The 2010s was the decade of the Entrepreneur.
The 2020s will be the decade of the Investor.
“It’s the wrong way to think, but the right way to win”
Paul Arden
Contrarian. And right?
There’s a particular feeling I get when I’m doing the opposite of what’s expected. It’s not adrenaline, not excitement, or recklessness — but I feel almost… giddy.
I’ve had this feeling when investing in an obscure startup that some very smart people have told me won’t work. They’re saying, “Don’t do it”, but I do.
Interestingly it has also happened when being pushed to do something I don’t want to do. Not for everything, but for the stuff that matters I just know I can be that little bit more stubborn than they are — the more they push, the less I’d give in1.
This genuine ‘giddy’ feeling is unusual, quite rare and perhaps it’ll trip me up sometime, but with the right framework around it it’s an instinct I’ve learned to trust.
This just doesn’t make sense
Take Unplugged. In early 2020 Hector and Ben started a startup that offers cabins for people to stay in and lock away their phones to disconnect from tech. In a world obsessed with AI, SaaS, and getting tech-tax-breaks2, backing a startup that’s anti-tech seemed crazy to many. “It’s too niche”, they’d say, “It just won’t scale.”
I invested when Unplugged had precisely zero cabins and I did that because I saw something others didn’t. A small number of people loved the idea.
Not just liked it — loved it. Those people loved their phones, loved the dopamine hit of a mention or a reply (don’t we all?). But they also desperately wanted to be off-line — they knew it would be good for them and Unplugged was the ‘excuse’ they needed to go and do a bit of digital detoxing.
The filter
I don’t think it’s about being contrarian for the sake of it. That’s just empty posturing. Sure, this “I’ve found something special” giddiness comes when I see something that’s under-appreciated but, critically, there also has to be evidence that it matters.
Early on, I mistook wanting the feeling for actually having it. I’d convince myself I was onto something, but now I have systems3 in place to make sure it’s the real deal and not just superficial excitement4.
You too?
So, when someone pushes back hard, or tells you something doesn’t make sense, will you see that as a signal to lean in?
Have you ever felt the same giddy excitement? That moment when everyone else says ‘no’, but you think you might be right?
Or am I alone in getting this ‘giddy’ feeling?
If you do, what does it tell you about what you really believe in?
In other news
🍻 The 9others Summer Party will be on Thursday 10th July in London. This is when everyone who has been to a meal with 9others, plus other good folks, to meet and help each other out. Details and signup here.
🥐 Thanks to Ollie and Barry for inviting me to a terrific breakfast they hosted last week in Farringdon (complete with coffee, croissants and jazz from a lovely Steinway).
📞 I occasionally do consulting work where I really dig into what makes people, businesses or investing tick. I have some availability until the summer so if you’re keen to get more dedicated time with me you can see what I offer startups, corporates and investors here. Just hit reply.
More from me?
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#CapitalAtRisk
I remember this also happening on a stag night in Edinburgh… someone pushing me to have whisky (no thanks), and the more they pushed, the more I enjoyed being pushed.
Yeah, this sort of thing has been on my mind again.
AKA: Frameworks, tools, mental models.
And — yet again — this is where my Golden Rule of, “If I meet you for the first time and you are raising investment then I will not invest in this round” comes in. That simple to implement, but incredibly powerful, rule helps any initial excitement calm down and genuine giddiness surface (if it’s really there).