Life is cumulative. It unfolds in a geometric progression and therefore, the timing of your initial wins has a major impact on future outcomes down the road.
Met someone earlier this week who has had a bunch of major outcomes as an angel investor. This sparked my curiosity and I asked him about his backstory and career trajectory. Turns out these venture outcomes were a result of a series of parlays and things coming together over a decade-and-a-half:
He was early at a leading startup in the mobile supercycle, which was acquired by a BigTech in a marquee transaction. He continued at the BigTech for a few years (which in hindsight, was still relatively small at that stage), thus rapidly compounding both his net worth and network.
His spouse was an early engineer at a now-leading BigTech, then left to become an early engineer at a startup that was acquired in another OG marquee transaction. Through this journey, she also built a deep relationship with one of the OG Tier 1 venture firms in the Valley.
The couple used the capital acquired from this track record to start writing angel checks. Alumni of all the companies they worked at gave them access to some of the best deals.
The guy also went on to join a venture firm later, which further added to his creds and network.
Essentially, as a direct outcome of their early individual successes, this couple benefited from a self-compounding flywheel of relationships and capital. Pooling these assets as a married-team further magnified their impact. To their credit, in addition to being highly capable, they had the hustle, risk appetite, and foresight to keep taking shots at various opportunities that came along their way.
Btw, this story is not that uncommon in Silicon Valley. Though the extent of financial outcomes might vary, I know of many such stories where people have benefited from similar flywheels in their tech careers. In fact, this is one of the things that makes the Valley a unique place as there is an adequate density of talent, capital, networks, positive intent, and implicit trust within a small geographical region, which enables such flywheels to take shape in people’s lives. PS: I had written about this idea in my post ‘The Success Flywheel‘.
This story also highlights the importance of something I think about a lot, even from reflecting on my own career – there is a massive advantage to putting points on the board early on in life.
Life is cumulative. It unfolds in a geometric progression and therefore, the timing of your initial wins has a major impact on future outcomes down the road.
Mark Spitznagel, famous tail-risk trader and Taleb’s Partner at Universa, talks about this concept in the context of financial portfolio management and risk mitigation in his book ‘Safe Haven‘.
We are not a casino, or a portfolio of our distribution of possible simultaneous returns. Rather, we are one wager compounded through time. We only get one chance, and, if we shine a bright light on that, we will avoid many mistakes—start thinking about the right things, with a better internal valuation metric: making sure this chance maximizes its chance.
The idea is simple but powerful – having early wins enables the player to parlay the fruits of that win into the next opportunity while also having a long enough time runway for significant geometric compounding.
Being in the right zipcode like Silicon Valley in tech or NY in finance, also provides a large enough sample set of opportunities for continuous parlaying as well as high rates of compounding given the inherent leverage in these ecosystems.
This idea also makes the case for why students try so hard to get into Ivy Leagues, or why VCs try their best to get into prominent logos early in their track records. It also frames the competitive advantage folks get by starting as a fresh undergrad Analyst at Goldman, engineers who joined Google in the mid-2000s straight out of college, or those in their 20s joining OpenAI right now. The difference in getting these early wins starts showing up a decade later when the slope of the curve of these folks is markedly steeper than those who didn’t.
Of course, logging early wins isn’t by itself a sufficient driver or a definite leading signal of holistic success later in life. Everyone has their own unique journey and has to walk their own path. Still, given the sheer leverage these early points provide, it’s worthwhile to have this at the back of your head while executing your career strategy.
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Seeing my kid get bombarded with activities in 1st grade prompted me to think about the relative importance of ‘discovery’ vis-a-vis ‘focus’.
While conventional wisdom talks about the importance of each in silos, I have come to experience that a healthy mix of both is needed to design a thriving career and live a fulfilling life.
My older son just started 1st grade. As expected with any kid growing up in the Bay Area, he is already being bombarded with tons of activities – from soccer classes & cricket camps to music classes, karate & regular play dates. This is in addition to a school schedule that to me, already looks super intense.
Just 2 weeks into the new school year, I have been compelled to bring up the importance of prioritization with my better half. With work commitments & regular school duties, there is only so much a kid and 2 working parents can get done in 24 hours.
My humble submission to the family has been that we need to be smart in picking our battles. Essentially, have the kid gradually start focusing on a few areas, instead of spreading himself thin.
This predicament has prompted me to look back at my own career and reflect on what I have experientially learned about this topic both directly while executing in my jobs as well as indirectly by observing others around me. In particular, what I have gathered from working with and studying founders & investors I have come to respect.
Reflecting on my journey – the ‘discovery’ part
Growing up, I was the kid who always wanted to try out a variety of things and experiences. Even for a specific school project, I would boil the ocean, reading every book and resource I could get my hands on. While preparing for IIT JEE, I would read every reference book any friend recommended, and try and do every practice test series that looked even remotely relevant.
I carried this same behavior into my professional career. Over a decade and a half, I worked directly or indirectly in multiple sectors (oil & gas, software, medical devices, consumer Internet, eCommerce, SaaS, etc.), dabbling in multiple functions (finance & investment banking, product, operations, strategy, BD, partnerships, etc.), operating across multiple regions (US, India, China, SE Asia, etc.) and stages of maturity (founding my own startup, Series B startup, tech conglomerate, institutional VC, operator-angel).
Luckily, I figured out last year that venture investing is my true calling and this type of career design actually feeds really well into pursuing it professionally. Be it public or private markets, the best investors have a diverse set of mental models and best practices from many different fields meshed in their heads. This helps them to connect the dots in unique ways while evaluating any opportunity, thus giving them the proverbial ‘edge’. The best example of this is Charlie Munger. PS: I wrote about how he thinks in ‘Munger’s Tao‘.
Having a rich tapestry of experience across many areas definitely helped me develop a unique ‘strategic 360⁰ product leader’ positioning as an operator vis-a-vis my peers, and is now helping me carve my path as a venture investor.
Coming back to the earlier retrospective exercise, though this story so far made sense, a specific question still kept bothering me – “Have I missed a trick by not focusing deeply enough on any one area?”.
As we operate in a cluttered and flat global marketplace where everyone has access to almost the same information, and it has become easy to create shallow narratives in any area, I started questioning whether I had peanut-buttered my career to my own detriment.
