Tag: Career Advice

Networking at Events for Introverts

I am petrified before attending any event!! There, I said it. Mixers, happy hours, cocktails, group dinners, you name it – the right side of my brain hates them all. Even attempting to “work the room” is equivalent to getting a root canal for me. Who to say hi to first? What does one talk about with a complete stranger? Why am I even here? My mind is fuzzy with these & many other questions, even as I attempt to fill out my name tag with an oversized marker, using my rarely-used & barely-legible handwriting, while awkwardly stooping over the registration desk.

But with experience, you learn to consult both sides of your brain. And while the right side of my brain is freaking out, the left side is reminding me of all the useful insights I have gathered, the wonderful collaborators I have met (many of whom have become close friends), & the positive energy I have taken away from these mixers, happy hours, cocktails & group dinners.

So yes, I am a self-confessed introvert who has been on a long journey of figuring out how to get myself to attend & do better at events. While I curse myself while driving over, palms sweaty, brain thinking through all the small talk I would need to be prepped for, admittedly I have been better off in my career & life after attending almost every one of those events.

Am sure you have heard of that old wisdom – “you should do what you fear the most ‘cos that’s where your growth is”. In that spirit, around the Fall of last year, I resolved to attend every good event I was invited to. But this time, I went in with an approach that I felt would work for me, incorporating all that I had observed about myself during & after these events.

Here are some ideas from this approach:

  1. Ask for an attendee list before the event – I figured that not knowing who I will be bumping into gives me major anxiety (yes, I am a prep-first kinda guy!). So I now ask for attendee lists upfront, so I can identify a few people I would definitely want to introduce myself to. This reduces uncertainty & guarantees at least a few interesting convos. PS: how do you do this when the guest list isn’t available, you ask? Simple – to begin with, I focus on having a good conversation with the event lead 🙂 Guarantees one valuable discussion at the minimum.
  2. Keep modest goals, quality over quantity – early on in my career, I used to put a lot of pressure on myself to meet the most number of people at an event, which made the whole thing really unpleasant for me. Over time, I have realized that spending focused time with a few quality people is significantly more valuable than exchanging business cards with tens of folks. So now, for an average close-knit event, my goal is to walk out with 1-3 quality connections that I can follow up with later. This reframing has been a real game-changer for me!
  3. For large events, set up 1:1 meetings on the sidelines – while attending large conferences, I didn’t even know where to begin, leave alone spending quality time with relevant folks. One hack I have developed is to avoid networking en masse at these conferences. I post on LinkedIn & Twitter that I am attending a particular event & then use outbound (using attendee list) + inbound (via social) to schedule 1:1 meetings on the sidelines. This takes the pressure off of working a large room & ensures a number of focused interactions.
  4. Connect on social post-event – events are just a lead-gen channel. The real value is in transforming these cold connections into warm relationships. Many times, in-person follow-ups are hard to schedule. I have found interacting on social (Twitter & LinkedIn) with these connections to be immensely useful in both giving us more context about each other, as well as maintaining momentum in the conversation. Personally, my social media game is much better than my events game, so this is one of my top strategies.
  5. Lastly, be genuinely curious! – my coach said something beautiful to me last year – “to form meaningful connections, replace judgment with curiosity”. Meeting new people with genuine curiosity, without overthinking about motives & outcomes, totally elevates the quality of human interaction. If I have to suggest just one mindset that can help you the most while meeting new connections, this is it! Whether we are introverts or extroverts, we all crave genuine human connection. And I believe that authentic curiosity is its strongest source.

This topic is very close to my heart so I hope these points are helpful as you initiate new connections at events. I am very much a work-in-progress at this, so please share your learnings too 🙏🏽

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Bouncing back in careers

It’s been a gut-wrenching last few days for us to witness several friends get impacted by Google’s RIF. My wife is a tenured Googler so naturally, we have built some outstanding relationships there & got so much value out of its community. This makes it even harder to see close friends & collaborators come to terms with this abrupt life change.

Folks who have built successful BigTech careers are typically pros at the job-hunting process, so I don’t think I can share any particularly new insights there. However, there is one idea I believe could be relevant in navigating this phase, & that I have been sharing with some friends over the last week. It’s the value of being “radically open-minded” while searching for your next adventure.

As we progress through our careers, especially beyond the first decade, we tend to build a certain self-image in our heads. It mostly reflects where we have seen the most external success in the past (titles, money, fame, influence etc.). But the reality is that the market is an ever-evolving beast that doesn’t really care about this self-image.

So while we might believe that we fit best into specific roles, or deserve certain compensation, the market may disagree. And this isn’t necessarily a negative reflection of one’s skillsets or experiences – in rapidly-changing industries like tech, the definition of talent-job-fit for the same role keeps shifting across eras, especially when the macros are hard. We don’t get exposed to this change while at a stable job until we start job hunting under pressure, which is when this reality hits us in the face.

