Tag: Fundraising

My Blindspots As A VC

On misreading founders, moving too fast, and why portfolio construction is my safety net.

Over the past few weeks, I have been doing a retrospective analysis of the Operators Studio portfolio. Given that I have adopted a “founder-first” investing style, I have been specifically trying to analyze cases where I got a wrong read on the founder.

Startups can struggle/ fail for N number of reasons. Especially as a seed investor, most of these externalities are out of your hands. Therefore, while doing such analysis, I like to keep reminding myself not to fall into the “Resulting” trap.

Annie Duke defines Resulting as “the cognitive bias of judging a decision’s quality solely by its outcome, rather than the decision-making process itself”. Top poker players are really good at avoiding Resulting while studying their plays post-facto.

So when outcomes turn out to be negative in a seed investment, rather than fixating on “why the company failed?”, it’s more useful to ask “how should the investing process be improved for future deals?”. And in my context, it’s typically the process of evaluating the founder.

Coming back to the retro analysis I have been doing on my deals, I have been able to identify a couple of blind spots that seem to be showing up repeatedly. Here’s a deep-dive on each of them:

1/ Getting blindsided by the founders’ pedigree

Sometimes, founders show up with just a jaw-dropping pedigree – IIT Bombay Computer Science, Stanford PhD, top leader at Big Tech etc. This pedigree is typically also accompanied by a strong show during the pitch meeting, demonstrating differentiated access & networks, and just overall self-belief that screams “I am awesome!”.

Looking back on such pitch meetings, it’s very easy as an investor to get carried away by this pedigree & show. However, as I am learning with some pain, pedigree doesn’t automatically translate to the many enablers of eventual success in a founder – grit, the ability to pound pavements selling stuff, controlling your ego, resolving conflicts, and frankly, eating glass during tough times.

One of my key maxims learned over a long venture career is to always distinguish whether the person is a strong professional or a (potentially) strong founder. Both are very different things.

Even with this hard-earned insight, it turns out that executing this day in and day out is extremely hard. Even the best of us get swayed by past track records.

This retrospective is a self-reminder to bring back this maxim as part of the core of my investing process.

2/ Pulling the trigger without spending enough 1:1 time with the founder

My natural style as an investor is highly instinctive. This often manifests in quick Yes’s during the first pitch meeting itself.

Over a long career, this has mostly benefited me. Almost all my major wins were quick Yes’s. But there is a difference between “moving with a pure initial instinct” and “being trigger-happy”.

In a few cases, I have pulled the trigger without spending enough 1:1 time to peel the layers on a founder. If I go one level deeper, in most cases, this was due to some fear – fear of being on the wrong side of deal heat & not getting allocation, fear of feeling disadvantaged as a relatively small check writer, fear of deployment pressure (“I need to do a deal this month”).

These fears are particularly amplified by the current investing environment, where seed deals move in days, where lead VCs have particularly sharp elbows, and where many founders fall prey to becoming over-transactional during the fundraising process.

I have come to realize that these fears are incredibly counterproductive to a long & sustainable venture career. Seed investing is at least a decade-long journey that is full of ups and downs. An important way to create a strong initial foundation that then delivers a consistently good experience to both the founder and the investor over multiple years is to dedicate enough effort upfront to build trust & a mutual connection.

When this trust & connection exists, the wins taste exponentially sweeter, and the pain of losses gets blunted.

Any diversified enough venture portfolio of decent quality is highly likely to catch at least a couple of winners. But the key to amplifying success over decades, both as a founder and as an investor, is to play repeated games with a set of highly trusted people. The starting point of these relationships is almost always the foundation of trust built during the first-ever transaction between two people.

Even empirically, if I study all my deals since 2011, whenever I have built a strong mutual connection with a founder upfront, the eventual outcomes have almost always been positive economically and/or experientially (the randomness has only been in “how positive?”).

Therefore, this is again a self-reminder that I should ensure I am devoting enough upfront time to build trust & a mutual connection with new founders I meet. And once I have built an informed instinct around a new person, given I now have 15 years of on-ground data on how it usually pans out, I should default to trusting & following my judgment without any fear.

The final line of defense against these blind spots…

Even at our most introspective and self-aware selves, we still have the same monkey brain that has been wired by hundreds of thousands of years of evolution. Even the best of us should expect to keep falling prey to various kinds of cognitive biases and blind spots across multiple deals.

The mark of growing up as a venture investor is accepting this truth and then acknowledging at a deep, internal level that the only line of defense against our own foolishness is portfolio construction.

As a young VC Associate way back in 2011, I used to always wonder why OG VC GPs kept harping on portfolio construction, spending hours poring over Excel sheets that frankly, had most of the numbers pulled out of thin air (an undeniable fact of any financial modeling efforts in early-stage venture).

Similarly, when I decided to come back into venture in 2023, I kept hearing how LPs care a lot about portfolio construction. And that it is the difference between someone being just an investor vs being a professional fund manager.

Studying my still fledgling portfolio today, I can already see how following even a rudimentary portfolio construction strategy has saved my a** several times already, and its impact will manifest in major ways over the remaining Fund life.

When you experience something working in real life, your buy-in starts growing organically, giving it higher chances of eventually becoming a sustainable habit. I can see this playing out with my rapidly growing appreciation of all the beauty and nuances of portfolio construction.

In fact, I can guarantee that 2026 will see my study and obsession with VC portfolio construction go many levels higher, and thankfully, I don’t need a New Year’s resolution to make it happen.

Note: My next post will be on some portfolio construction insights I have gleaned from listening to Roger Ehrenberg, Founder of IA Ventures. Stay tuned for that!

How to Get Warm Intros Right: My Ground Rules as a VC

Learn the ground rules for warm intros—double opt-in, reputation, skin in the game, and more. Avoid common mistakes & get intros right.

As a venture investor, warm intros are my lifeline, both as a receiver (new deals) and a giver (for portfolio founders & co-investors).

Given the sheer volume of the intro pipe I deal with, I also see the goods and the bads of it all. In particular, I see folks making 101 mistakes and breaking what have become fundamental rules of intros that the Valley plays by. Break them, and it screams, “I am not ready to play in the major leagues yet!” to the ecosystem.

