With AI disrupting middle-management roles, many professionals in their late 30s to 50s will need to reinvent themselves.
Anecdotally, in the Bay Area, Iâm seeing middle managersâparticularly at the Director levelâdisproportionately affected by recent layoffs at large tech companies.
The precedent was set by Meta in 2022/23 when Zuckerberg openly questioned the need for multiple organizational layers, arguing they slowed execution. Many of Metaâs layoffs were aimed at flattening teams.
Likewise, Elon Musk and Jensen Huang are known for engaging directly with frontline employees, even interns, to unblock key challenges. Brian Cheskyâs “Founder Mode” philosophy echoes this approach, encouraging leaders to dive into details and manage execution at the ground level rather than delegating critical projects to layers of managers.
Now, AI is accelerating this shift. By supercharging individual contributorsâturning them into self-sufficient, full-stack execution engines across coding, marketing, and salesâAI is reshaping how Big Tech structures its workforce. As companies prioritize efficiency, the middle management layer may be on the verge of disappearing.
In the last mobile/cloud/SaaS cycle, middle managers served as the bridge between executive leadershipâs vision and frontline execution. However, as tech companies swelled due to ZIRP-driven capital excess, Directors and Senior Directorsâwhether intentionally or notâbecame bureaucratic bottlenecks.
With AI disrupting these roles, or at the very least redefining their purpose and required skillsets, many professionals in their late 30s to 50s will need to reinvent themselves. This could mean re-skilling or up-skilling to become AI-native knowledge workers, transitioning to different industries, or even leaving core tech altogether to apply their experience elsewhere.
This may sound extreme, but itâs exactly what Iâm observing in my circles.
Zoom pitches demand quick engagementâcapture attention in 60 seconds, use visuals wisely, and keep slides concise. Bring personality and storytelling to stand out.
More than half of the pitches I take as an investor happen on Zoom. I also frequently pitch to LPs on Zoom, so Iâve gathered plenty of experience here.
Over the years, Iâve realized that pitching effectively on Zoom is a completely different skill from pitching in person. In fact, I almost always nail in-person meetings, but Zoom can be hit or miss.
In-person meetings have a consistent energy and settingâstandard surroundings, small talk, and even table arrangements. Zoom, however, introduces external factors that can impact the experience: audio quality, lighting, background noise, AI note-takers, joining delays, screen interruptions, and even the lingering mood from a previous (probably also Zoom) meeting.
TL;DR:
Attention spans and patience are significantly lower on Zoom than in person. Participants lose interest and get irritated much faster.
While first impressions, body language, and icebreakers set the tone in an in-person meeting, on Zoom, you have 60 seconds to capture attention and pull your audience into your pitch.
If thatâs true, Zoom pitch meetings should be structured very differently. Hereâs what I recommend:
1. Open with Your Strongest Points
With only 60 seconds to grab attention, avoid meandering intros or generic company overviews. People tune out fast on Zoom. Instead, start with the three strongest parts of your pitch in the first 30 seconds.
â BORING: “Iâm the founder of… Weâre based in SF and started three years ago after identifying this opportunity while working at…”
â INTERESTING: “[COMPANY NAME] is [1-line description]. Weâre at $X ARR/N users, growing Y% week-over-week. Our team comes from [COMPANIES], and hereâs our unique insight: [1-line unique value prop].”
Walking through slides one by one makes Zoom meetings boring. It also reduces face-to-face engagement, shrinking participants to tiny squares above a massive slide. This makes it harder for investors to read facial expressions, passion, and conviction.
Instead, use slide sharing only when diving into specificsâmetrics, product visuals, or key data points. If a conversation naturally leads to deeper discussions, screen-sharing makes sense. And if someone asks for more details, thatâs a great signâtheyâre engaged.
3. Prioritize Stories Over Generic Narratives
Broad business narratives and jargon make Zoom meetings dull. Theyâre harder to internalize and, in the worst cases, cause brains to switch off entirely.
Instead, use specific, personalized stories to make your points.
Rather than saying âOur product saves companies X dollarsâ, share a real customer success story.
Show how one specific customer (name, picture, and all) used your product and what impact it had.
Investors remember compelling stories more than numbers and percentages.
4. Leverage Visuals â Videos & Images Work Best
Spoken words are harder to absorb on Zoom, but visualsâespecially videosâhave a much stronger impact.
After your opening, incorporate relevant images or a short video to drive home key points. A well-placed visual can communicate in seconds what might take minutes to explain verbally.
5. Design Zoom Slides Like a TED Talk Deck
Verbose slides wonât be read. While your full pitch deck can be detailed, the version you present on Zoom should be simple, bold, and visualâlike a TED Talk deck.
Each slide should focus on one core idea
Use minimal text and large fonts
Whenever possible, let charts, images, or visuals tell the story
For inspiration, check out the following slides used by top TED speakersâthey prove that less is more.
TLDR: for Zoom meetings, like for TED Talks, less is more…
6. Let Your Personality Shine
Too many Zoom pitches feel roboticâmonotone delivery, deadpan expressions, and no effort to break the ice. Thatâs a missed opportunity.
The easiest way to be interesting? Be yourself. Show quirks, humor, and enthusiasm. Your journey, energy, and passion make the conversation engaging.
Your job isnât to blend inâitâs to stand out. If you canât get people to actively listen and engage, a future investment isnât happening anyway.
Closing Thoughts…
Mastering Zoom pitches is an evolving skill, but structuring them thoughtfully can make all the difference. Adapt your approach, test what works, and refine as you go.
Have you found any techniques that work particularly well in Zoom pitches? Would love to hear your thoughts!
Saw a post about how YC has been backing fewer India-based startups than before. I guess Antler, South Park Commons, and Entrepreneurs First are attempting to fill this gap to some extent.
With YC, the issue is that the quality and volume of AI founder talent in the Valley is so high right now that it doesn’t make sense to look outside.
Also, on a risk-adjusted basis, it’s unclear how India-based founders without global GTM experience/ networks will win against global competitors, especially given the rapid pace of AI evolution.
Personally, in addition to backing Indian diaspora founders in the Valley, am also tracking India-based founders who have specific product/ GTM/ verticalized superpowers and are hacking early US/global GTM in interesting ways.
For eg., am seeing a few India-based founders getting to $500k-$1Mn ARR with solid US logos by doing back-and-forth on B1/B2 visas. A few others are leveraging channel partner-based GTM cutting across multiple geos. In areas of deeptech’ish software/ hardware+software plays, the product itself tends to be fairly differentiated and sees relatively less competition from typical Valley/ YC companies, especially when you account for competitive pricing/ more value/ white-glove service/ rapid speed of iteration from India-based startups.
The enigma of junior VCs toiling-away to create market maps.
Probably one of the most mind-numbing jobs for a junior VC must be creating these frikkin’ market maps and thesis visualizations.
Imagine churning for days/weeks on a landscape doc, only for it to be obsolete in a few weeks/months with how AI is evolving.
And who do these docs eventually serve? Canât think of them creating any real value for seed founders. Perhaps LPs?
These market maps remind me of the âmarket slideâ that all consulting/IBs have in their deck. Hardly any customer cares about them much. They end up becoming junk collateral that some analyst/associate toiled hard to put together.