So how can one effectively deal with this challenge while job-hunting? The key is having a radically open-minded approach to this process. Borrowing from a beautiful piece of advice one of my mentors gave me when I was trying to bounce back post my startup – try & approach this phase the same way a founder tries to find product-market-fit:

  • Talk to many different types of customer segments
  • Deeply understand their pain points
  • Talk about your unique value proposition & how it can potentially solve these pain points
  • Observe where your value prop is resonating the most
  • Follow the highest-fidelity customer signals
  • Have an overall vision as a guiding North Star, to keep this process aligned with your internal compass

This approach is much more “discovery-based” (where does the market believe I can uniquely solve a problem), rather than “search-based” (this is what I want OR this is where I think I fit in the best). Similar to how market-pull takes startups in directions that the founders never originally expected, it’s worth being open to all kinds of re-framings & new opportunities that the market sees for you as a professional.

The curse of being an achiever is believing that you know exactly what’s best for you next. I call this a local maxima. But often, the market is giving you signals that can potentially take you to a global maxima in the long run, allowing you to become the best version of yourself. You just need to a) listen to the market & b) be brave to move in new directions. That’s what being radically open-minded is.

Humbly sharing these 2 cents from my own life experience, with the hope that it can give you a new tool to emerge stronger from this uncertainty. If I can help you in any way (listen/ brainstorm/ give intros), please don’t hesitate to DM me on Twitter. More power to you!

PS: in case you are interested in startup roles, especially in the US-India corridor, feel free to check out my portfolio. Happy to make intros.

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Building an anti-fragile career (& life!)

With the recent layoffs at Twitter, Stripe & Meta, alongside the implosion of FTX, this appears to be the decisive starting point of the tech downcycle in the US. While market leaders & institutional investors have adequate resources to ride this impending downturn, the real impact is going to be felt by tech workers, who designed their lives around the prevailing system of high cash comp, RSUs whose value kept going up (courtesy of a low interest rate fueled bull market over the last decade), fielding multiple job offers largely driven by their employer’s brand and work-from-home flexibility.

This downturn will shift the power back into the hands of employers. Many in their 20s & early-30s will discover that they are ill-equipped to operationally, financially & emotionally deal with this drastic reset in the tech job market. In most cases, the hardship they will go through will have nothing to do with their capabilities or contributions.

As we all prepare to face this downturn with little personal control over many externalities, I believe this is the right time to ask a really important question – “how do we build an anti-fragile career (& life!)?”. For those not familiar with this concept, it was coined by one of my favorite modern thinkers – Nassim Nicholas Taleb. Here’s how he defines it in his book by the same name:

Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure , risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better. 

From Antifragile: Things That Gain from Disorder (via Farnam Street)

Dealing with volatility, randomness, risk & uncertainty is an inherent part of an outlier tech career. Unlike other industries, tech is ruled by ruthless power law outcomes that are driven by tremendous leverage (software), high scalability with minimal marginal cost & top talent that creates intense competition by starting, operating & investing in new ideas. Given these dynamics, capital & talent rushes into prospective outlier companies, all of whom then execute with intensity. Ultimately, a handful of market leaders remain standing in each space, and the rest die. The cycle then resets – rinse & repeat.

While the above pattern seems obvious on reading, most tech employees remain oblivious to the “high risk-high reward” game they are playing. While early-stage founders, startup employees & venture investors understand this more than others, this downcycle is showing that even FAANG & scaled enterprise software jobs aren’t as derisked as everyone thought. This isn’t surprising, given the sheer pace & intensity of creative destruction in most tech verticals. And if we go by how things have played out since the dotcom crash in ’01, this disruption will only become more brutal in the next 2 decades.

So coming back to the anti-fragile career (& life!), I have been asking this question to myself for more than 5 years now. I started thinking on these lines much earlier than usual, probably ‘cos I have a tendency to keep disrupting myself in order to chase large opportunities & therefore, I have subjected both my professional & personal lives to significant stressors over the last decade. From leaving a lucrative VC career in India to move to the Bay Area with just 2 bags & no job in hand, to giving a shot at driving Alibaba’s global expansion pre-IPO when few knew about it, then doing my own startup through the pandemic in a very lean way, while in parallel to all these adventures, also angel investing with my own salaried money in 20+ companies, many of them at an idea stage.

Having been on every side of the table over the last 15 years (founder, startup operator, big tech operator, angel, VC), one thing I internalized very soon was that chasing large outcomes in tech is a high failure rate, multiple-shots-at-the-goal kind of game. It’s hard to know with high certainty what product/ company/ investment will become an outlier & when, so staying power becomes super-important. In this context, another mental model from Taleb (originated from his days as a public markets trader) really resonated with me:

Avoid risk of ruin.