For the benefit of everyone out there, sharing some of my ground rules for warm intros:

1/ Double opt-in

Internalize this deeply – double opt-in is the only right way to do intros. Violating this cardinal rule significantly reduces your credibility.

2/ Reputation

Implicitly underlying every warm intro is your personal reputation. In the venture ecosystem, judgment is everything, and who you are vouching for is a major signal for it. Think about that the next time you agree to introduce someone.

3/ Skin-in-the-game

I treat intros without skin in the game or demonstrated conviction as low-signal “favors”. Personally, I don’t do this type of intros at all. But definitely receive a ton of them.

As they say, talk is cheap. Or in the context of this post, “sending an email is cheap”. The signals underlying the email are what matter.

4/ Limited bullets

When I started my career in venture, one of the Partners taught me a valuable lesson that I follow to this day – “you only get 3 bullets with each relationship in a lifetime. So fire each bullet carefully”.

Being indiscriminate with warm intros is the worst thing you can do as a professional. It’s like spamming – your credibility goes down exponentially with each ask that hasn’t been thought through properly.

5/ Acceptance rate

Controlling the acceptance rate is as important as the send rate. As a constructive participant in the flow, you are individually responsible for ensuring no time gets wasted on either side.

So it’s important to control that carnal urge to “network” and vet each inbound request properly to ensure there is a high likelihood of mutual fit before the actual meeting.

It’s exactly like qualifying sales leads. Just because someone is doing a warm intro doesn’t mean it’s a good fit at this point in time.

Hope these rules are helpful. Wishing you a long track record of fostering interesting & useful connections.

That Series A Billboard On The 101

A reminder not to fall into the trap of first-order thinking.

My LinkedIn feed is full of posts making fun of that startup that has its Series A announcement up on a billboard on the 101.

This incident reminds me of a mental model I have learned & developed with experience over my career:

“When you come across something that looks stupidly irrational on the surface, instead of falling prey to first-order thinking, pause, take a step back, try putting yourself in that situation and think through some reasons why someone could indulge in that seemingly foolish or irrational behavior?”

In the case of this billboard, clearly the founders are smart enough & shrewd enough that institutional investors are handing them $25Mn. So it’s highly likely that they are trying to achieve some goal by putting up this cringeworthy sign.

Most likely, the goal was to drive awareness & word-of-mouth by making this meme-worthy. Similar to how celebrities say & do crazy, PR-worthy things strategically close to a big movie release.

While this billboard case is a bit frivolous, it highlights an important idea that we all should have in our mesh of mental models – when something doesn’t add up in plain sight, or when the herd has 100% consensus on an idea, it shouldn’t be believed prima facie. Rather, it deserves an even deeper investigation.

The crowd is largely a blob of first-order thinkers. Value almost always resides in second-order thinking & beyond. Train your cognitive radar to spot these signals & act accordingly!

How to cold-pitch your startup in 30 seconds to VCs at events

Putting your strongest foot forward quickly, coherently and in an interesting way is the key to getting VCs to lean-in during a cold-pitch at an event.

It’s been a hectic couple of weeks of tech events, with SaaStr, SaaSBoomi, VC mixers, and now Dreamforce. Meeting hundreds of founders cold across these events, I have noticed that most of them struggle to quickly pitch themselves/ their startups to investors.

In fact, in most of these meetings, I was only able to figure out their unique strengths, progress, and fit with the problem statement after 3-5 mins. into the conversation. Unfortunately, most investors have short attention spans and given they meet multiple founders daily, their ability to recall is even worse.

This means as a founder, you have to achieve 2 things while cold-meeting investors at events:

1/ Leave an impression in the first 30 seconds so that the investor starts leaning into the discussion and becomes inclined to spend 3-5 minutes more.

2/ Post this initial buy-in, leave the investor with something of high recall value so you have a higher chance of a post-event follow-up discussion.

A. The 30-sec pitch

For the first 30-sec pitch, I recommend having 3 parts to it:

[The Grandmother’s Explanation]

followed by…

[Social Proof of Team]

followed by…

[Proof of Business]

a) The Grandmother’s Explanation means explaining what your startup does in the way you would explain it to your grandmother. Yes, most investors aren’t domain experts in your field. They are likely investing across sectors, and aren’t living and breathing your specific area/ problem statement. Assume they are as ignorant about your business as your grandmother.

I am literally shocked by how most founders can’t explain their startup in simple tech-layman’s terms. Barring a few, true deep tech startups coming out of research labs and universities, most enterprise software, SaaS, and consumer Internet startups should be able to explain their business in simple words. This is the bare minimum signal of clarity in thinking.

TLDR: if an investor isn’t able to understand what you do in the first 5-7 seconds, there is no way in hell that investor is going to lean in. Even if the person might appear to be listening, in reality, they are actually zoned out/ looking through you.

b) Social Proof of Team means talking about your credentials in a straight-up manner, without beating around the bush. These could be:

Education-related – undergrad and grad schools, unique course work etc.;

Work-related – past employers, roles, needle-moving projects, accelerators like YC or Techstars etc.; and

Execution-related – products shipped, content created, social following, word-of-mouth etc.

Especially for founders in the US-India corridor – we are taught to be overly humble and in most social situations, we tend to talk down our achievements. Unfortunately, you are faced with intense competition in the Bay Area from talent coming in from all over the world. You have no choice but to talk about things that make you stand out from the crowd.

c) Proof of Business means talking about the business progress of your startup in tangible terms. Things like user base, retention, engagement, number of customers, revenue, customer acquisition etc.

It’s important to remember that while providing Proof of Business, both “absolute numbers” and “growth rates” are important. So, frame statements like “we have $Xk ARR, growing y% m-o-m” or “We have Xk users, growing y% week-on-week purely by organic word-of-mouth. People are also now starting to pay”.

Most startups attending these events don’t have enough Proof of Business yet.

  • For the ones who do, make sure you talk about it as traction trumps everything, and especially at the seed stage, any traction will help you stand out.
  • For startups who don’t have much Proof of Business, you can still talk about proxies of business progress like the velocity of shipping new features, people on the waitlist, early design partners, and how they are deeply engaging with your product etc.

PS: An important recommendation for the 30-sec pitch format:

If you have compelling traction, pitch [Proof of Business] first and then [Social Proof of Team].

