Soumitra Sharma

The Success Flywheel

Do you know what’s common between Shaq’s investment in Google, Ryan Reynold’s success as a marketer, the business dominance of Ivy Leagues & Peter Thiel’s investment in Facebook? A phenomenon I call the Success Flywheel.

In this post, I unpack this concept, including ways you can kickstart your own Flywheel.

Let me share a story that has 2 of my most favorite things in life – NBA and tech investing. Did you know that Lakers legend Shaquille O’Neal invested in Google’s Series A round in 1999 at a $100Mn valuation? Which, as we all know now, has turned out to be the biggest venture outcome of the last 25 years. So, how did an active basketball player get access to the deal of the century alongside Sequoia?

Shaq revealed the story behind his Google investment during his appearance at TheEllenShow a few years back. Apparently, he was hanging out at the Four Seasons in LA & started playing with a bunch of kids at the next table. In his own words – “I felt like I was babysitting this guy’s kids while he was in a meeting”. As it turned out, this stranger (Shaq didn’t disclose who he was) eventually let him into the Google deal.

Now, knowing Shaq’s storytelling skills, am sure this story is a bit jazzed up. And given he was already an NBA star in 1999 (he would go on to win his first ring in 2000), obviously this stranger must have recognized him. But even discounting for these possibilities, it’s clear that some amount of serendipity was definitely involved – meeting an important investor in a famous watering hill located in a powerful city led to him accessing a once-in-a-lifetime deal.

As you digest this, let’s cut to a similar story of another star, this time in Hollywood. Ryan Reynolds is now considered one of the savviest marketers & investors around. Look at his track record:

Became the brand personality for Mint Mobile, reportedly taking a 25% stake in the company. Mint recently got sold to T-Mobile for $1.35Bn!
In 2018, started promoting Aviation Gin and also took a stake in the company. The company was purchased two years later by Diageo for $600Mn.
In late 2020, co-bought a struggling fifth-division Welsh soccer team for 2Mn pounds. Used his marketing chops, including creating a Hulu documentary, to turn around the club’s attendance & revenues. It is now a thriving organization.

So, how does an active movie actor get access to deals that would be the envy of major private equity funds? And not just one-off – he keeps getting invited to the best deals one after another.

This is what I call the Success Flywheel at play. While the above are outlier examples related to top celebrities, I have seen the Success Flywheel working countless times both in my own career as well as those around me:

Repeat founders with prior success get access to the most venture dollars from the best investors. The other side of this coin – VCs with successful track records keep getting preferential access to the best founders.
The best recruiters (consulting, banking, investing, big tech) visit only the top campuses in each country for placements. So, these students get preferential access to the best jobs. And the flywheel doesn’t stop there – once you have any of these top logos on your resume, they act as preferential filters for subsequent jobs.
Early success brings folks to major economic centers like the Bay Area, NYC, London, Bangalore & Shanghai, either to study or work. Just by participating in the natural flow of information & people in these hubs, they get exposed to the best opportunities.

Morgan Housel of Collaborative Fund has a similar observation in his awesome post “Tails, You Win“:

The Success Flywheel is like a law of nature because it stems from fundamental human behavior. Across countries, cultures, sectors or even historical eras, at a fundamental level, humans are wired to maximize risk-adjusted returns while doing deals. Very crudely, there are 2 ways to do this – increase the numerator (return) and/ or decrease the denominator (risk).

Equally importantly, time is finite so people are looking to get to the most optimal risk-adjusted option, as efficiently as possible. This gives rise to the concept of “access” – how does one get in the flow of these people looking to do the best deals? ‘Cos they will quickly choose from people in their natural flow.

Having a prior event of success helps in getting repeated access to this flow as it creates a strong credentialing signal that plays really well to a crude heuristic that the human brain often uses – “if the person has been successful before, they are more likely to succeed again”. This signal drives 3 kinds of access: (1) Inbound (“I should talk to X”), (2) Referrals (“you should talk to X”) and (3) Serendipity (“have you met X?”).

1/ Inbound

The more socially-visible & externally-validated the prior event of success is, the more broad-based inbound access it drives to various kinds of flows. People looking to do deals proactively reach out even without any significant outbound effort (trying to sell yourself). Hence, visibly successful founders, investors, leaders, celebrities & experts keep getting access to opportunities.

