Philosophy crosses over into all walks of life and when put into practice, it enables the practitioner to create positive change in their lives and the lives of others. This has certainly been the case for Andrew McConnell, the CEO of Rented and author of Get Out of My Head: Creating Modern Clarity With Stoic Wisdom.
While Stoicism has been an influential philosophy in his life, McConnell doesn’t limit himself to only one train of thought, preferring to cherry-pick from different wisdom traditions. In this interview, we dive into how that shaped his journey as an entrepreneur, building a business with a philosophical mindset and being a parent.
On your entrepreneurial journey, what lessons has Stoicism and other schools of thought taught you?
I think Stoicism and philosophy in general teach the difference between theory and practice. So the armchair quarterback sitting and drawing up the best play. Well, if you’re not in the field, it doesn’t matter and the same goes for philosophy. You can be saying all the right things, but if you’re not living that life you talk about then it’s meaningless.
So, I think a big part of entrepreneurship is about going out and doing, rather than being stuck in your head. There’s another piece to that too in that time is our most finite resource and Stoicism teaches about what we can control and what we can’t. It’s being able to filter down the activities that you dedicate your time to.
Because if you’re spending all your time worrying about, or trying to work on things that you don’t impact, versus what you really do control, you’re far less effective, which carries over to your mental state.
Agreed. The conversation of Stoicism and time makes me think of Seneca and his quote about suffering more in imagination than in reality.
Now, given your work with Rented and everything you’ve done in the property industry I’m interested to hear what your definition of a home is. Because you’ve made a great analogy in other interviews about the idea of mind ownership instead of being tenants in our own heads.
This whole concept of ownership and what we own is fascinating. Because we can say we own our bodies, but historically that wasn’t always the case when you think of slavery. But in a modern context, viruses, bacteria and mental illness can also take our bodies away from us.
Then there are physical goods that we say we own in a legally prescribed world where our goods are protected. But those goods can be taken from us too. The one thing you can truly own is your mind and mental state.
Yet we spend so much time giving our minds away to other people and then we rent back the pieces. You quoted Seneca and another quote that comes to my mind from him is that we’re the toughest misers with our physical possessions and yet with our mind we just give it away. We pave the way to give it away to people who don’t even know they have it.
So, it’s about distilling down the idea of what we own, especially with our most precious resources and assets.
You’ve mentioned Seneca, but is there any other specific philosophers that inspire you?
With the publisher for my book Get Out of My Head: Creating Modern Clarity With Stoic Wisdom, I had the debate of whether we put Stoic in the title because I’m not just influenced by Stoicism. I think Lao Tzu with Taoisom and Buddha were wise in their thinking too and get back to the same essence of ancient wisdom.
Rather than cheering for a team or going with a single philosopher, I prefer identifying the commonalities of the human essence that is true. If you keep seeing the same ideas pop up over thousands of years across different cultures, then there must be something to them.
Ideas like being satisfied with what you already have, not chasing obsessively after physical wealth etc. Seeing how they all fit together like a puzzle piece of core truths is worthwhile.
In a former life, you were on the USA Open Water Swimming National team and there must have been a lot of discipline you needed to cultivate.
What sort of lessons did being an athlete teach you about entrepreneurship?
A friend of mine, who’s a very good swimmer once told me “there are two kinds of swimmers in the world. Those with talent and those who’re distance swimmers.” It’s the idea that those who don’t have a natural talent are willing to go the distance because so few people are willing to put in the work.
And if there are areas that are highly competitive and are easy for other people, but not necessarily for you, being willing to put in the work will make you stand apart. That’s when I went from swimming shorter distances to longer distances, like five hundred, to the mile, to 10ks and 25ks. You get to a world that’s smaller than the one you knew before and that allows you to be more driven in what you do.
I see a parallel there with my first business in the vacation rental industry. While I didn’t have any background in that sector, I had knowledge of data analysis. So, when I was started out I’d go and do all this data analysis and revise it.
Within the first year, I was speaking at the vacation rental World Summit as the trends expert for the industry. Within two years, I was the trends expert for the Vacation Rental Management Association. I wrote their trend updates because no one else was doing the work.
The lesson here is that it’s okay for something not to come naturally or easy. In fact, if it isn’t easy it becomes more accessible if you’re willing to put in the work.
That’s a great perspective and I feel that being willing to put in the work comes from developing the right habits.
It reminds me of another interview you did when you said you had a mechanism called a two by two matrix that lets you live in a certain space for a limited amount of time to do the things you love.