Reflecting on my journey – the ‘focus’ part
During discussions with some of my friends, mentors, and especially my better half, an interesting nuance hidden in my story was uncovered. Even while hopping across many fields, countries, and skills, the one parallel constant in my life’s equation was venture investing. Since stepping into VC for the first time in 2011, I continued to go deeper into it, studying and practicing it over the subsequent decade.
During 2011-13, when Indian VCs were yet to discover Twitter in a mainstream way, I was one of the most active investors on the platform, trying to replicate the playbook of Valley VCs on it. PS: credit to Shradha of YourStory for encouraging me to get on Twitter during those early days. Twitter has added value to my world in ways that are hard to quantify.
Subsequently, when I stepped out of the VC world and became an operator in the Bay Area, I continued deploying my salaried money into early-stage startups each year, a majority of which was invested in the first round at an idea stage. By the way, this was before it became fashionable to become an angel during ZIRP.
While working intense continent-hopping jobs, I continued to get on calls with founders at 2 AM, trying to work on strategies to save a company on its last breath. In between building products and founding a startup, I strived to keep making myself better as an operator-angel by studying the journeys & frameworks of the likes of Semil Shah (totally in love with his blog), Elad Gil (substack), Jason Calacanis (love his old but raw Angel Podcast episodes), Ron Conway & Pejman Nozad.
Purely as a result of following my natural curiosity, I had inadvertently ended up focusing and going extremely deep into the craft of venture investing.
Balancing ‘discovery’ and ‘focus’
Connecting the dots now with my kid’s 1st-grade predicaments, there is an idea here from my journey that I believe is relevant. Careers (and life) are about a balance between ‘discovery’ and focus’. While conventional wisdom talks about the importance of each in silos, I have come to experience that a healthy mix of both is needed to design a thriving career and live a fulfilling life.
It’s important to have enough room to discover – try different things & test different ideas, while still striving for focus and actively looking for leading signals that indicate what to focus on.
The relative proportion of discovery and focus will be dependent on each person’s context. While most kids and youngsters will naturally have a high proportion of discovery, we also know prodigies tend to start focusing really early in life (Tiger Woods took to golf at 6 years of age; Warren Buffet bought his first stock at age 11).
People in the middle phase of their careers typically tend to gravitate more towards focus, trying to climb the ladder at a specific company or type of job. A counter view would be that many of them would do well to increase the proportion of discovery in their careers, in order to get to a global maxima.
Folks in the latter phase of their careers organically become experts at something, thereby increasing the proportion of focus in their lives. A view worth considering here is whether increasing the proportion of discovery in their careers might help avoid getting jaded and bring in fresh perspectives into their field of expertise.
There are no right or wrong answers here. Everyone will need to find their own balance considering their holistic context – age, location, family structure, social setting, and economic circumstances. Although, just based on a sample size of 1 (i.e. my journey), is following your natural curiosity a good way to organically evolve an optimal mix of discovery & focus? Perhaps…
To close out, I would like to share a pictorial representation of this idea of balancing discovery and focus. I tend to think of ideas & mental models in terms of pictures; I guess there is some merit to that age-old wisdom of “a picture is better than a thousand words”.
To me, this balance can be represented as a free-flowing river being directed by its banks. The middle of the river is in discovery, having enough room for the water to go in any direction, form vortexes, change color, and experiment with constituents like soil, mud, rocks, etc. But, the banks give the river focus, ensuring it stays on a desirable path, moving within specific boundary conditions and ultimately, meeting its true calling of merging into the sea.
As a parent, I hope to be the river bank that provides focus to my kid’s discovery. As you reflect on your own journey, how might you strike the balance between discovery and focus in your career and life? Are there areas where you feel the need to freely discover more, and others where honing your focus could lead to breakthroughs? Would love to hear your insights and experiences in the comments below, or on LinkedIn and Twitter.
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As I started experiencing both time & mental bandwidth constraints, especially post becoming a parent, I started thinking through the golden question – “How do I get more leverage in my career?”.
Sharing 3 main forms of leverage that I have identified during my journey in tech as an investor, operator & founder.
The way I design my career completely changed when my first son was born in 2017. From the day I graduated from IIT, I implemented what I call a Brute Force strategy to climb the career ladder. The idea was to basically outwork everyone – worked deep into the weekend during my investment banking days, did every possible hustle during the venture capital gig, and was on a plane 15-20 days a month for 5 years at Alibaba, literally doing a round trip of the world (SF – Hangzhou – SEA – India – back to SF via EU).
Everything changed once a parallel day (& night) job landed on my plate – that of being a parent. Relative to Asia, raising kids in the US is especially hard given there are no support systems to fall back on, especially for a 1st gen immigrant like me.
The easy choice, of course, would be to step off the gas a bit, realign professional goals & essentially, accept the trade-off of more personal time & lower professional outcomes. And many at this life stage end up choosing this option.
But then, I have never been the guy who loves the easy way out. I set out to answer the golden question – “How do I get more leverage in my career?”. Essentially, figuring out ways to significantly improve the ratio of output (value created) to input (time & mental bandwidth invested).
Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.
Archimedes
As I churned on this topic in my head for a year or so, Naval Ravikant posted his now legendary “How to get rich (without getting lucky)” tweetstorm in 2018, where he wrote about leverage as one of the key ideas.
Fortunes require leverage. Business leverage comes from capital, people, and products with no marginal cost of replication (code and media).
Naval Ravikant
Having worked in tech as an investor, operator & founder, I had the opportunity to observe various forms of leverage at play from close quarters. Some examples that hit home hard for me over the years included:
I discovered legendary VC Fred Wilson’s “AVC” blog during my first year in venture capital. It blew my mind that Fred had been consistently blogging on startups & investing since 2003 when at the time most Indian VCs didn’t have a Twitter account. Cut to today, Fred still continues to write on the same AVC domain!
These examples highlight 3 main forms of career leverage I have come to identify in my journey. I call them the 3Cs – Code, Capital & Content.