This is also why conventionally successful professionals in any field still continue to productize & distribute themselves, building their personal brand & constantly growing their reach via networking, blogging, tweeting or starting podcasts. Putting oneself out there drives familiarity, which is key to inbound flow.

2/ Referrals

Everyone in these flows is typically in a consciously-cooperative mode, trying to optimize risk-adjusted returns for each other via referring opportunities, in the hope of future reciprocation. So, if a person has a prior event of success & on top of it, is also well-networked, it turbocharges referral-based access.

There is also a mini-flywheel at play here where a success event attracts people to your network, which drives referrals & more preferential access, thereby leading to more potential success & so on.

3/ Serendipity

Finally, even if you are not proactively looking for certain kind of opportunities (am sure Shaq wasn’t sourcing venture deals full-time), just being in the right flows puts you in the vicinity of serendipity that can take you in directions you never imagined. Shaq being at the LA Four Seasons at exactly the right time was the result of his outlier success as a basketball player, not his proactive networking skills.

The halo effect of success in one field generally transfers to other adjoining fields as well, which can drive massive serendipitous upsides. For eg. Peter Thiel’s track record as a co-founder of Paypal put him in the flows of Mark Zuckerberg in 2004, helping him become the first investor in Facebook. Or Jeff Bezos was able to invest in Google while it was still in the garage, courtesy of his success with Amazon.

Now the million dollar question – how does one leverage the Success Flywheel?

It starts by putting in the work to get your first event of success. The sooner the better so a sense of urgency goes a long way! And the good news is – unless one is born to privilege, most people start from scratch and build towards their initial success.

An event of success could be anything from cracking a top university, getting a coveted internship in a hot field, hustling into a brand-name job, hitting milestones with your business, creating a new product with buzz, publishing a paper, joining a board, building a social media following or just about any accomplishment in your context. Big or small matters less, it’s about getting a win on the score board to get the flywheel going.

While you are putting in the work towards your goal, also build a distribution network in parallel. This includes deep relationships & loose networks, both in the physical (IRL networking) & digital world (social media).

Once you get to that event of success, leverage your distribution network to amplify its impact. Make sure your success is visible, validated & shared in the ecosystem.

As Inbounds start, connect with people authentically, leave a good impression & look to solve problems for others.
To jumpstart Referrals, start using the tools & resources that typically come with success, to disproportionately give back to the network.
To leverage Serendipity, follow the golden rule of “showing-up” everywhere – meetings, events, calls, webinars, conferences, mixers, even birthday parties. PS: if you find networking at events a huge pain like me but still want to get better, check out my post “Networking at Events for Introverts“.

TLDR: the way to get a Success Flywheel going in your life is to first put in the work with a sense of urgency, and create an event of success, big or small. Once you get this event, make sure you “distribute” it well and ensure its compounding by continuous learning & effort.

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Meeting customers IRL still works

As the business world reverts to a blend of remote & in-person, meeting customers IRL is becoming important once again, especially in a slowing economy.

Sharing some thoughts on how jumping on a plane & meeting people could be key to unblocking growth for your business.

I was recently in a brainstorming session with a portfolio company that is struggling with stagnant growth. The company is profitable, has clear PMF as demonstrated by loyal top-tier customers, yet is unable to grow the business fast. It has major logos but the ACVs just aren’t expanding.

Now, as with any startup, stagnant revenue is a symptom & the causes could be many. In order to do a root-cause analysis & subsequently unblock growth, my immediate actionable input to them was simple – “go and meet customers in-person”.

When the bolt of lightning called Covid struck our planet, paradigms of doing business changed overnight. As workers went remote, so did interactions with customers. In fact, as companies were forced to do business with each other over video calls during the lockdown months, people discovered that it was both highly productive and profitable to drive the sales process sitting anywhere in the world with a laptop & a stable Internet connection, engaging customers living thousands of miles away over a shared screen.

As the world is stabilizing into a new-normal, many companies are now realizing that the success of a fully remote sales & BD process is highly contextual. In hindsight, its applicability & effectiveness became extraordinarily broad based in 2020 and 2021, mainly due to:

An excess liquidity fueled, demand-on-steroids environment, and
Altered social norms of human engagement.