What kind of habits do you find you’re able to cultivate in that space?
The two by two matrix comes from my consulting background. It’s on one axis and you have the things that you’re not good at and the things you’re great at. That’s the spectrum there and you also have the things you don’t enjoy all the way up to the things you do enjoy.
I find my days are more enjoyable and fulfilling when I spend my time on the things I’m really good at. So each quarter, I go through the exercise of asking myself what my unique skill set is and asking my team and network where I excel vs where I’m falling short.
I score those answers and audit my time based on the prior 3 – 12 months to see what activities got me energised and what sapped my motivation. This helps me redefine my schedule and make sure I’m spending my time in the top box of doing the things I enjoy and that I’m good at.
It’s not a one-and-done exercise because what we enjoy can change over time. And then we can change what we’re good at by investing our resources into improving what we’re not good at yet.
That chimes well with the concept of eudaimonia or flourishing. It’s something I try to apply in my own life and be discerning with those ‘I’m okay with this being enough’ moments and trying to have more self-awareness.
How do you reach those moments for yourself, whether professionally or personally?
I try similar practices daily. So, whether it’s meditation, swimming or playing with my daughter, I take a moment to think that no matter what else is going on or what I had, this is where I want to be in the moment. These are the things I value.
Then it becomes less about chasing what you don’t have and realising that so long as you’re crafting the day around what you do have, you can get the most out of every moment.
Speaking of your role as a father, I’d read your Forbes article about being an entrepreneurial parent and teaching your daughter the value of choosing her own path.
What are some takeaways you’d suggest for parents who’re trying to raise their own children with an entrepreneurial mindset?
The point of that article was about looking at children of entrepreneurs and how they were more likely to be entrepreneurs themselves. Then they went and looked at adopted children and compared both sides. But it wasn’t genetic. It was all nurture and not nature.
Instead of saying I want to steer my daughter into this path, it made me realise that very few people stop to ask themselves what they actually want. They follow the herd of wanting a new car or a bigger house. But even the people who stop to ask that question don’t go to the next step of asking why they want something.
So, in the research about the nature vs nurture entrepreneurship debate, kids were more likely to go into entrepreneurship and I don’t know if that’s a good or bad thing. The only reason they had gone down that path was because it was what they had seen and the environment they had grown up in.
You’re never going to be able to identify what it is that you really want to pursue if you don’t get to that next level of asking why. So, I’m not trying to encourage my daughter to be an entrepreneur.
I’d rather encourage her to ask the question of what she wants and why. It’s asking the question ‘do I want it for me or was it because my parents modelled that behaviour for me?’
I’m interested to hear your opinion on rhetoric as a way to steer people towards causes with substance and how it can be used ethically among CEOs and leaders.
Rhetoric can be used for good or ill. It’s much better for it to be used for good because it can tie into what people already value and to their aspirations. Bill Clinton said something like you can have good politics or good policy, but you can’t have good governance without both.
The same applies with having great ideas and rhetoric, but you won’t get good execution without both. You need the ideas for inspiring people and you need to be able to talk about them in a way that’s understood and resonates with a community for them to act.
What’s your opinion on knowledge and wisdom? To me, knowledge is something you learn and wisdom is applying it.
I think that is well put. You can accumulate knowledge like a stack of pebbles. But what’s the point of knowledge if it’s not in service to anything? That thought inspired me to start writing.
Reading is to obtain knowledge and in some ways is a selfish act unless you use it to benefit others. That could be just how you live or teach. It could be how you repackage and tie those ideas into a podcast or the written form.
That is where knowledge becomes wisdom because you’re living to impact others for the better.
Tying into the idea of wisdom, Socrates is a great example and I do prescribe to his perspective of the unexamined life isn’t worth living.
What’re your thoughts on the unexamined business isn’t worth building?
Our lives are just the sum of our days. Our days are a sum of what we’re doing and what we’re thinking about during that time. If a business is only out there to make money then the question becomes for everyone involved is there any fufillment there?
You don’t have to be a social justice warrior to have a sense of purpose in a business, but you have to ask yourself why anything of what you’re doing matters. Because all reaching for more money does is make you chase after more and there isn’t any true fulfillment.
It’s coming to the realisation that all that pressure you felt about reaching that one single metric of making more money was never the point. It was finding outer effectiveness and inner peace.
It’s the same point I made about having kids and being entrepreneurial. It’s asking what you want and why you want it.
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