1/ Code
Code is the strongest form of leverage that has come into existence in the last 50 years. It started from the days when one had to have access to a University with a Punch Card machine, just to run simple programs. Then, Apple and Microsoft together brought computers to regular homes, but coding languages were still complex & needed expertise. As personal computers got more powerful, the open-source ecosystem of programming languages started thriving, creating much broader access to software programming across the world (from s/w products in Silicon Valley to IT services in India). Now, with the rise of generative AI, it wouldn’t be a stretch to say that almost every knowledge worker can code & create products without deep expertise in specific languages.
Code provides game-changing leverage. Over the last 20 years, anyone with a decent laptop and an Internet connection could build a SaaS business, become a freelance developer, or get hired by a large tech company at extremely attractive salaries irrespective of location, background, or past credentials. As opposed to hourly jobs in the industrial age, coding just for more hours doesn’t necessarily translate into better outcomes. Quality of problem-solving matters much more than the quantity of hours, which is what gave rise to the 10x engineer phenomenon.
As someone who had neither the skillset nor the mindset to code, this extremely powerful form of leverage has always been out of my reach. That’s why I am particularly excited about how AI will make coding so much more accessible. At the minimum, it will both increase the global base of developers, as well as significantly enhance the productivity of the best ones (the 10x engineer now becomes a 100x?).
Given coding hasn’t been available to me as a leverage point in my career, I have had to double down on the other 2Cs, as I will explain below.
2/ Capital
Using capital to own assets is the oldest form of leverage that continues to stay powerful. The Vanderbilts made their fortune owning railroads, Carnegie in Steel, the Waltons & Jeff Bezos in retail, Buffet & Munger in owning full businesses as well as investing in stocks, Jobs & Gates in tech, Templeton, Soros & Jim Simons in public market investing, Stephen Schwarzman & Henry Kravis in Private Equity investing, and Don Valentine & John Doerr in Venture Capital investing.
Capital can be used to buy ownership in Real assets as well as businesses. The former benefits from scarcity (land is finite on this planet) & gives double-dip benefits of monthly cash flow + equity appreciation. But personally, I find the latter more interesting, purely because great businesses become long-term compounding machines, providing the prospect of exponential returns that Real assets can’t match.
As an example, Microsoft’s market cap has grown from ~$270Bn to $2Tn+ in 20 years. For any part owner via stock, everyone from Bill Gates to Steve Ballmer & now Satya Nadella has been putting in the work to give shareholders ~17% annualized returns.
Of course, the most powerful route would be to use your “sweat equity” & start a business, but that’s typically not an optimal option for most people.
Given my significant experience in banking & venture investing, I have gotten the most exposure to Capital as a form of leverage & ways to harness it across asset classes. In addition to developing expertise by working across institutions, investing in both public & private markets has also become my personal passion over the years. In a very organic way, I have always turned to the lens of markets & investing to decode life & human behavior.
As a result, I have doubled down on leveraging Capital to acquire ownership in businesses as a core form of leverage. I have been investing in tech startups for more than a decade, & plan to keep doing it for the rest of my life. My simple pursuit is to identify the best founders out there, & I believe this is where my professional Alpha is!
Compared to Code, Capital-based leverage is relatively hard to acquire. Accumulating own capital takes time & being able to manage other people’s money has a really high bar of trust, reputation & accountability.
The good news is – you can start young & with small amounts of capital. Compounding is your friend and as long as you are determined to save & deploy on a continuous basis for decades, every small step adds up. And sooner or later, my favorite model of “you only need to get a few right” kicks in, wherein a smart decision every few years will create a step function in your portfolio.
The first $100,000 is a bi**h, but you gotta do it. I don’t care what you have to do – if it means walking everywhere and not eating anything that wasn’t purchased with a coupon, find a way to get your hands on $100,000. After that, you can ease off the gas a little bit.
Charlie Munger
3/ Content
This is the newest form of leverage, & one of the most exciting ones. Pre-Internet, there were many gatekeepers in the way of getting ideas heard. Most regular people had almost no access to traditional media. One needed relationships with publishers & power brokers to put anything out in the market. Participating in a high-quality exchange of ideas happened within tight cliques – scientific, university, neighborhood, racial, socio-economic, etc. Essentially, the common man was blocked by “access”.
The Internet changed everything. Anyone could build a website to publish their ideas. With search engines, this content became discoverable by anyone across the world. As social media got created, distribution became turbo-charged with authors able to create holistic personal brands & interact with very specific audiences for their work. Now, powerful phones & software have transformed authors into “creators”, arming them with light-weight studios to create various forms of media, from vlogs & podcasts to tweets & reels.
I started writing online in 2011, mainly via blogging & tweeting. Over the years, my conviction in Content as a powerful form of leverage has only increased with time. As anyone who has taken a new product to market knows, it’s just not enough to have a great product. Communicating with your audience in a way that makes the product resonate in their minds matters the most. Case in point: Apple’s legendary 1984 Super Bowl commercial introducing the Mac (& in the process, convincing the audience that IBM is obsolete!). Even a product genius like Jobs spent an inordinate amount of time thinking about marketing (check out this snippet from Jobs on how he simplified Apple’s marketing message).
To me, the ability to influence human minds with your ideas is a superpower like no other. Writing & putting content out there helps me engage with people I would have never met otherwise. It helps me attract people with similar values, with whom I can solve problems. It helps me have a conversation with them even when one of us is asleep, or in a different time zone, or even when the encounter happens many years after the actual writing.
Early-stage investing is a long-tail game, with thousands of new startups getting created across the globe & tens of founders in the pipeline at any point in time. I realized very early that real-time meetings are unscalable, especially at my life stage, & that demand-gen is key.
Content is arguably the most scalable form of human interaction, with its engagement & subsequent impact reverberating for years & sometimes, generations (in the case of the best books). In fact, this post itself is a perfect example, wherein I have shared links to an Apple commercial from 1984, a Steve Jobs speech on marketing from 1997, and a Wall Street Journal article from 2000.
My belief is that Content in many ways provides more potent leverage than Capital – money can’t buy the best ideas, but the best ideas can attract money. And this friends, is why I write!
To summarize, employing various forms of leverage is key to creating large professional outcomes. As you design your career, think about proactively layering in one or more of Code, Capital & Content into it & equally importantly, commit to doing it over many decades.
