20VC Newsletter - 22nd June 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Larry Aschebrook, Founder & MP @ G Squared:
Download the full transcript:
My 7 key takeaways:
This Firm Made BNs on Spotify From a 22 Year Old Analyst
One of my first employees suggested buying some shares in Spotify.
We flew to Stockholm to get approved as shareholders & they asked if we could buy $150M worth of shares.
We said yes.
We didn’t have the money & only closed $125M on the fund.
Spotify Was 40% of the Fund...
We were buying up as many shares as possible.
We became a top 10 shareholder of Spotify: $380M.
It became a $1BN outcome for our LPs, but it was a very concentrated risk.
How We Made $800M on Coursera
We were the largest shareholders of Coursera through our strategy.
We owned 16% of Coursera when it went public.
We sold at $36/share and returned $800M to our LPs.
What I Learned From Being Sued by Theranos
We signed up for their secondary but something didn’t feel right.
We tore up the binding form. They threatened to sue & I personally settled for a few million dollars.
It was a bad process & bad outcome.
The Biggest Advice to Managers Raising Funds Today
Create a firm that is different.
The world does not need another fund.
You have to stand out.
Don’t Chase the MOIC, Chase F**king Cash Distributions
We made a 2x net over a five year period.
Cash returns, not shares.
We stopped distributing shares because LPs will blame you if they hold it.
The Whole Problem of Silicon Valley
People have lost focus on what they were hired to do.
They pay more attention to the lifestyle that comes with being a money manager.
At the end of the day it is all about the value you are creating for the people who have entrusted you with their money and making a difference for your underlying companies.
Behind the Scenes:
Thursday’s episode with Rory O'Driscoll, GP @ Scale & Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 5 key takeaways:
Scale Is a Dead Man Walking
The market is too dynamic.
They can manage $200M of its $800M revenue for 24 months.
There is no way they can recover from losing their founders.
Why Microsoft Has Leverage
They have leverage because it is not existential for them.
In situations of ambiguity, the person with the most leverage has the best chance to win.
Why Microsoft Will Decide When We Have AGI
AGI was an ambiguous term in their contract.
We will hit AGI when Microsoft & OpenAI litigate what AGI is.
Half a trillion dollars of value depends on that word.
What Chime’s IPO Pop Means for Public Markets
Investors were pretty Pavlovian because of ‘21-22 markets.
The narrative has changed in the last months.
They have effectively bribed the buying public to like IPOs again.
Can the "Old Guards" Still Compete
The old guard’s default playbook is to add AI on top of their existing platform.
The new guys have agents that work on any system of record.
The old guard’s right to win is in their existing customer base.
ServiceNow & Salesforce have big enterprise customers, but Dropbox does not.
Thursday’s episode with Cem Kansu, CPO @ Duolingo:
Download the full transcript:
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: Johannes Reck, Co-Founder & CEO @ GetYourGuide
Thursday episode: Jason Lemkin & Rory O'Driscoll
Friday episode: 20Sales
Thank you for reading 20VC.
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The world doesn’t need more of the same. It needs bold conviction wrapped in selfless execution.
Thanks for sharing your insights and reflections on fund success. 🎯