20VC Newsletter - 8th June 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Varun Mohan, Co-Founder & CEO @ Windsurf:
Download the full transcript:
My 7 key takeaways:
1. You Don’t Get an Award for Persisting With the Wrong Idea
If you don’t have a strong answer to the question “what is the reason we exist?”, you need to pivot.
We have pivoted three times.
We threw away real revenue to chase real product-market fit and it worked.
2. The Simple Test for a Great Idea? Even the S**t Version Feels Magic
The first Windsurf agent wasn’t good.
It hallucinated, broke GitHub, and forgot things.
But when it worked, it felt like the future.
3. Single-Person $1BN Companies Are BS
AI can amplify but it can’t replace coordination, leadership, execution.
The stack still needs a team.
4. Existential Dread Is Why Startups Beat Giants
Incumbents have time, startups don’t.
That pressure = speed.
Windsurf ships every 2 weeks. Big tech ship every 2 months.
That speed compounds quickly.
5. We Will End Up Fighting with Lovable and Bolt. The War is On.
We’re all attacking the same workflow from different angles.
Agents will be the battlefield. Infra and UX will decide who wins.
6. What Would Windsurf Do With Unlimited Resources?
We’d make far more bets, currently 50% of our bets fail.
Building technology for the future is expensive and painful.
One thing that works, pays for hundreds of failures.
7. What Windsurf Learned From Cursor: UI Matters
Cursor showed the dev world one thing:
If the UX is great, people will use it even if the backend is duct-taped together.
Hence, we rebuilt the whole stack: to own the interface and the infrastructure.
Thursday’s episode with Rory O'Driscoll, GP @ Scale & Jason Lemkin, Founder @ SaaStr & Sam Lessin, GP @ Slow Ventures:
Download the full transcript:
My 5 key takeaways:
Multi Stage Makes Life Harder for Everyone
“The existence of people with $10BN to spend makes it hard for people with $600M to spend it rationally.”
Two Core Elements to Do Seed Well
#1: You cannot sell the things that matter.
#2: Be honest with yourself if the thesis breaks.
You have to learn how to sell. Learning how to sell is just as important as learning how to buy.
It Is BS That if You Are Not in the Two to Three That Matter You Are Lighting Money on Fire
Insight made $400M for their investors on Hinge Health
20% of $400M is $80M.
People will still cash the check even if it is 3x: $80M is still real money.
AI Has Turned Cash Cows Into Cash Pits
The hyperscalers have turned cash-efficient businesses into CapEx hogs.
Microsoft, Amazon, Meta, Google have all increased their CapEx spend.
The investors don’t mind right now because their non-AI business cashflows have gone up as well.
Public Company Investors are Mean VCs on Steroids
One moment they’ll call the team in & say double the burn.
Six months later they’ll ask why are you spending so much money?
If the growth rate slows down on the hyperscalers we will likely see pressure to tone down the CapEx spend.
Friday’s episode with Matthew Pohlson, Co-Founder & CEO @ Omaze:
Download the full transcript:
My 6 key takeaways:
1. He Flatlined For 4 Minutes, and Came Back a Different Man.
Matt actually died. Like clinically.
for four and a half minutes.
Came back and the mission got real.
Not chasing success. Chasing impact.
2. The Truth Behind “Do Good and Do Well”
Omaze is not a non-profit.
It’s a machine built to raise millions for charity and make money.
Most people get this model wrong.
3. When the Charity CEO Told Him: “You Raised More Than Our Gala Ever Did.”
Traditional charity galas: 400 people in a ballroom.
Omaze: millions online and global access.
One campaign raised more than a decade of black-tie dinners.
Matt scaled philanthropy like a SaaS business.
4. When Ryan Reynolds Became Omaze’s Secret Weapon
They cold-DM’d Ryan Reynolds.
He replied. He did the video. It went viral.
It was one of the most successful campaigns ever.
5. We Went All In On Storytelling. It Changed Everything.
Forget landing pages.
Omaze focused on emotional arcs. Why the car? Why the house? Who are you helping?
Every campaign had a Pixar-level story structure.
6. The One Metric They Tracked Above All Else
Every Monday meeting started with a story.
It wasn’t the amount of revenue, it wasn't the number of entries.
Their north star metric wasn’t data, it was meaning.
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: Micha Kaufman, Founder & CEO @ Fiverr
Thursday episode: Jason Lemkin & Rory O'Driscoll
Friday episode: 20Growth
Thank you for reading 20VC.
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Too often the singers sing to the choir and don't hear the music