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rational vc .com
Learn from history's Greatest Minds — and find Timeless ideas you can apply to business and life.
Iman Olya
June 2024
After the biggest podcast episode in our history on The Black Swan, our brand has grown rapidly. Cyrus and I have been inundated with support and suggestions for more content. We have tinkered a lot over the years, and we are starting to see our barbelled approach to a shot at Extremistan bearing fruit. Taleb himself gave us a shout-out and we’ve managed to secure some Incerto nerds for an upcoming episode too. Watch this space.
More importantly, our long-awaited 4-hour mammoth podcast on Nassim Taleb’s seminal work ‘Antifragile’ is now live!
So much effort and love went into this episode. We studied the book multiple times. We dissected as many of Taleb’s talks and interviews we could find on Antifragile. We also read c.100 secondary sources and reviews of the book. Bringing all this together with our interpretations and experiences, we present you Rational VC’s take on Nassim Taleb’s masterpiece ‘Antifragile’.
As with all of Taleb’s books, they are to be studied, not read. We revisit them yearly. The Incerto Series is a masterpiece, hence why its philosophies and teachings have shaped our brand since inception many years ago (along with Poor Charlie’s Almanack).
Without further ado, let’s get into the mini essay that accompanies this megasode…
Relief, serenity and quiet confidence. Once I clicked the button to terminate my 8 years of employment at Strategy&, I knew I had made a decision that would finally enable me to focus. The act itself was anticlimactic: pressing a series of confusing switches on the ungodly Workday platform designed to manage human cattle. But the symbolism was strong: I was freed from the shackles of stress and mental preoccupation. I could now go all in on the one thing: Rational VC. I had skin in my own game.
But you see, that’s not how focus works. In fact, I spent the last 6-month sabbatical unlearning how to work relentlessly. I learnt to flâneur. And it worked.
“Rational flâneur (or just flâneur): Someone who, unlike a tourist, makes a decision opportunistically at every step to revise his schedule (or his destination) so he can imbibe things based on new information obtained. In research and entrepreneurship, being a flâneur is called ‘looking for optionality.’ A non-narrative approach to life.”
– Nassim Taleb, Antifragile
Stepping into uncharted territory
Just before you leave a corporate career, you feel the seeds you’ve sown and the “reputation” you’ve cultivated are about to be washed away. You feel your peers and your seniors are going to judge you. You feel you need to explain to every one of your “stakeholders” why you’re leaving. You need to make your decision fit into a neat Platonic Procrustean Bed.
But once you’re out the door, you realise how much unnecessary effort you placed into creating narratives so as not to upset your carefully curated relationships. Had I been salary-jumping to a Consulting competitor, my seniors may have been irked. But given my new, unorthodox path, most just wished me well, without truly understanding why I’d throw away a “stable” career to pursue Rational VC.
What they did not see was my pursuit of optionality.
As we learn in Taleb’s “Antifragile”, wealth is nothing without optionality. You can be a billionaire but what’s the bloody point if you have a packed calendar and a million shareholders to keep happy?
You can be a Partner at a prestigious Consultancy but what’s the point if you have to play political games with 899 other Partners and are always “on call”?
I learnt a great deal from my seniors in Consulting. I have huge respect for what they’ve achieved. They embody the epitome of how to build and leverage relationships (both inside the firms they operate and with the clients they sell to). They sacrifice a great deal to be where they are. And not least, they are always switched on and genuinely intellectual. In fact, I not only learnt from them how to tackle any problem, but also how to have confidence in doing so.
There was a problem I couldn’t solve though: I did not want to play that game anymore.
What I sought
Compare the life of Corporate Clive, a senior in Corporatistan to Fat Tony or say, an Iranian uncle with hairy knuckles and a belly that doubles as a stand for his iPhone when he watches political videos on his WhatsApp group chat with fellow self-made millionaire buddies. What you’ll innately realise is Fat Tony, or ‘Tehran Tony’ as we’ll call our fat uncle, has freedom beyond what is afforded to him by money. He naps when he wants, he plays Takhte Nard (Backgammon) when he wants, he eats copious amounts of Koobideh when he wants (even though his son, who of course, is a Doctor, tells him not to, for fear of an impending heart attack).
“ “F*** you money” - a sum large enough to get most, if not all, of the advantages of wealth (the most important one being independence and the ability to only occupy your mind with matters that interest you) but not its side effects, such as having to attend a black-tie charity event.”
– Nassim Taleb, Antifragile
Fat and Tehran Tony both have “F*** you money”. They live a different life to Corporate Clive. Although Clive seeks intellectual problems to solve, he does not choose those problems. They’re handed to him via RfPs from large corporations who want to shift the brunt of their complex, boring, untouched workload to overpriced 22 year-old grads.