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Here are some insightful ideas & quotes from Munger that stayed with me from David’s experience:
1/ Buy wonderful businesses at fair prices
Before Munger joined Berkshire, Buffet used to invest in Ben Graham’s “cigar-butt” style – buying super-cheap stocks, often trading below book value.
Munger gave him a new blueprint: “Forget what you know about buying fair businesses at wonderful prices; instead, buy wonderful businesses at fair prices”. This is what led to Berkshire becoming the compounding machine it is today.
2/ Cash is king
Through a company called Blue Chip Stamp, Munger & Buffet learned about the value of “float”- excess cash that a business throws up due to the timing difference between receiving payments & settling payouts. This excess cash could then be re-invested in profitable companies.
Through his early investing experiences, Munger started seeing the advantages of investing in better businesses that didn’t have big capital requirements and did have lots of free cash that could be reinvested in expanding operations or buying new businesses.
Munger advises keeping enough cash at all times, in order to take advantage of stock market crashes.
We made so much money because when the great deals came during an economic crisis, we had cash and could move fast.
Charlie Munger
3/ Acting on the few big ideas that matter
Munger says that very few times, you will be presented with an opportunity to buy a great business run by a great manager. Not buying enough when presented with this opportunity is a big mistake.
You have to be willing to act when the right opportunity comes along. ‘Cos great opportunities don’t last very long in this world.
Real wealth is created via concentration. Or to put it in another way, over time, one should expect 1-2 outlier winners to constitute a majority of the portfolio.
When Munger wrapped up his pre-Berkshire fund, Blue Chip Stamp accounted for ~61% of his portfolio.
Worshipping at the altar of diversification is crazy. One truly great business will make your unborn grand children wealthy.
Charlie Munger
5/ Chase unfair advantage
Competition is for losers! Why would you want to compete with people?
Some quotes from Munger on this:
“My idea of shooting fish in the barrel is to first drain the barrel”.
“Only play games where you have an edge”.
“Differentiation is survival”.
“Aim for durability”.
Munger talks about how size and market domination has its own kind of competitive advantage. When a company is deeply entrenched with customers, it acts as a deterrent for other players to enter the space.
Sectors that are generally considered to be “bad businesses” (eg. retail, textile, airlines etc.) are intensely competitive. Players beat each other over price and drive down profit margins for everyone, killing cash flows and bringing down chances for long term survival.
That’s why Berskhire looks for great businesses that have a durable competitive advantage.
Mimicking the herd invites regression to the mean.
Charlier Munger
6/ The power of Compounding
Find an exceptional business where underlying economics are going to keep increasing its value, and then hold on to it over time.
Quoting Munger – “Time is the greatest friend of an exceptional business. It’s the greatest enemy of a mediocre business”.
Compounding also works in knowledge. Munger gives an example of how over 50 years of consistently reading Barrons, he found just 1 idea worth investing in but that made him $80Mn, which he then gave to Chinese fund manager Li Lu, who turned it into $400-500Mn!
7/ The value of Rationality
To quote Munger:
“We don’t let other people’s opinions interfere with our rationality”.
“Life is like poker. You have to be willing to fold a much loved hand when new info or facts come to light“.
“It’s remarkable how much long term advantage people like us have got by trying to be consistently not-stupid, instead of being highly intelligent”.
8/ Focus is a super-power
Munger says:
“I succeed because I have long attention spans. People who multi-task give up their advantage”.
“You will always lose in a race to that one guy who sacrifices everything he has in service of one idea”.
“Extreme specialization is the key to success”.
“Intense interest in a subject matter is super powerful”.
He cites examples of how great companies tend to focus on optimizing one specific lever in their business:
Costco – optimizes costs
Geico – optimizes distribution via direct-to-consumer
Nebraska Furniture Mart – optimizes price for the end customer
What’s the one thing that both Warren Buffet & Bill Gates said was the key to success? Focus!
9/ Frugality drives value
Munger cites one common quality amongst all Berkshire businesses – they will go to great lengths to keep operating costs low. Even Berkshire itself demonstrates the same behavior:
It has no PR department.
It has no investor relations office.
For many years, its annual report was published on the cheapest possible paper & had no expensive color photos.
10/ Brands are magic
Munger says – “A great brand is a piece of magic”.
Brands like Coca Cola & See’s Candies have a piece of a consumer’s mind & therefore, have no competition. Charlie calls them “consumer monopolies”.
A lot changed the day Berkshire realized the power of brands.
11/ Business plans are useless
Munger says Berkshire has no master plan – “We always wants to be accounting for new information. We are individual-opportunity driven. Our acquisition style is driven by simplicity”.
He shares an interesting anecdote. When Mrs. B (Rose Blumkin), Founder of Nebraska Furniture Mart, was asked about having a business plan, she said – “yes, sell cheap & tell the truth”.
12/ Patience is rare
Human nature is all about being impatient. People just can’t sit around, waiting patiently. They want to feel useful. So they end up taking action and doing something stupid.
13/ Learning from mistakes is crucial
Learning from history is a big form of leverage. The biggest financial disasters get forgotten in a few years.
Munger says:
“Wise people step on troubles early”.
“Every missed chance is an opportunity to learn”.
“Be willing to take life’s blows”.
I love rubbing my nose in my mistakes. It’s an extremely smart thing to do.
Charlier Munger
14/ It takes many, many attempts to find your life’s work
For context, Munger started working on Berkshire in its current form only in his 40s.
15/ Finally, lots of life advice…
“Build relationships with A players”.
“Problems are a part of life. So why are you letting them bother you?”.
“The best way of reducing problems is to go for quality – Go for Great!”.
“It’s the strong swimmers who drown”.
“Envy has no utility. The key to living a well-lived life is killing envy”.
“The best armor for old age is a well spent life preceding it”.
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Earlier this year, my younger son got admitted to the same preschool that the older one attended in SF. As parents, we were elated! Our older one loved this school, we know the Principal and teachers really well, and it significantly reduces uncertainty for us given this school goes up to Middle. A win-win in every respect!