Btw this reminds me of when I was a junior VC. I had to ghost-write articles for the Partner and in the end, not even get credited for it. Even as a 27-year-old, I found it extremely discomforting that having joined the VC industry to invest in and support founders, I was spending inordinate time helping the GPs market themselves.
My (subconscious) revenge for the ghostwriting days? After a decade, have now turned blogger & podcaster with my own brand (An Operator’s Blog – blog + podcast) + investing in founders with my own world-view & conviction (my Fund Operators Studio), not begging GPs to âget a deal throughâ.
The backstory of Operators Studio investing in Breakout’s seed round.
Happy to share that Operators Studio has invested in the $3.2Mn seed round of Breakout, led by Village Global.
I have known Sachin Gupta since 2011 when we first met at the YourStory office in Indiranagar. He was a young IIT Roorkee grad and only a few months into starting HackerEarth. Since then, our paths crossed many times. He moved to the Bay Area a few years after I did, and we kept meeting through our respective journeys.
A few months back, Sachin reached out with just the figment of an idea of leveraging AI to fix holes in the top-of-the-funnel of enterprise sales. We brainstormed, and once he decided to go all-in, I literally became the first commit into what eventually became a marquee seed round.
So happy that Hitesh Aggarwal agreed to partner with Sachin on this journey. He is an incredibly accomplished product leader and a co-founder with very complementary skills.
What is Breakout?
Think of Breakout as an agentic workforce that grows your inbound pipeline by delivering personalized engagement to every website visitor.
Here are some of its key features:
đ¸ Personalized Interactions: Breakout uses third-party signals and first-party data to tailor conversations based on visitor personas, offering relevant content and case studies. đ¸ Live Demos: It can deliver interactive demos aligned with buyer interests. đ¸ GTM Insights: Breakout provides actionable insights, such as visitor segmentation, commonly asked questions, and competitor comparisons. đ¸ BANT Discovery: It naturally uncovers Budget, Authority, Needs, and Timeline through dynamic conversations. đ¸ Fast Onboarding: Breakout offers quick setup and easy maintenance, automatically updating its knowledge base.
If this has sparked your curiosity, consider joining the Breakout Growth Program where you will get the first 6 months free, in addition to dedicated onboarding & support, as well as the ability to join their exclusive community of GTM leaders and help shape the product roadmap.
PS: this partnership is another reminder that venture is a game of long-term relationships.
Most investors try to “slot” startups in their heads, whereas extraordinary venture outcomes lie in the “slot violations”.
A few weeks back, I was helping a portfolio founder put together the story and deck for raising the next round. This company is one of the true category-creators I have seen in my career and has now reached a PMF tipping point that will lead to explosive growth going forward. Customers and channel partners are literally pulling the product out of the company’s hands, and all metrics are going up and to the right.
Despite this, the founder was sharing how difficult it still is for him to explain the business, the market opportunity, and how this is an extremely differentiated play to investors. Having seen this startup’s thesis play out as an existing investor, my conviction on it is 200% but despite powerful operating signals, it’s still non-trivial to put together a narrative that investors “get” immediately.
This isn’t a new pattern. I have seen this repeatedly play out with truly groundbreaking companies, simply because most investors prima facie, try to “slot” the company in their heads within the first few minutes of the 1st meeting. These slots are pre-existing buckets created by years of pattern-matching, and not surprisingly, 90% of startups can easily fit into one or more of these slots – eg. big company exec stepping out to start an enterprise company, young engineers hacking a dev tool, repeat founder building in the same market, generalist founders executing really fast in SaaS etc.
The issue is this – history tells us that extraordinary venture outcomes are created in the narrative violations (or what I now call “slot violations”). These are companies that are hard to understand in the present moment, being built by founders who are quirky and/or with non-obvious backgrounds, or resulting from messy pivots. Well-known examples include:
When Evan Williams was shutting down Odeo and hacking around with a micro-blogging tool (which eventually became Twitter), it had no business model even in the foreseeable future.
Imagine how Canva looked as a deal when the founders came to the Valley to fundraise – an Australian couple, no revenue, competing with Adobe, raising at $25Mn cap.
Uber had massive regulatory risks that most investors couldn’t get their heads around.
Almost every major VC has mentioned Pinterest as a big miss. It was totally unclear how Pinterest could be a “business”. Ben Silbermann talks here about “why every VC passed on Pinterest“.
As a venture investor, I think a lot about what mental models to use in order to spot these slot violations. Thinking through the earlier discussion with the portfolio founder, it was clear that even though investors might struggle to slot the company at this moment, the market was clearly resonating with the product. In a way, the early adopters in the market had been educated by the founder and therefore, were already bought into the “insight”, whereas the existing mental models of investors were lagging in their appreciation of this insight.
I call this “Insight Arbitrage” – the delta between the market’s and investors’ understanding of a startup’s unique insight. At the pre-seed stage, this market understanding will be mostly qualitative and anecdotal. At the seed stage, this understanding will still be likely on a very small base of users.
Because a majority of investors find it hard to build conviction in the above two scenarios, an Insight Arbitrage continues to perpetually exist in the venture world. And I believe that this is where an opportunity lies for investors like myself to generate alpha, provided we show the courage to trust this arbitrage and put our money behind it.
I particularly found the part on what Ed calls “defense” highly intriguing – he says: “It just takes one weak link to finish you off”. Essentially, my understanding is that among other things, defense involves avoiding a bunch of things that when done repeatedly, could essentially wipe you out (as in, you die!).
Ed gives the example of “a terrible skiing accident” but other things that come to mind include say helicopter rides, binge drinking, bungee jumping, living next to a dangerous turn on a busy street etc. While the probability of death in a one-off instance of these games might be low, when done repeatedly, the chance of death becomes non-trivial due to repeated exposure.
Nassim Nicholas Taleb calls this concept Risk of Ruin, and I remember getting blown away when I read about it for the first time in his books ‘Skin in the Game‘ and ‘Antifragile‘. So much so that Ruin has become an essential mental model in my toolkit both personally and as an investor.
In particular, I love 2 specific examples of Ruin that Taleb frequently cites:
The Casino Experiment – let’s say we know that 1% of all gamblers playing at the Casino win. So for every batch of 100 gamblers that visit the Casino daily for 100 consecutive days, we know that each day, 99 will be wiped out and 1 will walk away with money. Now take a different case – one gambler visits the Casino daily for 100 consecutive days. In this case, his probability of getting wiped out at some point is 100%.
Russian Roulette (quoting Taleb directly here) – “Assume a collection of people play Russian Roulette a single time for a million dollars âthis is the central story in Fooled by Randomness. About five out of six will make money. If someone used a standard cost-benefit analysis, he would have claimed that one has 83.33% chance of gains, for an âexpectedâ average return per shot of $833,333. But if you played Russian roulette more than once, you are deemed to end up in the cemetery. Your expected return is ⌠not computable”.
Taleb calls the former case where different groups do an activity, and probabilities and expected values are computed “in average”, as Ensemble Probability whereas the latter case of a single person repeatedly doing an activity across time as Time Probability.
As common sense would tell us, Ensemble Probability represents a mathematically driven, academic (almost artificial?) scenario analysis, whereas Time Probability represents how we as individuals get exposed to risk in real life.
Time Probability suggests that there is an underlying Risk of Ruin in many more things & activities in real life than our brains can cognitively appreciate in the thick of the action.
