trading places

I Read the 308-Page SpaceX S-1 So You Don’t Have To

Aman read all 308 pages of the SpaceX S-1 so you don't have to. This week we break down every major number, surprise, and buried Easter egg in the filing — plus the biggest IPO week in recent memory across the AI holy trinity. SpaceX is pricing around June 12 and could open at a $2T+ valuation. We walk through all three business segments (Connectivity, Space, AI), the $28.5 trillion TAM claim, Elon's compensation plan that pays out $583B if he colonizes Mars, the unusual staggered lock-up structure, and the two breadcrumbs in the S-1 that suggest a SpaceX-Tesla merger could be coming. We also cover Anthropic's monster quarter ($10.9B in Q2 revenue, profitable, raising at $900B), OpenAI rushing to beat them to IPO after winning the Musk lawsuit, NVIDIA's $81B print growing 85% YoY, Mercury's $200M Series D at $5.2B, the US government taking equity stakes in quantum companies, and Nasdaq Private Markets suing Hiive over secondary market plumbing. A lot happened this week. 00:43 - [ tech news and vc ] 08:04 - Anthropic profitable, $900B looks cheap 🤯 13:38 - OpenAI rushes to IPO after courtroom win 🏃‍♂️‍➡️ 17:53 - NVIDIA $82B print $80B buyback 💰🫲 22:20 - Mercury $200M Series D @ $5.2B 🏦 25:35 - US Govt = Quantum VC ⚛️ 29:05 - NPM sues Hiive over 2ndry plumbing 🪠 30:58 - [ val corner: 308 page SpaceX S-1 ] 31:06 - SpaceX S-1 highlights 📸🔦 35:56 - $28T TAM includes Martians 🌎🌍🌏🌖✨ 37:00 - 3 core biz units: Connectivity, Space, AI 3️⃣ 47:05 - SpaceX-Tesla merger? 🤔 50:10 - board members revealed 👤 53:48 - unusual staggered lock-up period 🔐 1:01:00 - Dave sings a whole new Mars 🎶 [ links ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] Thank you for watching #spacexs1 #spacexipo #spacex #secondaries #venturecapital

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$900B Anthropic, SpaceX IPO Date, and the SPV Wild West w/ Clara Vydyanath | Trading Places Pod EP35

IPO season is here — and private markets are breaking at the seams. This week on Trading Places: Cerebras just had one of the best IPOs in years, pricing way above range and popping 68% on day one. SpaceX is targeting June 12th for its Nasdaq listing — and the prospectus drops next week. Anthropic raised $30B at a $900B valuation (up from ~$350B just three months ago) — and then told SPV operators to back off. And Anduril closed a $5B round at $61B, doubling its valuation in under a year. Then Dave and Aman sit down with Clara Vydyanath, a secondaries veteran who's spent eight years at Forge and Hiive, to break down what's actually happening in the SPV market — who's legit, who's a scammer, and what CFOs should be doing right now. Plus: retail VC part two, where Aman pits AngelList's USVC (Naval Ravikant + Ankur Nagpal) against Cathie Wood's Ark Ventures. One of them has a track record problem. Timestamps: cold open [ tech news and vc ] 00:53 - Warsh confirmed as new Fed chair 🪑 03:32 - Hormuz "you shall not pass" 🚢🧙‍♂️ 07:05 - Cerebras blockbuster IPO 📈 12:28 - SpaceX IPO date around June 12 🚀 15:56 - Anthropic raises $30B @ $900B valuation 💰 28:30 - Anduril closes $5B @ $61B 🛫 30:07 - [ intvw: Clara Vydyanath, 2ndry advisor ] What she learned at Hiive & Forge 🧠 33:52 - SPVs and Anthropic ✋ 39:43 - What will happen after IPO summer 🔮 44:20 - Wild West of 2ndries is only beginning 🤠 46:00 - CFOs tender offer playbook 📕 58:50 - [ val corner: retail VC part 2 ] Closed end funds: AngelList & Ark Invest 📝 1:00:33 - AngelList USVC portfolio breakdown 😇 1:02:35 - ARKK Ventures Ark Invest portfolio breakdown 🌈 1:05:10 - Portfolio strategy and fees faceoff 🥊 1:06:00 - Ankur Nagpal vs Cathie Wood 🤺 1:10:10 - second takes 😂 [ links ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ clara vydyanath = https://www.linkedin.com/in/clara-vydyanath-cfa-cpa-14287316/ | https://x.com/ClaraVydyanath ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] Thank you for watching #tradingplacespodcast #SpaceX #ClaraVydyanath #davemcclure #SpaceXIPO