Nassim Nicholas Taleb

I combined the 2 models of creating an anti-fragile career and avoiding risk of ruin, to design & practice my life in a very specific way. Sharing some of my key life rules for the benefit of anyone with similar goals & context:

  1. Embrace risk – rather than ignoring or avoiding it. ‘Cos risk will find you anyway. The best starting point for managing risk is to acknowledge its perpetual presence in your life.
  2. Regularly practice adapting to change – over a long lifetime, change will creep up on you whether you like it or not. It’s important to keep your muscles trained during peacetime, to deal with big changes during wartime. Going out of your comfort zone & routinely taking up low-risk, micro changes go a long way in building muscle memory. Eg. take up the mini-project at work that you don’t feel ready for, overcome your inertia & go to the networking event, or push yourself to have that tough conversation you have been avoiding.
  3. No complacency – remember the best-seller ‘Only the Paranoid Survive‘ by the legendary Intel Founder & CEO Andy Grove? Oh man, it’s so true! The key to thriving across cycles in tech is to never be complacent in your success. It only takes one black swan event, one war, one economic crisis, or one new competitor to take it away.
  4. Acquire & continuously improve real-world skills – whatever is the space, stage or timing in the economic cycle, core operating skills are always going to be valuable for building any business. In tech, the 2 core “L1” skills are a) ability to build a software product and b) ability to sell a software product. These are then surrounded by other “L2” skills such as operations, finance, human resources etc. Whether you are 25 yrs old or 45 yrs old, acquiring & improving these L1 skills (backed by specific L2 skills you are good at) should always be your North Star.
  5. Execute your skills with hustle – an armory of relevant skills is irrelevant unless it’s backed by strong execution. Be it a tech startup or a publicly-listed Big Tech, superior execution is key to winning & retaining market share. In this context, the word I really like to use is “hustle”. In my book, hustle means “doing whatever it takes to get the job done”. Unfortunately, everyone’s hustle-quotient goes down in bull runs, as returns become increasingly uncorrelated with effort & more correlated with (rising) macros.
  6. Hone your specific “competitive edge” – as with companies, talent gets rewarded the most when it figures out its specific edge & brings its skills+hustle to a team that needs that edge the most. Like the way any good founder or leader evaluates their product, view yourself as a ‘product’ too. Keep asking yourself the question – “where do I have the strongest product-market-fit?” to figure out what your edge is.
  7. Nourish a high-quality network – to start the go-to-market of your ‘product’ (skills+hustle+edge), you will need the support of your network to do lead-gen of relevant opportunities. The best opportunities are almost always behind the firewalls of relationships & cliques. And it’s difficult to break into it cold when you really need it. Important to keep investing in & nourishing a wide-enough network, especially as loose connections typically give the best access.
  8. Play repeated games with the most-valuable relationships – while building a wide network, it’s also important to identify a small set of people you have the most professional synergy & personal resonance with at any point in time. Once you know who they are (<10 people in most cases), consciously make an effort to reach out, help them achieve their goals & look for ways to collaborate with them. Behind every game-changing opportunity is prior trust & reputations at play. The best way to build real trust is to play repeated games with a small set of high-quality people & show up with consistency in them.
  9. Minimize leverage – history shows that the most frequent reason behind the ruin of both companies & individuals is leverage (debt). And interestingly, the propensity to take on more debt rapidly increases during bull markets. Of course, home mortgages are an important source of cheaper, long-term debt but even that needs to be done with discipline wherein your monthly cash flows should line up well even if the going gets tough. I grew up in a middle-class Indian household and as every Indian of this background will tell you, we are taught to be wary of debt since childhood. Now I know why!
  10. Maintain low household burn – even the highest salaries cannot sustain a lifestyle that goes beyond means, leave alone the scenario of tough times wherein the salary itself goes away for an extended period of time. To keep playing the game during both good and bad times, I always like to remember Benjamin Franklin’s age-old virtue of “frugality”. Living below your means is key to avoiding ruin & getting your freedom back.
    • Bonus point: to lead a quality life even while staying frugal, I have found “focusing on value-for-money (ROI) over penny-pinching” as a good framing to achieve goals that are important to you while minimizing personal conflict.
  11. Create multiple sources of income – as the current layoffs are showing, even if you are the most talented & hardworking employee, your salary can go away in an instant & due to reasons that are completely outside your control. I strongly believe that a monthly salary as the single source of family income is a major personal finance risk. Whatever your life stage might be, it’s important to continuously work towards creating other sources of income. These could be dividend income from public market investments, rental income from real estate, side-hustles like operating an Amazon store, weekend consulting or contracting work in your area of expertise etc. Though it might take several years of focus & discipline to put these non-salary cash flows together, once this system gets set, it will compound without much effort and give you freedom & flexibility when you call on it.
    • Bonus point: while setting up these supplemental income streams, it’s equally important to do the basics of personal finance & money management well. These include 1) paying off high-cost/ short-term debt (eg. credit card, auto, personal loans etc.), 2) saving x% of income every month & investing it in your desired asset classes, 3) taking full advantage of relevant tax benefits including maxing out retirement contributions (401k, Roth, IRA, 529 etc.), 4) avoiding large-ticket, cash-flow-foolish decisions at every life stage.