Over the years, as I have read/ listened to more thinkers across fields, many of them highlight this same concept of avoiding Ruin in their own words. Examples include:
It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent. – Charlier Munger
Never forget the six-foot-tall man who drowned crossing the stream that was five feet deep on average. – Howard Marks
The 1st rule of investment is don’t lose money. And the 2nd rule of investment is, don’t forget the 1st rule.– Warren Buffett
[Paraphrasing]“Arithmetic returns are false hopes; the truth lies in geometric returns” / “Profit is finite. Risk is infinite”. – Mark Spitznagel
Essentially, all these quotes are pointing to the same underlying idea:
The most important force that governs life, be it in health, relationships or portfolios, is compounding.
Given its cumulative nature, the optimal strategy for enabling the magic of compounding is combining avoidance of ‘Ruin’ (going to zero/ total destruction) with ensuring ‘Survival’ over a long enough period of time.
From my vantage point as a US-India venture investor, sharing what I observed in 2024 and my expectations from 2025.
As a venture investor in the US-India corridor via Operators Studio, I saw 2024 as the year of taking stock, of heads-down building for founders, and quiet contemplation for investors.
A. 2024 Recap
1/ AI(Enterprise)– after the unveiling of ChatGPT on Nov 30, 2022, and the peaking of the AI mania in 2023, 2024 saw a bit of dust settling down in the ecosystem. In the Bay Area, I heard more intellectually honest conversations amongst founders and investors, with folks going deeper into discussing operating details and how to best leverage this tech step function beyond the “AI is going to change everything” hyperbole.
(a) Focus on the Applications layer
Along similar lines, I saw US-India founders go into deep build mode in AI. Most appeared to focus on the Applications layer, which aligns well with their core strengths. Working closely with portfolio companies like Confido Health as well as interacting with several seed-stage US-India founders, it has been particularly heartening to see them doubling down on spending time with customers, while also ramping up on the latest developments in AI. They are actively leveraging new models and tools to quickly ship new features. A lot of early US-India SaaS vibes!
(b) Indian VC skepticism
In private conversations with many large VCs in 2024, I sensed a fair amount of skepticism on whether the current generation of Indian AI companies will be able to compete with global players. As a result, many of them are choosing to be extremely selective in terms of the number of deals, waiting, watching, and observing how things are playing out in the US, while occasionally backing de-risked repeat founders in one-off large deals.
A few are also experimenting with a multiple-bets approach, writing several small checks (up to $1Mn size) into high-potential teams and seeing how they execute. Tailored seed programs have been created to do this eg. Peak’s Surge, Accel’s Atoms, Chiratae’s Sonic etc.
2/ India-to-the-world deep tech
The domestic deep tech market opportunity clearly became mainstream in 2024, with a spectrum of 1st generation companies now well-established, ranging from public companies like ideaForge in drone manufacturing to growth stage space-tech startups like Agnikul, Pixxel, and GalaxEye.
Given these outcomes, almost all major Indian VCs now have a deep tech thesis, which bodes well for the next generation of founders in the domain.
(a) Rise of the 2nd-gen
In 2024, I saw the 2nd generation of deep tech founders like Sharang Shakti (anti-drone defense systems), Astrophel Aerospace (space tech) and Naxatra Labs (EV motors) emerge on the scene. They are piggybacking on the learnings and playbooks of their 1st-gen predecessors to move faster and think bigger.
(b) Global commercial traction
In parallel, I saw early green shoots of Indian deep tech startups starting to go global commercially in a more meaningful way in 2024. The biggest eye-opener for me in this regard was attending Speciale Invest’s Annual Summit in Nov’2024 and getting updates on their portfolio going global.
For instance, Ultraviolette has officially launched its EV Superbike ‘F77 MACH2’ for the European markets. Uravu Labs is starting to get some major international orders for its recycled water technology. Cynlr recently inaugrated its Robotics Design & Research Center in Switzerland. PS: for those interested in a few hours of deep-dive into the India deep tech ecosystem, the full-day recording of Speciale Summit’24 sessions is available here.
I saw similar signs of rapidly growing global traction in the Operators Studio portfolio too in 2024. Flytbase has now emerged as a clear global category leader in autonomous drone software, with major enterprise drone-dock installations across 16 countries. Cradlewise is one of the fastest-growing smart cribs in the US, and giving incumbents like Snoo a run for their money. Playto Labs has created a sharp niche of STEM learning using robotics kits and live instructors, with more than half of its revenue coming from outside India.
3/ Venture Capital
(a) No Enterprise exits
2024 continued to be a fairly tight year for VC financings in the US-India corridor. It feels like the VC ecosystem is still undergoing some sort of recalibration after the 2020/21 mayhem. While VCs saw some great IPOs at least on the consumer side, exits on the enterprise side were almost non-existent.
As a US-India venture investor, I primarily play in 2 areas – (1) AI/ Enterprise Software and (2) India-to-the-world deep tech. Exits in these areas are typically expected via M&A. With Indian acquirers being sparse, and the US M&A environment at a standstill under the previous administration, Indian enterprise exits saw virtually no action in 2024.
While smaller funds like Operators Studio can still generate healthy exits via secondary sales to growth investors, we as an ecosystem still need full company exits via M&A and IPOs to keep the liquidity pipeline flowing end-to-end over the long term.
(b) Limited seed capital
In the US, while the bar for Series As and Bs has moved significantly higher, seed-stage financings continue to see high levels of activity. In fact, most multi-stage firms like A16Z, Sequoia, and Coatue are also writing idea-stage checks into AI as we speak. Essentially, 2024 saw massive crowding at the seed stage in Silicon Valley, and given the bar for follow-ons has increased a lot, graduation rates have dropped significantly. As per Carta – “30.6% of companies that raised a seed round in Q1 2018 made it to Series A within two years. Only 15.4% of Q1 2022 seed startups did so in the same timeframe”.
India’s venture ecosystem behaved a bit differently in 2024. Established Indian VCs appeared to have become fairly risk-averse in the past year, reflecting both their larger Fund sizes (needing to deploy larger checks with more traction) as well as their efforts to triage the excesses of 2020/21. As I wrote in this post a couple of months back:
From what I am seeing in my deal flow over the last few months (and my focus is (1) enterprise software and (2) deep tech), I feel there is almost a dearth of quality, structured & consistent angel/pre-seed/seed capital in India right now.
From what Founders are telling me, almost all major Indian VC firms seem to be holding out & looking for late-seed/pre-Series A levels of traction even to start a real conversation. The proverbial $1Mn+ ARR, 2-3x y-o-y growth…
Anecdotally, it looks like only previously successful repeat founders are mopping up large seed rounds from these firms at the idea/pre-product stage. Pre-seed/seed seems to be significantly tighter for first-time founders.
Genuine question for myself and many India-based enterprise & deep tech founders out there who are fundraising – who are the angels/ seed firms in India that are comfortable in CONSISTENTLY writing checks at the true early stages in enterprise software and deep tech (idea/pre-product/MVP/design partner/some usage stage)? And by consistent, I mean doing 10-12 deals per year.
Essentially, 2024 turned out to be an extremely tricky year for US-India founders to raise seed capital, with rounds taking significant time to come together, investors wanting to see much higher levels of traction, and valuations fairly compressed especially relative to the amount of progress in the business.