Except, we were caught completely off-guard by how the first few weeks turned out. That the kid was having “adjustment issues” would be an understatement. Everything from sleep schedules & toilet training to eating & social behavior went majorly South. While this is normally expected when kids change schools, what surprised me was how much this derailed us as parents. We were maniacally struggling to manage the kid in this transition while trying to cope with all the mood swings & changes this was bringing to our daily routine.
Of course, things started improving after a couple of months & as we speak, the kid seems all settled in the new environment🤞🏽. But I couldn’t stop introspecting on why we got caught so off-balance in this episode, even when we knew the school intimately & had gone through this exact experience before with our older one?
This was a manifestation of what I call the Familiarity Conundrum. When we deal with things we are intimately familiar with, there is a double-edged sword at play. While familiarity arms us with high-fidelity, experiential data that can be incredibly useful in making a smart decision, it also creates overconfidence-driven blind spots in our ability to deal with the familiar.
In highly familiar situations, our brain tends to short-circuit the decision-making process, perhaps gathering comfort from past anecdotal experience regarding similar situations. The result is a quick decision based on 1st order thinking. We went through this in the above school episode – our brains used a quick, 1st order heuristic – “because this school was so great for our older son, it will be equally good for our younger one too”. We failed to ask even a basic set of questions regarding this decision eg. are the teachers the same this year, is our younger son starting at the same age as the older one, should we expect any changes to the school routines post-Covid etc. These are basic diligence questions that we would have definitely tried to answer had this been an unfamiliar school for us.
This Familiarity Conundrum often leads to sub-optimal decisions in other aspects of life as well. Some examples that I have personally experienced or witnessed:
When hiring someone we are highly familiar with eg. an ex-colleague or classmate, our brain tends to unfairly magnify our last, dated view of their strengths, not pushing us enough to evaluate them independently, especially with respect to fit with the current opportunity.
When a trusted person introduces us to a deal, say an investment opportunity, our brain wrongly transfers trust with the referrer onto the referred deal, without a rigorous evaluation of the deal on a stand-alone basis as well as the referrer’s true competence in the specific area being evaluated.
When operating in an area where we have prior work experience, we tend to under-diligence the opportunity & overestimate our likelihood of success. In areas of perceived expertise, our brain doesn’t push hard enough on 2nd & 3rd order thinking like figuring out ways in which this context is different from our prior experience, trying to see around corners for lurking risks etc.
So what can we do to effectively deal with this Conundrum? Based on what I have learned from my experience as well as studying great rationalists like Charlie Munger, here are a few ideas:
1/ First step is spotting it at the right time – training your mind to spot times when familiarity could be creating blind spots for you, is itself a major part of keeping biases at bay. Personally, I tend to keep a matrix of such mental models both layered in my head as well as often as part of a diligence checklist. For decisions that cross the bar of impact and/or irreversibility, I like to run them through this matrix to check for potential blind spots.
2/ Don’t deviate from the “checklist” – Dr. Atul Gawande argued for the importance of checklists as a tool to make surgeries safer in his popular book “The Checklist Manifesto – how to get things right“. Professionals as diverse as surgeons, pilots & public market investors leverage checklists to handle uncertainty & make better decisions under stress.
The key is not deviating from your operating process even when the context is highly familiar and your brain is pushing you to use crude heuristics to arrive at a quick decision. Like a pilot who will diligently run through the aviation checklist even on the best-weather days, one needs to strive to do the same, each time, every time while taking high-impact decisions.
3/ Always have an independent feedback mechanism – even in areas where you believe you have deep knowledge and/or extensive on-ground experience, it’s always good to get feedback from independent players who are likely to see the opportunity in an unbiased way.
During my early days as an angel investor, I had a tendency to predominantly rely on my own judgment of a startup & often made decisions without taking the time to gather feedback from other sources. Having learned from several missteps, I have now incorporated gathering feedback from several sources including market experts, customers, founder references & other investors, as a core part of my investing process.
In this context, I find the idea of having a “feedback buddy” incredibly useful. For important projects eg. buying a house, a product launch, a big investment, it’s good to have someone who is unrelated to the project be a sounding board to bounce off ideas, poke holes in current thinking & simply provide common-sense feedback.
The bottom line is this – as opposed to explicitly unfamiliar terrain where our natural survival mode gets alerted, familiar contexts are significantly more likely to get our brains in “lazy thinking” mode, creating blind spots that will catch us off-guard. Proactively spotting this dynamic, having the discipline to stick to a rigorous process at all times & consciously incorporating an independent feedback mechanism within it, goes a long way in offsetting this Familiarity Conundrum.
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I was discussing the SVB blowup situation yesterday with one of my friends who manages the public markets portfolio for a large family office. He and I both have deep financial services backgrounds, having worked across diverse services & asset classes (VC, PE, public markets, Investment Banking, debt etc.). Both of us came to the same conclusion regarding what has unfolded:
Given the complexity of financial markets, with many direct & indirect stakeholders, influencers, interconnections, interdependencies, manual & robo decision engines at play, it’s almost impossible for even the smartest operating teams & regulators to stay on top of systemic risks building up across thousands of organizations in our financial system.
Of course, this risk management challenge gets further exacerbated in pure capitalist markets such as the US, that consciously allow free market cycles, driven by excessive greed followed by excessive fear, to play out without much intervention.
Going beyond the macro discourse around SVB, of which there is enough now in the media & on Twitter, I want to highlight one learning that all of us need to pay attention to from this episode – the real risk in most things in life is in the “unknowable”, not the “unknown”.
What does this mean? In most planning exercises we do around risk management both professionally (eg. what’s the sensitivity around my company’s 2023 revenue?) & personally (if I plan to do a startup, how much personal runway do I need to be able to operate without a salary?), we focus mainly on outlining the “unknowns” – variations in outcomes of visible & obvious elements. Things like revenue from existing customers, attrition of top performers, house rent, holiday budgets etc.
Planning for unknowns is largely driven by first-order thinking. This includes the classic sensitivity analysis playbook of (1) listing out all obvious elements of the game, (2) thinking of a range of values for them (best case/ likely case/ worse case) & (3) using these values as inputs to model out various output scenarios that consequently drive the overall decision-making process.
But if most organizations & individuals follow this kind of solid decision-making framework, why is the real-world full of surprising blow-ups – bank runs, hedge fund unravels, fast-growing companies unexpectedly going bankrupt etc.?