Simply put, everyone wanted to buy so badly that the only bar the sales process needed to clear was to show up on a Zoom call. And, it also helped that nobody really wanted to meet a stranger in-person & take the risk of Covid transmission.

Now, as we sit in 2023, both these factors no longer exist:

Demand is contracting across industries, courtesy of the ongoing cycle reset driven by rising interest rates.
Post vaccine, broader social norms have reverted to a blend of remote & in-person. What proportion will they reach at steady state is hard to predict, although with the present return-to-office movements even with Big Tech like Amazon & Meta, my guess is 60% in-person & 40% remote (assuming a continuing trend of 3 days per week in office).

It’s critical for all founders & operators, especially those in early stage startups that typically have finite resources to deal with business headwinds, to quickly embrace this reality. In a 60-40 IRL:remote world with contracting demand, it’s unacceptable if founders & senior leaders aren’t getting on the plane to meet customers & build trust.

Meeting customers IRL has multiple advantages. First, leaders taking the time to travel & spend bandwidth in listening is a strong demonstration of commitment. It’s Strategy 101 that in most cases, it’s easier to grow a current customer vs land a new one. Even in consumer products, product leaders first focus on retaining existing customers + re-activating inactive ones, before filling up the top of funnel with new leads. In any business, growth is possible only when existing customers are happy.

Second, breaking bread with customers builds 1:1 trust with their execs, putting a human face to contracts, transcending beyond employers & current deals to opening up the possibility of these leaders becoming your personal champions for long after.

Third, getting informal feedback about their product experience as well as larger problems & challenges they are facing, & then connecting the dots across multiple such conversations, is the best way to do a root-cause analysis of “why are we not growing fast enough?”.

Going back to the portfolio company I mentioned in the beginning, I gave them a very simple & actionable plan for the next 8 weeks to unblock growth:

One founder to play what I call a ‘Key Accounts’ role.
Literally make an excel sheet of top 5-10 customers, hop on flights, meet key execs IRL, get feedback, hear their problem statements & build a personal rapport via drinks/ dinner.
As an output of each meeting, create a simple roadmap for (1) enhanced customer success, where customers are unhappy and (2) in-account revenue expansion via upsell/ cross-sell, where customers are happy & want to grow.
Finally, and most importantly, partner with relevant teams (product, delivery ops etc.) to unblock & provide execution momentum to these customer-wise revenue roadmaps.

The founder’s role shouldn’t end with token customer visits. Driving results by providing the necessary context, energy & cross-functional unblocking help to operating teams is the real output all stakeholders are looking for.

Btw, as I was working on this draft, star product operator & angel Gokul Rajaram posted this thought yesterday on the importance of building relationships in enterprise sales:

On a side note, willingness to get on a plane often is a career hack I used very successfully at Alibaba & something that I learnt from my then boss. While our international peers in US & EU offices loathed traveling to China & facing all the inconveniences (from jet lag & language to food & other cultural disconnects), me & my team would show up in Hangzhou every month, blending in with our local colleagues & building trust over meals, rice wine & karaoke. Slowly, we came to be known as the “true believers” – the only team willing to make the sacrifice & do a round-the-world trip every month to get s**t done. We gradually earned the right to be ‘insiders’, getting access to unique growth opportunities within the Group.

Now in this new phase of my career as a tech investor, am doubling-down again on this approach. As I ramp up venture investing in the US-India corridor, I am aiming to spend at least 2 weeks per quarter in India & devote more operating time to portfolio founders, grow new deal flow, cement old ecosystem relationships as well as initiate new ones.

Let me end this post with an article from Jason Lemkin of SaaStr that I really like – 10 Things That Always Work in Marketing. This is a must-read for anyone looking to unblock growth in their business. The suggestions go much beyond marketing, touching on all aspects of go-to-market. Reproducing the section on visiting your largest customers:

The 3Cs of career leverage

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:

When WhatsApp got acquired by Facebook for $19Bn in Feb 2014, it had only 55 employees and yet, had built a product with 450Mn MAUs.
Masayoshi Son of Softbank invested $20Mn in Alibaba in Jan 2000. When Alibaba went public in 2014, Softbank’s stake was valued at ~$90Bn, a 4,500x return. Similarly, Peter Thiel’s 2004 angel investment of $500k in Facebook turned into a ~$1Bn cash return when the company went public in 2012.
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.