Anthropic's $44B Revenue Run Rate, SpaceX's $75B IPO Problem, and the Retail VC Trap | Ep 34

Anthropic is now reportedly running at a $44B ARR pace, secondary markets are valuing it north of $1T, and demand is turning into full-scale FOMO. This week on Trading Places, Dave McClure and Aman Verjee break down: 00:00 — cold open 00:39 — [ tech and vc news ] 01:53 — Markets ATH during Iran war 💥 06:45 — SpaceX + Anthropic $4B deal 🤝 10:51 — New NASDAQ rules benefit SpaceX 🔔 15:21 — Anthropic raising $50B @ $900B, ARR accelerating 📈 18:20 — Sam and Elon courtroom drama 🍿 23:21 — Cerebras IPO 20x oversubscribed 🥊 25:14 — SaaS-pocalypse continues ⛈️📉 27:47 — [ valuation corner: retail VC part 1 ] Non-accredited investors want private stock 🙏 29:11 — Robinhood Ventures w/ Sarah Pinto & Vlad Tenev 1️⃣ 30:15 — Fundrise w/ Ben Miller 2️⃣ 33:00 — D/XYZ w/ Soheil Prasad 3️⃣ 36:39 — Which would Dave pick? 🤔 41:35 — [ VC secondary 101 w/ dave mcclure ] What is secondary? 🌈 43:03 — Size of the market 📈 44:53 — Why people buy/sell 🤷‍♂️ 47:41 — What are Secret Stallions 🐴 48:45 — Three deal strategies 🧠 [ links ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] Thank you for watching #tradingplacespodcast #secondary101 #vcsecondary #davemcclure #anthropicstock

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Anthropic at $900B, OpenAI Slipping | Sacra & Augment Power 20 Private Companies | Cohere Valuation | Ep 33

Anthropic is accelerating at a pace the tech world has never seen. In Episode 33 of Trading Places, Dave McClure, Aman Verjee, Marcelo Ballvé (Sacra), and Adam Crawley (Augment) break down the AI valuation frenzy, OpenAI’s growing pressure, hyperscaler spending, Cohere’s international AI strategy, and whether SpaceX’s trillion-dollar valuation has completely detached from fundamentals. Timestamps: [ tech and vc news ] 00:53 – Iran hits markets 💥 05:00 – Hyperscalers $700B AI CapEx 💸 12:31 – Anthropic raises $50B at $900B+ 🚀 13:51 – Musk vs Altman courthouse battle 🥊 18:22 – OpenAI eyes 2027 IPO 👀 21:35 – Cerebras IPO imminent 🏁 23:18 – Founders Fund $6B with 25% GP commit 😮 25:41 – Sierra raises $950M at $15.8B 🚀 29:16 – GameStop bids $56B for eBay 💰 31:39 – [ intvw: Marcelo Ballve @ SACRA + Adam Crawley @ Augment ] 33:16 – Why Anthropic beat OpenAI 🏆 35:35 – Defense tech crashes the top 20 🛡️ 41:06 – SpaceX at $2T — vibes or fundamentals? 🚀 47:35 – Most stretched valuation on the list 😬 54:51 – Retail VC fund trap 👎 1:02:24 – AGI in 18 months? 🤖 1:04:23 – [ valuation corner: Cohere @ $7B ] 1:05:40 – Canadian roots and team 🇨🇦 1:09:45 – Aleph Alpha German acquisition 🇩🇪 1:10:01 – The anti-US & anti-China play 🙅‍♂️ 1:13:08 – second takes 😂 [ links ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ adam crawley = https://www.linkedin.com/in/adam-crawley-b2146753/ | https://x.com/adamcrawley1 ] [ augment = https://augment.market/ ] [ marcelo ballvé = https://www.linkedin.com/in/marceloballve/ | https://x.com/ballve ] [ sacra = http://sacra.com/ ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] Thank you for watching **Please note: Inclusion in the Augment Power 20 does not predict future performance and should not be considered investment advice. For informational purposes only. Augment Markets, Inc. is a technology company offering software and data services with securities-related services offered through its wholly-owned but separately managed subsidiary Augment Capital, LLC, Member of FINRA/ SIPC. Read our full disclosure statement here. #tradingplacespodcast #sacra #augmentmarkets #davemcclure #cohere

