trading places

Anthropic had a massive week. The company is targeting $30 trillion in potential revenue, roughly the size of US GDP. A federal judge also struck down the Trump administration's attempt to label Anthropic a "supply chain risk,” a major hurdle cleared ahead of its IPO. The company also locked in a $45B compute deal with Enscale. Its AI infrastructure spending now tops $150B.

Nvidia had a big week too. The company posted a blowout $96B Q2 and purchased Hugging Face for $13B. Dave and Aman break down why Nvidia has shifted strategy. It's now fortifying the entire open-source AI ecosystem so no single LLM provider gets too much leverage.

Additionally: New details on that recent OpenAI hack of Hugging Face. Chinese open-weight models keep gaining user share. Meta settles a landmark $17B social-media addiction lawsuit - its implication for the industry going forward. Dave and Aman also break down Elon’s latest move.

Plus: a wide-ranging interview with Hoxton Ventures' Hussein Kanji on building a European venture firm from scratch, and a Valuation Corner deep-dive on Neoclouds.

[ links ]

[ invest =https://practicalvc.com ]

[ hussein kanji =⁠ ⁠⁠https://www.linkedin.com/in/hkanji⁠ |⁠ ⁠⁠https://x.com/hkanji⁠ ]

[ 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!

#husseinkanji #amanverjee #VentureCapital #PrivateMarkets #davemcclure

This week on Trading Places, Dave McClure and Aman Verjee break down Nvidia's expanding AI ecosystem, a billion-dollar stake plus exclusive licensing with Poolside, an investment in data supplier Mercor at $20B, and a bet on Perplexity as it raises at $30B. Plus: OpenAI's CFO signals a 2027 IPO, Chinese open-weight models overtake closed models in usage, the Cursor and OpenRouter deals officially close, investors cash out big while Sam Bankman Fried sits out his winnings in jail, fresh mega-rounds for Lovable, Higgsfield, and Lambda, PitchBook's Emily Zheng on the secondary market, and Aman's valuation corner on sports-franchise economics after the Lakers sold for a record $12.5B.

Timestamps:

00:00 - cold open

01:06 - [ tech and vc news ]

Aman plays the US Open and book launch 🎾

03:15 - Nvidia moves $19B on their open AI ecosystem 💰

09:08 - leaked timeline for OpenAI IPO ⏲️

10:45 - the Anthropic vs. OpenAI horserace 🐎

18:50 - open weight AI models usage is growing 📈

22:43 - investors cash out big on SpaceX-Cursor acquisition 🤑

25:00 - SBF sat out his big win in jail 🔐

26:45 - OpenRouter acquired by Stripe 🧾

30:11 - Lovable at $13B 💪

30:30 - Higgsfield raises at $5B 🚀

33:53 - Lebron bonds 🏀

37:01 - [ intvw: Emily Zheng, PitchBook ]

the state of the VC secondary market 🤔

39:45 - the next top-10 VC secondary startups 🏪

43:40 - the top sectors in Q2 2026 🎩

45:02 - potential trouble in the SPV market 😟

52:10 - the future of tender offers👂

57:45 - 2027 predictions 🗓

59:51 - the changing nature of the IPO 🔃

1:03:02 - [ valuation corner: Lakers sell for $12.5B ]

Lakers sale price breaks NBA record 🏅

1:04:30 - tax benefit to owning a sports franchise 📑

1:06:30 - breaking down the most valuable sports teams 🏟

1:09:11 - how different leagues manage revenue ⚾️

1:12:17 - why the Cowboys are the most valuable team in sports 🏈

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ emily zheng = https://www.linkedin.com/in/emzheng/ | https://x.com/EMZheng47 ]

[ 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 ]

Disclaimer: This is not investment advice. We may hold positions in companies discussed. Do your own research.

#Nvidia #AI #VentureCapital #Perplexity #PrivateMarkets

This week on Trading Places, Dave McClure and Aman Verjee break down the Anthropic roadshow numbers and leaked internal forecasts, Nvidia securing a $500B financing coalition of six Wall Street giants, and the SpaceX $60B acquisition of Cursor.

Plus: the Canva growth slowdown rattles its IPO case, Databricks becomes a top-5 private company at $190B, and Aman celebrates the NYC launch of his new book, A Brief History of Financial Bubbles.

00:00 – cold open

00:45 – [ tech and vc news ]

00:56 – Aman’s “History of Financial Bubbles” book launch 📖

01:20 – are we in a bubble right now? 🫧

02:00 – Anthropic IPO in Sept/Oct? ⏳️

05:30 – ⁠⁠Nvidia mobilizes $500B with 6 Finance Giants 🏢

11:22 – AI race: Anthropic is Secretariat, OpenAI is Twice a Prince 🏇

12:06 – potential timeline for OpenAI IPO 🤷‍♂️

14:22 – SpaceX acquires Cursor for $60B 🤑

16:11 – Canva growth rates slow down, valuation cut 😢

20:55 – Stripe acquires OpenRouter for $7B 💳

22:41 – Silver Lake takes Workday private 🔐

24:26 – Databricks valued at $190B 💰

26:17 – Kalshi and Cognition raise at $40B valuation each 🏅

29:02 – [ valuation corner: Hadrian @ $8B ]

33:00 – solving long-standing problems in weapons manufacturing 🏹

33:28 – can set up new production lines in months, not years 🏭

35:00 – signed massive contract with US Navy 🚢

[ 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 ]

Disclaimer: This is not investment advice. We may hold positions in companies discussed. Do your own research.

#Anthropic #IPO #VentureCapital #DefenseTech #PrivateMarkets

Is Bending Spoons really worth nearly $30 billion?

This week on Trading Places, Dave McClure and Aman Verjee break down the Italian software roll-up after its $2.25B acquisition of Airtable — and ask whether buying challenged SaaS companies at 3–4x revenue can justify Bending Spoons trading around 10x revenue.

Timestamps:

00:39 - [ tech and vc news ]

02:00 - historic Q2 earnings💲

05:18 - SpaceX stock rises 📈

09:53 - ⁠Elon scores AI wins after Grok 'miss' 💪

11:44 - Nvidia partners with Elon 💽

15:55 - Elon is planning the largest building in the world 🏢

18:10 - SpaceX buys Cursor 🚀

19:47 - OpenAI slashes prices  🔖

22:34 - Pitchbook Q2 report on VC Secondary Market 🛍

29:54 - Zach Dell starts energy company: Base Power @$13B🔌

30:38 - defense-tech startup Hadrian on the rise @8B 🪖

31:06 - AI power crunch fuels Valar Atomics @$6B ⚛️

34:45 - Palmer Luckey joins Elon, Bezos and Dorsey 🏦

37:57 - Bending Spoons buys Airtable 💰

42:14 - the SaaSpocalypse is real 🧟‍♂️

47:25 - [ valuation corner: Bending Spoons, Luca Ferrari ]

49:09 - unconventional background of Milan-based founder Luca Ferrari 🇮🇹

50:03 - buying up famous internet names 🏚

50:38 - determining if their current value is justified 🤔

52:26 - recent acquisition of Airtable 💨

54:14 - why the Bending Spoons business model makes sense 👍

57:35 - 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 ]

Disclaimer: This is not investment advice. We may hold positions in companies discussed. Do your own research.

Is Helsing becoming Europe’s answer to Anduril?

In this episode of Trading Places, Dave McClure and Aman Verjee break down the German defense technology company’s new $18 billion valuation, its AI-powered autonomous systems, its battlefield testing in Ukraine, and the growing pressure on Europe to build its own defense capabilities.

Aman compares Helsing’s software-first model with Anduril’s vertically integrated hardware-and-software approach—and explains why Helsing’s limited access to the U.S. defense market may be the biggest factor determining whether its valuation is justified.

Dave also sits down with Kelly Rodriques, CEO of Forge Global, now part of Charles Schwab, to discuss the rapidly expanding private secondary market.

00:00 – cold open

00:47 – [ tech and vc news ]

02:41 – The Fed votes to hold rates steady 🏦

07:20 – Q2 Earnings Week: how big tech did last quarter 📈

09:22 – how big tech makes their money - diagramed 📊

12:08 – Situational Awareness - Aschenbrenner loses his shirt 😢

16:11 – the highly volatile Korean stock market 🇰🇷

18:14 – SpaceX shares unlock August 6 🚀

22:14 – Anthropic and OpenAI models hack into systems of other companies 🚨

25:37 – Big Tech employee tender offers 🧾

29:44 – Uber founder's new company and jet ski commute 🚤

32:51 – [ intvw: Kelly Rodrigues, Forge Global ]

33:19 – his journey into private markets 👔

35:57 – why companies stay private longer now 🔐

37:00 – the new secondary market "middle world"🏬

40:20 – the Forge customer type 🙋‍♂️

46:30 – how to buy private companies on Forge 💳

49:00 – why Charles Schwab bought them out💲

57:04 – what SpaceX IPO can teach AI giants 🛰️

1:05:15 – predictions for markets in coming year 🕔

1:06:58 – [ valuation corner: Helsing @ $18B ]

1:07:12 – the Munich-based company raised $1.8B 🇪🇺

1:07:45 – inspired by Clausewitz 🪖

1:11:45 – how military budgets are changing 💶

1:12:32 – how Helsing compares to Anduril and Saronic 🚁

Trading Places is the world’s worst podcast about VC secondaries, private markets and high-growth technology companies.

