Alessandro Chesser

ok - dropping big dates/news for a16z speedrun: - starting TODAY, founders can apply for the 2026 program that runs July 27 to Oct 11 in SF here's the link: speedrun007.a16z.com/ac - we will be investing up to $1M and funding 70+ companies over the next few weeks - But there's also $5M in credits/tokens/etc from AWS/GCP/Open AI/Azure/NVIDIA/Deel/Stripe/etc. You'll also work with our amazing operating team (GTM, talent, brand, people, and more), and join our community of elite founders - we offer a Global Founders Program for international founders, to help with visas, banking support, relo recommendations - yes you can be solo (but better if you're further along, and have built a team). No you don't have to have an idea yet. Yes you have to know how to build (even if you're not technical) - Also, in other news: speedun is officially moving full-time to SF. (prev it alternated SF/LA) this is for all the obv reasons - we've continued to have an insane lineup of speakers, including the founders of Carta / DoorDash / Twilio / Figma / Zynga / Airtable / Twitch / and of course, lunch/dinners with Marc/Ben alongside a16z team - and much more - the deadline for applying is May 17!

Big news for NY startups! QSBS is here to stay. From @politico: the idea now “seems to be moot” following strong, coordinated engagement from across the tech community—including a @TechNYC letter with 1,600+ founders, early employees, and investors. This is a clear example of what’s possible when the ecosystem shows up together. We’re grateful to everyone who spoke out and helped ensure policymakers understood what was at stake. New York remains the best place to build. 🗽

Former Tesla President @jonmcneill says Elon Musk kept employees motivated post-IPO by "starving the balance sheet": "Even after we were public, we operated Tesla on a quarter's worth of cash." "I kept saying to Elon, 'I would like a little breathing room.' He's like, 'No. We've got to think like we're young entrepreneurs: if you're two steps from death—you operate differently.'" "I was like, 'Man, we have a quarter's worth of cash, but we have 70 days of payables. That means we have less than three weeks of cash. This is tight.' But that kept everybody sharp." "The experience of working in a Musk company is—you are literally on the biggest challenge you've ever faced in your life, with the best people, and you're doing the best work of your life. That's what keeps most people engaged—it's not the balance in their bank account."

Ignoring QSBS is like walking past a suitcase filled with tax-free Lamborghinis because bending down to pick it up seems inconvenient. The recent (2025) One Big Beautiful Bill (OBBA) has made QSBS even better. QSBS isn’t complicated. Here’s the old Cheat Code: * Hold qualifying startup stock for five years, and pay zero taxes on your gains. This applies to founders, early employees, and investors. * The benefit used to max out at either $10 million or 10x your investment (whichever is higher). But QSBS just got a big upgrade under the Trump OBBA. 1. Faster Wins: Now, you don’t even need to wait five years for partial benefits. * Hold stock for 3 years, exclude 50% of your gains. * Hold for 4 years, exclude 75%. * Hold for 5+ years, keep 100% of your gains. It’s like frequent flyer status, but for escaping taxes. 2. Bigger Tax-Free Exits: The lifetime exclusion cap jumped from $10 million to $15 million. That’s an extra $5 million in your pocket instead of funding another DMV renovation. 3. Larger Companies Qualify: OBBA increased the eligibility limit from $50 million to $75 million in gross assets, meaning most Series A companies no longer have to cry themselves to sleep. 4. Inflation Adjustments: Caps now automatically increase with inflation every year. QSBS is the tax benefit that ages better than Paul Rudd. 5. 10x Rule Lives On: You can still exclude up to 10x your original investment every year, no matter how much above the cap you are.  (your spreadsheet just popped a champagne bottle.) Let’s say two founders, Jenny and Sean, each make $15 million after selling their companies. Sean ignored QSBS and walked away with just under $10 million after taxes. Jenny planned carefully, met the QSBS requirements and took home the entire $15 million. That $5 million difference is: enough to fund your next company, buy a massive house, and hire a full-time chef who only makes artisanal breakfast sandwiches with avocados from the remote Andes. Why donate that money to the government? Yet, many founders and investors don’t structure their companies to qualify for QSBS, either because they are unaware or think it’s too bureaucratic, like assembling IKEA furniture blindfolded. It isn’t. To qualify for QSBS, check these boxes: * Your company (or the one you invest in) must be a domestic C-corporation. * You must acquire stock directly from the company for cash, property, or services. (SAFE notes? The clock starts when they convert, not when you start bragging about them.) * The company's assets must be below $75 million at and immediately after issuance. * The company must actively engage in a qualified business (most tech startups qualify unless your startup is “Meditation for Lizards” or something super really weird). * You can't hedge your investment (no offsetting short positions). at @flexcapital , we ensure every founder and LP maximizes QSBS benefits. A 3x seed fund with QSBS significantly outperforms a 5x fund. (Yes, we’re flexing. It’s in the name.)

Big news for NY startups! QSBS is here to stay. From @politico: the idea now “seems to be moot” following strong, coordinated engagement from across the tech community—including a @TechNYC letter with 1,600+ founders, early employees, and investors. This is a clear example of what’s possible when the ecosystem shows up together. We’re grateful to everyone who spoke out and helped ensure policymakers understood what was at stake. New York remains the best place to build. 🗽