Of course, the other side of this coin was that these same factors made the US-India seed ecosystem an attractive pond to fish in for investors in 2024. In fact, looking at both the quality of the teams I evaluated as well as the entry valuations I saw, I believe 2024 will emerge as one of the best vintages of Indian venture capital a few years down the road.
B. 2025 Expectations
As we enter 2025, here are some expectations I have from Global Indian founders. These aren’t predictions; rather, a wishlist of things I would love to see play out, again in the context of my US-India/ India-to-the-world focus:
1/ Thinking bigger
In 2025, I would love to see a “Path to $1Bn ARR” slide in US-India startup pitch decks. As I wrote in this post a month back:
I would like to encourage Indian founders building software companies for the world to think significantly bigger and more aggressive both in terms of how large their business can become and how fast can they get there (y-o-y growth targets).
Why? Because software TAMs and market growth rates are much larger than what our brains can imagine. Look at the growth rates of these public companies:
1. Shopify (Founded in Canada) is growing 21% at $8.2 Billion ARR. 2. Canva (Founded in Australia) is growing 40%+ at $2.4 Billion ARR. 3. Toast is growing 29% at $1.5 Billion ARR. 4. Monday (Founded in Israel) is growing 34% at $940Mn ARR.
I am now encouraging my portfolio founders to think beyond the proverbial âPath to $100Mn ARRâ slide and start strategizing a path to hit $1Bn ARR.
Itâs time we reset our internal narratives and think bigger and more aggressive as an ecosystem.
2/ Thinking non-incremental
One of my observations is that we as Indian founders at large still have a tendency to go after low-hanging problem statements. As AI gathers momentum, these will be automated away quickly and easily especially by incumbents, making it increasingly difficult for venture-backed startups to differentiate themselves.
It sounds counter-intuitive to the whole Lean Startup movement of the last decade, but I believe that in 2025, it will be easier to build a differentiated startup by going after harder markets and tackling hard-to-build products that need to exist in a future that isn’t fully here yet.
In 2025, I would like to see Global Indian founders build for the world in a category-creation mindset from Day 0, and not be afraid to play the game on hard mode.
3/ Founders physically moving to their target markets ASAP
If you are trying to build a venture-scale AI/ enterprise software/ vertical SaaS startup targeting the US, every year you spend not physically moving here will be a lost opportunity. Within the constraints of capital, immigration regimes, and family reasons, I would strongly recommend that US-India founders expedite their move to the US in 2025.
4/ Accelerating Deeptech exports
I would love to see Indian deep tech startups build on their global momentum and double down on exports in 2025. In particular, I see the Global South as an extremely attractive buyer of Indian technology in areas like space tech, defense, energy, and agriculture.
While the West is a harder nut to crack from a commercial standpoint, it can be leveraged to access growth capital as well as cutting-edge research talent. Soon enough, commercial traction from emerging markets will provide these companies with enough product maturity and credibility to be able to compete in the US and Europe in a meaningful way.
5/ Bounce back of seed VC
We are in the early stages of a massive global AI super-cycle, and there are several categories and pockets where US-India startups are likely to have a strong right-to-win. While remaining diligent in identifying these right markets to go after, keeping a high bar on founder-quality as well, and asking tough questions to them, I would encourage Indian venture investors (including angels, family offices, syndicates, and smaller funds/ Solo GPs) to actively deploy at the seed stage in 2025.
The seed stage is where outlier angel outcomes and fund returners get created and especially at this point in the economic cycle, the risk-reward ratios are extremely strong. By all means, it’s fair to keep the bar high. But the ecosystem needs more courageous risk capital to step up at the earliest stages of building truly innovative companies.
TLDR: for the US-India/ India-to-the-world venture story, while 2024 was the year of taking stock, I expect 2025 to be the year the ecosystem starts coming out of the bottom of the J curve.
Presenting a compilation of my best ideas & observations from 2024, sorted across 7 Chapters.
Happy Holidays to all my readers out there. I have a habit of routinely posting pithy and concise ideas and observations on LinkedIn and X. Topics range from Startups, Venture Capital, and the Economy to Careers and Life.
I feel that many of these get lost over time amidst all the noise on social media. Hence, have put together this compilation of my best ideas from 2024, sorted across 7 Chapters.
Note: this is a compilation of my short-form social posts. My long-form posts for 2024 are available on An Operator’s Blog, accessible via homepage shortcuts by year/ category/ tags.
CONTENTS:
Chapter 1: Startups
Chapter 2: Venture Capital
Chapter 3: Economy
Chapter 4: Careers
Chapter 5: Life
Chapter 6: India
Chapter 7: Other People’s Ideas
Hope you enjoy reading it!
_______________
Chapter 1: Startups
1/ “Closing” People
A simple tip to convert customers/ investors/ potential hires who are sitting on the fence:
Keep coming back to them with monthly/ quarterly updates, showing tangible progress and momentum.
Even the most hardened professionals canât resist a curve that is trending up and to the right.
If you bug them long enough (ranging from a few quarters, to up to a few years) with positive momentum, you are almost guaranteed to âcloseâ them eventually.
A very powerful technique with a high hit rate.
2/ Thinking Big
I would like to encourage Indian founders building software companies for the world to think significantly bigger and more aggressively both in terms of how large their business can become and how fast can they get there (y-o-y growth targets).
Why? Because software TAMs and market growth rates are much larger than what our brains can imagine. Look at the growth rates of these public companies:
(1) Shopify (Founded in Canada) is growing 21% at $8.2 Billion ARR.
(2) Canva (Founded in Australia) is growing 40%+ at $2.4 Billion ARR.
(3) Toast is growing 29% at $1.5 Billion ARR.
(4) Monday (Founded in Israel) is growing 34% at $940Mn ARR.
I am now encouraging my portfolio founders to think beyond the proverbial âPath to $100Mn ARRâ slide and start strategizing a path to hit $1Bn ARR.
Itâs time we reset our internal narratives and think bigger and more aggressively as an ecosystem.
3/ Time To Real PMF
In recent conversations with growth investors, a bunch of them asked about my experience on how much time a pre-seed company typically takes to achieve real PMF.
Based on my venture experience since 2011, hereâs what I have observed on average for pre-seed companies:
(1) Typical enterprise software/ SaaS in existing markets:
without a major pivot: 3-5 years
with a major pivot: up to 7 years
(2) Category creation plays in software: as long as 5-7 years
(3) Deeptech/ hardware: minimum 4-5 years
I am, of course, generalizing a bit here and outliers could get there sooner. But I feel these numbers are directionally correct.
Moral of the story: itâs a marathon for founders and seed investors. So, buckle up to play the long game!
4/ Investor Updates
Both as a founder in my past life, as well as a venture investor now, I have discovered that writing updates (to investors or LPs, as the case may be) on a consistent cadence over the years is an easily accessible superpower.
What it needs is basic discipline and intellectual honesty, which in turn, come from self-awareness, keeping imposter syndrome at bay, being comfortable in one’s own skin, and equanimity about monthly/quarterly wins and losses.
5/ Speed
If you think about it, the only real advantage a new entrant has against incumbents in any field (be it a startup or even an emerging VC manager) is speed. Speed of decision-making, speed of shipping, speed of learning & iterating, speed of taking risks.