Subscribe for weekly coverage of private-company valuations, tender offers, secondary transactions, IPOs and venture capital liquidity.[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ][ kelly rodriques = https://www.linkedin.com/in/kelly-rodriques-9b49418 | https://x.com/frgeglobal ]

[ 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 ]

Disclaimer: This is not investment advice. We may hold positions in companies discussed. Do your own research.

#Helsing #DefenseTech #VentureCapital #PrivateMarkets #Anduril #SpaceX #ForgeGlobal

SpaceX just reported earnings for the first time since going public — and the numbers were a rollercoaster.

Revenue beat estimates by a mile (+92% YoY), EBITDA came in strong, and every business segment posted growth. So why did the stock give up its gains and drop 8% after hours?

In this special breakdown, Dave and Aman dig into:

0:27 SpaceX first earnings report 🚀

5:45 how SpaceX makes money 💸

6:38 the importance of EBITDA 📖

8:04 detailing SpaceX revenue 📈

12:55 bull and bear case for SpaceX stock 🐂

17:13 chances of a SpaceX-Tesla merger 🤝

23:40 Dave’s 60th birthday 🎂

This is a special one-off episode — full episode with our regular format comes out tomorrow. Thanks for tuning in!

[ 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 ]

Disclaimer: This is not investment advice. We may hold positions in companies discussed. Do your own research.

Dave McClure and Aman Verjee break down why venture capital is pouring into autonomous defense companies, how Anduril, Shield AI, Saronic and a new generation of startups are challenging the traditional defense primes, and why expanding military budgets outside the United States could create an enormous new market.

They also discuss the growing threat Chinese open-weight AI models pose to OpenAI and Anthropic, including Kimi K3’s near-frontier performance at a fraction of the apparent cost. Could cheaper open models force the leading American AI labs to compete harder—or will Washington restrict access?

00:45 - [ tech and vc news ]

01:51 - the Iran war: will it ever end? 🛢️

03:15 - Google: first negative cash-flow quarter ever 😢

09:55 - SpaceX continues to fall 📉

12:21 - Chinese open-source AI vs. American AI 🤼‍♂️

16:47 - When will Anthropic go public? 📊

22:32 - most recent Chinese IPOs 🇨🇳

26:17 - massive valuation for Databricks 🤑

27:06 - Where is the IPO market headed? 🧾

31:57 - [ valuation corner: defense tech on the rise ]

32:03 - Anduril seeking $100B valuation 🛩

33:53 - why defense tech is soaring 🚀

35:37 - military-tech leaders: the new generation 🪖

38:04 - how military budgets are changing 🗃

47:49 - 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 ]

Thank you for watching!

#Anduril #saronic #shieldai #defensetech #venturecapital

The AI arms race just got a lot more interesting. Moonshot's Kimi K3 is topping leaderboards ahead of proprietary US models, DeepSeek is raising at a $71B valuation ahead of its own IPO, and Anthropic is quietly lining up bankers for a Q4 listing that could value the company at $2-3 trillion.

Meanwhile SpaceX has broken its IPO price, Stripe just made a $53B run at PayPal, and European defense tech is heating up with Helsing's $18B raise.

Then Adam Crawley (Augment) and Marcelo Ballvé (Sacra) join to break down the new Augment Power 20 — how the rankings are built, who's moving up (hello Neuralink and Crusoe), and their bold predictions for Q3.

We close out with a Valuation Corner deep dive on Crusoe, the neo-cloud infrastructure company reportedly raising at a $30B valuation, and where it fits into the broader AI stack.

0:00 - cold open

00:53 - [ tech and vc news ]

2:00 - post-IPO SpaceX: big flop? 📉

5:39 - Anthropic races to Q4 IPO 💰

7:26 - Chinese AI vs. US models 🇨🇳🇺🇸

14:26 - DeepSeek raises $1.5B @ $71B 🤖

16:15 - Stripe bids $53B for PayPal, not enough? 💸

22:49 - the European Anduril: Helsing 🛩️

24:46 - [ intvw: adam crawley @augment & marcelo ballvé @sacra ]

27:24 - how Power 20 rankings are calculated 💡

33:02 - most active 💪 Power 20 companies Q2 '26

40:08 - largest risers 📈 in price gains

42:15 - bold predictions for Q3 🔮

54:37 - [ valuation corner: crusoe @ $30B ]

55:03 - rapid revenue growth 🚀

58:29 - the AI "stack" breakdown 🍰

1:01:11 - pick-and-shovel play ⛏️🪏

1:05:07 - 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 #secondarymarket

Welcome back to Trading Places, the weekly show covering the biggest stories in venture capital, private markets, AI, IPOs, and secondaries.

This week, Jeff Bezos and Blue Origin make headlines with a $10B raise at a $130B valuation, igniting the next chapter in the battle with Elon Musk and SpaceX. We also break down OpenAI’s new multi-model strategy, the growing threat from open-weight AI models, Meta’s move into hyperscale cloud computing, Kalshi’s explosive valuation, and much more.

Then we’re joined by Shawn Bercuson, Founder & CEO of Earlyasset Capital, for an in-depth conversation about the future of venture secondaries, liquidity, SPVs, private market investing, and why the next decade could fundamentally reshape private capital markets.

Timestamps:

00:56 — [ tech and vc news ]

03:05 — setter top 30: the secondary scoreboard 🏆

07:53 — ⁠us vs anthropic ceasefire 🤝

12:11 — openai ships gpt-5.6: sol / terra / luna 🌕

13:24 — china vs us ai: does cheap/open reset the race 🌏

19:15 — meta back: low-cost models, rentable compute 🔋

21:17 — $SKHY raises $26B, mkt cap >$1T 💾

23:25 — blue origin: $10b on $130b 🚀

26:33 — kalshi raising at $40b, polymarket lagging 🎲

30:29 — [ intvw: Shawn Bercuson @ Earlyasset Capital ]

⁠from groupon to secondaries: an origin story 🍩

38:45 — bull vc: liquidity for distressed shares 🐂

43:30 — the law of 30 (really 50) 📏

46:18 — dailypay, SPVs, and the anthropic fallout ⚠️

58:20 — ⁠⁠the private market in ‘27 and ‘28 🔮

1:01:08 — [ valuation corner: Reflection AI @ $25B ]

the raise and the team 💰

1:04:35 — deepseek vs reflection: revenue and multiples 🇨🇳

1:07:05 — mapping the ai landscape: cost vs efficacy 🗺️

1:10:00 — coding assistants and the verdict on reflection 🤖

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ shawn bercuson = https://www.linkedin.com/in/shawnbercuson | https://earlyasset.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

#tradingplacespodcast #vcsecondary #SteveBercuson #davemcclure #BlueOrigin

DeepSeek just raised $7.4B at a $50B valuation 🇨🇳and there's no cap table access. It's structured through an SPV, no voting rights, no board seats. CEO Liang Wenfeng put in $3B of his own money and controls the vehicle.

Meanwhile Anthropic is trading above $1T on the secondary market despite Mythos getting staged by the government, and SpaceX just locked in its Nasdaq 100 slot with a $2T valuation on a float of only ~6%.

Plus: Michael O'Keefe of CAZ Investments breaks down how a $12B GP stakes portfolio actually gets built.