It’s because the real world is a complex adaptive system with emotion-driven humans as actors. Michael Mauboussin, legendary analyst, academic & public markets investor, beautifully outlined the qualities of this type of system in his recent conversation with Tim Ferris:
So, “complex” means lots of agents. Those could be neurons in your brain, ants in an ant colony, people in a city, whatever it is. “Adaptive” means that those agents operate with decision rules. They think about how the world works, and so they go out in there and try to do their thing. And as the environment changes, they change their decision rules. So that’s the adaptive part, their decision rules that are attempting to be appropriate for the environment. And then, “system” is the whole is greater than the sum of the parts. It’s very difficult to understand how a system works, an emergent system works, by looking at the underlying components.
Michael Mauboussin
In such a system, while some risks fall under “unknowns”, a majority of them are “unknowable” given the system is self-evolving & therefore, impossible to predict at a granular level. Many words are used to describe these unknowables – edge cases, tail events, black swans etc.
Even if we do get some additional visibility into a few of these probabilistic unknowables & can foresee their 1st-order impact to an extent, their 2nd & 3rd order effects are really hard to model out.
Given this context, classic risk management approaches work well most of the time, until they don’t. And when they don’t, participants are caught unaware, unprepared, & often facing the Risk of Ruin.
So, how can organizations & individuals prepare better to deal with the unknowables? The following steps can help:
Start by recognizing the presence of “unknowables” – a major first step is to acknowledge one’s ignorance, & consciously keep overconfidence bias at bay by reminding oneself that even after all this data & analysis, there is a lot that is just not possible to predict. Approaching risk management with humility & in defense mode creates a conducive mindset for this.
2. Add a significant “Margin of Safety” on top of your analysis – while a rigorous Sensitivity Analysis will cover the unknowns well, adding a Margin of Safety goes a long way in providing a buffer for the unknowables. How much of it you want to add depends on context but given we live in a highly risky world, it should be significant enough. As an example, legendary value investors like Buffet & Munger insist on a 50% Margin of Safety while buying public securities (buying at half of the intrinsic value of a company).
Btw, this isn’t anything new. Engineers who design everything from trains & storage tanks to nuclear reactors & space shuttles, recognize error rates in their assumptions & therefore, always include an “allowance” in their computations. Millions of lives depend on this method!
3. Routinely stress-test & update your assumptions – with software continuing to eat the world at an exponential pace, cycles are becoming shorter & feedback loops quicker. The Fed raised rates from under 0.5% in Mar’22 to ~5% in less than a year! With information transmitted in real-time, especially via networks like Twitter, & decisions manifested at the push of a button, we saw how SVB unraveled in literally a day. Given this speed of change, it’s important to frequently stress-test your state-of-state, accounting for changes in external & internal environments & updating your assumptions (esp. Margin of Safety) accordingly.
While the Treasury, the Fed & FDIC have joined forces to save everyone impacted by this specific SVB case, most of us can’t count on such White Knights bailing out our families or our startups each time. A pragmatic & defensive risk management approach that accounts for unknowables, incorporates a healthy Margin of Safety, & includes periodic stress testing, can help us cope with outlier events & keep us in the game.
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Growing up in India, where inherent chaos makes sure most things don’t go according to plan, I got organically trained to always have a Plan B. The classic fallback option – the bylane you take when the main road is clogged because a minister is scheduled to pass through, the backup college seat you block in case you ranked low in the entrance exam for your top preference, or the autorickshaw you hail when the car refuses to start.
Look, I get it! Now that I am a father to 2 boys, I see the instinct parents have to ensure their children are tangibly & emotionally “safe” in all situations. So, I can appreciate why my middle-class upbringing was designed this way. To top it up, my technical education & early analytical jobs further pushed me into the world of scenario analysis & fail-safes.
Down the road, as I entered the risky world of startups, I naturally brought this instinct with me. While building, operating & investing in high-risk-high-reward endeavors, my animal brain would always push me to have a Plan B in my backpocket:
If this startup doesn’t work, I can always go back to Company X.
What if this investment fails? Let me spread my resources & take a smaller bet.
If I don’t like living in Country Y, I can always go back to India.
A few years into taking these asymmetric bets (presumably backed by Plan Bs), I expectedly started encountering failures, both big & small, one after another. They ranged everything from major projects going South & unforeseen external risks coming to the party to unexpected company restructurings & gross misjudgment of certain people’s skills & intent.
During a recent introspection of these adverse experiences, something interesting jumped out – every time I attempted to call on a Plan B for a specific situation, more often than not, it wasn’t really there. In some cases, the “backup” companies had changed their strategy & weren’t a fit anymore. In others, I had grown in a different direction & going to a fall-back option would be a negative step. Many times, people I was relying on to help materialize a certain Plan B had either fallen out of touch, were themselves dealing with adversity, or had changed their context & therefore, relevance.
So this was my lightbulb moment that inspired this post – in high-risk-high-reward situations, Plan Bs are….fictitious. The very nature of extremely risky situations is that they take you in unpredictable directions, change your context in unimaginable ways & leave you with baggage that’s hard to foresee. And all this happens in parallel to a rapidly-changing external environment that in most cases, becomes increasingly incongruent with your endeavor (most asymmetric projects are by definition, contrarian in relation to established rules of the game that the majority operates by).
This complex system renders even the most thought-through Plan Bs useless. Given asymmetric bets are driven by power laws (a few will drive a majority of the total outcome) & compounding (need a long enough timeline for ideas to mature, which is when outcomes start growing exponentially), positioning yourself to be on the right side of these rules requires going all-in for a significant period of time.
While having a Plan B provides the initial psychological space to initiate a risk, in my experience, it unfortunately also creates a mental mechanism to cop out of it, & even worse, often doesn’t provide the safe landing space it initially promised.
Going forward, my aim is to ditch the “Plan B” mindset in all asymmetric bets. A fall-back instinct comes from a place of fear, and while controlled fear can be a useful tool to drive alertness & urgency, it becomes adverse when acting as a roadblock to going all-in & persevering on a thoughtfully-chosen path.