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Anthropic Hits $1T, OpenAI Struggling, Elon Reloads with $60B Cursor Deal | Trading Places Podcast E32

Anthropic just crossed a $1 trillion valuation… and may have officially passed OpenAI. Meanwhile, Elon Musk is making moves—SpaceX is partnering with (and possibly acquiring) Cursor in a $60B deal, while OpenAI races to stay competitive with new releases like GPT-5.5 and Images 2.0. This week on Trading Places, Dave McClure and Aman Verjee break down one of the wildest weeks in AI, venture capital, and secondary markets: — The Fed shakeup and what it means for interest rates — Iran war tensions and global market implications — Anthropic’s meteoric rise past OpenAI — SpaceX’s massive AI bet with Cursor — OpenAI’s latest product push — AngelList opening venture capital to retail investors — The rise of prediction markets like Polymarket and Kalshi Plus: a deep dive into Cursor—the fastest-growing SaaS company ever—and why SpaceX wants it. 00:00 – cold open [ tech and vc news ] 01:22 – Warsh fed chair moves Up 🪑 03:52 – Iran war ends when 🤔 06:15 – Anthropic $1T valuation 💰 08:10 – Cursor & SpaceX engage 👰‍♀️ 14:21 – OpenAI launches GPT 5.5 + images 2.0 🚂 17:54 – AngelList launches USVC 💸 25:11 – Polymarket & Kalshi double down 🎲 29:25 – [ valuation corner: Cursor @ $50B ] what is Cursor 🤖 31:24 – CEO & MIT team 👥 33:12 – Why SpaceX wants Cursor & vice versa 💍💒 38:23 – early investors a16z + Thrive 🤑 39:56 – Sam Bankman-Fried almost won big 🙅‍♂️ [ spv: Equitybee ] 44:27 – why we invested in Equitybee 🐝 46:15 – how you can join the SPV 👍 46:53 – spinal cap debut 🎶 [ links: ] [ equitybee SPV invest = https://practicalvc.com/eb ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ aman verjee = https://www.linkedin.com/in/aman-verjee/ | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] #cursorspacex #spacexcursor #venturecapital #secondarymarkets #secondaries

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SpaceX, Saronic, and the New Era of Defense Tech Investing | Trading Places Podcast Ep31