00:00 – cold open

00:54 –  [ tech and vc news ] 

02:33 – SpaceX joins Nasdaq-100 🚀

08:39 – Anthropic hits $1T valuation & IPO outlook 💸

14:45 – OpenAI builds its own chip + 2027 IPO delay 🤖

18:07 – AI memory demand surges (Micron wins, Apple/customers pay more) 💾

20:24 – Cerebras falls below its IPO price 📉

22:46 – AI token costs rising; customers shift to Chinese open-weight models 🔄

28:24 – Bending Spoons targets ~$19–20B IPO on profitable roll-up strategy 🥄

32:56 –  [ intvw: Michael O’Keefe @ CAZ ]  

33:22 – CAZ manages $12B AUM 💰

36:04 – What is GP stake investing? 📊

44:19 – Typical check sizes & fund sizes

45:45 – How GP stakes are valued 📈

56:52 – Where CAZ is investing today: AI, energy, sports 🤖

1:00:05 – The secondary market boom 🔥

1:02:45 – [ valuation corner: DeepSeek @ $50B ]

1:03:40 – Largest seed round ever? 🏆

1:04:45 – SPV mechanics & stockholder structure 🛠️

1:07:40 – Users and revenue growth 📈

1:10:25 – DeepSeek vs. OpenAI comparison 🆚

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ michael o’keefe = https://www.linkedin.com/in/mjoii/ | https://cazinvestments.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

#tradingplacespodcast #SpaceX #ClaraVydyanath #davemcclure #SpaceXIPO

SpaceX just finished its first week as a public company. Anthropic just had its newest model frozen by the US government. And Jeff Bezos just raised $12B for a startup that's been alive for about a year.

Dave and Aman break it all down — from SpaceX IPO mechanics and gamma squeeze risk, to the Dario vs. Washington standoff that could derail the Anthropic IPO, to Bezos's $41B physical AI bet, a massive Salesforce acquisition of a 500 Startups alum, and why Mistral and Cohere just became the Dr. Pepper of AI.

Plus: the Valuation Corner returns with Powerlaw (PWRL) — the new retail-accessible VC fund from Ben Black and Mike Dinsdale backed by Acadian. Dave and Aman break down the portfolio, the price-to-NAV, and whether it's worth the ride.

00:48 - [ tech news and vc ]

02:58 - oil down, defense up 🚀

10:31 - SpaceX week one on the tape 📈

15:15 - Anthropic gets frozen 🧊

30:30 - SaaS enters valuation winter ❄️

33:42 - Bezos bets $12B on an AI engineer 🤖

36:30 - Mistral doubles to $23B 💸

42:15 - Saronic unmanned ship saves lives 🛟

43:20 - [ val corner: PWRL Ben Black ]

how Power Law gives retail a chance 🙏

46:06 - portfolio breakdown 💼

47:15 - strategy pros and cons 👍👎

49:29 - manager accolades 💐

[ 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

#spacex #anthropic #mistralai #secondaries #venturecapital

The SpaceX IPO just happened. Dave and Aman break down the grades, the winners, and what comes next — then sit down with CJ Gustafson, recovering tech CFO and founder of Mostly Metrics, to dig into the private market pricing mechanics that most investors get completely wrong.

This week: SpaceX Day 1 results and the $75B raise that dwarfed an entire year of VC-backed IPOs. The updated Private Mag Seven — who stays, who goes public, and who replaces them. OpenAI vs. Anthropic: which IPO is actually stronger and at what price. Google raising $80B in equity (not debt) with Berkshire Hathaway coming in. Cognition at $26B and the AI coding land grab.

——

00:36 - [ tech news and vc ]

01:52 - Big 3 Race to Go Public 🏁

04:15 - Google $85B Equity Raise 💰

22:48 - SaaSpocalypse Over? 🫨

29:46 - AI-coding Cognition Raises $1B 💸

32:32 - Databricks Past $134B & Revolut Past $100B 🚀

40:01 - [ intvw: CJ Gustafson, recovering tech CFO ]

44:32 - Raising $1B in 18 Months 💸

46:16 - SaaS Multiples: From 20x to 4x and the Road Back 📉

1:17:00 - Stay Private, Get to $1B ARR Before You IPO 🏰

1:20:26 - [ val corner: Aman grades SpaceX IPO ]

1:25:12 – What happens to stock price next 6 months 🤔

1:29:45 – Who made the most money 🤑

——

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ][ cj gustafson = https://www.linkedin.com/in/cj-gustafson-13140948/ | https://x.com/cjgustafson ]

[ run the numbers podcast https://www.youtube.com/@RuntheNumberswithCJ ]

[ 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 ]

Trading Places is the only VC secondary podcast on the internet. Hosted by Dave McClure and Aman Verjee of Practical Venture Capital.

Subscribe for weekly coverage of private markets, AI company valuations, and the deals most investors never see coming.

#spacex #spacexipo #spacexstock #secondaries #venturecapital

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

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 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

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

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

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

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

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 ]

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

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

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

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

The biggest private round in history just got bigger.

This week on Trading Places, Dave McClure and Aman Verjee break down:

• OpenAI’s rumored $100B raise at an $830B valuation

• Anthropic’s $380B valuation surge

• Stripe’s $140B employee tender

• Databricks at $134B

• Harvey AI jumping to $11B

• SCOTUS striking down Trump’s emergency tariffs

Then we go deep with Tyson Hendricksen, Founder & CEO of Notice.co, on private market pricing transparency, broker networks, secondary liquidity, and what’s really happening beneath the surface of today’s AI concentration.

And in Valuation Corner:

OpenAI vs Anthropic — who actually wins?

Let’s unpack it.

⸻

00:00 - cold open

00:53 - [ tech & vc news ]

02:09 - ⁠OpenAI @ $830B🥇

02:56 - ⁠ Anthropic @ $380B🥈

04:02 -⁠ ⁠Stripe tender @ $140B 💸

06:38 -⁠ ⁠Databricks @ $134B 🧱

08:39 - ⁠Harvey AI @ $11B👨🏽‍⚖️

11:07 -⁠ ⁠SCOTUS rejects Trump Tariffs 🙅‍♂️

22:30 - [ intvw: Tyson Hendricksen / Notice.co ]

23:17 - ⁠olympic training to 🍍 farmer

26:21 -⁠ ⁠founding Notice.co 💼

33:48 -⁠ ⁠product walkthrough 🚶‍➡️

37:58 -⁠ why people need transparent pricing 👀

55:50 - prediction markets 🎰

[ val corner: OpenAI vs Anthropic ]

1:03:20 -⁠ ⁠OpenAI raise history 🚀

1:08:04 -⁠ ⁠OpenAI vs. Anthropic 🥊

1:13:43 - ⁠who wins Gold 🥇

1:18:07 - second takes

⸻

[ links ]

[ invest = https://practicalvc.com ]

[ donor-advised fund webinar signup = PracticalVC.com/DAF101 ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ tyson hendricksen = https://www.linkedin.com/in/tyson-hendricksen | https://x.com/thetyson ]

[ www.notice.co = https://www.linkedin.com/company/noticedotco | https://x.com/noticedotco ]

[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.

If you care about private markets, AI dominance, and secondary liquidity — this is the episode.

👇 Drop your vote in the comments:

OpenAI or Anthropic?

#OpenAI #Anthropic #AIvaluation #privatemarkets #venturecapital #secondarymarket

Space, AI, SaaS carnage, secondary liquidity, and the biggest merger of all time.Welcome to Episode 23 of Trading Places — and this one covers everything from venture DPI math to Mars colonization strategy.This week, Dave McClure, Aman Verjee, and returning guest David Zhou break down:🚀 The $1.25T SpaceX + xAI merger📉 Why SaaS multiples just collapsed💰 How VCs can generate DPI before year 10🧠 The future of AI infrastructure (data centers in space?)📊 What secret “stallions” investors should actually buy🧾 Why most VC funds have 0 DPI at year 7Timestamps:00:00 – cold open00:53 – [ News ]02:03 – $1.25T merger: xAI + SpaceX 🚀05:33 – SaaSpocalypse 📉💣13:46 – $68B → $11B: Figma slides 🛝17:30 – Tether $20B backpedal 🕺19:35 – ElevenLabs $11B valuation 🗣️21:00 – Cerebras $23B benchmark 🤖24:48 – [ Interview: David Zhou 2.0 ]25:35 – DPI or ☠️32:38 – why fund cycles are broken ⛓️‍💥37:42 – how to get DPI before IPO 💼48:11 – what nobody tells GPs 🤔53:07 – SPVs are everywhere 📦56:47 – the 5 types of unicorns 🦄1:09:22 – [ Valuation Corner: SpaceX + xAI ]1:09:30 – $1.25T merger examined 🧐1:12:28 – East India bull case for SpaceX 🐂1:16:20 – the Tesla puzzle piece 🧩1:20:42 – investors weigh in 🏋️1:27:38 – Dave singing + second takes[ links ][ invest = https://practicalvc.com ][ trading places socials = www.linktr.ee/tradingplacespod ][david zhou =   / davidjzhou   | https://x.com/cupazhou ] [aman verjee =   / aman-verjee   | https://x.com/amanverjee ] [dave mcclure =   / davemcclure   | https://x.com/davemcclure ] *This content is for informational purposes only and should not be considered investment advice. #venturecapital #spacexxai #mergersandacquisitions #tradingplacespod #davemcclure #amanverjee

Welcome back to Trading Places — the terrible, very bad, absolutely horrible VC secondaries podcast with Dave McClure and Aman Verjee.

