My Biggest Lesson on Reserves Four Funds In:
"My first three funds. I did do reserves and I did some great reserve investments.
I put 15% of my third fund into @owner@adamguild their series A.
So that was a good investment, but I realised the opportunity cost of that investment given where I come in, it could be 20 to 30 pre-seed investments and the value creation at the pre-seed is so high that I decided for my fourth fund, no reserves, just everything up front." @Joshuabrowder
What do you know now about reserves that you wish you had known when you started @chadbyers@NWischoff@honam@infoarbitrage@jasonlk?
Josh gave me a place to stay right after moving to SF and would ask if he could 50k more, every day as I would work my ass off even before my pre-seed round. One of the best investors on my cap table
https://t.co/0RzyWORvac
I am going to piss off so many friends by saying this but if I could invest in one emerging manager sub $50M fund, it would be @Joshuabrowder.
A few things you need to know about Josh:
- He makes the founders he invests in live in his spare room at the Four Seasons until they raise their seed
- He turned his $100K Thiel Fellowship grant into a $10M angel portfolio
- He was one of the first cheques into Micro1, Yuzu and many more
- When he found out his father had been taken by the Russians, he was playing poker… (legend!)
I have never had founder references like the ones I got on Josh. I spoke to 12 founders. He averaged 9.2/10 across all 12.
This is one of the best episodes we have done in a long time and my notes below:
1. Why I Believe Young Founders Make the Best Founders
Young founders have no safety net and no option but to win. Corporate engineers often default to hiring big teams, while young founders stay focused on building the product. Their grit is much higher. Without that level of dedication, most people quit at the first real obstacle.
2. How I Test Founder Commitment Before Investing
To filter out tourist founders, schedule a pitch meeting at 11:00 PM. Elite founders accept immediately. Mediocre ones push it out by weeks.
During the interview, ask rapid-fire questions. If they claim a specific revenue number, have them pull up their live Stripe account on the spot. Look for tactical customer acquisition goals, not vague partnership promises.
3. Why I Make Founders Live With Me After Investing
The best early investments come from deep day-one relationships. Living together creates a focused, one-person accelerator where founders get a three-week crash course and avoid years of mistakes.
The rule is simple: co-founders share one room near the Four Seasons and cannot check out until they raise an institutional seed round.
4. Why Pre-Seed Companies Fail
Startups usually fail for three reasons: they run out of money, they run out of hope, or the co-founders break up.
Money problems usually come from weak pitching, which is why founders should drop the deck and show the product live. To maintain hope, ignore Silicon Valley vanity signals and focus on customer progress. To avoid team blowups, handle mechanics like vesting early.
5. What Founders Need to Know About Signing With a VC
VCs will say almost anything to get you to sign on the spot. They reverse-engineer your desires and claim they know every customer you want to meet.
Impressionable founders fall for it, but the promised intros often never happen. Never sign in the room. Take the night to think clearly.
6. My Biggest Lesson on Reserve Investing
Holding back reserves for later rounds has a huge opportunity cost. The biggest value creation happens at pre-seed, so saving capital for a Series A follow-on can limit your upside.
Deploying upfront into 20 to 30 pre-seed companies can produce far better long-term returns. Go all-in early.
(links below)
This morning I sat down with @HarryStebbings for the spiciest podcast I have ever done. We are both 29, English entrepreneurs, who went global (me physically and him metaphorically, building the @twentyminutevc International Media Brand). Airing soon! Stay tuned!
Actor has raised a $4M seed round. I am excited to show a snapshot of what our deployed robot models can do in the real-world.
We're incredibly grateful to be supported by investors from Eniac Ventures, Hyperion Capital, Hummingbird VC, 2048 Ventures, Nova Fund, Vanderbilt Alumni, and many incredible angels.
If you are interested in deploying machines with us, contact me : )
I guess I'm a Thiel Fellow now?!
I'm building AI models at @AntifraudCo to catch fraudsters who defraud the American taxpayers. We're qui tam laws to sue the fraudsters directly, and keep 15-30% of the recovery.
Today, some fraudster's day got a bit worse... (also we're hiring!)
Today, Yuzu announces their $35M Series A led by General Catalyst; I couldn’t be more proud as a pre-pre seed investor.
I’ve known Russell Pekala for over 8 years. We worked together at DoNotPay and even lived together at the house in Palo Alto where Facebook was started, later immortalized in the movie “The Social Network.” When he told me he was starting a company with his Harvard classmates, Max Kauderer and Ryan Lee, writing their first $500k check was an easy decision. (It felt only right to invest the same amount in Yuzu as Thiel’s first check into Facebook, given the house we shared).
