for an entrepreneur to take, but it can also be hugely rewarding. If you suspect it may be the route you wish to take in business, your professional life will be busy, hectic, and often stressful – but it may also allow you to make the most of your innate entrepreneurial spirit, and be able to achieve your goals all the faster.

Mark Asquith

That British podcast guy, Mark is co-founder of Captivate.fm, the world's only growth-oriented podcast host. A Harvard, TEDx, Podcast Movement and Podfest speaker (amongst many more!), he's a wildly approachable Brit and Star Wars/DC Comics geek.

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