This week is a full-spectrum market tour: the latest rumors swirling around Elon’s empire (SpaceX + Tesla + xAI), the mega-rounds and IPO chess games of Anthropic + OpenAI, the reality check hitting public SaaS multiples reported by Jamin Ball, and a deep dive into secondaries, LP liquidity, and why DPI is suddenly the only thing anyone cares about.

We’re joined by Anurag Chandra (operator → investor → allocator) for a rare look inside how real capital allocators think: risk budgets, time horizons, pension constraints, and why governance + incentives matter more than “manager genius.”

Then we head to Valuation Corner LATAM with Karin from the Practical VC team for a breakdown of Latin America unicorns, the IPO window reopening, and what could be next after PicPay’s IPO — plus why Brazil’s Pix changed the game.

Timestamps:

0:00 – cold open

00:53 – [ news ]

1:13 – Elon Inc: xAI + SpaceX + Tesla 🚀

6:06 – Anthropic doubles to $350B 💰

8:16 – OpenAI Q4 IPO 🏁

12:25 – Ethos Technologies $200M US IPO 🔔

13:55 – AI eats SaaS 🍽️

16:00 – Kevin Warsh Fed chair nod 🪑

19:04 – Waymo $110B valuation 🚕

21:37 – Social media goes on trial 👩🏽‍⚖️

24:11 – MoltBook viral swarm AI 🦞

30:31 – [ intvw: Anurag Chandra ]

32:05 – $2B VC money managed 💪

33:12 – Family office fundamentals 💼

37:40 – San Jose Pension Fund success 🙌

38:17 – Future of San Jose 🔮

1:01:32 – [ val corner: PicPay $2.5B IPO ]

1:02:07 – Analysis: LatAm exit market & liquidity history

1:03:43 – top LatAm unicorns 🦄

1:11:44 – PicPay & fintech competition

1:17:46 – second takes

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ anurag chandra = https://www.linkedin.com/in/anchandra/ ]

[ karin tenenboim = https://www.linkedin.com/in/ktenenboim/ | https://x.com/LadyChutzpa ]

[ 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.

#secondarymarkets #secondaries #venturecapital #tradingplacespod #davemcclure #amanverjee

In this episode of Trading Places, Dave McClure and Aman Verjee break down what’s driving markets right now, and what it means for liquidity in private tech.They’re joined by Ravi Ravulaparthi (CEO & Co-Founder, Qapita).Together, they unpack what’s actually happening across IPOs, secondaries, SPVs, and late-stage price discovery:

• Why public markets rallied and what’s underwriting the optimism 📈• EquipmentShare’s strong IPO vs BitGo’s weak debut (and what investors are rewarding) 🏋️🟠• Capital One buying Brex at $5.15B a “down round exit” that’s still a real outcome 🤝• Secondaries getting institutionalized (EQT–Coller) + Evercore’s volume signals 💰• Pinegrove’s $2.2B venture secondaries raise and what it implies for DPI 💸• Zipline’s $7.6B valuation + the hard path to real-world drone delivery 🛩️• SPVs scaling fast (Sydecar at $4B AUA) and why they’re becoming default infrastructure 🏦• OpenAI’s move toward ads and the principles they claim will govern it 📸• Qapita’s playbook: equity management + secondary infrastructure across India/Singapore → US 🌎• Valuation Corner: Anduril - hardware + software in defense tech, and the $14B → $31B step-up 🛡️If you’re tracking IPO windows, secondary liquidity, SPVs, and how private markets are evolving in 2026, this episode is a clean map of where the pressure (and opportunity) is building.Timestamps00:00 – cold open[ tech & vc news ]00:36 – Why public markets bounced 📈03:18 – EquipmentShare $7.2B strong IPO 🏋️03:51 – BitGo $2B weak IPO 🟠06:15 – Capital One acquires Brex $5.15B 🤝08:55 – EQT buys Coller Capital for $3.7B 💰11:02 – Pinegrove raises $2.2B 💸12:00 – Zipline $7.6B valuation 🛩️13:21 – Sydecar hits $4B AUA 🏦15:39 – OpenAI starts ads 📸18:11 – [ intvw: Ravi Ravulaparthi / Qapita ]18:50 – From Singapore to USA 🇸🇬➡️🇺🇸18:52 – What Qapita does 🧐21:48 – India investing dynamics 🇮🇳27:05 – SPVs go global 🌎33:24 – Where 2ndary volume concentrates: IPO-window names 🎯[ val corner: Anduril ]53:49 – Anduril overview: defense tech + disclosure 🛡️54:17 – What Anduril does (defense tech framing) 🧠55:17 – Founders Fund + Palmer Luckey origin story 🧩55:40 – Valuation step-up: $14B → $31B examined 📈01:01:14 – Final riff: “ready to rally… or we’ve lost our minds” 😵‍💫[ links ][ invest = https://practicalvc.com ][ trading places socials = www.linktr.ee/tradingplacespod ][ ravi ravulaparthi = https://sg.linkedin.com/in/raviravulaparthi ][ qapita = https://www.qapita.com/ ][ qapita socials = https://www.linkedin.com/company/qapita/ | https://x.com/qapita ][ 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 #PrivateMarkets #Secondaries #SPVs #Anduril #DefenseTech #Qapita

In this episode of Trading Places, Dave McClure and Aman Verjee dive deep into the rapidly evolving world of private tech markets.

They’re joined by:

• Noel Moldvai (Founder & CEO, Augment Markets)

• Adam Crawley (Co-Founder, Augment Markets)

• Marcelo Ballvé (Founder, Sacra)

Together, they unpack what’s actually happening beneath the surface of AI, secondaries, and late-stage private companies:

• Why the bar for IPOs keeps moving higher

• How secondary markets have become a primary source of liquidity

• What SPVs, tender offers, and structured secondaries really solve

• Whether today’s AI valuations reflect fundamentals—or momentum

• Why many “private” companies now behave like public companies without public rules

If you’re tracking AI, private markets, or venture liquidity in 2026, this episode explains where price discovery is really happening—and who benefits from it.

Timestamps

00:00 – cold open

00:59 – [ tech & vc news ]

01:15 – California billionaire tax 🤌

09:06 – China IPOs in 2026 🇨🇳

13:10 – JP Morgan & secondary market 📈

15:49 – BlackRock–Microsoft $12.5B partnership 🤝

17:47 – Cerebras AI new $22B valuation 💰

22:04 – [ roundtable: Marcelo Ballvé / Adam Crawley ]

22:47 – Adam Crawley, co-founder of Augment 👨‍💼

23:31 – Marcelo Ballvé: CB Insights → Sacra 🚀

24:19 – Augment Power 20 🔍

31:39 – How Sacra gets data 📊

34:42 – Up-and-coming private companies 🐎

39:51 – Going public vs staying private 🆚

[ val corner: Mistral AI ]

56:13 – Top 10 French unicorns 🇫🇷

58:03 – $2B → $13B 👍

59:00 – 100x on “maybe” revenue 👎

1:02:53 – Valuation prediction 🔮

[ intvw: Noel Moldvai / Augment CEO ]

1:04:02 – Value proposition of Augment 💰

1:06:40 – The rise of SPVs 💸

1:11:17 – Tokenization of private companies 🟡

1:15:38 – Future of secondary markets 🤔

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ noel moldvai = https://www.linkedin.com/in/noelmoldvai/ | https://x.com/noelregrets ]

[ 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

#VentureCapital #StartupInvesting #secondaries #VCSecondaries #mistralai #augmentmarket

In this episode of Trading Places, Dave McClure and Aman Verjee break down the reopening IPO market, sky-high AI valuations, and the growing push for private-market liquidity — before diving deep into Latin America’s venture ecosystem with Nathan Lustig (Magma Partners) and Karin Tenenboim (Practical VC).

Karin explains why Latin America has quietly outperformed other emerging markets on $1B+ exits, how Brazil’s Pix payments system changed fintech overnight, and why secondaries are still underdeveloped across the region. The episode closes with a valuation corner on Discord, including its rejected Microsoft offer and what its IPO might look like today.

