Exit Learnings From the Airtable Acquisition

Airtable’s recent acquisition shows why seed investing still works, why seed VCs must know when returns are good enough to exit, and why smaller funds can benefit from exits of all sizes.

One of the venture darlings of the SaaS cycle, Airtable got acquired by BendingSpoons this week for $1.285B enterprise value and $2.25B equity value. As of June 2026, the company was reportedly doing ~$480M ARR but only growing ~20% YoY.

As an emerging manager at the pre-seed/seed stage, the most valuable insights I am taking away from the Airtable acquisition are around DPI and timing of exits:

1/ Even at a fairly low exit revenue multiple, Airtable seed investors like Caffeinated and Freestyle have reportedly generated anywhere from a 30-50x multiple on invested capital (~30-35% IRR) over an 11-year hold period.

While they might have been holding this position on their books at multiples of this due to the 2021 inflated growth round, on a standalone basis, this is still a solid seed exit, especially if the fund sizes were relatively small.

This should be a great proof point for both LPs and emerging managers that as long as you can do seed at the right valuations (which means you have to do non-consensus-and-right deals), even in a relatively sub-optimal exit outcome, investments can still move the needle massively, especially for smaller fund sizes.

As a corollary to this insight, I get extremely uncomfortable when I see post-YC demo day seed deals at $50-100M cap and some marquee researcher-led companies raising seed at $1-5B valuation.

As a smaller fund, if I am doing such deals, I better be right. Which is unlike, say, a General Catalyst or a16z, who can spray-and-pray without bothering about seed valuations, as they just need to catch a potential outlier in the fishing net and crowd in gobs of follow-on capital into it.

2/ Airtable had raised a Series F in 2021 at a ~$11B pre-money valuation. Based on what I saw in that era, large incoming investors like Coatue, Greenoaks etc. would have had significant appetite to buy out older investors in secondaries during that round.

As per Grok, Airtable’s seed round was at a ~$7.3M post-money valuation, and by Series F, seed investors had seen 80-90% dilution. Assuming 80% dilution and say a 20-30% discount on Series F primary, Airtable seed investors would have had the opportunity to sell secondary at a ~220-250x MOIC in 2021 (I’m sure a bunch of them did at least partial secondaries).

So, given changing macro conditions, driven by a major technology shift in this case, seed investors saw a theoretical MOIC compression by a factor of 5-8x.

A learning for me here is that as seed investors, once we have got a more than adequate risk-adjusted return, we should look to actively sell and pass on the baton to later-stage investors in the capital stack who are more suited to the current risk-reward dynamics. Especially if the seed position has been held for 5-7 years & beyond.

Based on my own experience, this requires a major emotional re-balance, and when things are going up, greed kicks in massively, and the brain finds it incredibly hard to play devil’s advocate and evaluate risks that are still inherent in the business.

Also, we as seed investors are emotional & optimistic by definition (or else, we wouldn’t back people with just an idea). For this personality type, keeping commitment and consistency bias at bay becomes even more difficult, especially when 3rd parties are finding your sh*t as sweet-smelling as you 🙂

There are a few ways emerging managers, especially solo GPs like me, can enforce exit discipline:

  • Establish a rules-based exit framework, and stick to it. It might lead to leaving money on the table in specific instances, but over a long time scale and across multiple deals, it will serve fund managers well in terms of risk management and exit discipline.
  • Lean on your Investment Committee, LPAC, or, in the case of solo GPs with smaller funds, a set of experienced GPs who can be your informal GP advisory board. Ask these folks to proactively play devil’s advocate, look at the deal on the table from the outside, call out your potential biases, and essentially help you evaluate the exit opportunity holistically.

3/ The Airtable seed MOICs further support why smaller funds find it so much easier to generate outsized index-beating returns.

For a sub-$10M fund, a 30-50x MOIC deal would likely return at least the fund in most cases. Whereas for a $50-100M fund, unless they concentrated enough capital into what turns out to be an eventual winner (something that is really hard to do in practice and requires insane judgment), it might only return 25-50% of the fund even with a winning exit.

Hence, I keep going back to this famous line from Mike Maples of Floodgate – “Your fund size is your strategy”.

Why AI Valuations Aren’t That Odd

AI is an exponential technology and therefore, the “winners” deserve significantly higher valuations. But few can access them. Therefore, the quest for non-consensus-and-right still stands.

I think all of us are still systematically underpricing the extent of value AI is going to unlock for both enterprises and individuals.

As with compounding, the human brain isn’t wired to grasp exponentials. And the outcomes AI will drive over the next few decades are honestly unfathomable in humanity’s current context.

If you operate with this premise, it makes sense why category-defining companies are being valued at trillions, compared to going public at $10-100B in the 2010s.

This dynamic should reflect across the startup financing stack, and the reason why early and growth investors today are paying up for the best companies.

As long as you can be more-right-than-wrong in underwriting these companies as category-winners, beyond a certain level of de-risking/ PMF, the entry valuation really doesn’t matter because the commensurate exit valuations have also gone up dramatically.

I think a16z was one of the earliest VCs to grasp this change and also have the mental plasticity and capital war chest to execute behind this philosophy.