As an upstart, if you aren’t fast, the odds are against you.
6/ Boring Zoom Pitches
The majority of first-pitch meetings tend to happen on Zoom these days. I find remote pitching especially challenging for founders. A big part of venture investing is catching the vibes and personal energy of the founders. That’s super hard to communicate on Zoom.
Leaving the detailed nuances of Zoom pitching for another post, I want to leave founders with this one thought – at the minimum, avoid being “boring”! I have been through too many Zoom pitches where it seems like founders are just going through the motions, pitching in a monotone with an almost deadpan expression, and spending little time or care on breaking the ice and vibing with the other person.
Especially on days packed with back-to-back Zooms, you should assume that the investor is coming in with Zoom fatigue. If you don’t grab their attention and get them to lean in during the first five minutes of the meeting, even though they might appear to be listening and nodding through your monologue, they have mentally zoned out.
So, be interesting, and don’t be afraid of bringing your personality to Zoom. It will at least get the other side to actually hear you out and engage with you, without which, an eventual investment is not possible anyway.
7/ Cold-pitching Your Startup To VCs In 30 SecsAt An Event
For the first 30-sec pitch, I recommend having 3 parts to it:
[The Grandmother’s Explanation]
followed byâŚ
[Social Proof of Team]
followed byâŚ
[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 arenât domain experts in your field. They are likely investing across sectors and arenât 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 canât explain their startup in simple tech-laymanâs 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.
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.
Execution-related – products shipped, content created, social following, word-of-mouth etc.
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.
Itâs 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”.
Most startups attending these events donât 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 donât 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 donât have compelling traction, pitch [Social Proof of Team] first and then [Proof of Business].
The idea is simple â always lead with your strongest suit.
8/ Pitch Decks
I see an overemphasis on creating sophisticated-looking pitch decks at the seed stage.
While an eye-catching deck is always nice to have, have seen terribly basic & verbose decks getting funded simply because the underlying business was super differentiated & therefore, interesting.
PS: this changes at the Series A & beyond stages, where the pitch materials areheld to a much higher bar by larger institutional investors.
9/ Over-capitalization
These lines from a post by Christina Farr on X resonated with me:
“One of the top reasons companies die in health tech is overcapitalization. I canât tell you how many growth-stage founders Iâve talked to lately who told me they wished theyâd raised less and at a lower valuation. Huge problem, rarely discussed.”
This is a smart observation. The underlying reason seems to be that most health tech companies either tap out at a certain revenue scale or tend to grow slower than what enterprise s/w VCs expect. Overcapitalization then artificially distorts execution velocity and/or makes it harder to exit.
This point actually applies to more verticals of enterprise software than folks realize. Many of them can’t support very large outcomes and yet, if they can be capital efficient, can still lead to meaningful outcomes both for founders and early investors.
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Chapter 2: Venture Capital
1/ Liquidity
As a GP, it helps to have gone through some personal experiences that teach you the value of liquidity, why cash is king, and how itâs not around when you need it the most.
This helps develop empathy for your LPs and how unrealized paper gains canât be used to pay medical bills, take care of kidsâ tuition, build homes, and support pension liabilities.
As much as sourcing & picking the best investments, another core job of a GP is to proactively create liquidity for LPs so the cash can be used towards human needs.
2/ Psychology
One of the biggest changes I have seen in myself as an investor over the last decade – I now spend significantly more time studying the psychology of both the markets I am playing in as well as specific individuals I am working with.
3/ 1st-Time vs Repeat Founders
While second-time founders are great risk-adjusted bets, I keep reminding myself that a majority of generational tech companies were started by 1st-time founders both in the US and India.
4/ Non-Consensus-And-Right
2024-25
“Hot” theme of the year: Gen AI
What I have been investing in:
(1) AR/VR
(2) Edutech
(3) Robotics
(4) Drones
Periodic reminder: outlier venture returns are non-consensus-and-right.
5/ Alpha
Given AI is leading to massive competition in every obvious software opportunity, perhaps a good way to improve the odds of true venture returns in the portfolio is to index on âpotential for category creationâ much more than ever before.
This will require being open-minded to narrative violations, leaning in on products that look implausible/ hard to understand at this point, believing that future winners are unlikely to be simple extrapolations of the past, and having the courage to act on this belief.
However, one thing remains the same. The fundamental traits & qualities of a top-notch founder donât change across cycles.
So, rather than thematic or market-driven, perhaps a truly âfounder-firstâ venture investing style (backed by a humble admission that itâs hard to predict how markets will evolve over the next decade and which products are likely to eventually win) is better poised to do well.
Founder-first style + looking for category-creation plays = Alpha?
6/ Value-Add
What founders need help with the most is customer introsâŚ
BUTâŚfew investors can repeatably & scalably help with this.
ALTHOUGHâŚinvestors can introduce you to connected cliques who in turn, can potentially connect you to customers through a chain of intros.
THEREFOREâŚa major value add investors can bring to the table is connections to cliques that founders can then mine.
7/ Top 5 Learnings From A Decade Of Angel Investing
(1) Choose a âstrategyâ âĄď¸ many can work, focus where you have an edge.
(2) Take enough âshots-on-goalâ âĄď¸ adequate diversification/ portfolio size but watch out for âdi-worsificationâ.
(3) Respect âpower lawâ (few winners will account for the majority of the returns) âĄď¸ hence, Point (2) is important.
(4) âAccessâ is everything âĄď¸ watch out for adverse selection.
(5) Brace for long periods (10+ yrs) of illiquidity to let compounding kick in âĄď¸ Knowing âwhen to sellâ is going to be super-important, and unfortunately, it is an art rather than a science.
PS: for your own good, see this chart once daily đđ˝(Source: David Clark of VenCap).
One nuance though is that smaller pre-seed/seed firms can start returning DPI in phases through secondaries in growth rounds, while still holding on to a chunk for harvesting during the eventual main exit (IPO or M&A event).
âYour Fund size is your strategyâ holds truer than ever before.
9/ “Access” vs “Picking”
In a venture upcycle, âaccessâ becomes more important.
In a venture downcycle, âpickingâ becomes more important.
Currently, we are in the latter.
10/ Power Law
Venture Capital is all about “finding the best companies”, not just “doing deals”. The power law is so extreme that the latter almost guarantees failure.
11/ TAM Fallacy
Having very rigid views on TAM at seed stage is a classic VC fallacy. The best founders either create new markets or expand to adjacent markets over time. So the TAM keeps growing.
If a startup remains sub-scale, in most cases it tends to be due to founder motivation, quality of execution and team/culture issues, rather than available market.
At the seed stage, better aspects to evaluate include 1) founder-market fit and 2) competitive differentiation/ right to win (I call it ânon-incrementalityâ).
12/ LP Updates
In an undistorted venture market, valuation markups should always follow operating progress toward PMF. This order got reversed during ZIRP, where markups happened in anticipation of progress.
The right logical structure should ideally, also be reflected in LP update emails from VCs.
The primary section upfront should cover operating updates from the portfolio [revenue, ACVs, product releases, key logos, churn, patents, team additions, etc.].
This should be followed by a “financial” section, positioned as an enabler of the operating progress. This can cover follow-on rounds, mark-ups, runways, etc.