The team has exceeded every expectation. Congratulations @EryDayImRusslen, @maxkauderer and @up_to_nonsense; this is just the beginning!
I'm excited to announce Posh’s $37M Series B, led by @FirstMarkCap.
6 years ago, people told us a better events platform was a solved problem. 8m users and $350M in GMV later, we're just getting started.
For more on our vision and what's next: https://t.co/EQ9QuH0Peg
Legal judgement is one of the most important forms of human expertise. Proud to serve on the Board of Directors of micro1 and co-author this research on contextual evaluations for law, with my friends @aliansarinik and Isabel Yishu Yang.
I would also like to share our prior round which was never formally announced.
In late 2024, Bain Capital Ventures and A* led a $55M Series B into Whop. As part of this round, we also welcomed several new angel investors including Guillermo Rauch, Jawed Karim, The Motley Fool Ventures, Signal Fire and many others.
As always, we are very grateful for our earliest supporters Cory Levy, Justin Mateen, Justin Kan, Peter Thiel, Eric Cohen, Guillaume Pousaz, Josh Browder, The Chainsmokers, Insight Partners, and many others for believing in us when Whop was just a sneaker bot rental marketplace.
We are excited to announce that @tether, the largest stablecoin company in the world, is making a strategic investment of $200M into Whop, valuing us at $1.6B.
Our partnership with Tether marks a major step in building the world's largest internet market. Tether is committed to enabling everyone in the world to participate in the new internet economy. The way humans work and create value is changing fast. The world needs both an open internet market giving people a platform to conduct business, as well as a transparent payments network.
Tether and Whop together will work to bring a sustainable income to billions of people throughout the world. There is enormous opportunity when you combine Tether’s global scale and wallet technology with Whop’s community of next generation entrepreneurs.
My co-founders and I met as teenagers on the internet selling software. We first launched Whop as a way for us to sell our own software to people in Facebook and Discord forums. Prior to Whop, the place we found customers was different from the place we collected payments, different from the place we talked to customers, and there wasn’t a central place to “do business” on the internet.
In partnership with Tether, we will be scaling infrastructure in real-time for new business models as they emerge across the globe.
The job is just getting started.
🚀
Last night @AndreaShuyuWang and I spoke to the amazing AIEB club at Berkeley. So many amazing companies have come out of this club, including @greptile!
Human judgment is the bottleneck in AI. The world keeps changing, which is why human data is becoming a trillion dollar market with @micro1 at the frontier
https://t.co/6KXsKmC5ls
humans have been middleware between siloed applications for too long
@Adapt has already meaningfully accelerated us at Wander, very excited for the future of the product
Hosted 30 incredible students from the Princeton classes of 2026 to 2029 (and incredibly alums) at my house this evening for their twice a year “TigerTrek.”
Archie (@archiemckenzie_) and Katie (@katieruthmishra) have a tradition of cohosting these incredible future founders!
Nothing like epic investor updates on 1/1/26. First up is @owner:
👩🍳 One of the best companies I've ever invested in is @owner — AI for restaurants. A great example of AI Vertical B2B.
They dramatically accelerated in 2025:
• Growing almost ~3x YoY, accelerating towards $100M ARR.
• 83% of growth comes from their AI products.
• Truly S-tier team and jaw-dropping velocity.
The key is massive ROI from AI. Massive & nearly instant.
Great work on a great 2025, Team @Owner@AdamGuild@DeanBloembergen. Proud to have led the seed round at @SaaStrfund.
Proud to be the first investor in Jibran and the exceptional team at Haladir. As is standard, I hosted Jibran in my spare bedroom and convinced him to drop out of Carnegie Mellon.
When he was staying with me, he woke me up at 3am to tell me he had made a major breakthrough; he had exceeded the benchmark of a leading A.I. lab. It was worth waking up!
I was proud to introduce Haladir to @chadbyers, @AndreaShuyuWang, truly amazing investors. This is just the beginning for @jibranhutch, @josephtso914 and @quanmhuynh. Congratulations!!
Earlier this year, 24 year-old @aliniikk was running an AI recruiting startup. @micro1_ai pivoted into AI training, and in 8 months the company is now making $100 million a year, and fielding offers at a $2.5 billion valuation.
https://t.co/Us7BjiikG5