If you are very early and don’t have compelling traction, pitch [Social Proof of Team] first and then [Proof of Business].

The idea is simple – always lead with your strongest suit.

B. The post 30-sec-pitch part

Ok, so you delivered an amazing 30-sec pitch to Investor A. The person is now leaning in and wants to have a longer conversation for the next 5-7 mins.

In this part of the convo, your main job as a founder is to leave a high-recall impression on the investor. The person meets tens of new founders every week. Your job is to ensure that post this interaction, you go into the deal flow software for the VC firm at the minimum, and ideally, the person remembers you for some standout qualities and/or stories.

This is the “art” part of having a good conversation. There are no specific rules for how you build camaraderie and leave an impression. Everyone has their own style, and everything from body language and listening skills to storytelling and tonality has a role to play.

While I can’t offer you any specific hacks for this, here are some things I have seen work well in my experience:

a) Tell an interesting story – people don’t remember facts, but they remember stories. Instead of bombarding an investor with jargon, business numbers and technical info while having a cocktail, focus on telling an interesting story. Could be about your childhood, maybe something from your past life, or even something quirky that has happened while building the startup.

The biggest risk you have in a cold-pitch situation is to make it boring for the other person. A good story is something that brings a smile and/ or a questioning look on someone’s face. Basically, it interests them.

b) Bond on commonalities – the classic sales technique of finding commonalities to break ice always works. Humans are wired to want to belong to certain identities – A New Yorker, A Delhi-wala, A Knicks fan, a worshipper of Sachin Tendulkar, a backpacker, a wine connoisseur, a Japanese food lover etc. The moment they meet someone who belongs to the same identity, there is an instant connection that gets established, which is the first step towards building trust.

As you are chatting with the investor at a mixer, try and probe for some commonalities (where they grew up, went to school, worked, where they are living now). It will give the conversation much more substance and make it enjoyable for both sides.

c) Be genuinely curious…and listen – in my previous posts ‘Curiosity As A Networking Cheat Code‘ and ‘Networking at Events for Introverts‘, I have talked about the power of being genuinely interested in other people. It usually manifests in you asking good questions and listening more than talking.

As much as you are trying to ‘pitch’ in the conversation, don’t make it a one-way street. After the 30-sec pitch, focus on consciously giving talk-time to the investor by asking questions that spark an interesting discussion vs a founder-to-investor monologue.

C. Closing thoughts

I was feeling so frustrated listening to some awesome founders give such broken and unengaging 30-second pitches at recent events that I had to write this post.

Essentially, all the above inputs are based on 2 core ideas:

#1 Put your strongest foot forward as quickly as possible, and in a coherent structure.

#2 Make the conversation interesting. Tell stories. No one likes to be bored.

Happy pitching!

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Notes From India Trip Q2’24 – Elections, Deeptech, Fundraising

Notes from my Q2’24 India trip – everything from post-election vibes to public markets and the state of the venture ecosystem.

Just returned from my quarterly trip to India. With the recently held elections (and a bit of a surprising result there!), it was interesting to get a pulse of what’s happening on the ground. Here are some key takeaways from my meetings with founders, investors, and operators in the ecosystem:

1/ Real reasons behind BJP’s weakened mandate

While Modi created a massive pre-election narrative of the BJP coming back to power with an even bigger majority than in 2019, it ended up losing ground in the actual results tally.

Honestly, I didn’t see it coming but talking with people on the ground, one of the major reasons behind the weakening of BJP seems to be shrinking employment opportunities, especially for young graduates. While the India macro story stays strong, there are pockets of economic distress in the poor states and amongst the lesser-skilled parts of the population/ those graduating from non-top-tier universities.

It’s clear that while Modi focused a lot on infra buildout over the last 2 terms, one of his core focus areas in the 3rd term needs to be continuous job creation for all sections of society. This might require some bold reforms.

2/ Investors are largely unperturbed by the election results

Given that the BJP-led NDA coalition still has a comfortable majority in the Parliament, and Modi continues to be the PM with a largely unchanged cabinet, Investors are expecting political and economic continuity in this 3rd term of the govt.

So, expect continued momentum on key execution tracks from the last 2 terms, including physical infrastructure buildout, expansion of digital public goods, and focus on technology startups.

3/ General Catalyst acquiring Venture Highway

The news of GC acquiring VH broke out while I was in Bangalore. While it could be a one-off development, it’s still a positive greenshoot that a large Silicon Valley-based, premier capital pool is allocating to the India venture market.

Personally, I also believe it’s a smart move from Hemant Taneja to acquire a high-performing team that is local and has developed on-ground expertise, versus parachuting people in from the Bay Area or doing the fly-in-and-out model.

Not recruiting and empowering a high-quality local leadership team is a classic India entry mistake that both Y Combinator and AngelList did, which is why they have struggled to crack the market.

4/ All VCs talking deeptech now

Similar to the Valley, deeptech has now clearly become the flavor of the season. Even a few years back, major Indian VCs spending time at the IIT incubators or looking at sectors like manufacturing and semiconductors was unheard of. This time, I heard multiple instances of VCs writing large seed checks into deeptech companies.

My only fear is that based on past history, the Indian VC ecosystem tends to behave in steep emotional cycles, flooding hot sectors with capital in tandem like a herd (eCommerce 15 years back, fintech 10 years back, lending and SaaS 5-7 years back), and then abandoning verticals also in tandem like a herd (eg. no one is touching edtech now).

These emotional cycles are incredibly counter-productive for long-term company building, and also tend to be incredibly disturbing, especially for younger, 1st-time founders. As the deeptech wave begins, I hope some lessons are learned and implemented from previous cycles.

5/ Angels suffering from 2021 vintage markdowns and illiquidity

One of my observations on the Indian venture ecosystem has been many new-gen angels tapping out in 2023/24. While some of the marquee spray-and-pray ones, as well as the conventional IAN/Mumbai Angels persona, continue to be active, many high-quality operator angels seem to have bowed out of the game.

On bringing this point up with folks, they confirmed that the portfolios of many new angels who started deploying in 2020 and 2021 are suffering from either major markdowns and writeoffs or prolonged illiquidity of marked-up positions. I would also add layoffs, salary rationalizations, and a lack of broader ESOP liquidity (barring a few cases here and there) to the list of reasons behind many angels bowing out of the game.

