Founders Lose 22% Equity Due to Multiple SAFE Caps
A founder raised 3 SAFEs at different valuation caps. $4M cap. $6M cap. $10M cap. When they got to Series A, they expected to own about 60% of their company. The actual number? 38%. They'd given away 22% more of their company than they thought — and they didn't find out until the cap table was modeled at conversion. This happens constantly. SAFEs feel simple. One short contract, no valuation negotiation, money in the bank fast. That's why Y Combinator created them in 2013.
Slow Growth Squeezes Early Investors; Prioritize Revenue From Seed
When startups don’t grow quickly enough, early investors are squeezed. Later rounds dilute all shareholders (investors, founders, employees), and this is especially painful when the round is flat or down. It's one reason we're so focused on revenue +...
Join Monastery Accelerator: $2M Funding for AI Unicorn
Go join Monastery accelerator with our friends @cyberfund $2m uncapped note, 12 week program, let's see if we can get the 1 person AI-assisted unicorn
Back Bold Founders; Crazy‑smart Often Looks Crazy
Can't agree more with Adam (yet again) As I always tell my team, "there is a very fine line between 'crazy smart' and 'crazy' and when we're writing a very early check we have to be willing to get this wrong...
Skip Costly SPVs; Invest in Anthropic Directly
people trying to get Anthropic exposure through 15-layer SPVs and 50% fees getting clapped when they could have kept investing simple like this guy https://t.co/W6M2amsQqw
Early‑stage Angels Win by Backing Frontier Founders
to be a good angel investor you need to spot great founders building on the frontier as early as possible and take the risk to back them before anyone else. high risk, high reward. by series A (esp these days)...
Weekend Fund IV Democratizes Venture Investing for All
Announcing Weekend Fund IV, backed by operators and founders (and maybe you). When we raised Weekend Fund III, we did something different. Toward the end of our raise, we announced the fund in public and accepted applications from LPs. Our goal was...
YC Seeks Fintech Innovators at NYC Live Pitch Event
YC is coming to NYC on May 21! Calling all fintech builders. We're hosting live interviews for the S26 batch. We're interested in tokenization, stablecoins, prediction markets, AI trading, and more. Come pitch us the future of finance. Apply at https://t.co/9hUZ0buEiU https://t.co/z1qZFOJIxj
Write Off Up to $100K When Small Startup Fails
A weird tax loophole with early stage startup investing that almost no one knows about: If you invest in a small startup that has raised less than 1M in funding And the business fails You can write off up to 50K (single) or...
USVC Opens Startup Investing to Everyone with $500
In 2026 you can buy any shitcoin you want. You can bet on Polymarket for how long Trump shakes someone's hand. All perfectly legal. But investing in a startup? Accreditation wall. Apparently retail investors can’t be trusted to invest in...
Fund's Fake “Alumni Priority” Window Is a Scam
I got a mass email from a fund that claims they invest in YC startups "during the Alumni priority investment window." In fact there is no such thing as an "Alumni priority investment window."
Term Sheet Mistakes Can Cost Founders Millions
Once you sign a term sheet, the deal is 90% done. Every clause inside that document is set in stone for the next 5 to 10 years of your company's life. I've negotiated 100s of these as a startup lawyer, and I've...
Ron Conway Shows Generosity Is Silicon Valley’s Winning Strategy
When future historians write about Silicon Valley, they’ll have an entire chapter dedicated to the Ron Conway way: how he turned generosity, warmth, and showing up for founders into a winning strategy.
Supabase Execs Invest After Dreambase Impresses Them
Exclusive: Supabase Execs Were So Impressed With Dreambase, They Became Investors In Its $3.7M Round https://t.co/77oCaZRoZe via @crunchbasenews
VCs Should Prioritize Growth over Early Cash Positivity
I was asked if startups must now get to cash flow positive after raising early stage VC. My take: No. VCs should not be interested in that. I want to invest in founders that consistently grow at least 15% MoM...