20VC Newsletter - 1st June 2025
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Jack Zhang, Co-Founder & CEO @ Airwallex:
Download the full transcript:
My 6 key takeaways:
The Best Angel Investment in History
When I was starting Airwallex I met with a girl called Lucy.
She decided to invest $1M for 20% of the company.
Today that investment is worth over $1BN today.
Matrix Pulled a Term Sheet and the $BN Mistake
Matrix signed a term sheet for $2M on $10M post and then pulled it.
I had already rejected every other VC except Gobi VC, who put the $2M round together.
Yuri Milner Did Not Ask Me Anything About the Business and Then Gave Me $100M
Yuri asked me a few questions about my personal life, how I grew up etc.
And then decided to invest $100M at $1.1BN valuation.
We agreed the terms in two hours.
100% YoY Growth for 8 Years and Revenue Scaling
We never grew below 100% YoY from 2015 to 2023.
We reached $500M ARR last August, $600M in November, then $700M in January.
We are still growing 90% YoY.
The $10BN Investment Meeting With Tencent
I waited for 3 months to meet with Tencent. It was the biggest meeting of my life.
Our invoicing product failed during the demo. I thought I was going to lose the deal.
Turns out James did not need much convincing: He knew cross-border payments was going to be a large market & convinced Pony to invest the day after.
I Did Not Have a Budget and Realised We Were Running Out of Money
I did not have financial discipline.
I was hiring as fast as possible.
At one point I realised we were going to run out of money.
Behind the Scenes:
Thursday’s episode with Rory O'Driscoll, GP @ Scale & Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 7 key takeaways:
1. OpenAI Spent $6bn on Jony Ive
This is the age old “Hardware Paranoia” felt by all big tech.
Meta’s VR Headset & Microsoft’s Surface Pro both failures, both driven by paranoia.
History says this will fail.
2. How to 3X a $700M Fund in This Market
Late-stage funds now rely on 100+ exits and push 20–30% of the fund into one breakout winner.
No 10xers. Just lots of 2–5x wins and one massive win.
They’re playing a different game now.
3. The IPO Market is Open. Deals are getting done.
The window is open and you don’t have to be doing $500m in ARR.
You need $200–$300M in revenue, rapid growth and a real margin.
4. Late Stage VCs Are Getting F***ed on Hinge Health
They raised at $6B. IPO’d at $2BN–3BN.
Preferred shareholders got stuck with non-interest-bearing blocks that don’t convert till $77/share.
The public market? Doesn’t care.
The lesson: You can’t block liquidity anymore. The market will move on.
5. Has YC Won?
They have a structural advantage.
The brand is a magnet for the best founders on the planet.
It’s not just a great fund, it’s a great business.
6. Elon Could Be Worth $500B Within 12 Months
If SpaceX gets revalued, if X raises again, if Tesla holds — Elon clears $500B.
No one else has the leverage.
Private markups don’t care about fundamentals — just the story.
7. VCs’ In NYC/California Are Taking a Big Hit
Trump's “Big Beautiful Bill” is looking very expensive for US VC’s.
State tax deduction gone. Pass-through workaround gone.
It’s effectively a 7% tax hike.
Friday’s episode with Kyle Norton, CRO @ Owner.com:
Download the full transcript:
My 6 key takeaways:
1. Early Stage Founder = Head of Sales
Outsourcing the sales process too early is suicide.
Founders must understand the customer problem firsthand.
Compress the distance to the frontline.
2. Inbound, Outbound, Partnership. You Need All Channels
We swung from 90% inbound to 70% outbound and back again.
Each channel ebbs and flows, the only way to win long-term is to build all them early.
Multi-channel is non-negotiable.
3. BDRs Only Get Paid on Closed Revenue
We don’t care about how many demo’s you book.
Everyone’s comped on what matters, real money in the bank.
Alignment is key.
4. Scorecards > Gut Feeling in Hiring
My hiring framework: DNA (mindset), Craft (skill), Knowledge (domain).
SMB = 70% DNA. Enterprise = 70% Knowledge.
Scorecards scale better than gut feeling and question marks.
5. Personal Brand on LinkedIn = The Most Efficient Recruitment Funnel
I’ve consistently posted on LinkedIn for 7 years, and now have 100,000+ impressions per post.
The first BDR hire came through LinkedIn, now 9 people have joined from the same company.
The compounding returns from content are massive.
6. We went from 3% to a 16% connect rate
How?
We built a proprietary lead engine with in-house tools
Got DataLane for mobile enrichment.
Now every BDR is booking 2 meetings a day, everyday.
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: Varun Mohan, Co-Founder & CEO @ Windsurf
Thursday episode: Jason Lemkin & Rory O'Driscoll
Friday episode: 20Growth
Thank you for reading 20VC.
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This just proves that the right capital and a good story can change everything. Keep grinding.
The episode with Kyle is a masterpiece! Thanks Harry.