Markets hit all-time highs in 11 trading days. Someone shorted oil 20 minutes before Trump spoke. SpaceX wants to raise $75B at a $2T valuation. And an autonomous naval defense startup just hit a $9.25B valuation — and almost no one's talking about it. Dave and Aman break down the biggest stories in venture and tech: the OpenAI executive exodus, why Stripe and Databricks still won't IPO, the continuation vehicle boom reshaping VC fund structures, and a deep valuation dive on Saronic — the defense tech company building autonomous warships for the US Navy. Timestamps: 00:00 — Cold open 00:36 — Tech & VC news 01:56 — OpenAI C-suite exodus 💨 05:52 — Markets ATH despite Iran War 🚀 11:56 — How to price the SpaceX IPO 🤔 19:53 — Cerebras IPO is greenlit 🟢 21:43 — VC top 15 mega raise 💰 25:48 — Iconiq: celebrity wealth advisor to the stars 📸 27:27 — Stripe, Databricks, Canva IPO mirage 👻 30:15 — Continuation vehicle boom 🚖 33:26 — Valuation Corner: Saronic @ $9.25B 🛳 41:44 — Second takes [ links: ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ aman verjee = https://www.linkedin.com/in/aman-verjee/ | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] #VentureCapital #SpaceXIPO #StartupValuation #TechInvesting #Saronic

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Anthropic Passes OpenAI ($30B ARR), SpaceX Lost $5B & How EquityBee Unlocks Employee Equity | Ep. 30

Trading Places is the only VC secondary podcast on the internet. Each week, Dave McClure and Aman Verjee break down the biggest stories in venture capital, tech, and private markets — with the insider perspective most shows don't have access to. This week's guest is Oren Barzilai, founder and CEO of EquityBee — the platform that funds startup employees' stock option exercises via forward contracts, giving them access to liquidity most never see. 00:00 — cold open 00:45 — [ tech and vc news ] 01:28 — Iran war vs. markets 💥 03:49 — OpenAI c-suite shakeup 🪇 05:29 — Anthropic $30B ARR goes BRRR 💸 10:48 — Claude Mythos mystery 🫆 13:47 — SpaceX financials leaked 🫗 16:13 — CoreWeave deal with Anthropic & Meta 🤝 18:17 — [ intvw: Oren Barzilai @ EquityBee ] 18:29 — What EquityBee does 🐝 21:08 — Who uses EquityBee 👤 31:02 — How much do people sell 💰 31:41 — Which secondary stock is most in demand 🫴 34:50 — Risks and rewards of stock options ⚠️🚀 42:21 — PVC + EquityBee partnership 🙌 49:08 — [ valuation corner: Whoop vs. Oura ] 49:14 — Whoop vs. Oura use cases 🏃‍♂️ 50:50 — Whoop ideal customer 💪 52:22 — Oura ideal customer 💍 54:57 — Whoop vs. Oura financials 🧐 57:22 — Who IPOs first? 🏁 [ links: ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ oren barzilai = https://www.linkedin.com/in/orenbarzilai/ | https://x.com/orenbarzilai ] [ aman verjee = https://www.linkedin.com/in/aman-verjee/ | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] #VentureCapital #DaveMcClure #AmanVerjee #equitybee #OrenBarzilai

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SpaceX $2T IPO ?!? 🚀 Shield AI = next Anduril 🛩️ Shri Bhashyam Sydecar grows to $4B SPVs | Ep29