Doing more with less

As an angel, one of the strongest leading signals I look for in a startup is progress per unit of capital – how much forward movement has the team achieved & the resources it has consumed for it.

My thoughts on why a capital-efficient mindset is so important for early-stage tech founders.

Having seen 1000s of deals across a decade of investing my own as well as institutional money, I rarely cringe while evaluating a new company. As an investor, I have often seen the same goods-and-bads in other deals several times before. As an ex-founder, I have walked the path & made the same unforced errors so almost every time, I can empathize & almost pre-empt why a founder is doing things a certain way.

However, there is one specific thing that is guaranteed to make me cringe – a founder attempting to raise an amount that is totally out-of-sync with where the business is. In many cases, this is accompanied by other precursors:

No intent to bootstrap from idea to “some” traction.
Wasteful handling of the last round.
Coding & building product for months at a stretch without putting anything meaningful in front of customers.

Personally, one of the strongest leading signals I look for in a startup is progress per unit of capital – how much forward movement has the team achieved & the resources it has consumed for it, especially when evaluated relative to other comparable startups.

I remember an interesting learning from my time at IDG Ventures (now Chiratae). Sudhir Sethi, the Managing Partner & the lead investor who had backed Myntra (Zappos of India at that time; was eventually acquired by Flipkart for ~$300Mn in 2014), often cited how when he went to meet Mukesh Bansal (the founder) for the first time at the Myntra office, he observed they were working out of a dingy space in a classic Indian neighborhood market with the ground floor occupied by a fruit & vegetable vendor. Sudhir used this as one of the positive signals for the team’s ability to execute in a cut-throat eCommerce vertical like fashion.

Fast forward a few years, and I got a similar insight yet again in the retail context. While working with Alibaba, I saw how frugal the Group was in terms of saving every dollar of operating cost. eCommerce works on wafer-thin margins, especially in highly competitive & price-conscious markets like Asia. And one could see this by comparing the bare minimum facilities & perks we got at the US HQ in San Mateo vs even well-funded growth startups, which were offering everything from catered meals to draft beer stations at that time.

Why is a capital-efficient mindset so important for early-stage tech founders? It’s because they are playing a game where the odds are hugely stacked against them. Where 9 out of 10 new startups fail on average. Where the starting point and end point of companies are vastly different, with each year choked with iterations, a major pivot every few years, and team members jumping on & off the ship.

Setting yourself up to have even a remote chance of winning such a game requires many shots at the goal, many course corrections, and many resets. At the same time, capital is scarce at the pre-PMF stages even for the best teams. Capitalism is brutally efficient, throttling money when relative risk is high, & opening the faucet once success is highly certain (typically post-PMF).

Building even a decently sized company can take anywhere from 6-8 years, & up to 15+ years. In such a long period, both the overall economy as well as your specific market will go through several cycles. The key is surviving long enough, even with limited capital, to be able to walk this arduous path.

This is what the best founders bring to the table – using investor capital like their own, each dollar wisely deployed towards only what’s truly necessary for the stage, raising each round with specific milestones in mind, and realizing that ownership is everything, with each bps of dilution being the costliest trade shareholders can make. To me, this mindset & building approach is perhaps the biggest signal of perseverance in a team.

Come to think of it, in the non-tech world where starting a business isn’t called “doing a startup”, entrepreneurs typically use their savings to get going, & once there is enough business confidence & profitable revenue flowing-in, grow using either internal accruals or debt. Initial bootstrapping creates skin-in-the-game, profitable revenue creates high confidence that customers want what you are making, & debt creates financial discipline around managing cash flows while preserving the founder’s ownership to compensate for all the risk they have taken.

This model has been used by everyone from Sam Walton to Richard Branson, & continues to survive in all parts of the SMB economy. While the venture capital model definitely works for building tech companies, which are asset-light, highly scalable & operate in winner-takes-all dynamics, I believe the founders who are in it for the long run build with a similar philosophy – planning for the next basecamp & raising conservatively, maintaining discipline around cash & giving high importance to ownership.

On a related note, I wanted to share something I recently wrote on Twitter regarding a fundraising pitfall specifically for serial founders:

Often see serial founders who have seen success before (scale and/ or exit), raise large rounds at high valuations at the idea stage!