These are some core rules I have discovered while attempting to create my own anti-fragile career (& life!). The virtues behind them are all from grandma’s wisdom – discipline, humility, less ego & more sacrifice. As it turns out, grandma’s wisdom is more relevant than ever in this age of AI & Crypto 🙏🏽

Sending you my very best wishes, as you navigate these turbulent times. This too shall pass, and when it does, I hope to see you stronger (& anti-fragile) on the other side ⭐️

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Reflections from the last decade as a banker->VC->operator->founder

Starting the 2010s as a fresh b-school grad, the last decade has been grueling, challenging, uncomfortable, full of highs & lows but significantly net positive on professional & personal satisfaction. Post-facto, if I have to give it a theme for myself, it would be “taking risk & embracing change”.

I distinctly remember watching the legendary Steve Jobs Stanford commencement speech on YouTube in mid-2010, while I was going through a phase of disillusionment and feeling a strong disconnect with the way I perceived the world to be operating. As I saw him speak, for the first time, I got a life-approach framework that finally made sense to me — my job was to execute on my “voice” (instinct/ conviction/ belief/ interests/ enjoyment), create enough “dots” (businesses/ opportunities/ relationships/ products/ investments) and trust the universe that these dots will all connect in hindsight and reveal the overall picture much later in life.

Following this approach, I consciously put myself through a series of diverse experiences that positioned me to create enough of these dots. These spanned various sectors & functions (investment banking, venture capital, startup operator, big tech, angel investor & now, founder) as well as markets (US, India, China, SEA). Over the last decade, I lived/ spent considerable time in Hyderabad, Chicago, Mumbai, Bangalore, Hangzhou, and San Francisco. Of course, a lot of this was a result of spotting & reacting to opportunities that presented themselves in an organic flow of life, but there was always a strong underlying intent behind taking risks, stretching limits, keeping oneself uncomfortable & embracing change.

I have been fortunate that in this last decade, this approach has resulted in several professional dots — investing in the first Internet wave of India, VC portfolio companies going public/ getting acquired, being part of $2Bn+ of tech investments from angel to late-stage, taking businesses global out of the US and China, being part of products that have touched 100s of millions of users globally, supporting & working alongside so many world-class founders, investors & colleagues, working under the leadership of the likes of Jack Ma and Joe Tsai, traveling the world and operating across cultures to get things done. My hope is that all these dots will start connecting in the next decade, and a worth-while picture shall emerge at some point.

Given the last decade has been a “foundation” phase for me professionally, I thought it will be useful to pen down my experiential learnings, with the hope that it might benefit you. The caveat is that these are all very specific from my context. I hate generalizing and therefore, will request that you absorb these for what you feel they are worth to you. Also, rather than making an overall list, I will capture the top points for each functional phase of my career during the last decade, so you can pick & choose what is contextually relevant for you. I have also ordered the sections chronologically, from the earliest to most recent.

Top professional learnings for the decade of 2010s:

A. As a VC

  • Identifying & backing awesome founders as early as possible is still the main driver of returns.
  • High-quality & timely “deal access” is key to VC success, as is identifying the winners early and doubling down on them.
  • As a VC professional, if top-quality founders want to take your check and have you onboard irrespective of the firm brand behind you, that’s when you know you are doing a good job.
  • Trusting your conviction on the “fundamental value” of a company and holding on to it even during chasms, leads to potentially outsized returns.
  • It takes a long period of time (min. 5 to a max. of 10+ years) for value to accrue & then get realized.
  • There is space for many different types of funds & investing strategies. The key is to survive the bad times.
  • In good times & bad times, the flywheel of “raise-deploy-exit-raise” needs to continue. Capital has to keep churning.
  • Important to create a few but really deep co-investor relationships, to be able to partner & grow together.
  • Creating an authentic & consistent personal brand (digital + offline word-of-mouth) is a source of significant professional leverage as a VC.
  • The world is a big place and there are many sources of capital with varying belief systems. Sometimes, just one person needs to bite the bullet for a company to be king-made.
  • Finally, however smart you think you are, it’s still extraordinarily hard to pick. Important to still maintain a diversified portfolio.

B. As a startup operator

  • Despite how much capital or how large a team the company has, it’s still damn hard to build & regularly ship a decent working product that customers like.
  • Despite how much capital or how large a team the company has, it’s still damn hard to achieve product-market fit. You will be surprised by how many well-known and well-funded companies might, in reality, have no PMF.
  • More often than not, over-capitalization induces bad behavior across multiple levels in a company.
  • The best way to drive positivity in the culture is rallying people around business momentum (users, revenue, shipping product etc.). No momentum = disillusioned employees + too much time to have negative water-cooler conversations + internal political struggles = screwing-up culture bit-by-bit each day.
  • Over-hiring is one of the biggest crimes in a startup.
  • Irrespective of stage & functional skillset, a solid execution ninja will always merit a place on the team.
  • Rigorous ops & program management is an often under-valued skillset.
  • In every aspect of the startup — focus, focus, focus.