SpaceX just filed its confidential IPO prospectus — and prediction markets say it will be June 3rd, Elon's birthday, during a rare 6-planet alignment. Anthropic is on a generational heater — Opus 4.6, Cowork, enterprise momentum — while OpenAI cuts Sora and kills the Disney deal trying to find focus. Prediction markets now say Anthropic IPOs first, 60/40 chance. In Episode 29 of Trading Places, Dave McClure and Aman Verjee reshuffle the Private Mag7 – Anthropic jumps, OpenAI slides. Shield AI breaks into the conversation after closing at a $12.7B valuationJeff Bezos announces a $100B AI manufacturing fund — and Dave says it's 100% getting raised, probably oversubscribed. The Meta/YouTube social media addiction verdict that spooked the entire tech sector.Plus a deep dive with Shri Bhashyam, COO of Sydecar, on how SPVs are becoming a permanent part of every investor's toolkit — and why layered SPVs aren't always the villain people think they are. Timestamps: 00:00 — cold open 00:49 — [ tech and vc news ] 00:49 — #7 of private Mag7 02:21 — Iran war end when 03:35 — Why June for SpaceX IPO 05:34 — First to go public: Anthropic or OpenAI 10:23 — Bezos seeks $100B 14:02 — Meta & YouTube found liable 19:12 — Ex-Kalshi launch 5cc 21:27 — [ intvw: Shri Bhashyam @ Sydecar] 21:52 — Forge ➡️ EquityZen 24:22 — SPV secondaries vs primaries 29:04 — Trajectory to $4B AUA 41:40 — SPV fee structure warning 51:05 — DEAL act to set privates free 54:50 — [ valuation corner: Shield AI @ $12.7B ] 55:59 — Shield AI marvel story 56:40 — What Shield AI does 57:41 — Anduril playbook 1:01:04 — Future of defense tech 1:02:02 — second takes [ links: ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ aman verjee = / aman-verjee | https://x.com/amanverjee ] [ dave mcclure = / davemcclure | https://x.com/davemcclure ] [ shri bhashyam = / davemcclure | https://x.com/ShriBhashyam ]

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Polymarket vs Kalshi ($20B), OpenAI vs Anthropic (IPO?), Tesla & SpaceX create Austin Terafab | Ep28

Dave and Aman break down a packed week in VC and tech — from macro headwinds threatening the IPO window to the big question of whether SpaceX and Tesla are quietly becoming one company.The Private Mag7 gets a full ranking debate: SpaceX is comfortably #1 at over a trillion, but Anduril's surprise $20B DoD contract has it punching into the top three. OpenAI just raised the biggest private round ever — so why is the CMO telling everyone to stop doing side quests?Valuation Corner goes deep on the prediction market arms race. Kalshi hit $260M revenue in 2025 and is now running at a $1.5B run rate. Polymarket is still early on monetization but sitting on massive on-chain activity. Both just crossed $20B valuations. Dave and Aman stack them up against DraftKings and FanDuel — and make their call.Plus: Kraken pulls its IPO, PayPal finally launches stablecoins in 70 countries, and a $55M prop bet on Cardi B turns into a legal mess.00:00 — cold open[ tech and vc news ] 0:33 — "you shall not pass" straits of hormuz ✋2:58 — private mag7 rankings 🏆6:04 — elon terafab in austin 🔋7:21 — Tesla x SpaceX super merger? 🤝10:26 — OpenAI abandons sidequests 🫳11:41 — who will take no. 7 🔔14:57 — Kraken freezes IPO plan 🥶16:25 — PayPal expands stablecoin 🌏[ valuation corner: prediction markets ] 18:07 — Kalshi vs. Polymarket 🥊20:15 — the incumbents: DraftKings & FanDuel 👴🏻27:42 — which is best bet? 💰28:40 — the tale of cardi b 💃30:45 — second takes[ links: ][ invest = https://practicalvc.com ][ trading places socials = www.linktr.ee/tradingplacespod ][ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ][ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ]#VentureCapital #DaveMcclure #AmanVerjee #TradingPlacesPodcast

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Nvidia $4.4T vs Cerebras $23B Val | Why Private Prices Are Wrong with Nick Fusco of PM Insights | Episode 27