Timestamps

0:00 - cold open

[ tech & vc news ]

1:24 - 2026 IPO market opens 🏁

4:31 - a16z raises $15B across several funds 🥇

6:38 - Top 10 VC firms in the world

12:36 - China blocks Manus ✋

16:16 - Bill Gurley on AI

24:15 - Anthropic, OpenAI, xAI valuations 💸

32:15 - Discord & Strava IPOs 🔔

37:29 - G Squared + Nasdaq team up for private market liquidity 🤝

40:09 - [ intvw: Nathan Lustig / Magma Partners ]

40:26 - Nathan Lustig background and moving to Chile

40:34 - Karin Tenenboim on PVC LatAm strategy 🌎

49:25 - Brazil Pix payments breakthrough

52:45 - Mottu vertical stack (Motorcycle leasing/logistics) 🏍️

1:07:30 - Investing strategy in LatAm

1:08:56 - PVC + Magma LatAm 2ndry Fund partnership 🥳

1:33:59 - [ val corner: Discord IPO ]

1:34:36 - What is Discord 🗣️

1:42:07 - 2021 valued at $14.7B / $15B 📈

1:43:24 - Rejected $12B Microsoft offer 🚫

1:43:24 - Valuation today 🤔

1:44:19 - second takes

[ links ]

[ invest = https://practicalvc.com ]

[ trading places socials = www.linktr.ee/tradingplacespod ]

[ nathan lustig = https://www.linkedin.com/in/nathanlustig | https://x.com/nathanlustig ]

[ magma partners = https://magmapartners.com ]

[ karin tenenboim = https://www.linkedin.com/in/ktenenboim | https://x.com/@LadyChutzpa ]

[ 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

#VentureCapital #StartupInvesting #LatinAmericaTech #VCSecondaries #DiscordIPO #NathanLustig

Episode 18 of the @TradingPlacesPod featuring James Riney from Coral Capital is out now!This week: Dave and Aman kick off 2026 with their macroeconomic predictions (GDP growth, Fed rate cuts, and tax refunds), break down the IPO market outlook (SpaceX at $1.6T?!, OpenAI, Anthropic, Databricks), and dive deep into the secondary market dynamics for companies that won't go public in 2026. Plus, we explore the private Mag 7 vs. public Mag 7 in our [valuation corner] to answer the big question: where would you rather be—public or private markets?Then, Dave sits down with James Riney, founder and managing partner of Coral Capital in Tokyo, Japan. James shares how he went from JP Morgan to founding one of Japan's largest crypto exchanges (Coin Check) to launching 500 Startups Japan (now Coral Capital) at age 26. They discuss Japan's explosive VC growth (from $700M to $7-10B annually), the rise of "hidden unicorns" (companies that IPO'd before hitting $1B), why secondaries weren't a thing in Japan until recently, and Coral's massive $100M secondary sale in SmartHR—the largest secondary exit ever in Japan that returned 6X on their fund while still holding half their stake.[ timestamps ]00:00 – cold open01:07 – [ tech & vc news ]01:29 – macro growth picture 🖼️07:40 – 2026 IPO predictions 🔮10:24 – 2ndry market game plan 🏈16:43 – Nvidia gives Groq $20B 💰22:00 – SoftBank buys DigitalBridge $4B 🌉23:01 – Google acquires Intersect $4.75B 💸25:42 – Meta hands Manus $2B 👋27:25 – hot IPO Market in China31:35 – [ intvw: James Riney / Coral Capital ]31:46 – $100M 2ndry sale of SmartHR 🧠34:44 – Japanese founding story 🏯36:15 – Japan startup scene 🇯🇵41:35 – Coral Capital strategy 🪸43:54 – China vs Japan vs USA 🌏1:13:59 – [ val corner: mag7 public vs private ]1:13:59 – public mag7 analysis 🔔1:18:38 – Tesla Elon magic 🪄1:22:00 – private mag7 deep dive 🕵️1:27:10 – 2026 2ndry strategy 🧐1:30:51 – second takes[ links ] [ trading places podcast = www.linktr.ee/tradingplacespod ] [ james riney = https://www.linkedin.com/in/jamesriney | https://x.com/jriney ] [ coral capital = https://coralcap.co ] [ 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 ]Pod highlights this week:-2026 macro setup is strong: 4% GDP growth, Fed quantitative easing starting, and the biggest tax refunds ever hitting Q1 (tips, social security, overtime exemptions)-IPO predictions: SpaceX targeting $1.6T valuation, OpenAI and Anthropic likely to go public, plus Databricks, Stripe, Canva, Kraken in the mix-Private market reality check: top 10 AI companies getting all the attention, but the real secondary opportunities are in the next 200-300 companies trading at discounts-Nvidia's shopping spree: $20B for Groq (talent + inference tech), $100B in annual free cash flow to deploy—expect more acquisitions-Japan VC market exploded: from $700M (2015) to $7-10B today, with companies IPO'ing at series B/C stage instead of staying private for 12 years-SmartHR secondary: Coral Capital's $100M sale to General Atlantic = largest secondary in Japan history, 6X return on fund, still holding half their stake for the IPO-Hidden unicorns in Japan: 42+ companies hit $1B valuation within 12 years but were already public—so they don't count in "unicorn" stats (definition = private company)-Valuation corner showdown: Public Mag 7 trading at 7-10X revenue with profits; Private Mag 7 top tier (OpenAI, Anthropic, X.AI) at 20-30X revenue with no profits—priced for perfection-Dave's take: avoid the froth at the top (OpenAI, Anthropic, SpaceX), hunt for value in second-tier private companies (Canva at 7X revenue, Databricks at 20X revenue) trading at discounts outside organized tender windows

Episode 17 of the Trading Places Pod featuring Javier Avalos of Caplight is out now!This week: the IRS as your hidden secondary buyer, why banks need private market solutions, how platform acquisitions are reshaping secondaries, and whether AI companies are in a bubble or just getting started. Plus, Oracle's cash flow crisis, TikTok's $38B deal, and why mega VC funds might be destroying returns.Hosts Dave McClure and Aman Verjee dive deep with Javier Avalos, CEO and co-founder of Caplight, on the explosive growth in VC secondary markets, transaction data from $3.5B+ in deals, and why 83% of trading volume concentrates in just 15 companies. Javier shares insights on SPV structures, fee loads that make no sense, and why secondary markets are becoming the third leg of the exit stool alongside IPOs and M&A.[ timestamps ]0:00 – cold open1:04 – intro[ tech & vc news ]02:05 – TikTok new owners 🕺07:07 – 2025 AI hype cycle review 🤪10:02 – Tomasz Tunguz on AI junk bonds 🗑️

12:33 – Elon launches DATA CENTERS IN SPACE!!! 🚀🛰️14:29 – Lightspeed $9B megafund ⚡️16:53 – Dragoneer raises $4.3B 🐉17:39 – OpenAI $750B val & deal with Amazon 💃21:51 – Databricks $134B valuation 🧱23:22 – Waymo $100B val drive 🚕24:14 – Lovable, Unconventional & Notion 💰30:18 – [ intvw: Javier Avalos / Caplight ]30:27 – from Forge to Caplight 👨‍💼35:30 – top 20 startups vs the rest 🌎36:26 – $3.5B closed trade data in 2025 💵39:07 – concentrated VC funds 🎅🏼40:10 – good SPV check list ✅[ val corner: xAI @ $230B ]1:15:11 – what actually is xAI? 🤖1:18:02 – financial analysis 📊1:21:34 – xAI big backers 🧑‍🧑‍🧒1:24:48 – which Elon company to back? 💸Links:[ trading places podcast = www.linktr.ee/tradingplacespod ][ javier avalos = https://www.linkedin.com/in/javier-avalos-caplight ][ caplight = https://framer.caplight.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 ]Pod Highlights This Week:Secondary markets = new exit option: Javier reveals Caplight is tracking $3.5B in closed trades in 2025—up 50% YoY—making secondaries a viable third leg alongside IPOs and M&AConcentration is extreme: Top 5 companies = 54.7% of all trading volume; top 20 = over 80%; if you're not in the top 50, you're less than 10% of the marketAI pure play thesis: Only place to get direct AI model exposure—public markets bundle it with advertising, cloud, social mediaBanks racing to acquire platforms: Schwab/Forge ($660M), Morgan Stanley/EquityZen, Goldman/Industry Ventures—if you don't have a private markets solution for clients, you're behindSPV explosion: Now 50% of market activity (up from 15% in 2021) as mega AI rounds require co-investment vehicles—but beware triple-layer 4-and-40 structuresOracle's cash flow crisis: Went from $14B free cash flow (2021) to NEGATIVE as CapEx commitments balloon—bet on OpenAI backfiring?AI bubble or justified?: 25% of volume but 50%+ buyer interest; if more sellers come to market, 2026 could see even more dealsMega funds destroying returns?: Lightspeed $9B, Dragoneer $4.3B—history shows mega funds underperform smaller strategic fundsNotion's patient playbook: Raised at $11B in 2021 bubble (100x revenue), then grew revenue 10x to "only" 20x multiple—rare flat round successx.ai at $230B: Is this about Elon's network or fundamentals? Valor, Ira, Jensen, Sequoia, a16z all in—do you bet with or against them?Javier's insider wisdom: "If you're buying a triple-layer SPV with 3-and-30 that closes in 24 hours, just say no—there's no FOMO worth that"#davemcclure #tradingplacespod #vcsecondaries #secondarymarket #caplight #javieravalos #forgeglobal #schwab #openai #oracle #AI #venturecapital #SPVs #privateequity #liquidityevent #unicorns #spacex #stripe #databricks #xai #elonmusk #secondaries #techvc

Episode 16 of the TradingPlacesPod featuring Adrien Gautier of Bridgespan VC is out now!

