20VC Newsletter - 23rd March 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
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Monday’s episode with Yamini Rangan CEO @ HubSpot:
Download the full transcript:
My 7 key takeaways:
Wartime vs Peacetime CEOship
When you are in wartime, you are optimizing for speed of execution.
When you are in peacetime, you are optimized for getting a consensus around what you’re trying to do.
The best CEOs need to know how to do both.
Going Upmarket Is Not That Hard: Everyone Gets It Wrong
Don’t hire entirely new enterprise reps – This will break the culture.
You need to improve your product in increments until it is the perfect fit for the next segment.
You also need to uplevel your sales & support org simultaneously.
How HubSpot Competes With Salesforce and Why B2B Is Not Winner Take All**
All the B2B apps in HR, finance, recruiting, CRM all have multiple players.
We have a great go-to-market fit for 2-2000 person companies.
Salesforce has a great enterprise segment but our overlap is small.
Does AI Kill the Margin of SaaS Products
The model and inference costs have come down significantly since 2023.
They will likely continue to decline. There will be no margin degradation.
WTF Does HubSpot Do When SEO Dies?
We have looked at diversifying our content strategy even before the AI era.
We are expanding into podcasts & newsletters.
These get daily coverage which grows our distribution.
What the $30BN CEO of HubSpot Learns From Satya Nadella
Three things:
Foresight in making massive bets on cloud & AI.
How he used culture to pivot the company.
How he instilled this growth mindset & curiosity within a company that seems super siloed.
Is HubSpot No Longer Woke
We made a change from unlimited vacation times to flexible time off.
This was implemented during COVID where support was necessary.
Now we are refocusing the company in terms of customer outcomes.
Behind the scenes:
Wednesday’s episode with Peter Singlehurst Head of Private Companies @ Baillie Gifford:
Download the full transcript:
My 7 key takeaways:
How One of the World’s Biggest Investors Determines Value in an Investment
Our underwriting process is simple:
Growth: What is the growth opportunity in the next 5-10 years?
Determinants of Success: Product, competitive advantage, organizational culture – How will these change & evolve?
Financial: Can this be a high return on equity?
Losing 100s of Millions on Northvolt
We were too enamoured with the idea of energy sovereignty in Europe.
What we got wrong was the team’s ability to execute.
When we saw those signs we pulled back on additional capital.
There Are Good Mistakes and Bad Mistakes in Losing Money
Not all of our bad investments are necessarily mistakes.
Investing means predicting uncertain futures & sometimes the odds are against us.
Real mistakes happen when we miss clear signals or fail to weigh the risks correctly.
Why It Is Better to Be Private Than Go Public?
There are too many distractions being public.
Share misalignment, heavy reporting burdens, competitor visibility…
Companies have greater focus by remaining private for longer.
How Do Investors Get Liquidity When No One IPOs?
We are seeing more company-facilitated secondary rounds.
Stripe, Databricks, etc…
These will likely become the primary source of liquidity for investors.
Why ByteDance China Is Such a Good Business
TouTiao & Douyin are market leaders in online advertising in China.
They are #3 in e-commerce in China.
Shutting down TikTok won’t make any difference to ByteDance.
The Investment Case for Anduril
They’ve developed software-enabled products that solve hard technical hardware problems.
They operate in large markets that have not changed & have clear waters between them and the next competitor.
It is the same pattern we’ve seen in Tesla & SpaceX.
Behind the scenes:
Top comments from the show:
My gosh I could listen to Peter for hours. Harry this was one of your best chats, you two have such great chemistry. Would love to see Peter here at least two times a year! Thank you, best business podcast in the game! - @markom001 (YT)
One of the best interviews! Great guest and a lot of insights - @Plokhoj (YT)
Friday’s episode with Elias Torres, Founder & CEO @ Agency AI:
Download the full transcript:
My 5 key takeaways:
Does It Make You Happy to Sell Your Company for $1.2BN
It hurts the ego – there’s new management & suddenly you don’t matter in your own company anymore.
I spent the next 10 months finding myself.
How Cushy Culture Killed My Company
Drift was my biggest failure.
I wanted to build something great & sustainable.
If I wasn’t giving out candy bars & trophies I would have a public company by now.
What Do I Know That I Wish I Had Known When I Started
Things are not as hard as they seem.
We think everything is too hard & put so many roadblocks ourselves.
Why Incumbents Are So Slow
There are too many people who only care about promotions & work-life balance.
Nobody gets fired for saying no so they will not buy/build the right products.
They are swamped in approvals.
The Only Way Big Companies Can Survive
Do what Twitter did.
Drastically reduce the team, build great products, break all their pricing models.
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:
Andrew Feldman, Founder & CEO @ Cerebras
Antoine Martin, Co-Founder & CEO @ Amo
Julia Hoggett, CEO @ London Stock Exchange
Thank you for reading 20VC.
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