It’s important to add here that while ditching the Plan B outlook, I will still proactively focus on avoiding the Risk of Ruin at an overall life level. Asymmetric bets require multiple shots at the goal & therefore, safeguarding the ability to keep playing is paramount.
On a related note, a mental heuristic I have recently started using while making asymmetric decisions I am 50-50 on – “which option is the fear side of my brain asking me to choose?”. In most cases, I then lean towards the other option!
I have found the following quote by Swami Vivekananda to be hugely inspiring in driving this mental transformation:
Take up one idea. Make that one idea your life – think of it, dream of it, live on that idea. Let the brain, muscles, nerves, every part of your body, be full of that idea, and just leave every other idea alone. This is the way to success.
Swami Vivekananda
As you consider this approach, I want to leave you with this outstanding scene from Christopher Nolan’s ‘The Dark Knight Rises’. As a frustrated Bruce Wayne is trying to catch his breath after yet another failed attempt at climbing out of the pit (he was using a rope each time), an old & wise prisoner gives him the mantra for successfully making the climb:
You do not fear death. You think this makes you strong. It makes you weak.
How can you move faster than possible, fight longer than possible, without the most powerful impulse of experience – the fear of death!
Make the climb…as the child did. Without a rope!
The Dark Knight Rises (2012)
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As a long-time student of Charlie Munger, I eagerly wait for his musings at the Daily Journal Shareholders Meeting every year. This time was no different! Here are some of my notes capturing Charlie’s wisdom at the DJCO 2023 meeting:
Importance of under-served markets in software
Both Munger & Buffet are big believers in moats. Having witnessed the natural creative destruction of even the best companies like Kodak & Xerox, they understand the power of competition & what it can do to long term returns of investors.
Munger spoke about how the software business of DJCO, which offers a solution to automate legal courts, is operating in a large yet unaddressed market that incumbent software companies hate. It’s an unsexy business that has long sales cycles & as Munger himself said – “it will be a long grind”.
However, these same reasons also limit competition in the space. Munger believes that this combination of a large, underserved TAM + low competition is likely to drive superior long-term returns, as long as DJCO shareholders are prepared to ride through the grind & hold over the long term.
In my view, this idea also has some interesting insights for venture investors in the enterprise software/ SaaS space. Too often, investors start chasing the hot market of the year without realizing that a space that is obviously popular will end up attracting disproportionate competition & investor $$. And as history shows us, too much competition in a market drives down returns for everyone.
Therefore, there is some merit in looking at startups going after unsexy or under-served verticals. These non-obvious nooks & crannies often hold the most potential for contrarian-and-right bets.
2. Holding is tax-efficient
Munger spoke about how he hates to sell his holdings as California would straight-up take 40% away in taxes. As he went on a brief rant about how California is driving businesses away with its tax policies, the underlying insight stayed with me – how holding securities over the long term is a brilliant strategy for tax efficiency. A simple rule that anyone from Berkshire & DJCO to common folks like you and me can follow in our lives.
As the likes of Robinhood have leveraged the excess liquidity environment over the last several years to create a generation of young day traders, many of them don’t realize how tax-inefficient frequent trading is.
3. #1 bias is denial
When asked what the #1 behavioral bias is, Munger said “denial”. And it’s so true. Often times, when the present reality is too brutal to bear, our brain tricks us into living in a delusion. While this stems from an evolutionary survival mechanism our brains have developed, taking major decisions under this denial state can cause havoc in our lives.
Proactively trying to see & live in one’s reality at any point in time is the best way to behave rationally. If one thinks of all of grandma’s wisdom handed down to us in popular sayings (eg. “live within your means”), they all urge us to recognize & live within our own realities.
4. Betting big when the right opportunity knocks
I loved this sentence from Munger – “What % of your networth should you put in a stock if it’s an absolute cinch? The answer is 100%”.
While I am positive that Charlie wouldn’t like this to be construed as a stance against diversification, which is important for almost all portfolios in varying degrees, the spirit of this sentence is this – a few times in your life, you will come across a no-brainer opportunity with massive asymmetric upside. It will happen very infrequently, but when it knocks on your door & you are convinced about it, go all in & bet really big. Over a lifetime, these bets will drive the majority of your returns, financial or otherwise.
If there is one thing that separates the likes of Buffet & Munger from other investors, it’s the mindset of betting really big when the odds are extraordinarily in your favor. During the meeting, Munger mentioned how Ben Graham made 50% of his money from just 1 stock – GEICO. Also, he illustrated the importance of power laws by sharing how Berkshire’s initial $270Mn investment in BYD (made in 2008) is now worth $8Bn!
Munger admitted to having used leverage to buy Alibaba stock in the DJCO portfolio. When asked why he violated his own rule (his famous quote being “there are only 3 ways a smart person can go broke – liquor, ladies & leverage”), Munger responded with another fascinating quote:
The young man knows the rules. The old man knows the exceptions.
Charlie Munger
The insight behind this is something I say a lot – context is everything! Rules & checklists are great for driving overall discipline & avoiding foolish behavior but as Munger demonstrates, it’s not wise to become a prisoner of your own rules. With experience, one should learn to spot exceptions & when the context is favorable, be bold enough to break the rules.
6. On long-term economic trends
While both Munger & Buffet generally hate to predict macro trends, Charlie mentioned a few interesting observations:
-Inflation is here to stay over the long run, given most democratic govts. globally have shown an ever-increasing inclination to print money.
-Most govts. across the world are going to be increasingly anti-business, with tax rates steadily going up.
-If one looks at economic history, the best way to grow GDP per capita is to have property in private hands & make exchange easy so economic transactions happen (the essence of capitalism).
If these trends are even directionally true, it makes sense to hold assets that can fight inflation (eg. stocks), as well as invest in a tax-efficient way, over the long term. Developing an investor mindset that can operate in a high-inflation environment will be important.
7. The playbook for success in life – Rationality + Patience + Deferred Gratification
When asked the thing that’s helped him the most in life, Munger said – rationality! Loved this line from him:
If you are constantly not crazy, you have a huge advantage over 90% of people.
Charlie Munger
To significantly improve the odds in your favor, Munger prescribes combining 3 things:
-Rationality (which is often, just doing the obvious)
-Patience (take advantage of compounding)
-Deferred gratification (live within means, save & invest)
Like most things Munger says, the above ideas are simple & profound, yet hard to consistently follow for most people as their biases come in the way.