C. As a big tech operator

  • Actively chase roles that have the potential for max impact.
  • Align with most-empowered & internally-influential leaders. You are unlikely to make fast progress under a weak leader.
  • Focus as much on building internal relationships, as external ones.
  • Focus as much on building your internal personal brand, as the external one.
  • Stay away from any role that makes you a paper-pusher.
  • Identify & double-down on what uniquely sets you apart from the clutter of peers.
  • Figure out the “game” as soon as possible (it varies for each company and often, even amongst teams). Be ready to play the game, else be prepared to get sidelined. Ideal scenario — if you have the capability & backing, change the “game” itself.
  • Follow-up —be persistent, don’t take no for an answer, control your ego.
  • Over-prepare — every meeting is important & needs prep. Every “let’s grab a coffee”, “let’s have a quick call”, “let’s do a quick huddle” will influence your perception & trajectory within the company.
  • Learn how to position & sell…your vision, your story, your plan, your headcount reqs, your budget, and yourself.

D. As an angel

Have invested in about 18 companies over last 5 years via my investing platform Operators Studio. Here’s what I have learned:

  • Write checks only of amounts that you can immediately write-off mentally.
  • No one can pick at an angel stage. Create an extremely diversified portfolio.
  • Diversify across multiple vectors — sector, vintage, markets, stage.
  • If you are personally convinced of the sheer ability of a founder, just write a check.
  • Be reasonable about what operating value-add you can realistically provide. Don’t overpromise.
  • Assume that in 50% of cases, co-founders will split.
  • Post 24 months of investment, you will likely lose all touch with founders and receive minimal company updates/ info.
  • Ideally, have some sort of a broad investing framework. Assume it won’t work in most cases, but will likely improve your odds.
  • Follow your playbook, but don’t stop being opportunistic. If you are getting a chance to board a potential rocketship, frikkin’ take it.

E. As a founder (still very early days for me)

Still in nascent stages of building Workomo, but here are my recent learnings as a founder:

  • Doing “0-to-1” is extremely hard.
  • There is no “playbook”. You have to figure things out and make your own way.
  • All popular startup narratives & playbooks are post-facto, polished versions of reality. Discount them heavily.
  • Figuring out what people want is damn hard. Making & shipping it is even harder.
  • In the first 2–3 years of starting-up, your biggest enemy will be your own mental state (negativity, envy, anger, hopelessness, anxiety, frustration, disappointment). Manage it proactively on a daily basis.
  • Try to keep your self-worth disconnected from your startup’s progress & outcomes. As Taleb says, outcomes in this world are highly random anyway.
  • Keep multiple anchors of happiness — family, friends, travel, health, interests, community. Don’t over-index your life on just your startup. It’s a part of your life, not your whole life.

Hope you found these decade-long learnings helpful. Let me know what you think.

Do this to become a true contrarian in your career

Taken from Talk at Google presentation by Bruce Flatt, CEO of Brookfield Asset Management

“Contrarian” is one of the favorite words of Silicon Valley. Investors want to be contrarian in their picks, founders want to be contrarian in their ideas, employees want to be contrarian in the company they choose to join. In today’s age of near-perfect information flow, one has to be a contrarian to generate any sort of “Alpha” as a professional. This is in terms of both spotting opportunities, as well as timing your entry and exits. Of course, just being contrarian isn’t good enough. As Howard Marks (legendary value investor and Founder of Oaktree Capital) cheekily says, “you have to be a contrarian…and you have to be right!!”.

Over my career, I have made several moves that, at least at the time, I thought were fairly contrarian. Left a Partner track VC job to move to the Bay Area and start from scratch as a startup operator in a brand-new ecosystem. Had 2 startup offers — one from a pre-IPO enterprise software company and other from a maverick Series B startup trying to beat Google in search; joined the latter. Left a meaty role at Alibaba to start Workomo at a tricky mid-stage of my career. Invested in several companies at Operators Studio, where the businesses were (and are) considered “unsexy” from a VC perspective. Whether the above moves turn out to be right or wrong, I need a decade more to find out 🙂

Am a believer in what Robin Sharma says “if you do what everybody else is doing, you will get the results that everybody else is getting” (which is, being average). Through-out my career, I have consciously sought risk and tried to keep myself uncomfortable.

Since early 2018, when I started institutionalizing the Operators Studio investing thesis as well as ideating for my startup, I noticed something interesting. When I discussed some of my previous contrarian moves with friends & colleagues, while they perceived them as “hard to understand” or “highly risky”, I was able to naturally see those opportunities as “an obvious gap” or “the downside is really quite limited”. Clearly, these choices were taking me down a different path compared to my peers, and therefore, perhaps I was being contrarian in spotting & evaluating those opportunities. But I hadn’t articulated the mental model that I was intuitively using while making those decisions.

