20VC Newsletter - 27th April 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Jason Wilk, CEO @ Dave:
Download the full transcript:
My 7 key takeaways:
How We Got Mark Cuban as Our First Investor and Why He Capped Our Salary
I had to try and convince him for a year to put money into our $300K seed round.
He capped my salary at $30K/year until we could get the company profitable.
Raising capital was different back then.
Why SPACs Are a Good Mechanism and Bad Companies Damaged Their Brand
You get to raise a guaranteed amount of capital at a set valuation.
In a traditional IPO, capital raised is uncertain and the process can take 9–12 months due to regulatory prep and compliance.
If it wasn’t for the lower quality companies, SPACs would be a more common way for good companies to go out.
Why Timing Fucked Us and the Savage Ride From $5BN to $50M
We went public in January 2022 & the market completely fell apart on April 20th.
All of our pipe investors from our IPO bailed before the lockup expired, our valuation dropped from $5BN to $50M.
Had we gone public 9 months earlier we would have raised more capital.
My Investors Fucked off When I Needed Them Most
When the market was uncertain I called some of my investors suggesting a private round.
Their response was, “Don’t worry, if the stock goes down we will buy more.”
They were out in a matter of weeks. I had no support in my stock & we were fucked.
Why Tesla Trades at a Premium Being Public vs Private
They have developed a cult following.
They have pushed the price above any sort of reasonable EBITDA multiple that they would be trading as a private company.
If they were private they would not be a $TN company.
Why Pref Stacks Make Acquisitions Impossible
Pref stacks kill their optionality.
There are a lot of small companies that would have been bought by now.
But because they raised a couple hundred million dollars of pref, it makes their inevitable outcome impossible.
Are pref stacks killing a huge amount of acquisitions today @fintechjunkie @howietl
The Most Successful Fund Strategy No One Has Done
If you had a VC fund that wrote blank checks into every successfully exited YC founder’s second company, you would have one of the most successful VC funds on the planet:
Jason Wilk: Founded AllScreen (acquired for $85M) before founding Dave
Eric Wu: Founded Movity (Acquired by Trulia) before founding Opendoor
Patrick & John Collision: Founded Auctomatic (Acquired for $5M) before founding Stripe.
Second-time founders are willing to take more risks once they have a bit of money in their pocket.
Thursday’s episode with Rory O'Driscoll, GP @ Scale & Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 6 key takeaways:
Why I Admire Sam Altman for Acquiring Windsurf
He saw 3 massive use cases for AI:
Direct chat: ✅
Coding: 🤔
Customer Success: TBD
OpenAI is moving down the to-do list – it may or may not work but not making a move is akin to losing.
How a Generation of VCs Are Ditching Their S**t Track Records
They are leaving the mega firms & starting their own funds.
Not only are they ditching their colleague’s track record, they are also ditching their own.
They will never be questioned about their mega fund return as long as the new fund works.
Are Endowments Fucked and What Does This Mean for Fundraising in the Next Few Years
The endowments are hurting right now.
They are typically one of the best funders of new designer funds but they may not do these deals anymore.
‘25-26 will be much harder to fundraise.
If I Was CFO of a Ivy League University This Is What I Would Do
My cash planning for this year will be dramatically different.
Bonds, index funds, accessible cash at a moment’s notice when 30-40% of my revenue could disappear.
If someone came in my office & said we need more illiquid assets, I would tell them to get out.
If You Are 100% Sure You Will Make 5X, Do It
You should do it irrespective of ownership or valuation.
It may not return the fund but you will not regret it.
I Have Never Understood the Positioning of an Investment Before Investing
I will do a lot of internet diligence.
But if you haven’t come out of that space it will take you at least 6 months to truly understand the market.
You cannot fully figure it out before you invest.
Friday’s episode with Mayur Gupta, CMO & Growth GM @ Kraken:
Download the full transcript:
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: Taavet Hinrikus, Partner @ Plural
Thursday episode: Jason Lemkin & Rory O'Driscoll + Guest
Friday episode: 20Sales Episode
Thank you for reading 20VC.
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