Portfolio Entrepreneurs

Type the phase ‘Portfolio Entrepreneur’ into Google

You’ll find a number of academic articles suggesting it’s a wonderful form of entrepreneurship – that results in greater success, less stress and better outcomes for both society and the entrepreneurs involved. It should be much encouraged, it seems. 

Yet there are few mentions beyond academia. The prevailing narrative within the startup ecosystem is that entrepreneurship requires singular focus. Doing multiple things in parallel, is foolish, distracting and likely to result in failure, or at very least worse outcomes. Ask a dozen entrepreneurs ‘in real life’ what a portfolio entrepreneur is, who they know that fits the mould, or how to become one, and you’ll be met by blank stares. 

In the last few weeks, I’ve watched coronavirus destroy startups, or reinforce them – regardless of the smarts, effort or strategic brilliance of their founders. No investor would invest in a single stock – but that’s what all entrepreneurs do. Plus listed companies are far, far less risky than startups. 

Two years ago, I wrote an article called ‘A Founder, Not a CEO’, which struck a chord amongst the entrepreneurs I shared it with. Its premise was that entrepreneurs are often not managers, or leaders but are usually forced to become them. I wondered if a lot of the issues – mental health, frustration and failure rates amongst startups – might be caused by shoehorning people into an unhelpful and inaccurate narrative that has been borne out of the survivorship bias of a few edge cases.

In my case, I’d burned out after 15 years of being the kind of entrepreneur people had told me to be, rather than the one I wanted to be, and collected enough savings and enough residual sleeplessness and stress to not want to do much for a while.

Two years provides plenty of perspective and recovery time to be able to double check whether an idea holds true.  For me, I’m doubly committed to becoming a ‘Founder, not a CEO’ – or, as I’ve since discovered it’s called – a portfolio entrepreneur. I have found my calling within a calling and am ready to begin (again). Yet despite my excitement, identifying my new tribe and wandering hand-in-hand off into the sunset hasn’t happened. The route ahead is hazy and less well-trodden than I’d hoped. 

According to that academic literature, 12-33% of entrepreneurs are ‘portfolio entrepreneurs’. So why the disconnect between the studies and reality? Where are they all? Why is it that there is a pent up desire for people to become portfolio entrepreneurs amongst both entrepreneurs,  governments and society, yet no one knows that it is an option, and it’s mostly discouraged? Why is it that the UK’s leading (or perhaps I should say highest profile) entrepreneur, Richard Branson, is a portfolio entrepreneur, (and in the US – the same is true of Elon Musk) yet entrepreneurs are taught to focus on single projects or at best serial projects, but encouraged to never get distracted by multiple things at the same time? Why are so many entrepreneurs forced into becoming CEOs, managers and leading their companies, when their skills are in creation and it’s painfully obvious they’ll make terrible leaders? 

Being an entrepreneur is hard enough without realising you’ve been doing it wrong and having to invent new bits. It’s been frustrating to unearth more questions than answers, but with the benefit of the harnessed mojo that comes from taking significant time off, I’ve enjoyed the process of digging in both practically and theoretically. 

In the next post, I’ll share some of the thoughts and theory of portfolio entrepreneurship. First up, I need your help – by sending me a tweet telling me about the portfolio entrepreneurs you know, so I can delve further into this research with better real-world examples.

6 thoughts on “Portfolio Entrepreneurs

  1. Great stuff Tom, some of this reminded me of Originals by Adam Grant, his exploration into different types of entrepreneurs and thinkers… success rates, etc.

    Maybe worth a look/read if you have not yet… also Justin Basini might be a good person to put on your list of Portfolio Entrepreneur, and possibly Jeremy Gutsche.

    Hope all is well out west!


  2. Thanks for the great read.

    I’ve used the distinction 0:1 founder vs 1:N founder previously which I think gets at the heart of your founder not CEO distinction.

    The zero to one stage of a company versus the one to N stage is a natural inflection point where different skillsets, personalities, and mentalities are required.

    I am personally very much a 0:1 founder or in the parlance of this article, a portfolio entrepreneur. 💯

  3. This is a very interesting take , after having been in two startup ventures , I burned out. The last one in particular was extremely stressful both in the business and coming out of it.

    The idea of portfolio entrepreneur is very intriguing, I’m probably heeding to call now where id like to be a manager rather than a founder. I’ve realized that I’m not very good at being a founder but someone who can establish very good structures and procedures for longevity.

    Self realisation plays such a huge part of being an entrepreneur. I suppose there are so many flavours of entrepreneurship, makes little sense to settle to the only version of being a founder entrepreneur

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