dolan.

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)