The last 2 years have shown that private valuation mark-ups are transitory anyway. Core operations are the real building blocks that stay and continue to compound across cycles.
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Chapter 3: Economy
1/ Top vs Bottom
With the S&P500 hitting ATHs post the election results, many are wondering if we are at the top.
Sharing my post from last year wherein I covered John Templeton’s framework of thinking about market cycles. As we stand today, it seems to be playing out perfectly. Stage 2 (“grow on skepticism”) seems to have ended and we seem to be at the beginning of Stage 3 (“mature on optimism”). This stage can last a few years, till we reach the “point of euphoria” (the last one being Nov 2021).
I follow the mental models of Charlie Munger and therefore, know that the future is unknowable and predictions have little value. However, I also follow Howard Marks and believe that it’s still useful to estimate where we are in the market cycle.
Enjoy Stage 3 of the cycle!
2/ Liquidity Cycles
The way the world works…
When you really need the capital, no one is ready to give it to you. And when you really don’t need it, they trip over each other to hand you the cheques.
This is the way liquidity cycles work.
Source: hard knocks from multiple cycles.
3/ Mean Reversion
Mean reversion is one of those laws thatâs so powerful and yet, is actively utilized as a mental model by only a few. One can see it in everything from stock multiples and startup valuations to BigTech headcount.
If understood and used well, itâs a really powerful tool for scenario analysis and being prepared for various eventualities.
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Chapter 4: Careers
1/ PMF Approach To Careers
My career arc started changing the moment I started trying to figure out:
1) What I am uniquely good at, relative to competition
2) What’s the best way to bring that unique value to the world
3) Who will pay me for it and how much
The key is to approach it like a PMF-finding process for a product, indexing more on “discovery” and “inputs”, as opposed to “outputs” like compensation, title, and career trajectory.
The key is to get the input strategy right, align your mindset, lifestyle, and family goals to it, and be patient enough to execute it for decades, taking feedback and iterating along the way.
As simple as that.
2/ Networking
Whether one likes it or not, networking (I prefer the words “relationship-building”) is a key skill to succeed at anything in the real world, particularly as a founder.
During Web 1.0 and 2.0, the Internet rewarded “volume” of content. But now with AI, anyone can churn volume.
So, what matters now? Hypothesis:
(1) Targeting sharply-defined niches
(2) Going deep into concepts
(3) Keeping a high bar on quality
(4) Sustaining adequate volume while doing #1-3
4/ Clarity
Speed is an outcome of Focus.
Focus is an outcome of Clarity.
Seek Clarity of Thinking.
5/ Make It Interesting
Even if you are writing what you believe is the most helpful (or technical) content on a topic, you still got to make it interesting for readers.
Helpful but boring content wonât work at scale.
6/ Getting On A Plane
Getting on a plane to meet people you are doing business with is an execution superpower that is accessible to everyone.
7/ Urgency
A sense of urgency is a superpower not just for founders but also investors. Unfortunately, while itâs a standard expectation from the former, I donât see much of it in the latter.
8/ Superpowers
The best career advice can essentially be distilled down into one sentence:
“Find your superpower and double down on it.”
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Chapter 5: Life
1/ Personal Burn
The person/business with the lowest burn usually ends up winning.
2/ Life Is A Marathon
Quick note to all youngsters out there:
Based on what I have seen across the world in my life so far, you should assume that achieving reasonable success at any endeavor in life will most likely require a decade of focused work on that craft.
Account for these timelines as you plan your career (& life).
3/ Immigrant Mindset
As immigrants, we have no choice but to be brutally driven and almost emotionless while making important life decisions.
The reason is that we and those around us have sacrificed way too much. We literally can’t afford this not working out.
4/ Courage
The real arbitrage in the world is âcourageâ.
Those with courage become owners.
Those without courage serve the owners and make them rich.
5/ Name Dropping
Life has taught me to instantly get my guard up when someone starts name-dropping in the first few mins of a conversation.
6/ Winning
Winning in the short term vs winning in the long term – two totally different things!
7/ Opportunities
As a founder/ employee/ investor, you will likely stumble upon only 2-3 truly asymmetric-upside opportunities in your lifetime. So when you know you have one, try your best to make it count.
Rest of the time is spent grinding towards creating a funnel that hopefully, someday, will get you to these 2-3 opportunities.
8/ Upper Middle Class
The upper-middle-class are the true suckers in an economy:
(1) High enough income to get royally taxed. Yet low enough to keep them on the treadmill.
(2) Not large enough economic outcomes so need to keep aspiring for downside protection for kids (eg Ivy League education). But just enough assets to be able to afford this protection (keep saving in 529 plans for 18 years).
(3) Just enough W2 to put a downpayment and get a mortgage on a âstretchâ house. Yet, slow income growth so keep paying the mortgage for 30 years.
A decade back, all Indian VCs were flipping their portfolio companies, especially those in the SaaS/ enterprise space, to the US (Inventus Law was a big beneficiary of this move).
Then, as YC doubled down on India, everyone stopped discussing this issue. Whether consumer or enterprise, if you went to YC, you did a Delaware C-Corp.
Now in the last few years, with Indian public markets ripping and showing a major appetite for IPOs (including SME/mid-sized ones), founders are getting blanket advice to domicile in India to take advantage of this market.
A few things to consider on this topic:
Even in the Valley, IPO outcomes are rare and outliers. Most exits happen via M&A. If you are playing the odds, this is an important idea to keep in mind as global acquirers are generally reticent to acquire Indian-domiciled companies, especially in software. This could change, and I hope this changes going forward, but this is the present state of things.
Indian public markets being gung-ho right now doesn’t guarantee how they will behave after 5-10 years or when you are ready to go public. Though, it’s reasonable to expect that macro secular tailwinds will continue over the next decade.
It makes sense for domestic consumer companies like Razorpay and Groww to re-domicile to India, given their business is domestic consumption-based and they are already late stage/ IPO ready.
Indian public market demand for domestic consumption themes might not necessarily translate to other areas/ sectors in the future. Would Indian markets have an appetite for your specific deep tech or enterprise business N years down the road? Something to think aboutâŚ
Right now, there seems to be more than enough INR/domestic capital demand for consumption-themed companies across the early->growth->late stage/pre-IPO spectrum of VC/PE. But is that the same case for enterprise and deep tech? Would these companies have a higher reliance on global growth capital in Series C and beyond rounds?
This is a highly nuanced topic and I am not a legal or tax expert. But what I will say is that like most things in business, your specific context as a startup is very important. And many of these calls are extremely hard and expensive to reverse later on.
So, while I can’t offer broad-based/ cookie-cutter answers on this topic, I would definitely encourage both Indian founders and VCs to avoid thinking in broad strokes on this matter, and partner with cross-functional experts to together explore the nuances of each case.
2/ India’s Seed VC Landscape in 2024
From what I am seeing in my deal flow over the last few months (and my focus is (1) enterprise software and (2) deep tech), I feel there is almost a dearth of quality, structured & consistent angel/pre-seed/seed capital in India right now.
From what Founders are telling me, almost all major Indian VC firms seem to be holding out & looking for late-seed/pre-Series A levels of traction even to start a real conversation. The proverbial $1Mn+ ARR, 2-3x y-o-y growthâŚ
Anecdotally, it looks like only previously successful repeat founders are mopping up large seed rounds from these firms at the idea/pre-product stage. Pre-seed/seed seems to be significantly tighter for first-time founders.