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You know, the ideas that I have had in my life are quite few. But the lesson I can give you is, a few is all you need, & don’t be disappointed.
When you find the few, of course, you have to act aggressively, that’s the Munger system.
Charlie Munger
As I was ruminating on blogging about my experience of this idea, Warren Buffet did a timely reminder in the recent Berkshire 2022 Shareholders Letter:
The lesson for investors: The weeds wither away in significance as the flowers bloom.
Over time, it takes just a few winners to work wonders. And, yes, it helps to start early and live into your 90s as well.
Warren Buffet
The idea that you only need to get it right a few times in order to lead a rich life is so powerful! Through it, Munger & Buffet also underline the importance of power laws in almost everything worthwhile. That a few decisions & outcomes will drive most of our respective lives.
About a decade back, this idea was an intriguing concept for me, but only at an academic level. Since then, I have experienced, & therefore internalized it, across multiple aspects of my life. Even though I would consider myself a perpetual hustler who has worked in 8 companies, tried multiple functions across diverse industries, lived in many cities across US & Asia, and invested in 20+ startups, I can boil down where I am in life today to a handful of decisions that acted as step-functions:
Where I ended up studying for undergrad, as that’s where I met my (future) wife.
Pursuing & marrying her several years later.
A cold email to a VC firm that eventually became my entry point into tech.
Deciding to move from India to Silicon Valley with no job in hand, no existing networks, with just faith that I will figure it out.
Casually meeting the husband of one of my wife’s friends back then, who eventually led me to join Alibaba.
That’s it! If I take any of these decisions out of the equation, my life would look very different.
At a more specific level, I see this dynamic play out in my angel portfolio too. I have been investing as an operator-angel since 2014, & now with enough data from my own experience, can confirm that 1-2 companies will end up driving a majority of my returns. The countless hours I have spent turning over stones, meeting hundreds of founders & working in the trenches with portcos, translate to just a couple of needle-moving outcomes over a decade. But yes, they are expected to move the needle by a lot (major step-functions, as I like to call them).
Same with content – sometimes I feel like I have written the most thoughtful post or a super-smart tweet, & no one reads it. And then, I write some crazy anecdote from my past lives & it goes viral.
Translating this “only need to get a few right” idea from purely academic to a lived & internalized one becomes important as it helps to frame risk-taking in the right way, particularly dealing with failure.
It has taught me many lessons:
Outcomes in creative & high-risk-high-reward pursuits are random.
Multiple failures don’t matter (& should be expected), as long as the few successes are outlandishly large.
Given success is sporadic, need enough shots at the goal to get odds in your favor. Take more chances with asymmetric upsides.
Given success is intermittent, plan for & evaluate things over a long-enough timeline. Patience is key!
When you get it right, let it compound. Milk every success to the fullest.
While specific outcomes are uncontrollable, a few decisions will always be make-or-break points in life – where you study, who you marry, which city you decide to settle down in, whether you have kids or how many, what house you buy & when etc. When faced with these questions, appreciate their importance, take your time & try to make the best possible decision in your capacity.
Finally, rather than getting fixated on episodic successes & failures, zoom out to look at the bigger picture & visualize your life as a curve. The goal is to have it trending up & to the right over a long timeline.
So, keep playing the game, be patient & wait until you get your “few” right!
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I recently tweeted a really interesting insight I heard from Mike Maples, Jr of Floodgate at a recent Draper University closed-door event:
This is so true, and a common mistake that founders & product leaders make while building new products. Looking back on my own startup, while I rigorously tried to execute Paul Graham’s “Do things that don’t scale” philosophy, I still created unreasonable expectations in my own head around user growth for each MVP iteration. This was probably due to the baggage I was carrying from my previous experience of working at large companies like Alibaba, where numbers were talked about in Millions & sometimes, Billions.
When the absolute user numbers weren’t met, my morale as a founder would get hit with each iteration. In hindsight, hitting numbers shouldn’t have been the goal at all. The ideal 0-to-1 mindset is like that of a scientist, with curiosity being the core driving emotion, backed by an iterative product development approach. The target outcome of this approach should be to gather insights that help refine the hypothesis.
Similar to how scientists drive their research process one experiment at a time, I have realized that building any new product or service from grounds-up requires moving one “unit” at a time. It’s up to you to decide what that unit should be – acquisition, activation, frequency of use, revenue or even just getting qualitative feedback!
In a scientific process, more than just the number of experiments run, what’s important is taking the learning from each experiment & applying it to the next one so it becomes better than the first.
Similarly, a good approach to building anything new is to delight one person at a time. This automatically focuses the building process & anchors it on an actual customer, thus making it easier to ship something that solves a monetizable problem for someone in the real world. Trust me, this is a non-trivial hurdle that many startup teams are unable to cross.
The 0-to-1 stage can be highly fuzzy but breaking it down into one unit at a time helps give more clarity to the team around the exact short-term goals.
The most profitable way for a product to grow is via word-of-mouth. The above approach naturally optimizes for it. And once the testimonials & organic growth start kicking in, traction compounds with minimal incremental effort.
Of course, the key to executing this building approach well is patience. Again, think of a scientist. A larger research budget or more headcount can’t necessarily speed up a breakthrough. Similarly, building one unit at a time requires a small team committed to iterating over a long enough timeline for customer compounding to kick in. A lean & capital-efficient operating model is a requirement of this approach as a long runway significantly improves the odds of success.
Learning from my mistakes as a founder, as I have now started working towards regularly putting useful startup & investing content out there, I am consciously following the approach of publishing & learning one unit of content at a time – blog post, Twitter thread, LinkedIn post etc.
Same for my angel investing, wherein I am trying to help each founder, co-investor & startup employee I meet, one week at a time, with whatever resources I have – network, expertise, capital etc.
This approach is helping me to first put the core enablers of my venture investing craft in place that then, hopefully, self-compound. Therefore, I feel much better this time about hitting my long-term goals.
Also, in case you are interested in other similar startup insights shared by Mike Maples at the DraperU event I referred to earlier, check out my Twitter thread on it.
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