Episode 27 of Trading Places asks a simple question: Are we pricing AI companies completely wrong? This week, Dave McClure and Aman Verjee are joined by Nick Fusco, founder of PM Insights, a private markets intelligence platform focused on tracking valuations, secondaries, and what assets are actually trading for beneath the surface. From Cerebras at $23B to Nvidia at $4.4T, the spread in valuations is massive — but the underlying dynamics are even more confusing. Meanwhile, Anthropic is adding $5B in ARR in a single month, robotics startups are raising at extreme multiples, and secondary markets are quietly revealing what assets are actually worth. So what’s real… and what’s mispriced? If you’re investing, building, or just trying to understand AI right now — this episode breaks down where the market might be getting it wrong. Timestamps: 00:00 — cold open 00:50 — [ tech & vc news ] 00:50 — Private Mag 7 + 3 Impostors 🧐 04:34 — Anthropic vs OpenAI 🥊 05:23 — Figure Robotics $39B val 🤪 08:00 — Iran: Straits of Hormuz vs. Price of Oil 🔮 15:00 — Oracle & Meta Layoffs 🚶‍♂️‍➡️ 19:43 — VC MAG 7 🏆 28:11 — Atoms: Travis is BACK 🤖 30:20 — Mind Robotics raises $500M 💰 31:17 — Replit $9B val 💸 33:16 — [ intvw: Nick Fusco, PM Insights ] From public to private markets 🙇‍♂️ 41:05 — Their competitive advantage 💪 42:40 — Databricks example 📝 49:58 — Down rounds and repricing 📉 1:02:43 — SpaceX IPO & Robinhood private stock 🤔 [ val corner: Cerebras @ $23B ] 1:04:17 — Cerebras vs NVIDIA 🤺 1:06:37 — 5x revenue in one year 📈 1:07:01 — S1 weakness 💣 1:12:05 — second takes [ links: ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ nick fusco = https://www.linkedin.com/in/nickfusco/ | ] [ PM insights = https://www.pminsights.com/ | https://x.com/P_M_Insights | https://www.linkedin.com/company/pm-insights/ ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] #VentureCapital #PrivateMarkets #SecondaryMarkets #TradingPlacesPodcast

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Iran Tanks IPOs | 2026 VC Outlook with PitchBook & CB Insights | ByteDance @ $550B | Ep26

Dave and Aman break down how the Iran conflict is rattling markets — and what oil futures backwardation is signaling about how long it lasts. Then: Anduril closes at a $60B valuation (a portfolio company for Dave and Aman — they got in at $14B), Palmer Luckey vs. Dario Amodei, Anthropic getting flagged as a supply chain risk by the Pentagon, Kraken connecting to the Fed, Robinhood's $RVI fund underwhelming at launch, and the secondary market hitting a record $226B in 2025. We bring in Emily Zheng (PitchBook) and Jason Saltzman (CB Insights) for a deep data dive: 53% of unicorns are worse off year-over-year, AI companies are raising multiple rounds within 12 months, and LP appetite isn't coming back fully in 2026. Plus their bold predictions for the year ahead. And in Val Corner: Aman goes solo to break down ByteDance at $550B — a full sum-of-parts across Douyin, TikTok International, and TikTok US. Was it a bargain at $330B last fall? Is $550B the right price now? Spoiler: China still controls the algorithm — and gets paid 20% of TikTok US revenue to prove it. 00:00 - cold open 00:53 - [ tech & vc news ] 01:04 - Augment Power 20 🏆 01:53 - Anduril $4B raise on $60B 🛸 03:00 - Palmer Luckey vs Dario Amodei 🤼‍♂️ 06:30 - Iran war shocks NASDAQ, oil, & IPO markets 💥🛢️ 11:28 - Can Cerebras IPO in 2026? 🤷‍♂️ 13:27 - Robinhood public VC fund $RVI launch 🏁 16:51 - Secondary deals hit $226B in 2025 🚀 20:17 - Decagon tender offer @ $4.5B 💰 25:09 - Kraken connects to Fed 🐙 27:46 - [ intvw: Emily Zheng & Jason Saltzman ] 28:23 - Emily gives Pitchbook 2025 recap 🙇🏻‍♀️ 31:36 - Jason gives CB Insights 2025 recap 🙇‍♂️ 35:50 - Emily gives Pitchbook 2026 predictions 🔮 57:53 - Jason gives CB Insights 2026 predictions 🔮 1:00:56 - [ val corner: ByteDance @ $550B ] 1:01:20 - Sum of Parts analysis 🧩 1:05:09 - What is TikTok US worth? 💃 1:09:33 - China still controls algorithm 🇨🇳 1:12:53 - second takes 😂 links: [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ emily zheng = https://www.linkedin.com/in/emzheng/ | https://x.com/EMZheng47 ] [ pitchbook = https://pitchbook.com/news/author/emily-zheng ] [ jason saltzman = https://www.linkedin.com/in/jason-salt/ | https://x.com/saltzman_jason ] [ CB insights = https://www.cbinsights.com/ ] [ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [ dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] #venturecapital #secondaries #secondarymarkets #tradingplacespod #davemcclure #amanverjee #pitchbook #cbinsights