6/ Seed capital is plenty but wants more traction. Series As continue to be hard.

Similar to the Bay Area, I heard that while there is plenty of pre-seed/seed capital available in the ecosystem right now, the bar for raising Series A has significantly gone up. As a result, companies are seeing both larger seed rounds as well as extension/ top-up rounds happening as we speak.

Several seed investors shared with me that one of their learnings from doing many idea-stage deals in 2021 is how companies are taking so much longer than they initially estimated to go from zero to even $100k ARR. This is adversely impacting the IRRs of seed portfolios. Also, given valuations have now massively corrected, the next round markup isn’t in line with the time it’s taking to get to early traction.

Given this dynamic, many seed investors are now tracking companies and waiting to see more traction before pulling the trigger on idea-stage companies. Btw, am seeing similar behavior even in the late seed/ pre-Series A/ Series A spectrum too, where VCs are waiting to see a long enough timeline of revenue growth, retention, and other metrics before engaging seriously.

Another related observation – growth capital for tech companies is a major gap in the India venture ecosystem right now. Many strategics and hedge funds that were writing large checks post-pandemic have either completely exited the market (eg. Softbank, Alibaba, and Tencent) or are triaging their current portfolios. Recent cases like Prosus writing off its entire ~$500Mn investment in Byju’s isn’t helping to build confidence either.

7/ Public markets continue to rip, lots of FO appetite for pre-IPO rounds

After a brief blip post-election results, Indian public markets have continued to rip. There is a whole new generation of young Indians who are leveraging new-age brokerage apps like Zerodha and Groww to actively participate in the markets. In fact, recent F&O retail trading numbers suggest that a majority of this activity might in fact, be speculative rather than long-term, fundamental investing.

It is noticeable to see frequent ads on Indian TV channels encouraging everyone to invest in mutual funds. An uncle who recently visited us in SF was bragging over chai about how he “made 55 lakhs in the market already this year”.

During this India trip, I saw my father casually opening and checking his brokerage app dashboard multiple times daily. I also noticed that a majority of YouTube consumption by this age group is financial influencer and stock tips content.

On a similar note, a few institutional investors shared how domestic Family Offices are showing an increased appetite for pre-IPO investments in companies like Lenskart, FirstCry, and Oyo. In fact, with the domestic index doing really well, FOs are more skeptical of taking LP positions in venture funds right now, preferring to either stay liquid in public markets or take relatively de-risked, later-stage positions in pre-IPO private companies.

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Tips & Insights For Emerging VC Managers – Notes From Camp Hustle’24

My notes from attending Camp Hustle, a unique LP-GP gathering. Includes actionable tips for those raising Funds 1 and 2.

It was a great experience to attend Camp Hustle last week. I have been following the work of Elizabeth Yin (co-founder of Hustle Fund, a pre-seed fund that organized this event) on X for some time now. All this while, I kept seeing posts from the last 2 editions of the event.

This time, I was in town, in a relationship-building zone, and looking to add new and interesting LP-GP folks to my community. So, I landed up at the event (who would say no to spending 2.5 days in the idyllic surroundings of Los Gatos and Saratoga anyway!).

Honestly, I didn’t arrive with a specific agenda or expectations from the event. I just went in with an open mind and knowing the vibe of the Hustle Fund team, I instinctively knew this would likely be the best frame of mind for this gathering.

The event turned out to be a pleasant surprise. Now I know why the name has the word “Camp” in it – the entire event had an informal, outdoorsy, campy, yet energetic and authentic vibe to it. Everyone agreed to an informal social contract – no explicit pitching, no so-called networking and no shallow talk. Everyone bought into the idea of just getting to know a bunch of folks and really bringing their whole, authentic selves to the event.

While the free-flowing, candid conversations amidst nature were the highlight of the event, I did end up with some really actionable insights shared by the Hustle Fund team, other emerging managers as well as a few LPs. Sharing my notes below:

1/ Fundraising for emerging fund managers – via Charles Hudson (Precursor Ventures) and Virginie Raphael (Full Circle)

  • While interacting with potential LPs, focus on making them a “fan” of the fund first. That is the first step towards eventually converting to an LP.
  • One common mistake during fundraising as a first-time manager is chasing people too aggressively. The key is to put out your story and let people come to you.
  • A great way to engage potential LPs is to send out a monthly/ quarterly newsletter. Also, Virginie mentioned doing informal LP meets in the Spring and Fall, so folks stay connected with the fund.
  • The majority of potential LPs you meet today might eventually invest in Funds 2 and 3. So, it’s important to start building relationships from now.
  • I asked Charles a question on ways to increase conversion on warm intros that a GP gets via existing LPs. While intuitively one might expect a healthy conversion on this type of lead, Charles confirmed that in his fundraising experience, the conversion on these referrals was indeed lower than expected.

2/ Venture investing learnings from the Hustle Fund team

During an informal AMA, Hustle Fund co-founders Elizabeth, Eric, and Shiyan shared the following top venture investing learnings from their anti-portfolio:

  • Always bet on your friends.
  • Don’t penny-pinch on valuation (they passed on an initial round of one of the largest consumer Internet outcomes because of valuation).
  • “Good deals have legs” – when you like a founder, push as hard as possible to get into the deal. Don’t be afraid of being perceived as a pain, if it can help you get into the deal.
  • Don’t over-index on what a market or company looks like right now. Learn to imagine what the market or a company can become “over a period of time”.

3/ Tips from an institutional LP

Courtney McCrea (Co-founder of Recast Capital) is one of the most experienced institutional LPs out there. In a candid Bonfire Session, she shared some insightful tips for emerging managers:

  • During an LP pitch, don’t be afraid to talk about how great you are. In fact, spend the first 3 minutes in a pitch just talking about your unique superpowers.
  • If you are having trouble creating a unique narrative for why your fund is different, ask your portfolio founders why they picked you and how they would pitch you to their friends.
  • LPs look at who you co-invest with and who does follow-ons in your companies, as signals for the quality of your deal flow.
  • There are so many LPs out there who aren’t pitched very often. Try and focus on them to improve your odds. Don’t underestimate the amount of capital that is out there looking to be deployed.