Over last year or so, I have tried to de-construct the above decision-making process, and then put it together again to arrive at what I call my “Zone of Real Contrarianism”. One caveat — this is my deconstruction of how I attempt to act in a contrarian way during big decisions. Not claiming this as a universal mental model but perhaps, you might derive some value out of it.

The diagram is pretty self-explanatory — to me, real contrarianism is at the intersection of what you have really high personal conviction on, and what the majority are unable to see or agree with. However, it’s important that your personal conviction is:

  1. Authentic — needs to come from an authentic place inside you; represents your personality, values, ideals, and what you stand for (not copied or overly influenced/ inspired by others)
  2. On-the-ground — original beliefs result from exhibiting skin-in-the-game in this world; being out there, understanding & playing the game (not deriving ideas & conclusions from being a desk-jockey or paper-pusher)
  3. Execution-led — observing your environment as you execute; the unpredictable, unplanned & idiosyncratic nature of execution makes it a prime breeding ground for non-obvious ideas & gaps

Nassim Nicholas Taleb defines complex systems as where the behavior of individual elements doesn’t explain the behavior of the collective or the ensemble (eg. while people are individually sane, they are prone to exhibiting irrational mob behavior as a collective). My thesis is that due to this very nature, complex systems are a gold-mine for contrarian ideas, provided you operate with skin-in-the-game in it. As a professional, I seek them out proactively (starting companies, venture investing, white space opportunities in large companies, operating in radically-new geographies & markets) to at least have a shot at generating career alpha.

Would love to hear your feedback on this mental model, and your thoughts on how to be a true contrarian in one’s career (& life).

PS: am currently building Workomo, a smart & simple professional relationships management hub for the new-age professional. If you find it intriguing, do sign-up for free private beta access.

Low burn is a career superpower

Living costs are increasing rapidly across major economic cities globally, be it SF, NY, Sydney, Shanghai, Bangalore or London. A key reason is concentration of knowledge opportunities in specific centers in each country, with other cities lagging behind in new job creation and salary growth.

At the same time, professionals in these geos are also searching for more flexibility compared to previous generations — things like remote work, ability to travel frequently, taking sabbaticals to work on a personal mission, more involved parenting etc.

In order to reconcile higher living costs with more life flexibility, I think an under-rated superpower is keeping your household cash burn low. It means proactively living below your means & cutting unnecessary expenditure, essentially as a trade-off for more freedom. It’s very similar to a low burn startup, which always seems to have much more runway & options of building the business in an agile way, compared to its extravagant peers.

With all our careers exposed to so many external risks that are frankly, uncontrollable, having a ‘low burn’ life provides the necessary resilience to manage uncertainty, tide over tough times and still live with the freedom you want.

As one grows older, one realizes that true success is actually freedom to make your own choices. So the next time you are about to take on an expense that increases those monthly payments, think about it as a trade-off with your overall freedom to make life choices.

True competitive advantage is a “Mesh”

Today, I was remembering my strategy professor from ISB Prof. Prashant Kale. All my batch-mates will agree that he was probably one of the best, if not the best, professors that year for Class of 2010. In particular, one of his classes where he taught the legendary Southwest Airlines strategy case is imprinted in my consciousness — I even remember exact drawings he created in the class.

The key takeaway from that class was that the competitive advantage of Southwest Airlines wasn’t a single linear element; rather, it was a “Mesh of inter-connected, inter-dependent, self-reinforcing activities” that was almost impossible to replicate by competition. Eg., turning around a plane in 15 mins (fastest in the industry), which required the gate staff to operate at a certain cadence, which in-turn, required the check-in staff to do certain activities at a certain speed etc. Essentially, executing any precedent element well made the next dependent element even stronger; conversely, if one of the elements was poorly executed on, the entire mesh advantage ceased to exist. This Mesh model has been a transformative strategy concept for me, and has been a key foundational element of my thinking.

Illustrating the proverbial “Mesh of Competitive Advantage”

I recently got reminded of this concept again after a decade, this time in an entirely different context of public market investing. I was reading the Q1 2019 Quarterly Investor Letter by O’Shaughnessy Asset Management (OSAM), a top quant asset management firm founded by the legendary public markets investor Jim O’Shaughnessy. This letter is particularly fascinating, as it talks about how to cultivate real edge as an investment firm.

OSAM defines the following framework for real investing edge (quoting the letter):

  1. “Real investing edge should (instead) be cultivated at the organizational level.”
  2. “Properly built, an edge should be very difficult or impossible for others to replicate.”
  3. “Ideally, the edge naturally increases over time — something venture capital investor Keith Rabois calls an “accumulating advantage.”

Specifically, OSAM does 2 things that drive the edge — 1) consciously building a Research Graveyard, which essentially means doing lot of research, data analysis and number crunching projects that don’t necessarily lead to immediately improved investing outcomes but increase the overall ideation & knowledge of the firm in a compounded way over the long term; and 2) building tools (data-sets, software and combos thereof) and then deliberately opening them up publicly for other researchers to use (like the way Amazon opened up its cloud infra to developers, creating AWS), whose usage, in turn, has generated some of the best research insights for OSAM.