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OpenAI $110B Raise, Stripe at $159B, and the Donor Money Tax Hack VCs Use | Trading Places Podcast E25

OpenAI just closed a historic $110B funding round — the largest private raise ever. At the same time: • Stripe surged to a $159B valuation • Anthropic is selling $6B of employee shares • The Pentagon reportedly blocked Anthropic from defense work • Sam Altman quickly picked up a DoD AI contract • ByteDance hit a $550B valuation • And Jack Dorsey laid off 4,000 employees citing AI productivity Welcome to Episode 25 of Trading Places, where Dave McClure and Aman Verjee break down the biggest stories in venture capital, AI, and private markets. In Valuation Corner, we analyze why Stripe now commands a $159B valuation — and whether PayPal could become an acquisition target. Then we’re joined by Daniel Blake (UI Charitable) to explain a powerful strategy many founders and investors overlook: How Donor-Advised Funds (DAFs) can turn illiquid startup equity, fund interests, or crypto into major tax deductions. If you’re a founder, VC, or startup employee sitting on paper wealth, this episode is worth watching. ___________________________________________________________ 00:00 - cold open 00:47 - [ tech & vc news ] 02:07 -⁠ ⁠OpenAI historic $110B raise 😲 06:14 - Anthropic $6B staff share sale 🕺 07:45 -⁠ ⁠Pentagon cancels Anthropic 🧨 11:08 -⁠ ⁠Sam Altman grabs DoD AI bag💥 14:26 -⁠ ⁠SaaSpocalypse update 📉 18:20 -⁠ ⁠Jack Dorsey lays off 4,000 🚶‍➡️ 21:37 -⁠ ⁠ByteDance @ $550B 💃 24:11 - ⁠Plaid tender offer @ $8B 🔒 25:49 -⁠ ⁠Robinhood $1B private fund 🤺 27:24 - [ val corner: Stripe @ $159B ] 29:58 -⁠ ⁠Competitive analysis 💪 32:40 -⁠ ⁠PayPal acquisition target 🎯 39:23 - [ intvw: Daniel Blake - UI Charitable ] 40:09 - introducing Daniel Blake and UI Charitable 👋 40:43 - the problem with selling privately held complex assets 🧐 42:39 - intro to Donor-Advised Funds 🤲 49:03 - DAFs for founders + employees 1️⃣ 52:10 - DAFs for investors 2️⃣ 1:01:54 - donate your crypto holdings 💛 1:03:43 - not all DAFs are created equal ≠ 1:05:07 - case studies 📖 1:10:20 - get in touch with UI Charitable 📞 1:10:43 - second takes ___________________________________________________________ [ links ] [ invest = https://practicalvc.com ] [ trading places socials = www.linktr.ee/tradingplacespod ] [ daniel blake = https://www.linkedin.com/in/drblake/ ] [ donor-advised fund info = https://www.uicharitable.org/ ] [aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ] [dave mcclure = https://www.linkedin.com/in/davemcclure | https://x.com/davemcclure ] *This content is for informational purposes only and should not be considered investment advice. #VentureCapital #OpenAI #Stripe #Startups #AI #PrivateMarkets #TechNews

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