4/ Other helpful convos

  • Matthew Stotts of Cerulean Ventures shared that outlining the 10-year vision and story of what the fund is looking to do, goes a long way in generating excitement as most LPs are looking not just for financial returns but also for impact in whatever their personal mission is.
  • To re-engage with potential LPs in your funnel, try going back to them when you have an interesting development or story to share from the portfolio (eg. “we invested in Company X at the pre-seed stage and now, 12 months later, they just cracked a $XMn ACV deal”). This could also be done with a new differentiated investment or interesting deal flow.
  • [Via Rahul Vohra, Founder and CEO of Superhuman] One of the best pieces of advice Rahul got while building Rapportive was to pick a strategy to go from Point A to Point B, never change your mind about it, and continue relentlessly executing it. The goal could be say reaching 1Mn users, $100k MRR, or any other metric. The key is to stick with it.

Hope these notes help emerging managers out there. Once again, thanks so much Team Hustle Fund for creating this unique event format. Am excited for the next one!

PS: For those in SE Asia, the next Camp Hustle is in Bali in September🏖️

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One Person’s Conviction For Easier Fundraising

As a fundraising founder swimming in the rough seas of skeptical investors, sometimes all you need is a high-conviction intro from one sponsor to tip the scales in your favor.

As a venture investor, referrals from people in my network is one of my top channels of deal flow. There are hundreds of startups that reach out for fundraising discussions every month. Having someone you know vouch for a founder automatically gives initial comfort around taking a meeting.

Over the years, I have observed that these referrals fall into 3 categories:

1/ Weak intro: beyond being a friend, the referring person doesn’t know much about the founder’s idea or the reasons behind pursuing it. These referrers are usually the founder’s weak acquaintances and are only helping out with connecting to a bunch of investors.

While even a weak intro ensures that I pay attention to the startup, conversion to a live interaction is usually low.

2/ Warm intro: the referrer has deeply known or worked with the founder in the past, and has a fair idea about their personal mission, goals, and personality. Typically, these referrers are ex-direct managers, peers, college friends who have stayed in touch, and other direct collaborators. They might or might not have an understanding or appreciation of that particular startup idea but believe in the founder.

These intros are solid, especially as the founding team is the top-most investing criterion at the early stages. In most cases, I will typically schedule a 30 min. video call with the founder at the very least.

3/ Conviction intro: the referrer has spent significant time either organically or consciously, to develop a deep conviction in both the founder and the startup idea. These referrers are usually founder execs, senior operators, angels, and VCs.

In the best cases, the referrer is also showing skin-in-the-game via either investing significant money and/ or time in the startup.

Conviction intros are gold and a great signal of the quality of an investor’s deal sourcing. For almost all such intros, I end up scheduling a 1-2 hour deep brainstorming session to get into the weeds. Interestingly, by the end of these sessions, the judgment on whether to invest or not gets immediate clarity.

Adding more nuance…

I would like to go one level deeper on Conviction Intros, and talk about what I call ‘One Person’s Conviction Intro’.

Those who regularly read my blog would remember the post ‘An Investing Framework to Find Startup Diamonds‘. In it, I talk about the ‘High-Signal-Non-Consensus’ quadrant where the best startups are to be found at the early stages.

Deal ScreenConsensusNon-Consensus
High-Signal🪙🪙🪙
Low-Signal
Consensus vs Signal 2×2 ©Soumitra Sharma

(4) High-Signal-Non-Consensus – these are the opportunities we as venture investors live for. They are highly non-consensus, with the investor-crowd struggling to access, understand, evaluate risk and build a positive view on them. Yet, these startups have high-quality leading signals, which could be external and/ or internal.

  • External – eg. a respected investor, sometimes a domain expert, has taken the time to evaluate & build high conviction around the company. Or a visionary customer is taking a bet, partnering with them in building the early product.
  • Internal – extraordinary founder-market fit eg. the founder has spent a decade just going deep in the field. Or a backstory that provides an authentic “why” behind pursuing this idea. Or an execution track record in the startup’s arc that is outstanding on important elements like capital-efficiency, iteration velocity or organic customer acquisition.

This quadrant is the hardest to source for and requires having a really differentiated network of relationships (for referrals) and a personal brand that attracts interest from these types of founders.

An Investing Framework To Find Startup Diamonds

As mentioned in this excerpt, the High-Signal part comes from someone credible putting in the effort to build conviction, demonstrating skin in the game via committing any type of valuable currency, and then risking their personal reputation to socialize the opportunity with their trusted networks.

This opportunity might still be Non-Consensus, with the investor-crowd struggling to appreciate it. Yet, this referrer (or perhaps ‘sponsor’ is a better word in this context) is willing to be contrarian and follow their own conviction built from first principles.

When this sponsor refers a deal to me, this One Person’s Conviction Intro sits at the peak within the universe of Conviction Intros, simply because it has a high likelihood of being a key to the High-Signal-Non-Consensus quadrant.

However, even an investor with the highest quality deal flow can only expect a handful of such intros every year. The reason is most founder execs and operators don’t have the time and/ or incentives to build independent conviction. And most angels and VCs tend to demonstrate herd behavior, preferring to lazily piggyback on the conviction of others versus taking the time to do independent thinking.

So, even though my investing style is predicated on searching for these intros, the world is supply-constrained with respect to them. However, what I can do is swing really hard when I do get a few of these fat pitches every year, and maintain discipline at all other times. Venture investing is a very forgiving game where one isn’t reprimanded much for the losers, as long as you get a few right in a big way!

For founders, getting warm intros to investors has now become common knowledge, and frankly, table stakes. However, what could give you an edge over hundreds of other fundraising founders is inculcating that one sponsor – someone who can build independent conviction on your yet-unvalidated startup, show skin in the game, and socialize their commitment to other investors.

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Storyteller vs Scrapper Founders

At the seed stage, how does one distinguish between and evaluate the top-down ‘Storyteller’ vs the bottoms-up ‘Scrapper’ founder personas? And can one grow into the other?

At the pre-seed/ seed stage, I have generally observed 2 founder personas – the ‘Storyteller’ and the ‘Scrapper’:

A. The Storyteller

Extremely articulate at painting the vision and market opportunity. This persona typically comes from pedigreed educational institutions (hence, great communication skills). Often, they have been execs at large corporates, Big Tech companies, and/ or brand-name, growth-stage startups.

