20VC Newsletter - 18th May 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Immad Akhund, Founder & CEO @ Mercury:
Download the full transcript:
My 5 key takeaways:
Sequoia Did the Most Work of Any Fund
I’ve pitched over 20 funds for my series C.
Sequoia did the most diligence with customers & asked the best questions.
They do not take their position lightly.
Founders You Should Take the Highest Price
It is very hard as an entrepreneur not to chase the highest valuation.
We did our series B at 120x ARR back in 2021.
I would do it again.
Why Serial Entrepreneurs Are Better
Being an entrepreneur is irrational but being a serial entrepreneur is especially irrational.
They know how hard it’s going to be & they’re still willing to do it again.
They have a huge chip on their shoulder & something to prove.
Labour Replacement Revenue Is Total BS
AI companies are charging customers a third of their labor costs.
But there is very little moat & network effect against it.
Once you have 3-4 competitors in the same space the actual margins will get dramatically compressed.
Two Reasons Why Being Public Is Shit and Broken
Complexity: The costs are high & there are too many rules around being public.
Visibility: Passive index funds dominate, so sub-scale companies get no investor attention.
Thursday’s episode with Rory O'Driscoll, GP @ Scale & Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 6 key takeaways:
Is SBF the Best Investor of the Last 5 Years?
Early Anthropic. Early Cursor.
He picked 2 of the most important companies before the ChatGPT moment and nailed it.
Coatue’s New Fund Is Because Companies Do Not Want to Go Public
Founders want to stay private.
Going public sucks — scrutiny, slow cycles, no upside until you’re massive.
Coatue’s retail fund isn’t about “democratising venture,” it’s a workaround.
Rory’s take: “These companies should be public…Fidelity Growth Fund could do 'em at 70–50 bps instead of Coatue doing them.”
Individuals Should Not Invest in Venture Funds
The illiquidity is brutal.
Most people won’t see anything for several years & the stress is not worth it.
99% of people, including in tech, should only be in liquid investments.
Why the Big Funds Are Betting on Perplexity
Right to play the game: First with web search + LLMs, real users, real revenue growth
They’re a credible shot against OpenAI & Anthropic.
Even if they end up third, it is worth the downside.
The Weirdest Thing About OpenAI Is Its Org Chart
They have 2 non-technical CEOs running the #1 AI business.
Companies like these usually fail – the rate of change is so fast, non-technical CEOs just can’t understand it.
BUT OpenAI is breaking the rule & so far it’s working.
Microsoft’s 3% Layoff is Just the Start
A lot of execs quietly know they don’t need 80% of their staff.
Most teams are bloated, slow, and still playing by 2018 rules.
3% is not enough & the CEOs know it.
Friday’s episode with Yuhki Yamashita, CPO @ Figma:
Download the full transcript:
My 6 key takeaways:
How Dylan Got Designers to Care About Figma
He built a social graph of the most followed designers on Twitter.
He DMed them personally, collected feedback & got them excited about Figma.
Design Twitter influenced each other a lot & it worked.
How Many Developers Will Figma Have in 5 Years?
Most teams today have 8–10 engineers per pod, one PM & one designer.
That ratio will shrink – design, product, code will all converge.
Figma will do more with fewer engineers.
The Wrong Kind of Constraints Kill Products
Most teams build around legacy rules they never questioned.
That is a bad constraint & results in a subpar experience.
Being able to recognize those constraints is an important part of product thinking.
Are PMs the CEO of the Product?
Yuhki’s first manager told him: “You’re a glorified secretary.”
PMs are there to unblock their developers.
The best PMs aren’t running the room — they’re making the ‘why now’ existential.
Why Joy & Playfulness Matter More Than You Think
One of Figma’s cultural values is play – in the way they work & the product itself.
It’s the little details you’re excited to work on not because they had an OKR to fulfill.
The pride in the craftsmanship shows the human behind the product.
Why Waymo Is Already Such a Great Product
Their attention to detail & little cues is incredibly impressive.
Alerts you before a biker passes, warnings if you forget your bag…
They make an average ride one of the best experiences you’ve had.
Behind the Scenes:
Let us know what your big takeaways from this week’s shows were in the comments below!
Thank you for reading, and don’t miss the great guests we have next week:
Monday episode: Severin Hacker, Co-Founder & CTO @ Duolingo
Thursday episode: Jason Lemkin & Rory O'Driscoll
Friday episode: Luke Harries, Growth & Engineering @ ElevenLabs
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