What is unclear to me is: while the power law winners in both public and private markets will keep going up in value without any real ceiling, does the median venture exit outcome also similarly increase in value? Eg., does the $100-250M M&A/ secondary sale outcome from the 2010s become the $5-10B outcome in 2030?

‘Cos if that’s the case, then it makes complete sense why entry valuations in YC have gone up from $10M a decade back to $50M today. And all pre-seed and seed investors like us should willingly pay up for whatever we deem to be the “best” consensus companies in our deal flow.

Another point: for pre-seed & seed stage micro VCs like Operators Studio
, I expect secondary sales during growth rounds to constitute a large portion of our exit outcomes. I asked ChatGPT to analyze how Series C pre-money valuations in US startups have evolved over the last decade.

Interestingly, the median Series C pre-money valuation rose from approximately $75M in 2016 to $320M in 2025, a little over 4x. Here’s the annual trend:

So, it’s not illogical that seed valuations should be expected to go up by a similar factor during this time period, especially in an efficient venture market like the Bay Area.

It’s obvious now that accessing growth rounds in the very best companies is delivering early-stage-like venture returns in this market. However, the reality is that beyond a handful of top VCs, most of us fund managers neither have this access nor the fund size to do these types of deals.

For us emerging managers, the equation still stays the same – our best bet is to find non-consensus-and-right companies early enough.

It’s hard to find non-consensus teams in consensus fishing ponds like Stanford, ex-foundational model folks, repeat unicorn founders, and celebrity execs stepping out to startup.

We will need to look beyond these channels, back non-obvious people from non-pipeline backgrounds, perhaps fish outside the US.

PS: If you are curious about how to be non-consensus-and right, you might find these posts of mine interesting – A Talent Scout Mindset For VC, An Investing Framework to Find Startup Diamonds and Staying In The Ring Long Enough.

When To Sell? – Part 2

A pandemic unicorn, a 400x Indian compounder, and a public SaaS unwind.

At first glance, unrelated. But there’s a single thread connecting them that provides an answer to the eternal question: when should you sell?

Recently, I came across a podcast clip on X where a European seed investor was reminiscing on how she had written an angel check in Hopin (a hype-unicorn from the pandemic era), which got crazily marked-up from a ~$2.5M pre-seed valuation in 2019 to ~$7.6B Series D valuation in 2021, and she didn’t sell even while the founder took $200M off the table via secondary.

This reminded me of my “When To Sell” post from Sep 2023. I think this is a good time to do Part 2 of that and add some recent examples to this discussion.

Fractal Analytics

An Indian analytics company called Fractal Analytics, which was founded in 2000, recently went public in India. What is fascinating is that their first angel investor, Gullu Mirchandani (who had started Onida Electronics back in the early 80’s, and launched India’s first-ever color television), continues to hold his initial position more than 2 decades out, even though it has run up by more than 400x. Note: check out this excellent post by Rahul Mathur (DeVC) on this investment by Gullu.

Freshworks

Girish Mathrubootham, founder of iconic Indian cross-border SaaS company Freshworks, stepped down as the CEO in Sep 2025 and became a full-time AI VC.

With the recent rout of SaaS stocks and the market consensus being that these companies are going to face secular headwinds from AI going forward, in hindsight, the Freshworks founder stepping down was a leading signal that the SaaS story was decisively over.

While folks can make up many reasons behind his departure, the fact is that a founder who is barely 50 years old is voting for where he’d like to devote his energy, relative to the opportunity cost of all the things he can pursue. Note: I asked ChatGPT to do a quick analysis of all Freshworks stock sales done by Girish. He sold zero shares in 2022. But post the launch of ChatGPT, sold ~$39M of stock in 2023 and ~$49M in 2024.

Essentially, any public market investor who didn’t entirely exit their Freshworks holding when Girish stepped down needs to have their judgment severely questioned.

Map To The Founder

What is a common learning from these cases of Hopin, Fractal, and Freshworks? It’s a learning related to exits that all experienced GPs frequently cite:

Investors should map their exit to the founder. If the founder is selling, you should sell. If the founder is holding, you should lean towards holding.

Applying this framework to the above 3 cases:

1/ Assuming that the Hopin angel knew that the founder was selling (even if the exact amount was unknowable), she should have immediately sold at least some part of her holding.

2/ Fractal had 5 co-founders in the beginning. Three of them left in 2007. But even as of today, 2 original co-founders continue to hold fort in full-time operating roles – Srikanth Velamakanni as Group CEO and Pranay Agrawal as US CEO.

This is perhaps why Gullu didn’t sell over all these years – he astutely mapped his position to the founders, and as long as even a couple continued to believe in the business and were competent enough to run it, he continued to hold.

3/ In the case of Freshworks, every significant stock sale by the founder should have been a warning signal for public market investors to re-evaluate the business as well as the price relative to underlying business quality.

On the founder’s full exit in Sep 2025, astute investors should have mapped their strategy to how the founder is voting with his time and money, and completely exited their position.

So, the experienced venture GPs were actually right! Adding a simple mental model for the “when to sell?” decision for myself as a VC – map to what the founder is doing.