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.