Corporate Clive puts everything into his job. He makes very good money and if he gets lucky (market conditions, overall sales of the business and generosity of his seniors permitting) makes a big bonus every year. He works crazy hours on PowerPoints and spreadsheets, usually formatting and correcting errors his work-from-home 22-year-old juniors failed to pick up. He sits on 6-8 hours of calls when working from home, or jumps from meeting to meeting while in the office (on mandatory “in-person” days), asking politely for those in meeting rooms that are running over their booked time slot to leave so he can hop onto his “important” (usually process-focused) call. He makes friends with everyone (or so he tries to) without being too friendly, in case he offends them or makes them feel “triggered”. His relief is (usually) a pint with Corporate Alan and Corporate Tom; but only if they can spare a couple of hours on Sunday afternoon, once they’ve caught up with their emails that were not priorities for the past week.
Corporate Clive lives for his holidays where he thinks “this is the life” but reverts to checking his work emails to make sure he’s not missing anything “urgent” or “important” while he’s away with his kids.
I could go on.
The point is not that being Tehran Tony is better than being Corporate Clive. Some people thrive with Clive’s lifestyle. The point is rather, most do not thrive in this environment but most do work in this way.
Further, most do not get to experience optionality. They can’t “switch off” because they are conditioned to think this is optimal for a high-functioning human.
“Most humans manage to squander their free time, as free time makes them dysfunctional, lazy, and unmotivated - the busier they get, the more active they are at other tasks.”
– Nassim Taleb, “Antifragile”
The reality is we are built for flâneuring. You should not feel you can only get things done when you’re actively thinking about things. To-do lists are the devil in disguise. You need to be comfortable being off.
The highest performing people, those who solve our biggest problems, flâneur organically. They are almost always switched off. Einstein’s initial breakthroughs on the Theory of Relativity emerged from a dream (about cows). August Kekulé discovered the structure of benzene after a dream about snakes. Werner Heisenberg discovered the foundations of quantum physics while going for aimless walks and choppy swims on a trip to a remote archipelago on the North Sea. Charles Darwin was even a flâneuring walker.
Naval describes this phenomenon using a lion as an example. These kings of the jungle sleep for 20 hours a day, outsourcing their hunting to their very capable females. But once every month or so, they get hungry and they hunt themselves. Once or twice a year, they fight young pretenders. The apex predator only works when necessary.
However, most of us are not built to be “high-performing”. It is a noble pursuit to be your best self. But your best self may actually only emerge when you loosen control and learn to flâneur.
Friend of Rational VC, Vizi Andrei has recently written a book about this very topic, called ‘The Sovereign Artist’. Vizi explains the value of sovereignty emerges from freedom of time and a lifestyle aligned to, as he puts “an avant-garde dolce far niente.” It is often in this way of living that you find life to be truly sweet.
Clive will see Tehran Tony and immediately invoke the notion that Tony’s lifestyle is not intellectually stimulating enough or too slow-paced and even, lazy. Tony can live like this because he got lucky as “90% of businesses fail” and “he was one of the lucky few who made it”. It also helps that he bought property in the 90s. Tony is also not that smart; he could never build a slick deck or financial model like Clive.
Clive is afflicted with an all-too-common disease: the Green Lumber Fallacy. He bases his judgment on seen variables as opposed to unseen (and often more important) conditions. Tehran Tony is the king of negotiation. What he learnt in the bazaars of Tajrish (one of Tehran’s bazaars) are far more applicable to deal-making, M&A and boardrooms than the ability to identify the inflection point (and infer a made-up CAGR on a graph) in the customer numbers and sales of an obscure market.
Tony has real-life experience and a true appreciation of risk. Clive will never have or understand this.
To reiterate, optimising for optionality alongside wealth is more important than anything else when designing a “working” life.
Further, the reality is Clive is fragile. Last year, as the Consulting market was tanking, Clive was given a “generous” redundancy package. All those years of selfless slide-making and formatting, forgotten in one fell swoop. His kids’ private tuition, his huuuge monthly mortgage and car payments and not least, his prized country club and golf memberships, all now a very real burden. But worst of all, the shame.
Tehran Tony never let his (or his eccentric wife’s) demands get too high. Given the fluctuation of his income, he learned to manage his expenses and never became addicted to regular income.
What I learnt
Deep down I am an Iranian Uncle. I am no less ambitious than Corporate Clive but I ultimately realised I’d rather have less (or more, if lucky) money than Clive but with the option to roll a double six in Takhte Nard at 1pm on a Tuesday and then play tennis with my other Tony mates at 3pm.
In other words, I wanted to become at the very least, robust. I am shooting for antifragility.