Genuine question for myself and many India-based enterprise & deep tech founders out there who are fundraising – who are the angels/ seed firms in India that are comfortable in CONSISTENTLY writing checks at the true early stages in enterprise software and deep tech (idea/pre-product/MVP/design partner/some usage stage)? And by consistent, I mean doing 10-12 deals per year.
3/ Indian Elections 2024
The 2024 Indian elections almost turned out to be another 2004 âIndia Shiningâ. Probably the delta this time was the personal charisma of the PM.
The Indian economy is already close to a tipping point so the current govt getting an opportunity to continue the work it started in 2014, for another 5 years is a good sign.
Finally, this election just goes to show that this economy is underpinned by a vibrant democracy that has all the checks-and-balances that the likes of China continue to struggle with.
To global investors – India will continue to lift millions out of poverty, put more disposable income in the pockets of its citizens, build world-class infrastructure and digital public goods, export innovation via its tech startups, and deliver growth that is sustainable for all stakeholders.
4/ Domestic Hardware
Wanted to throw out a challenge for Indian founders – in this next generation of the ecosystem, can we aim to build our own domestic smart EVs to compete with BYD and Xiaomi?
In the last cycle, I had a ringside view into how in smartphones, Indian companies like Micromax and Lava had massive dependence on Chinese OEMs and ultimately, ended up bowing out to OnePlus and Xiaomi.
Given the ambitious goals we are setting for the Indian economy, itâs time we invest towards controlling the hardware stack too. From what I am hearing about all the work already happening in semiconductors, automotive, space and manufacturing in general, this is totally doable if we have the courage.
I also believe that there is enough global capital available that is positive on India and will be ready to back this courage. Or perhaps our Indian conglomerates can also step in there with INR capital?
The role model here is how Sachin Bansal and Binny Bansal stood up to US and Chinese competition in eCommerce, ultimately ensuring a homegrown & enduring market leader Flipkart continues to thrive to this day.
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Chapter 7: Other People’s Ideas
1/ Network Density
As always, massive insight-per-sentence from Fred Wilson on how “density” matters a lot while building networks.
2/ ACV Expansion
The key to ACV expansion đđ˝
3/ Emerging Managers
For all emerging managers out there who are trying to understand the world of LPs:
This 10X Capital episode on How to Pick Top Decile Venture GPs is awesome. Albert Azout of Level Ventures candidly shares some amazing insights on how LPs evaluate emerging managers, what separates the best GPs from the rest, common pitching pitfalls etc.
4/ Talk Less
This is a very, very important and practical insight for fundraising, or any sales process for that matter. Thanks Hugh Geiger for putting this out there!
(1) “Doing more with less” by leveraging creative thinking.
(2) Moving fast with campaigns to keep up with the speed of culture vs getting caught up in analysis-paralysis and bureaucratic over-planning.
6/ Stay In The Game
If you are going to read one thing today, please read this (especially if you are a parent).
7/ An LP’s Perspective On VC
Nice convo between David Clark (VenCap) and Jason Calacanis. Was interesting to hear a top LPâs perspective on venture capital, manager performance and portfolio construction.
Across a sample of 12,000 companies that VenCap analyzed, only 1% were âfund returnersâ. Power law in venture is intense.
Venture is a game of finding outliers. The best managers arenât afraid of high loss ratios. In fact, loss ratios are surprisingly similar across various percentiles of funds. Even the best strike out a lot.
The best managers have the confidence to let their winners run. You might have 1 fund returning outcome in a portfolio of 50 companies so if you donât let it run, it is a bigger sin than not having invested in it at all.
Breakout private companies with real businesses tend to hold their value. But when these companies go public, VenCap has seen the stock going down by a lot in subsequent years in many cases.
In WeWork, the only people that won were Benchmark (exited pre-IPO with a $2Bn outcome) and Adam Neumann (via secondary sale).
In venture, less capital is more capital. If you get too big, you become more of a capital allocator than a venture investor.
Under-performing managers tend to put more capital into their under performing companies vs the winners. The opposite is true for the best performing managers.
PS: also check out this amazing X thread where David shared raw insights on power law in venture.
8/ Learnings From Scaling To 10Mn ARR! – via Bessemer Venture Partners
Attended an awesome US-India SaaS event organized by Bessemer Venture Partners in Redwood City. Key takeaways below:
Session 1 – Learnings from a decade of building Manychat
Mike Yan shared candid founder learnings from 8 years of building Manychat (a marketing platform for chat eg. IG DMs, WhatsApp etc.), wherein the company had to be completely reset during Covid before reaching tens of millions in revenue at present.
(1) The art of decision-making with limited data:
One of the key jobs of a founder in the 0-to-1 stage is to take strategic direction bets with very limited data. Eg. Manychat pivoted in a specific direction with only 40 beta customers by asking, “Are what these 40 customers doing representative of millions of other businesses?”.
Being able to develop the right judgment even with limited data comes down to how deeply the founder understands the market. To quote Mike – “your mental neural net has to get to the level where you can say with 80% confidence that this is going to work at scale”.
(2) In the initial stages of building products, it’s important to remember that data acts as a rear-view mirror into the past. It doesn’t necessarily show you the future.
(3) Value of focus:
To compete as a startup, it’s important to sharpen your product and business knife by saying no to a lot of markets, features, geographies etc. That’s how you get to a point where no one can compete with you in your sharp niche.
(4) Importance of Events for demand-gen:
Manychat has found holding flagship events to be very successful in demand-gen. The company works with influencers and paid marketing to drive maximum traffic and sign-ups for these events.
Events are also a good internal forcing function around new product launches, feature rollouts, fresh campaigns etc.
Interestingly, Manychat charges a small registration fee to ensure attendees are invested in the event. Also, all the content gets hosted on the event portal. They have found hundreds of people browsing through it daily many days after the event.
It’s important to note that events only work when a product has a basic resonance with the market.
(5) Key to differentiate in a crowded market:
To differentiate as a startup, it’s important to have a clear ICP and nail down messaging just for that ICP, and no one else.
One common mistake is talking about the technology more than the benefits to the ICP. Eg. while most of Manychat’s competitors were talking about how cool Facebook Messenger was when it was launched and where all they could integrate with it, Moneychat’s messaging focused on what its ICP (email marketers) could do with FB Messenger, how they could run a campaign on it and what outcomes they could drive from it.
Session 2 – Selling to large enterprises
Ashwin Ballal, ex-CIO of Medallia, shared the following insights on what founders should keep in mind while selling to large enterprises:
(1) For a customer CXO to take a startup seriously, you must solve a deep-seated personal problem for the exec. Else, it won’t be important enough to warrant their bandwidth.
(2) Every enterprise shouldn’t be a “customer” for your startup. It is important to be surgical and focus on an ICP.
(3) There are essentially only 2 high-priority problems that any customer is looking to solve – (1) growth and (2) cost optimization. A startup needs to hit the core of these problems. Everything else like productivity improvement is a nice-to-have.
(4) Given weak macros over the last 2 years, cost optimization has become so important that CEOs are mandating the CIO and CFO to work together and bring down costs by being willing to adopt cheaper software even with relatively inferior UX.