This week: Oracle's debt crisis sends shockwaves through AI infrastructure stocks, the IPO market heats up for 2026 with SpaceX, OpenAI & Anthropic eyeing historic exits, and Adrien Gautier reveals how Bridgespan's unique employee stock option financing strategy gets them 30-70% discounts vs. preferred share pricing 💰

Welcome to Trading Places, the extremely terrible, very bad podcast on VC, secondaries, and all things tech. Hosts Dave McClure and Aman Verjee break down market volatility, the Fed's rate cut uncertainty, Oracle's leverage problem, and the explosive IPO pipeline for 2026—before diving deep with Adrien Gautier on how employee stock option financing creates a capital-efficient secondary strategy with built-in downside protection.

In Valuation Corner, the team tackles the autonomous vehicle wars: Waymo vs. Tesla vs. the rest of the auto industry, exploring whether software-first companies deserve their premium valuations and why traditional OEMs can't catch up.

[ TIMESTAMPS ]

00:00 – cold open

00:53 – [ tech & vc news ]

01:15 – Oracle’s bad week

06:09 – 2026 IPO market

11:49 – SpaceX IPO update

13:15 – Wealthfront flat IPO

14:56 – Medline $55B valuation

22:51 – Boom Supersonic raises $300M

23:49 – Goldman Sachs invests in Harness at $5.5B

25:19 – New fed chair & rate cuts

30:44 – Invest Act coming soon

33:07 – China rejects US Nvidia H200s

35:43 – [ interview: adrien gautier / bridgespan ]

36:12 – Bridgespan VC focus

42:15 – tender offers

43:24 – when can companies IPO

46:16 – EquityBee partnership

47:54 – portfolio management strategy

1:12:45 – [ val corner: waymo @ $45B ]

01:28:29 – second takes

LINKS

[ trading places podcast ]

www.linktr.ee/tradingplacespod

[ adrien gautier ]

https://www.linkedin.com/in/adriengautier

[ bridgespan ]

https://www.bridgespanvc.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

POD HIGHLIGHTS THIS WEEK:

-Oracle's leverage trap: 500% debt-to-equity ratio means a 50% drop in enterprise value = 60% equity wipeout. Credit default swaps hit highest since 2008​

-2026 = IPO supercycle: SpaceX ($800B), OpenAI ($500B), Anthropic ($350B) could each break Alibaba's $25B IPO record​

-Bridgespan's edge: Employee stock option financing gets 50-70% discounts vs. latest preferred rounds—with non-recourse downside protection​

-6 exits in year 1: Bridgespan's Fund I generated DPI from 36 investments, with Firefly Aerospace delivering 10x in 60 days​

-Disney + OpenAI = new playbook: Characters licensed to Sora (minus voices)—Ursula's contract confirmed​

-Fed uncertainty: Only 8-10 of 12 voters likely support December rate cut; jobs data showing negative growth 3 of last 5 months​

-Invest Act passes: House approves 49% secondary cap for VC funds (up from 20%), 250→500 LP limit, $10M→$50M emerging manager threshold​

-Tender offer trends: Now standard for companies $10B+ with $100M+ revenue—Bridgespan's primary exit strategy alongside IPOs​

-Autonomous driving wars: Tesla/Waymo trade at 15x revenue; GM/Ford at 0.5x. Software is better than hardware. Helm.ai aims to democratize FSD for legacy OEMs​

-Adrien's wisdom: "If you don't like the public market valuation 6 months post-IPO, we may hedge. But our strategy? 1) sell at lockup 2) return capital to LPs 3) repeat."​

#davemcclure #tradingplacespodcast #venturecapital #secondarymarket #bridgespan #employeestockoptions #tradingplacespod #IPOmarket #SpaceX #OpenAI #Anthropic #Oracle #AIbubble #Waymo #Tesla #autonomousdriving #tenderoffer #VCfundraising #InvestAct #Firefly #equityB #Helm #EmploymentRate #BLS

Episode 15 of the Trading Places Pod featuring Ben Black of Akkadian Ventures is out now!Welcome to Trading Places, the extremely terrible, very bad podcast on VC secondaries. Hosts Dave McClure and Aman Verjee break down the biggest news in venture secondaries, late-stage funding rounds, and this week's exclusive interview with Ben Black, founder and Managing Partner of Akkadian Ventures and creator of the legendary RAISE Conference for emerging managers.Ben shares his wild journey from losing his biggest LP in the 2008 crisis to building one of the most successful secondary funds in venture. He reveals how a green Ferrari purchase taught him about dealing with sellers, why he rejected 200 LPs last year for not being "real enough," and the secret to managing LPs (spoiler: it's way more important than picking deals).In Market News, we cover SpaceX's insane $800B valuation (doubling in months), Anthropic's potential $300B raise, OpenAI's code red, Netflix acquiring Warner Brothers for $83B, and why prediction markets (Kalshi $11B, Polymarket $15B) are coming for DraftKings' lunch money.In Valuation Corner, Professor Verjee analyzes Vercel's explosive growth to a $9B valuation—200M+ ARR growing 70-100% YoY with their AI cloud platform setting industry benchmarks.[ timestamps ]00:00 - cold open[ tech & vc news ]00:56 -⁠ ⁠SpaceX @ $800B leapfrogs OpenAI @ $500B 🐸05:35 -⁠ ⁠Anthropic hires IPO attorneys 💰⚖️08:23 - ⁠OpenAI code RED 🚨10:35 - ⁠Netflix offers $83B for Warner Brothers 🎥20:00 -⁠ ⁠Hasset new Fed Chair @ 75% 🪑📊23:12 -⁠ ⁠Kalshi $11B valuation 🤯25:00 -⁠ ⁠Harvey AI @ $3B… $5B… $8B 📈👨🏽‍⚖️27:00 -⁠ ⁠Databricks @ $134B val 🧱28:47 -⁠ ⁠Meta VR ashes 💸30:56 - [ intvw: ben black / akkadian ]31:05 -⁠ ⁠Ben Black 2ndry pioneer 🏁33:26 -⁠ ⁠Akkadian fund history 6️⃣45:30 -⁠ ⁠how VCs raise funds 🙏52:00 - ⁠how to manage LPs 🗣️57:47 -⁠ ⁠magic of RAISE summit 🪄1:10:20 [ val corner: vercel @ $9.3B ] 1:13:19 -⁠ ⁠ai-powered app dev platform 🤖1:14:38 - ⁠due diligence details 🔍1:13:19 -⁠ ⁠Vercel vs Digital Ocean 🆚1:14:54 -⁠ ⁠Vercel vs Replit 🥊1:18:14 - second takes (outtakes)links:[ trading places podcast = www.linktr.ee/tradingplacespod ][ ben black = https://www.linkedin.com/in/benblack | https://x.com/benblackvc ][ akkadian ventures = https://akkadian.vc/ ][ raise conference = https://www.raisevc.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]Pod Highlights This Week:Ben Black reveals brutal truth: "Managing your LPs is such an important part of your job and people think this job is about investing"—quarterly updates, annual in-person visits, and personal calls matter more than picking unicornsRAISE Conference origin story: Started with 140 people in 2015, now 1,000+ applications from emerging managers competing for 124 stage spots—and Ben rejects 200+ LPs annually for not being "real enough, big enough"Market concentration in secondaries: Top 5 companies = 54.7% of all secondary trading volume; top 20 = 80.4%. If you're not OpenAI, SpaceX, or Databricks, good luck finding buyersSpaceX valuation insanity: From $400B to $800B in months—is this Elon's ego competing with Sam Altman's $500B OpenAI? Dave's skeptical of 50x revenue multiplesBen's emerging manager advice: "What is your competitive advantage? How are you going to build a community around yourself?" Differentiation is better than "I know people and I'm smart"#davemcclure #amanverjee #tradingplacespod #benblack #akkadianventures #raiseconference #vcsecondaries #secondarymarket #emergingmanagers #vercel #spacex #netflix #warnerbrothers #anthropic #openai #polymarket #kalshi #predictionmarkets #databricks #harvey #IPOs #DPI #LPmanagement #venturecapital

Welcome to Trading Places, the extremely terrible, very bad podcast on VC secondaries. Hosts Dave McClure and Aman Verjee unpack the biggest news in venture capital, late-stage funding, crypto valuations, and this week's explosive valuation corner on why Grayscale's IPO might be heading for disaster.