Courtesy of this top-tier background, this persona has a naturally strategic, top-down view of the market they are going after, including the “why now?”, secular growth trends, market gaps, competition etc.

This persona is also great at spotting and riding waves, and therefore, is often building at the edge of hot trends (eg. Web3 a few years back, AI now).

This persona has a thoughtful view of how the ‘company’ will scale in the coming years. Everything from hiring and global expansion to marketing and M&A. In general, this persona will talk more about the opportunity, market, growth and scaling, and less about getting the 1st customer, writing early code, design and other aspects of building.

It’s easy to visualize this persona as the Founder and CEO of a multi-billion $ company. Therefore, Investors love this person. Period.

B. The Scrapper

Natural tinkerer in a very specific space. Typically, this interest germinated during teenage or through college. In many cases, this interest was considered obtuse or nerdy by mainstream observers, and hence, this persona is relatively less understood, perhaps viewed as quirky and therefore, underestimated.

Their creative energy manifests in hacking software, teaming up with friends on specific projects, building products as a hobby, or doing side hustles on the weekend.

This persona typically doesn’t have much capital, nor are investors lining up outside their door. So either by choice or fate, there is no option but to build in scarcity.

In fact, this persona is less likely to view their work as a ‘company’. They have a deep and unending curiosity about something and just want to put it out in the world, hoping that maybe a handful of us will ‘get’ it.

This persona thrives in a bottoms-up view of their space – their eyes light up when discussing technology, code, features, users, and anything related to building. They suck at top-down, so-called strategic discussions of possible markets their work could serve.

It’s hard to visualize this person as the Founder and CEO of a multi-billion $ company. Therefore, Investors largely pass over this person.

C. The Scrappy Storyteller

The dream is to spot a founder who blends the attributes of the Storyteller and the Scrapper. Someone who can both build with their own hands, as well as explain with utmost simplicity and clarity, why what they are building matters to the world.

©An Operator’s Blog

As I was drawing this Venn diagram, the one founder who immediately came to my mind was Peyush Bansal of Lenskart. I still vividly remember him pitching to our entire investment team for Series A in 2011 – it was a poetic combination of Storytelling backed by Scrappy execution. Peyush stays as a gold standard founder persona in my head to this day.

So, how does one spot the Scrappy Storyteller? Anecdotally, I have seen a few contexts where this persona lives:

  • Fresh grads of good universities, with a builder DNA.
  • Repeat founder with sub-scale outcomes in previous startups and/ or ‘a point to prove’.
  • ‘Hacker’ personality with good communication skills and a high-potential side project.
  • Deep domain/ research expertise with commercial DNA, often building in university labs.
  • Solid professionals who are under-estimated or ignored as per mainstream social criteria.
  • First-time founder who is executing on fumes, clawing and scrapping to early customers.

Of course, these are just some examples from my lived experiences as a venture investor. The whole point that makes venture capital extremely challenging and exciting as a vocation is that there is zero predictability in where the best founders can be scouted. It’s like going on tiger safaris in India – you might spot one in the wild during the first trip itself, or it might take multiple trips over several years.

D. Can one persona gradually grow into the other?

While all investors are on a perpetual quest to repeatedly find the dream Scrappy Storyteller persona, the reality is most founders would be more indexed on one side, to begin with.

However, the beauty of entrepreneurship is that it’s an extremely long game of survival. Therefore, irrespective of the starting point, founders with a growth mindset can gradually evolve into incorporating the strengths of the other persona, becoming an ideal blend of the two over the journey.

So the key question then becomes – how does one spot which Storyteller can eventually transform into a Scrapper? Or which Scrapper can grow into a Storyteller?

Here are some heuristics I have been experimenting with:

1/ Storyteller ➡ Scrapper

It’s very hard to convert someone into a builder. It’s like what they say in cricket – you can’t teach a fast bowler to bowl fast. Either one has it or doesn’t.

If one hasn’t developed Scrappiness as a muscle through life experience, then the only way to develop it is to go through the fire during the startup journey and not give up while at it.

Surviving for long requires grit. And grit is an outcome of an underlying emotion, which is “How badly do you want to win?”. Whenever I meet a Storyteller, I try to spot signals that help me get conviction around this single question.

2/ Scrapper ➡ Storyteller

I believe that while Scrapping is a muscle that is built over many years via braving adversity and hardships, Storytelling is a learned skill that can be honed with expert coaching and practice.

In my own venture career both institutionally as well as individually, I have seen numerous examples of Scrappy founders gradually becoming awesome Storytellers. More global exposure, as well as tools and guidance provided by VCs, really helps in this.

However, while the odds of a Scrapper becoming a Storyteller are generally positive, one still needs to evaluate how quickly and to what quality can a particular founder evolve?

In this regard, I have come to look for the following signals:

  • Basic communication skills – like command over the language, elementary articulation, clarity of thinking, logical thinking, creating arguments, and basic persuasion skills. It’s like scouting for fast bowlers in Pakistan – if the kid is bowling fast bare feet, with a tennis ball on an uneven dusty playground, the raw material is there for a premier fast bowler.
  • Coachability – self-awareness to recognize personal gaps, humility to seek solutions from experts, listening skills to assimilate feedback, and courage to work on it and become better.

E. The key message

As individuals, we all have our strengths and weaknesses. Ideally, we should choose to play games in life where our natural strengths give us an ‘edge’. Entrepreneurship is the toughest of such games. If you do choose to play it, I believe it’s important to have the self-awareness to map your gaps, and the growth mindset to work on them. If one can follow this approach and survive long enough in the game, success is almost inevitable.

PS: this post is a result of a recent brainstorming session over WhatsApp with my friend and deep tech VC Arjun Rao of Speciale Invest. Thanks so much for your thought partnership in framing this 🙏🏽

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India Startup Valuations, Corporate Governance, And Other Good Stuff: Notes From The Recent Trip

From valuations drastically coming down and hard questions around SaaS, to the unlock of INR LP capital and rise of deeptech – sharing candid notes from my recent India trip.