A new solution has to create a minimum of 25-30% cost savings to have a chance at displacing the incumbent solution.
Customers look at this potential cost-saving both in terms of being able to boost the bottom line or being able to use it for extra headcount to drive growth.
(5) Large enterprises are increasingly looking to adopt “bundled software” to reduce IT costs. They are also looking to transition from per-seat pricing models to consumption-based pricing. These elements are going against specialist incumbents which turn out to be significantly expensive.
(6) There has been a trend over the last decade where software buying decision-making shifted from the IT/ CIO org to functional teams. Now, with capital becoming scarcer and more expensive, cost reduction is back at the forefront, and therefore, CIO/ IT orgs. are again becoming important stakeholders.
Startups often make the mistake of not looping in the CIO org early on in the deal and not building relationships within that team. This often derails deals at late stages. In addition to functional champions, important to have a parallel champion within the CIO org too.
(7/) Nobody is doing AI in production at scale. Most projects are still POC stage so long way to go in the space.
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About the Author
I am Soumitra, a venture investor focused on the US-India corridor. I invest in Global Indian founders via my Fund Operators Studio.
I like to say that “I am a writer in the costume of a VC”. I write about Startups, Investing and Life on An Operator’s Blog. Also check out the AOB Podcast on YouTube.
While the venture industry thrives on standard pattern recognition, outlier outcomes often lie in narrative violations of these patterns. But how does one spot these diamonds hiding in plain sight?
As I was analyzing some patterns in the kind of deals I was seeing over the last few months, something stood out. Most deals that I see tend to fall into 3 buckets:
#1 Clear “No” – it’s clear that there is a lack of mutual fit. Easy to move on.
#2 Clear “Yes” – I want to thump the table and invest. The bar for this is high and therefore, deals in this bucket would be max. 1-2 per quarter.
#3 Not sure – I like a few things about the opportunity but also see major question marks in other areas.
Bucket #1 accounts for the majority of any VC’s deal flow. A typical investor will evaluate hundreds of deals in a year and will invest only in a handful. So the VC job description itself is to reject at scale and anyone in the industry either already has or goes on to develop the mental capacity to do this.
Bucket #2 is a dream for any VC as these deals inspire high internal conviction in a very organic way. Though this conviction may or may not align with what other investors think, still one feels great about doing such deals as strong VC investors tend to be independent thinkers and follow their internal compass. If this conviction also aligns with other high-quality investors, then even better! Examples of this Bucket that I have seen in my career include Lenskart, Delhivery, and (I would like to believe) a majority of the Operators Studio portfolio.
Bucket #3 is what I call the “Middle Zone” of venture deals. In these opportunities, there are some things to intensely like and also a few question marks to temper these positives. Some personas of the Middle Zone from my recent deal flow include:
Strong founder going after a bad market.
A talented founder but weak founder-market fit.
A market with massive tailwinds, but weak founder-market fit.
A pedigreed founder who has just stepped out of a Big Tech, only with an idea and zero traction.
A very young (therefore, generalist) founder, often <2 years out of undergrad, with a limited track record and/or traction to diligence on.
A startup that has been around for a while and is now raising a bridge.
While I am not really “feeling” the opportunity, someone who I rate highly/ who understands the space deeply/ has spent a lot of time with the founders, and has high conviction/skin in the game.
As a venture investor, I am spending a lot of time thinking through the best way to identify & evaluate these Middle Zone deals. While the venture industry thrives on standard pattern recognition (repeat founders, domain expert founders, young generalists, ex-Stanford founders, co-investing with Tier 1 VCs etc.), outlier outcomes often lie in narrative violations of these patterns.
As an example, in my post ‘Three unicorns and a VC‘, I wrote about how Amagi was an unpolished diamond hiding in plain sight that most venture firms missed. I don’t want to miss the next Amagi that comes to me!
As accomplished angel & now VC investor Ben Narasin once said on a podcast:
There are deals we should do, there are deals we shouldn’t do, and then there are the ones in the middle. We make all our money in the middle ones.
-Ben Narasin
The fact that Middle Zone deals are non-obvious makes them less competitive and therefore, inefficiently priced, lending them well to giant outcomes when the bet turns out to be right. Hence, every VC investor worth its salt needs to have some mental models and heuristics in place to deal with them.
Here are some high-level guiding principles I have learned and am using for Middle Zone deals (more detailed heuristics are my secret sauceđ):
Middle Zone Case
Approach
Strong founder going after a bad market.
Mike Maples of Floodgate says (paraphrasing) – “A strong founder will ultimately pivot to a good market”.
My investing style is founder-first. So, strong founders going after supposedly bad markets are fair game for me. Though I would definitely try and ask – “If this founder is strong, why has she chosen this market to begin with?”
Also, I don’t find spending time on market sizing at the seed stage to be particularly beneficial. For why I believe this, check out my post ‘The TAM Fallacy At Seed Stage‘.
A talented founder but a weak founder-market fit.
If a founder is strong but the founder-market-fit is weak, I try and answer the question – “Can this market be won by first-principles thinking and hustle?”.
Many areas in Consumer Internet and Enterprise Software lend themselves well to young generalists, while areas like hardware can be excruciatingly painful to execute on and require a founder persona who is prepared for it.
A market with massive tailwinds, but weak founder-market fit.
This one is tricky. A working POV is that a “hot” market will get crowded very quickly and therefore, a founder without a clear right-to-win in it will struggle to build a large, enduring business.
A pedigreed founder who has just stepped out of a Big Tech, only with an idea and zero traction.
This case needs all art. Every context will be different but as an approach, important to understand: (1) Backstory of identifying the problem statement and leaving a cushy job to start up.
(2) Personal life story – motivations, adversities, aspirations, chip-on-shoulder.
A very young (therefore, generalist) founder, often <2 years out of undergrad, with a limited track record and/or traction to diligence on.
Again, this stage is all art. I like to look at 3 things here: (1) Does the founder fit a few “spiky” personas I like to back? A few I have written about before include storyteller vs scrapper and engineering dhandho. I would also include the college builder/hacker in it. A catch-all I like to use for these personas is born-to-be-founder.
(2) Does the market they are going after lend itself well to young generalists?
(3) Has the founder been able to acquire some early users/ customers that I can speak with?
A startup that has been around for a while and is now raising a bridge.
While I am not really “getting” the opportunity, someone who I rate highly/ who understands the space deeply/ has spent a lot of time with the founders, has high conviction/ skin-in-the-game in the opportunity
While I am not really “feeling” the opportunity, someone who I rate highly/ who understands the space deeply/ has spent a lot of time with the founders, and has high conviction/skin in the game.
This will vary a lot by context but as I said in my post ‘An Investing Framework to Find Startup Diamonds‘, one way of sourcing high-signal-non-consensus opportunities is (quoting the post): “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”.
While evaluating these signals, especially when they are from other investors, I find it useful to ask: “Is this deal amongst this investor’s best ideas?“.
I know that’s a lot to digest so let me give you the TLDR of what all the above analysis is trying to say:
Given Power Law, the most important thing in venture capital is getting into the companies with monster outcomes. Only the hits matter.
Based on history, many of these monster outcomes looked like weird companies in the beginning. Hence, having a strategy to sift these out of the Middle Zone is what gives a VC the Midas touch, and what at least I aspire for.
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