As a finance and investing person, while both these elements are individually interesting to me, the real deal was this sentence (again quoting the letter):

“These things — software, data, research partners, our graveyard, even the podcast and our twitter activity — all link into and depend on each other, which makes each more valuable and harder to copy.”

“Think back to the ownership data project. Without other connected tools, that would have just been a dead idea — time wasted. But now the ownership data set has become a critical piece of another software tool we use for clients called Portfolio X-Ray. It is now also a new data set available to research partners, who may find something interesting that we did not.”

This is the “Mesh of Competitive Advantage” all over again. A set of activities that, while look replicable in isolation, are almost impossible to replicate by competition as an inter-dependent, inter-connected, self-reinforcing system. This, my friends, is where true competitive advantage comes from!

This is the same reason why, despite having an incredibly transparent investing strategy, framework, terms, processes & activities, other venture firms are unable to replicate the Y Combinator model. This is the same reason why I saw Alibaba winning in China eCommerce (a rhythmic mesh of commerce, payments, logistics, cloud and advertising that is perhaps, impossible to replicate even with infinite capital). It’s the same reason why, as Prof. Kale told us in 2009, Southwest won in the US airline market.

As I think more about this concept in the context of tech startups & Silicon Valley, I believe the following execution elements are important drivers of on-ground success:

  1. Mesh creation has to be deliberate — it’s really hard to defend individual, linear advantage elements in the long run (eg. just having more capital than competition).
  2. Constituent elements of the Mesh need to flow from an authentic place residing inside founders/ leadership teams — what we call as DNA, else it’s hard to sustain.
  3. The Mesh strength compounds over time — demands consistent execution over a long-enough period of time.
  4. This is why true diversity in the team is important — underlying this Mesh of Competitive Advantage, is really, a Mesh of diverse people, each contributing a uniqueness that, combined as a whole, is a super-power. Like the YC Founders or Paypal Mafia.

Would love to hear how you have created competitive advantage for yourself/ your companies.

Side-note: the “Mesh of Competitive Advantage” can also be used to differentiate yourself as an individual professional. Instead of being linear in your career, try to create your own cross-functional, cross-sector, cross-cultural & cross-market Mesh of skills & experiences that, while individually might not look compelling enough, combine together to give you a truly differentiated world-view and approach to life. In today’s age of automation & tech-driven leverage, having this type of Mesh is worth its weight in gold as it can’t be replicated by software; rather, software & tech tools can be used to leverage it up & further magnify its impact.

Related note for parents raising kids in Silicon Valley: given we live in an echo-chamber, with template approaches to pretty much everything (from hiking at the same spots, wearing similar Patagonia vests, to starting up and listening to the same podcasts), it’s important we consciously expose our kids to the non-Silicon Valley world. We would do well to nurture their authentic qualities and original habits, whether they fit with the Valley way of doing things or not. In fact, I would argue that the more contrarian or differentiated these intrinsic personal qualities are, the more we as parents, should encourage them. This will set them up as adults to create their own, authentic “Mesh of Competitive Advantage” that stands the test of time and disruption.

The Student Loan crisis will hurt us exponentially more than 2008!

Over past month or so, have been thinking a lot about the US student debt issue (US student debt balloons past $1.5tn; 74% of all debt owed by US 25–34 year old’s is student debt, up from 10% in 1989).

Apart from the sheer size of this debt obligation (which, like any type of debt, will obviously be a great source of emotional and financial strain on an entire generation), what worries me most is that the end-product that people have leveraged themselves for, will end up continuously declining in value over coming decades.

For the foreseeable future (say next 5-10 years), a good-quality university degree will still, broadly speaking, continue to be a relevant filter for majority of jobs out there. However, once you start looking beyond next 10 years, it’s hard to believe that this will continue to be the case.

Students are taking on debt, essentially to get the following 3 elements from a university:

  1. ‘Foundation’ knowledge & skills — given the pace at which the working machinery of this world is changing, essentially driven by technologies whose future impact is hard to predict even for the most informed and privileged (VCs, large tech company execs, policy makers etc.), it’s hard to see a university curriculum keeping pace with these rapid changes. Perhaps, it will require almost a Just-In-Time approach from both the skill givers and receivers, which a static education paradigm like the present university system will struggle with. Continuous training, perpetually-upgraded skilling methods and a vocational approach will become vastly more important. While I am painting this in broad strokes, you get the drift!
  2. Networks — while there is merit in having a common university bond that helps set up a base network, the reality is that as life goes on, other networks (the companies you work for, your neighborhood, the community initiatives you support etc.) continuously get added and their summation becomes far more important than just your university networks. Carrying forward the earlier thought of rapid tech-driven change, the ‘relevancy’ of your networks will also evolve quickly. For instance, as a design under-grad, you might know lot of other designers. However, you might end up eventually building your career designing digital healthcare products and therefore, might need more healthcare professionals in your network rather than just designers. Finally, with networking initiation, build-out & maintenance happening more online than offline, importance of campus relationships and old boys clubs is definitely going to decline. The point is simple — in the pecking order of networking elements, campus schmoozing & alumni events are going to be replaced by leveraging tech platforms, creating your personal brand in the digital world and good-ol’ hustling. PS: my belief is also that elitism in recruiting (eg. Company XYZ only goes to these 2–3 campuses for hiring) will reduce drastically. As the required skill-sets for all professions evolve dramatically in the 4th Industrial Revolution era, employers will become more open-minded and honestly, will have no option but to go where the skillset is (if US universities aren’t producing enough data scientists, companies will go and hire wherever they are available, be it Warsaw or Trivandrum).
  3. Credentialing — the tech industry has already taken the lead in adopting alternate credentialing mechanisms such as hackathons, internships or in the blockchain & crypto world, publishing a solid white paper :). In a rapidly changing business environment, credentialing provided by relatively slow-moving and static university channels is frankly, declining in importance. Similar to the paradigm of continuous learning, credentialing will also become a continuous phenomenon that is driven by practical skillsets & real-life outcomes delivered on the job.

As the above scenarios play out, taking on an unrealistic amount of student debt that is decoupled with the real long-term value of the asset itself, doesn’t make much sense. Why does this delta exist and how can it be brought down going forward are of course, key questions that educational institutions and policy-makers face today.

Some life-strategy suggestions:

For Millennials with significant student loans: would be good to prepare a detailed and practical financial plan to pare down this debt. Have the discipline to stick with this plan, and make the necessary sacrifices of ‘living below your means’ to accomplish it ASAP. As the loans come down, create a fresh capital allocation for ‘continuous learning’ via online courses, certifications, networking events etc. In the long-run, this will be money well-spent and give you a massive ROI.

For students about to enter university soon: rather than taking a less-thoughtful approach that is driven by historical precedence and herd-mentality, be brave enough to take a fresh approach to evaluating your options. This is a massive investment of your time and money, so think like an investor. Deeply compare the long-term ROIs of public vs private universities. Be sensitive to tuition & overhead costs of specific courses, and compare them against the tangible post-graduation prospects they offer. Think about every angle — univ. brand vs the actual course, full-time vs part-time, location with associated living costs and career options. In a rapidly changing economic environment, things like financial freedom & employment flexibility are going to be very important in the long term. Include these aspects in your career math. It’s hard to think on these lines as an 18 year old, so the role of parents, teachers and other experienced stakeholders will be very important in guiding them through this process.

As a society, we have already made the mistake of burdening our newest generation with this student loan problem. Similar to issues like the environment, everyone needs to come together and start working on removing this albatross from the necks of our students.

Moving one step a day towards true leadership….

Have been thinking a lot lately on what true leadership really means. Back in Jan 2014, I moved from doing Venture Capital in India to becoming a tech operator in Silicon Valley. Life has been a roller coaster since then…to say the least. Met people that willingly ‘punt’ on quality talent, as well as jacka**es that suck the life out of them. Worked with some awesome individuals, as well as shockingly dysfunctional teams. Experienced world changing visions, as well as weak products that did no justice to them. Each day has been fun, gut-wrenching and full of countless moments wherein I have questioned all my assumptions…and life choices.

In particular, one question, more than others, stares at my face daily — “What does true leadership mean”? No matter how many management books, expert blogs and leadership training you go through, none of them gives you solutions to the ambiguous problems that life throws at us — what to do when a team member who is well-intentioned and great at the job, is actually destroying team culture? How do you give feedback to a senior leader? How do you communicate in a different country’s culture where even the language isn’t shared? How do you react in a political work environment — do you participate or stay away from it?

To counter these situations, the advice always is “to do the right thing”. But what is the “right thing”? Isn’t the “right thing” always contextual? What if your “right thing” is different from my “right thing”, given our different personal compasses?

I have no answers to these questions — perhaps, navigating these challenges successfully day-after-day, year-after-year and decade-after-decade is what creates true leaders. Standing today, to me it seems true leadership is a path, a journey, a series of battles that need to be fought (not necessarily won!). You have to be brave enough to walk down this path, and keep walking. Even with all the business knowledge, models, frameworks and networks in the world, nothing can quite prepare you for this journey. You just have to experience it, fall down, cry, curse, get up, learn from it, move on and make the best of it. And maybe…just maybe…years later…you would have moved closer to becoming a true leader. After all, it took more than 25 years each for Mahatma Gandhi and Nelson Mandela. And they were still questioned!!

Personally, as I have started walking down this path over last few years, following Robin Sharma and Sadhguru has given me fundamental concepts and energy that has helped me tremendously. What has helped you as you walk down your own path? What is your idea of true leadership and doing the “right thing”? Would love to hear your thoughts.

Will leave you with this quote by Robin Sharma that has left a huge impact on me — “To lead is to serve”.