Just came back from one more of my quarterly trips to India. Based on meeting scores of founders, investors, and operators, here are a few interesting insights on the current state of the Indian startup ecosystem:

1/ 4-6 quarter lag between US and Indian private markets

There appeared to be investor consensus that the real shakedown in overfunded/ overvalued tech startups in India hasn’t really started yet. Most VCs believe that 2024 will be brutal for many of their portcos that are on the wrong side of things and are, therefore, expecting brutal downrounds and recaps.

Given that the US private market correction started sometime in mid’22 and is still ongoing (eg. Convoy, a digital freight brokerage last valued at ~$3.6Bn, recently shut down reportedly under stress from creditors), there seems to be a significant lag between the US and Indian private markets.

With US VCs expecting startup shutdowns to peak in 2024, assuming the above lag, we are potentially looking at a weak fundraising environment in India continuing deep into 2025.

For India-based founders, this underlines the importance of having enough runway to tide the next couple of years out.

2/ Current fundraising environment is worse than I thought

Over this trip, I heard of at least 10 deals falling through at the final legal documentation stage. Anecdotally, I could identify a couple of reasons:

  • Smaller funds are facing capital call challenges with LPs, given tough global macros and general pullback from venture as an asset class.
  • The bar for financial diligence has really gone up. Funds are willing to walk away if even a few issues crop up in the typical Big 4 fin DD. A common issue I heard is a founder signing a term sheet on the claim of say $1Mn ARR, and post-fin DD, true recurring revenue as per accounting standards turns out to be $200k. This is a deal-killing red flag!

3/ Valuations have significantly compressed

Based on triangulating numbers from convos with multiple investors, these are the generally prevailing valuation ranges for each financing stage right now in India.

Note:

(1) These numbers are highly anecdotal and will vary a lot case-by-case depending on sector, team, and traction. However, I validated these broad ranges from multiple Indian VCs.

(2) Am also including a comparison with current US benchmarks as per Carta.

Pre-Money Valuations (as of Oct’23)IndiaUS
Pre-seed$3-5Mn$5-10Mn
Seed$5-10Mn$10-25Mn
Series A$10-20Mn$25-70Mn

What’s striking to me is how compared to the US, the valuation ramp with each stage of maturity is relatively low in India.

4/ The rise of Rupee denominated capital in venture

I remember the Managing Partner of the VC firm I used to work for more than a decade back, having a strong thesis that similar to China, India’s venture ecosystem will truly be unlocked by the participation of domestic capital pools. On this trip, I saw encouraging green shoots of this view, with Family Offices like the Mariwalas and Hindujas allocating to venture capital both actively and passively.

One interesting trend here is how the younger, next-gen heirs to these family businesses want to play an active role in working alongside the new crop of Indian founders. I sensed a passion and excitement in their approach, which transcended from startups being mere wealth management or portfolio allocation decisions.

To me, unlocking INR LP capital is a hugely encouraging trend and one that will make the local innovation economy more resilient to geopolitics and global shocks.

5/ Deeptech becoming a mainstream venture theme

Deeptech seems to have transitioned from being a fringe venture theme for many years, to now being one of the core theses of all mainstream VCs. Peak XV’s latest Surge batch is dominated by AI and deeptech, Accel is running an Industry 5.0 program via its Atoms accelerator, deeptech specialists like Speciale Invest and Pi Ventures are busier than ever, and I heard of many investments in-process in the semiconductor space.

The cornerstone of my investing thesis is – “India started by exporting software services in the 90s-early 2000s. It then moved up the value chain to become the global hub for software products/ SaaS from the mid-2000s till 2020. Over the next 20 years, India will move even further up the value chain and export cutting-edge innovation to the world”.

This time, I saw strong signs of this thesis on the ground in India.

6/ Corporate governance clean-up in progress

It was clear that both founders and investors are owning up to the corporate governance mishaps over the last year. The problems have been recognized, accountability taken, causes diagnosed, and learnings accepted and assimilated. I heard many instances of deep clean-up happening within companies, right from the board to the lower operating levels.

I see this as a major growing-up moment for the Indian venture ecosystem as a whole, and post this clean-up, everyone will be better off for it. I expect a whole crop of young founders and venture investors to emerge battle-hardened from these experiences, and from here on, focus their energies on building generational companies.

7/ Hard questions being asked of application SaaS

Similar to the sentiment at Bessemer’s recent Cloud100: Rise of SaaS in India Brunch 2023** in SF, Indian VCs are now starting to ask some hard questions about competition and product differentiation to application SaaS startups.

The Zoho playbook worked in the early 2000s. The Freshworks playbook worked in the 2010s. In this rapidly changing, post-AI world, whether these old paradigms are still applicable needs to be questioned and discussed in an intellectually honest way.

**Key SaaS takeaways from this event here.

8/ Very early signs of the domestic B2B software opportunity

While the India cross-border SaaS opportunity is now well established, I am also hearing scattered anecdotes of startups going after large ACV, domestic B2B opportunities. While VCs continue to be generally bearish on domestic B2B software, founders have started taking note of the journeys of the likes of Perfios and Netcore. Some of these companies have shown that though it takes time, it’s possible to build large ($100Mn+ ARR) domestic software product businesses.

In fact, over the last year, I have seen several enterprise startups reach $3-10Mn ARR by serving large Indian customers. Maybe it’s time to be more open-minded and take a nuanced view of the domestic B2B software opportunity?

9/ Tech-enablement of legacy domestic verticals

Applying technology to improve the growth and efficiency of legacy verticals like construction, procurement, automotive parts, logistics etc. is emerging as a key business opportunity. While horizontal B2B commerce platforms like Udaan, OfBusiness, and Moglix are already mainstream, am also seeing the rise of a new set of more specialized, vertical platforms.

These are really large TAM opportunities given the amount of GMV that changes hands in the brick-and-mortar portions of the economy. As India grows from a $3.5Tn to a $10Tn economy, the tech-enablement opportunity in these broader spaces will grow even faster.

10/ Didn’t see a clear thesis on AI

While almost all Indian VCs are deploying in AI startups, I didn’t hear any clear thesis or POVs from most of them. Not to be too harsh on them as barring the emerging hyper scalers like OpenAI and Anthropic, the early stage AI scene is pretty fuzzy even in Silicon Valley. PS: check out my recent post ‘AI Musings #1 – How The Odds Are Stacking Up?‘.

