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.