From what I have seen, even the most successful founders have operated in phases where a lack of capital could have potentially killed their startup. That’s probably why on the 2nd attempt, they try and take that risk out of the equation at the beginning itself.

Oddly enough though, having a capital-rich Plan B to fall back on reduces the scrappy iterativeness, discipline & underdog mindset that startups usually need to succeed. And which probably contributed to their success the 1st time too.

In asymmetric bets like startups, to reference The Dark Knight Rises, “the way to climb out of the pit is without a rope”.

Hopefully, as this cycle resets, all of us founders & investors will go back to the drawing board & start appreciating Benjamin Franklin’s age-old virtue of frugality as a key to success in business & life.

Conviction vs Randomness in Venture Investing

Recently came across a fascinating Twitter thread from June 2020 by Dave McClure, ex-founder of 500Startups, where he talks about how “investing with conviction” is a myth. This tweet captures his sentiments well:

I agree with several arguments in this thread:

1/ Picking winners in early-stage investing is really hard. Power laws govern the best venture portfolios, driving down the hitting %. Per Horsley Bridge data, even for a top VC firm like Sequoia, ~4.5% of portfolio companies generate 2/3rd of aggregate returns.

2/ Intelligent venture investing, by its very nature, involves making both Type 1 and Type 2 errors. Therefore, even high-conviction deals are likely to exhibit unexpected outcomes, both positive & negative.

3/ There is a lot of hindsight bias in the way investor narratives are created around companies that turned out to be successful – “Look, I had high conviction on this deal & it turned out exactly as I expected. Ergo, I can predict the future”.

So in games like this where outcomes are random & often uncorrelated with the level of effort that goes in, does it make sense to discard the input process?

Based on more than a decade of venture experience, I tend to view it differently. I believe it’s still important to have a rigorous process of building conviction and to keep improving it bit by bit with each experience. Even though eventual outcomes might still be random, this approach helps tilt the playing field a little in your favor every time. Over a long enough time horizon, as one keeps taking more shots at the goal & with continuously improving odds, the hope is that a home run arrives sooner than later.

Particularly at the earliest stages (angel/ pre-seed/ seed), especially with the advent of small check investments ($1-5k via syndicates/ SPVs) attracting a new generation of 1st-time investors, it’s easy to assume that outcomes are randomized & therefore, fall into the trap of doing spray-and-pray that isn’t backed by an intelligent investment process.

It’s important for new angels to first deeply study the asset class & build their personal investment process – areas of expertise, focus sectors, stages, target founder persona, deal flow engine, unique value-add to get into best deals etc. Post which, the odds of success are significantly better.

While being a champion of a “conviction-building” investment process, I also agree with the 3 takeaways that Dave closes the thread with, regarding having enough shots on goal:

Even with the most intelligent investment process, venture investors need to acknowledge their limited picking ability & therefore, keep taking enough intelligent shots at the goal for the odds to work in their favor. Semil Shah of Haystack wrote a great post titled “Shots on Goal” on this idea a while back.

Equally important as portfolio diversification via numbers, is making asymmetric investments – ensuring that the few winning bets have huge outcomes so that even with a high loss ratio, the returns math still works at the portfolio level. The smartest thing a venture investor can do is to befriend the power law, and work towards being on the right side of it!

To summarize, acknowledging the randomness of venture outcomes doesn’t need to be at odds with running a rigorous & continuously-evolving investing process. In fact, such a system should be intelligently designed to account for this randomness, combined with other considerations like power laws, compounding, economic cyclicality etc. Even a few points of “edge” that is systematically created with each experience, can slowly accumulate into a sizable alpha over the long term.

Munger’s Tao

I recently came across this awesome Tweet & Podcast from David Senra of Founders Podcast, wherein he captures learnings from his dinner with Charlie Munger, as well as his reading of The Tao of Charlier Munger.

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.

Good ideas are rare. When you find one, bet big.
Charlier Munger

4/ Portfolio concentration creates outlier outcomes

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”.

PS: If you love Charlie Munger’s wisdom, you might enjoy my post capturing his musings from the 2o23 Daily Journal Shareholder’s Meeting.

The Familiarity Conundrum

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.