11/ Promise of IPO’ing in India

I heard distinct excitement around the potential of late-stage startups doing IPOs in the Indian market. Over the last couple of years, Indian public markets have shown a strong appetite both for tech growth stocks as well as small to midcap SMB stocks.

I spoke to a founder who recently listed his tech services company at a relatively small scale. His experience in managing the compliance and related overheads of running a publicly listed company in India has been fairly smooth so far. In fact, he has enjoyed both interacting with and learning from well-prepared large institutional investors.

Similar to INR LP capital, unlocking domestic public markets for IPOs of new-age companies will be a huge boost and de-risker for the local innovation ecosystem.

Other memorable moments…

LetsVenture, my very first angel investment, completed 10 years. I still remember the first brainstorming session with the founders when it was just an idea on a blank sheet. The company has since emerged as the leading infrastructure layer for private market investing in India. I am in awe of the tenacity of Shanti Mohan (Co-founder and CEO), and how she has selflessly contributed and fought for organizing private market investing in India. PS: some special moments at the celebratory dinner with early backers – Subrata of Accel, Sharad Sharma of iSpirt, and others are here.

LetsVenture’s achievements over the last decade

I was also on a panel at LetsIgnite with one of my oldest friends Anirudh Singh (Avataar Ventures), alongside Vishesh Rajaram (Speciale Invest) and Uday Sodhi. It was an unfiltered discussion on everything from portfolio construction, diversification, and power laws to entry prices and exit approaches. It was also the first time I presented my investment strategy to any external audience, so this particular event will always stay close to my heart. PS: some key insights from the panel are here.

LetsIgnite’23 panel on venture portfolio construction

Towards the end of the trip, I partnered with my friend and collaborator Arjun Rao (Speciale Invest) to do a closed-door, no-holds-barred type session with select infrastructure SaaS founders in Bangalore. The main theme was the US-India corridor. I like to keep these sessions very raw, no-gyaan, only brassstacks around operating and financing challenges that US-India enterprise founders are dealing with daily. PS: some key takeaways from the session are here.

Closed-door session on US-India corridor, in partnership with Speciale Invest

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Cheetah in the Rainforest: 2021 Vintage of Venture

“A firm writing seed checks without specific competence in that stage is like a cheetah in the rainforest. The beast is a wonder of nature that can run at a top speed of 60-70 mph in the African grasslands. But place it in the Amazon rainforests, and all its wondrous capabilities will amount to zilch. It’s just not built for it!”

Most 2021 vintage startups got VC ‘cheetahs’ on their ‘rainforest’ Boards. Surviving the new reality that faces them, will require a cathartic reboot.

Had an interesting conversation with a Bay Area-based founder a few weeks back. His startup is in the high-ACV enterprise space wherein the product is solving an intense and wide-ranging problem that is especially applicable to large companies. He got off the blocks in 2021 with a mid-single digit $Mn pre-seed round by a top-tier VC at the idea stage itself. A start that most founders dream of!

However, now two years down the road, the situation on the company’s Board is far from rosy. The company has gone through tumultuous times that are typical for any 0-to-1 startup. While the founder has kept his chin up during this phase, he is very disillusioned with the VC’s advice, behavior & general stance so far. When he shared some specific examples of this with me, my first reaction above all else was that this firm clearly has little past experience of portfolio management at the seed stage & in particular, what founders need in order to navigate its inherent complexity.

As I started relating this to many other founders I have met this year, a pattern is clearly emerging in the 2021 vintage of startups. Specialist VCs who have mainly invested in the Series A & beyond space in the past, went upstream & wrote massive pre-seed & seed checks with minimal or no traction. They were probably under pressure to deploy or get early dibs on the best teams as later stage valuations were going to stratospheric levels.

Seeing these companies now, after most of them have almost consumed their 24-month runway, I am seeing how the lack of milestone-based capital sequencing & strong stage-firm fit has created many fundamental issues with their core:

1/ Armed with big checks from large AUM firms, founders ignored the scrappy, capital-efficient approach right out of the gate. Instead, they bulked up teams & spent disproportionately on go-to-market even before problem-solution fit. Now in hindsight, they have ended up creating fragile organizations that are at the mercy of the macroeconomy & availability of follow-on capital.

2/ Many of these VC firms have put relatively inexperienced team members on the boards of these companies. My guess is because in their overall AUM game, these types of really early investments are probably considered highly risky “option bets” with low stakes in general & therefore, good learning opportunities for more junior members.

While experience by itself doesn’t make anyone a good or bad VC, pre-seed & seed stages of venture capital demand much more art & judgment in company building from all stakeholders. A firm writing seed checks without specific competence in that stage is like a cheetah in the rainforest. The beast is a wonder of nature that can run at a top speed of 60-70 mph in the African grasslands. But place it in the Amazon rainforests, and all its wondrous capabilities will amount to zilch. It’s just not built for it!

It’s a bit counter-intuitive but in my view, the best VC talent (best = strong fit from a personality & skills perspective) needs to be involved in the earliest stages of company building. There is a reason why YC has a strong moat in that stage, & why while most fresh MBAs can invest & do portfolio management at Series A & growth funds, pre-seed & seed needs artists like Paul Graham & Semil Shah that are few & far between.

One of the things I would like to see coming back into the startup ecosystem foundation post this venture downturn is the importance of “capital staging” – rigorously thinking through how the company should be capitalized at the earliest stages, what kind of investors should be assembled for it, the mindset, approach & time a specific company would need to iterate towards problem-solution fit & eventually, product-market-fit.

I would like to see the return of angels, domain operators & specialist boutique VCs partnering with founders at the earliest stages of venture. We need some version of the Arthur Rock & Ron Conway models but modified for this age. These types of stakeholders in turn, would educate and/ or encourage founders to be scrappy, agile and perseverant during the 0-to-1 stage, supporting them in building the most optimal path to the next base camp.

Closing thoughts specifically for the 2021 vintage startups – while it’s not easy to rewire the foundational DNA of a company, it’s not impossible. While the lesser gritty teams will flame out, I am also seeing founders who are acknowledging both the mistakes of the past as well as the new reality that faces them and are determined to learn & re-invent themselves. Even though as an investor, I am not too excited about the 2021 vintage the way it looks & is behaving right now, I will be more than eager (& rightly so!) to back its re-invented & re-wired v2.0.

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