This Thanksgiving episode dives deep into Michael Burry's controversial claims that Big Tech is cooking the books, comparing Nvidia and the hyperscalers to WorldCom-era fraud. The duo analyzes whether Burry is the modern-day Cassandra or just crying wolf (again). Plus: Luma AI's massive Saudi-backed raise, Revolut's $75B secondary completion, India's emerging IPO market, and Professor Verjee's bearish breakdown of Grayscale's $31-33B valuation.

[ timestamps ]

00:00 – intro

00:45 –  [ tech & vc news ]

01:05 – Michael Burry vs NVIDIA 💥

01:44 – who is Cassandra Unchained ⁉️

05:54 – hyperscaler accounting 🧮

06:14 – worldcom’s fraud 🚨

11:52 – will Burry be right? 🔮

14:19 – luma AI lifted by saudis 🇸🇦

15:12 – genspark’s unicorn status 🦄

17:04 – meesho’s indian IPO 🇮🇳

19:03 – revolut’s $75B secondary sale 💰

20:53 –  [ val corner: Grayscale @ $33B ]

21:04 – Grayscale’s “digital asset platform” 🟡

22:23 – S-1 form deep dive 🤿

27:03 – something smells fishy 🐠

32:07 –  second takes

links:

[ trading places podcast = 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]

Pod Highlights This Week:

Burry is back: The Big Short investor claims big tech is cooking the books—but is he right or just crying wolf (again)?

Cassandra curse: Burry successfully called 2008 but has been wrong about bubbles in 2019, 2020, 2022, and 2023

Accounting deep dive: Why Google, Meta, and Oracle extended depreciation schedules from 3 → 6 years and what it means for earnings

WorldCom redux?: Burry compares hyperscalers to telecom fraud era—we break down why this comparison falls short

1999 vs 2025: Cisco's debt-laden telecom customers vs Nvidia's cashflow-positive hyperscaler clients

AI CapEx boom: $300-500B/year spending now equals 1% of US GDP (same as 1999 telecom bubble)

Luma AI rockets: $2B raise at $8B valuation backed by Saudi PIF—first major AI investment on Saudi soil

Revolut secondary done: $75B valuation secondary completed despite questions about bank-like revenue mix

India IPO surge: Meesho's $600M IPO signals India as viable alternative to US public markets

Grayscale disaster incoming?: Trading at 60x revenue with 88% concentration in 2 products seeing massive outflows

Fee comparison shock: Grayscale charges 1.5% for Bitcoin (vs BlackRock 0.12%) and 2.5% for Ethereum (vs Fidelity 0.25%)

Professor Verjee's verdict: Grayscale is bearish—overvalued, losing market share, and competitively unsustainable

Episode 13 of @TradingPlacesPod featuring Emily Zheng (@Pitchbook) is out now!

Welcome to Trading Places, the extremely terrible, very bad podcast on VC secondaries. Hosts Dave McClure and Aman Verjee (with special guest Amber filling in) break down the biggest news in venture secondaries, late-stage funding rounds, market dynamics, and this week's exclusive interview with Emily Zheng from Pitchbook.

Emily walks through Pitchbook's Q3 2025 VC Secondary Market Report, revealing that secondaries have officially arrived as a mainstream exit option alongside IPOs and acquisitions. The trio discusses macro headwinds (jobs recession, Bitcoin crash, Fed uncertainty), AI company valuations (Anthropic, Google Gemini 3), prediction market mania (Kalshi, Polymarket), fintech growth (Ramp, Kraken), and platform consolidation (Schwab/Forge).

In Valuation Corner, Professor Verjee analyzes Ramp's meteoric rise to a $32B valuation—doubling from $16B in just 5 months on the strength of $1B+ ARR and triple-digit growth. The team compares Ramp vs Brex and discusses the competitive spend management landscape.

[ timestamps ]

00:00 — intro

00:38 — market volatility hits: Bitcoin, Mag 7, Nvidia concerns

07:42 — Fed rate cut uncertainty & macro headwinds

11:43 — Gemini 3 launch: Google back in the AI race?

14:20 — Anthropic raises $15B from Microsoft & Nvidia

17:24 — Ramp raises $300M @ $32B valuation

20:33 — Kalshi ($11B) vs Polymarket ($15B): prediction market arms race

22:02 — Kraken raises $200M @ $20B (Citadel backs crypto)

26:13 — Fair's $100M+ tender offer

29:28 — General Atlantic invests in SmartHR (Japan secondary)

40:31 — Meta wins FTC antitrust case: M&A implications

[ interview: emily zheng, pitchbook ]

43:37 — introducing Emily Zheng, Pitchbook's VC secondary analyst

47:02 — Q3 2025 VC secondary market report highlights

50:31 — secondaries now on par with IPOs & M&A ($95B market)

53:41 — direct secondaries surge 31% to $80B annually

57:28 — top 5 companies = 54.7% of all trading volume

59:01 — top 20 companies = 80.4% of secondary market

01:04:30 — SPVs explode: 682% increase in secondary SPVs

01:07:07 — single vs double-layer SPV structures

01:11:42 — tailwinds for recent fundraisers vs 2020-2022 vintage

01:17:06 — discount dynamics: 0-8.5% for recent rounds, 33-61% for 2020-2022

01:20:33 — Hiive raises Series B @ $650M valuation on own platform

01:24:50 — Schwab acquires Forge ($660M), platform consolidation continues

01:28:04 — industry trends: more tender offers, ROFR dynamics

[ valuation corner: ramp ]

01:32:16 — Ramp @ $32B: from $16B to $32B in 5 months

01:36:22 — $1B+ ARR, 133% YoY growth, profitable

01:40:31 — Ramp vs Brex comparison

01:43:37 — competitive landscape: can they beat SAP Concur?

links:

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ emily zheng pitchbook = https://pitchbook.com/news/authors/emily-zheng ]

[ 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]

Pod Highlights This Week:

-Secondaries = new exit option: VC secondary market hits $95B annually—now matching IPOs ($105B) and M&A ($107B) as a viable exit path​

-Market concentration is real: Top 5 companies account for 54.7% of all secondary trading volume; top 20 capture 80.4%​

-SPV explosion: Secondary SPVs increased 682% in deal count and 1,340% in capital raised (2023 vs 2025 Q1-Q3)​

-Discount math matters: Recent fundraisers (2024+) trade at 0-8.5% discounts; 2020-2022 vintage faces 33-61% haircuts​

-Bitcoin volatility: Down 35% from $125K peak to $84K amid Fed uncertainty and jobs recession signals

-AI wars continue: Google's Gemini 3 impresses (Altman and Musk congratulate); Anthropic raises $15B from Microsoft & Nvidia at $350B valuation

-Prediction markets heat up: Kalshi ($11B) and Polymarket ($15B) both raising massive rounds—coming for DraftKings' and FanDuel's lunch money

Episode 11 of the Trading Places Podcast featuring Daniel Blake from UI Charitable is out now!

This week: the IRS as your secret secondary buyer, donor-advised fund (DAF) strategies that turn illiquid assets into tax savings, and the wild world of prediction markets—where Polymarket and Kalshi are coming for DraftKings’ and FanDuel’s lunch money.

Timestamps:

00:00 - Intro

01:05 - Tech VC secondary news

01:20 - Big tech selloff?

03:02 - OpenAI / Amazon deal

05:58 - Anthropic leaks revenue numbers

08:51 - Schwab acquires Forge

14:10 - IPOs: Beta Technologies, BillionToOne

16:32 - Ripple raises $500M @ $40B valuation

18:16 - Metropolis raises $1.6B

19:45 - David Sacks a16z interview

27:56 - Interview: Daniel Blake, UI Charitable

28:04 - UI Charitable = tax-efficient impact philanthropy

39:15 - What is a Donor Advised Fund (DAF)?

43:08 - Founder journey / acquisition

48:13 - Donating illiquid assets (startups, VC funds)

50:31 - Fair Market Value (FMV) and tax deductions

54:50 - Donating crypto / bitcoin / digital assets

1:07:07 - Val Corner: Prediction Markets

1:17:40 - PVC SPV: Helm.ai

Links:

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ daniel blake = https://www.linkedin.com/in/drblake/ ]

[ aman verjee = https://www.linkedin.com/in/aman-verjee/ | https://x.com/amanverjee ]

[ dave mcclure = https://linkedin.com/davemcclure | https://x.com/davemcclure ]

Highlights:

• Daniel Blake explains why donating appreciated stock beats cash—and how you can reset your cost basis while earning tax deductions.