SMB SaaS at Scale: Founder Learnings from HubSpot

SMB SaaS is hard. Getting the positioning right, increasing ACVs, controlling churn – it all becomes harder when your customer is a small business that is resource constrained & perpetually dealing with its own execution challenges.

Despite this, given SMBs are the most frequent early adopters of new products, the reality is that most startups tend to start mid-market. Though, in my experience, a majority get stuck in unfavorable economics of this customer segment & are unable to achieve breakout PMF.

So, what is the secret sauce founders can learn to effectively scale SMB SaaS? Hubspot is a great case study. I recently came across this SaaStr podcast with the HubSpot CEO Yamini Rangan, where she shared some of the company’s SMB strategy & learnings. Here are the key highlights:

Go after a large TAM: given the fragmented nature of SMB verticals, it’s really important to have a large TAM. HubSpot made the smart decision to transition from marketing automation to CRMs, basically going after Salesforces’s lunch.

Mid-market verticals tend to have open opportunities for startups as SMB customers are usually sandwiched between either buying a host of solutions & stitching them together or buying an expensive, enterprise-grade solution. In this context, I had recently posted a Twitter thread about how Zoho followed a similar multi-use case bundling strategy to position itself as an “operating system for SMBs”. This strategy works well as SMBs have a tendency to simplify their tech stack & procurement processes by buying multiple solutions from the same vendor.

2. Customers gravitate towards competitively-priced, mission-critical products: in times of economic uncertainty like today, SMBs tend to become really sensitive about budgets. Customers start asking tough questions internally around (1) where are they spending?, (2) do they have a clear path to getting enough value from the spend? and (3) can they do more with less?

Acting per this analysis, SMB customers are then likely to consolidate their tech stack to a handful of mission-critical platforms that are competitively priced & deliver the most value. This is the bar startup products need to cross while selling in this tough macro environment.

3. PLG-based distribution is king: to achieve break-out growth in SMB SaaS products, startups need to have the widest possible distribution. The front door needs to be big enough so that most people can come in.

For the first 8-9 years, HubSpot was mainly driven by a sales motion comprising Direct Sales & Partner Sales. Around 2016-17, in order to exponentially grow distribution, the founders made a counter-intuitive bet to go from sales motion to product motion. Today, HubSpot has a massive user base of ~1Mn WAUs to monetize off of.

4. A strong “free” product is key to PLG: One of HubSpot’s truly differentiated product strategies has been to offer a strong, full-featured free product. Rather than making a “free” product free just for the sake of it, they have focused on making it really valuable.

Some important benefits of having a strong “free” plan:

Drives high top-of-funnel growth & user engagement, improving the probability of monetization once the value is proven out.
Puts product org. under pressure to deliver enough features at the top, in order to maintain the competitiveness of paid versions.
Forces the product team to maintain a “consumerized” ease of use, which benefits all customers, free or paid.

Irrespective of whether your GTM is sales-led or PLG-led, a founder should never give up on the “free” plan as it’s key to keeping your product competitive.

5. North Star Metric should be Net Revenue Retention: NRR is the best health indicator of an SMB SaaS business given it represents whether or not: (1) you are retaining the customer, (2) you are continuing to drive enough value so they buy more from you and (3) you are protecting yourself from churn.

6. Don’t underestimate the value of a Partner ecosystem: once you reach a certain scale, PLG & Direct sales aren’t enough. A thriving partner ecosystem can be a strong GTM moat. Interestingly, a majority of HubSpot solution partners *only* sell & deploy HubSpot as a CRM, thus creating valuable network effects for the company.

7. In geo-expansion, less is better: PLG-driven companies will always have customers in many countries eg. Hubspot has 130+. But in order to deeply localize for elements like language, currency, customer support etc., it’s important to focus only on a few markets. As an example, HubSpot has chosen 7-8 markets to deeply localize their offerings in, based on factors like TAM, existing installed base, net ARR growth being seen & the company’s ability to serve the market locally.

While SMB SaaS can be a tricky business model, it compounds beautifully once the founders figure out its key levers, as HubSpot has shown.

PS: if you enjoyed this post, you might also find this post on Top 10 enterprise SaaS learnings from a unicorn founder helpful.

The real risk is the unknowable, not the unknown

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.

The futility of Plan B

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)

Author: Soumitra Sharma

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The real risk is the unknowable, not the unknown

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The futility of Plan B

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