During my sabbatical, I ultimately learnt that success is nonlinear. I learnt this via negativa.
To start my sabbatical, I fell into the old Intellectual-Yet-Idiot trap. I mapped out all the things I wanted to try and achieve. Whilst I traveled to multiple countries, I forced a period of idea-fication: noting down every single business idea I could fathom and every piece of content I wanted to write about.
I quickly learned that this was not effective as I was forcing creative pursuits. Ideas come from experiences. To truly experience you must be present. You need to let shit happen without naively intervening.
Not only that, but you need to feel fluctuations and stressors in life to become antifragile. Eating into my savings, sometimes stressing about money and my financial runway were important uncertainties to expose myself to. I could now learn through hormesis.
“Hormesis: A bit of a harmful substance, or stressor, in the right dose or with the right intensity, stimulates the organism and makes it better, stronger, healthier, and prepared for a stronger dose the next exposure. (Think of bones and karate.)”
– Nassim Taleb, Antifragile
Focus on Rational VC came from stripping away all the ideas, putting myself in a somewhat low tail-risk stress situation (quitting without a plan but having already built Rational VC) and then flâneuring. Of course, I had barbelled by building Rational VC on the side while still in Consulting. But when I left, we still were not generating income.
“Barbell Strategy: A dual strategy, a combination of two extremes, one safe and one speculative, deemed more robust than a “monomodal” strategy; often a necessary condition for antifragility.”
– Nassim Taleb, Antifragile
I also went back to my childhood. Naval Ravikant talks about finding what you’re good at. He calls this “specific knowledge”:
“So, specific knowledge is found much more by pursuing your innate talents, your genuine curiosity, and your passion. It’s not by going to school for whatever is the hottest job, it’s not for going into whatever field investors say is the hottest.”
– Naval Ravikant
“When I talk about specific knowledge, I mean figure out what you were doing as a kid or teenager almost effortlessly. Something you didn't even consider a skill, but people around you noticed. Your mother or your best friend growing up would know.”
– Naval Ravikant, “The Amanack of Naval Ravikant”, Eric Jorgensen
So I lent into who I was as a kid. Obsessed with sport, reading, writing and history. I started playing tennis with my dad again. Seeing my parents more often. Spending more time with my friends and just doing more normal stuff. I read multiple books when I felt like it and went down random historical rabbit holes. I traveled extensively, and went back to Iran to enjoy time with my aging aunts and uncles (they really know how to live a life of flâneuring).
Now I don’t want to create a narrative of what worked ex-post and I certainly haven’t got it all figured out. In fact, I now have more questions than answers. I am no fool of randomness. And I hate prescriptions.
I am, however, sure that our recent growth at Rational VC and our constant tinkering is bearing fruit. Not just because I made it my focus, but because I prioritised this focus by simplifying my life.
“Take a simple idea and take it seriously”
— Charlie Munger
It took 8 years in Consulting, rising up the ranks and applying a iatrogenic lens to big business problems, to realise instead of building my perfect life via positiva, I needed to invert.
And again as the late, great Mr Munger explained, borrowing from mathematician Carl Gustav Jacob Jacobi:
“Man muss immer umkehren” (or “Invert, always invert.”)
“[Jacobi] knew that it is in the nature of things that many hard problems are best solved when they are addressed backward.”
— Charlie Munger
So my plea to those feeling stuck in the hamster wheel of slide-churning and aimless “this could’ve been an email” meetings, is to get back to first principles.
Answer the question: “What do I not want my life to be like from a professional perspective?”
Note all the things you don’t want. Then think of a plan to do the opposite of those things.
Often, the answer comes after taking a break from the rat race. And it really is difficult to answer that question. But it is infinitely easier than answering the reverse: what do I want my professional life to look like?
With this via negativa approach, you bound the question and ironically, you unbound the possibilities for your future.
In fact, Paul Millerd is a huge proponent of taking sabbaticals to find your direction. He’s the writer of the phenomenal book “The Pathless Path” where he explains that you must embrace times of uncertainty and time off to reassess your path, gain new perspectives and redefine your goals. If you’re anything like me, and you don’t take prolonged breaks, you lose sight of your North Star and end up grinding for the sake of it. Don’t fall into this trap.
Horizons
I write this as a lion re-entering the jungle searching for prey. I have secured a job in Mediocristan at a late-stage fintech. But my goal is to tinker in Extremistan on the side, and make Rational VC my life’s work. I now step foot into the dense jungle with my eyes wide open. The flâneur in me is itching to get out again.
Check out our 4-hour megasode, where we cover everything from modernity, nonlinearity, naive interventionism, convexity, optionality, the Green Lumber Fallacy, the Lindy Effect, via negativa and much, much more…
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