• The IRS as your secondary buyer: fair market value appraisals on 2021-era valuations can generate 30–50¢ on the dollar in tax savings.

• Charitable UI accepts everything: S-corps, carried interest, crypto, even your hobby farm greenhouse.

• Schwab pays a 75% premium for Forge Global at $660M—the third major secondary platform acquisition after Goldman/Industry Ventures and Morgan Stanley/EquityZen.

• Polymarket ($9B) and Kalshi ($5B) are positioning to eat DraftKings’ and FanDuel’s $45B+ sports-betting duopoly.

• Dave’s hot take: donate your worst illiquid assets (2020–21 vintage anyone?) before values drop further—capture the tax savings now.

• PVC SPV: Co-invest with Practical Venture Capital in Helm.ai—the AI autonomous driving software democratizing Full Self-Driving (FSD) for every automaker not named Tesla or Waymo.

#davemcclure #tradingplacespod #donoradvisedfunds #philanthropicstrategy #universityimpact #secondarymarket #polymarket #kalshi #predictionmarkets #taxstrategy #illiquidassets #venturecapital #openai #forgeglobal #schwab|

Episode 12 of the @TradingPlacesPod featuring Sean Engel from Top Tier Capital Partners is out now! 

This week: Are we in an AI bubble (again)? Data center capacity constraints meet infinite hyperscaler ambition, SoftBank sells Nvidia (again!) to bet on OpenAI, and venture secondaries are the new must-have strategy for every LP trying to escape the 15-year fund cycle.

00:00 - cold open/intro

00:53 - [ tech & vc news ]

01:01 - 2025 IPO roundup

02:00 - IPOs: Klook, Pine Labs, Groww

06:56 - Indian IPO market

07:57 - AI datacenter growth (6 charts)

15:54 - China solar growth (4 charts)

16:45 - Softbank sells NVDA (buys OpenAI)

18:43 - xAI raises @ $200B val

21:46 - Robinhood ETF in AI startups

24:46 - Cursor @ $29B, Lovable @ $6B

27:59 - Gamma AI @ $2B

30:01 - [ intvw: sean engel / top tier capital ]

30:54 - “started from the bottom…”

32:18 - Paul Capital spinout -> Top Tier 

32:18 - core thesis: VC Fund-of-Funds (FoF)

32:58 - Velocity: Co-invest, LP/GP 2ndry 

39:59 - Bubble or not? (yes, a bit)

44:00 - secondary discounts, bargains

38:44 - selling secondary to generate DPI

51:34 - more acquisitions in 2ndry market?

32:18 - VC FoF + VC 2ndry partnerships

1:09:55 - [ val corner: kraken / crypto exchanges ]

01:10:05 - kraken vs. binance, coinbase

01:15:55 - robinhood moving into crypto 

01:17:06 - profile: arjun sethi / kraken, tribe

01:20:34 - valuation update

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ sean engel = https://www.linkedin.com/in/sean-engel-toptier ]

[ aman verjee = https://www.linkedin.com/in/aman-verjee | https://x.com/amanverjee ]

[ dave mcclure = https://linkedin.com/in/davemcclure | https://x.com/davemcclure ]

Pod Highlights This Week: 

Sean Engel on bubbles: "There are pockets of bubbles playing out right now for sure." Seed-stage AI deals at multi-billion dollar valuations on a promise? Scratching our heads on risk-adjusted returns.

The beauty of venture: Liquidity events let you harvest all that hard work that wasn't obvious along the journey—but you gotta be patient (or sell smart).

Top Tier's Velocity Fund: Target 2X base case, 3X good days, 1.5X bad days—tighter standard deviation than traditional VC, with DPI in 4-6 years instead of 10-15.

Tale of Two Cities: AI-native companies at 300%+ growth vs. traditional SaaS at 40-50% growth trading at massive discounts. Both can win, but LPs need blended exposure.

2021 Lessons Learned: GPs are finally taking 10-20% liquidity off the table early instead of swinging for another turn. Zero-interest rates made everyone look like geniuses—until they didn't.

Secondary market maturation: GP-led continuation vehicles and LP portfolio buys are coming to venture from PE-land. Top Tier sells AND buys to optimize liquidity every single year.

SoftBank's Nvidia regret: Sold its entire stake for $6B to invest in OpenAI. They sold in 2019 for $3.3B too—would've been worth $150B today. Sellers' remorse is real.

Data center capacity crunch: Hyperscalers planning 60+ gigawatts of capacity by 2027, but energy and permitting constraints mean 5-10 year build-out. To justify hundreds of billions in spend, you need trillions in revenue. That's more than Apple's entire annual revenue.

Kraken at $15B: 10X sales, raised from Thrive Capital and Sequoia China (now HongShan). Then Citadel dropped $800M hours after we recorded. Ken Griffin warming to crypto = institutional legitimacy unlocked.

Cursor raises $2.3B at $29B valuation: From $1M to $100M to $1B ARR in three years. Might be the fastest startup ever. Jensen Huang called it his favorite enterprise AI service. 30X this year's ARR.

**#davemcclure #tradingplacespod #toptier #secondarymarket #venturecapital #fundoffunds #bubble #aibubble #kraken #coinbase #binance #citadel #softbank #nvidia #openai #datacenter #hyperscaler #cursor #gamma #robinhood #ipomarket #dpi #tvpi #thrivecapital #valuationcorner

This week on Trading Places, hosts Dave McClure and Aman Verjee cover the latest tech news, including OpenAI's path to a trillion-dollar IPO, Big Tech's massive AI spending spree, and Tether's $500 billion valuation. Plus, we sit down with Rick Baker, Managing Partner at Blackbird Venture Capital, to discuss the incredible Canva story, secondary transactions, and building Australia's venture ecosystem from the ground up.

📰 THIS WEEK'S NEWS

🤖 OpenAI's IPO Plans

-Potential $1 trillion IPO target-Microsoft ownership restructure (49% → 27%)

-California AG blesses for-profit transition

-Sam Altman hints at revenue north of $100B

💰 Big Tech AI Spending

-Microsoft, Amazon, Alphabet, Meta spending $125B/quarter on AI infrastructure

-Meta raises $30B in corporate bonds

-Oracle raises $38B for data center expansion

-Power constraints emerging as key bottleneck

📈 Secondary Market Consolidation

-Morgan Stanley acquires EquityZen

-Goldman Sachs acquired Industry Ventures

-Signals expansion of secondary market opportunities

🚀 IPO & Funding News

-Navan's challenging IPO (down 20% on day one)

-Mer raises $350M Series C at $10B valuation (5x step-up)

-Securitize going public via SPAC at $1.2B valuation

🪙 Stablecoin Market

-Tether considering $500B valuation round

-Coinbase reportedly pursuing $2B acquisition of BVNK

-Stablecoin revenue growing 300M+ per quarter

🎙️ FEATURED GUEST: RICK BAKER, MANAGING PARTNER @ BLACKBIRD VENTURES

The Canva Story

-Rick shares the incredible journey of Blackbird's investment in Canva—from a $250K seed investment to a company now valued at $40B.

GP-Led Secondary Transactions

-Rick walks through Blackbird's 2019 secondary sale:

-Sold ~$120M (1/3 of Fund I) at 93% of NAV

-Returned 3.5x to LPs while maintaining 9.5x exposure

-Used Lazard to run a competitive process

-StepStone + Australian super fund won the bid

Managing Concentration Risk

Owned 15% of Canva at peak, now ~11%

-Balance between maximizing returns and managing risk

-LP perspectives range from "sell everything" to "hold forever"

-Strategic sales during primary rounds to unlock growth capital

Australian VC Ecosystem

-Superannuation system: 12% of salary mandated into pension funds

-$4T AUD pool of long-term capital

-Reset after GFC: Blackbird, Square Peg, Airtree, Main Sequence

-Circle of life: Atlassian/Canva alumni starting next wave

💎 VALUATION CORNER: TETHER @ $500 BILLION

-Deep Dive on Tether

-Aman analyzes whether the world's largest stablecoin issuer is worth a $500B valuation:

-$13B+ in annual profit (2x BlackRock's profitability)

-75% market share vs. Circle's 20%-36x P/E ratio vs. Circle at 240x

-Medium transparency, aggressive reserve policy-Regulatory uncertainty in U.S. market

🔑 KEY TIMESTAMPS

01:12 - [ tech & vc news ]

01:21 - OpenAI Restructuring | $1T IPO?

08:24 - Big Tech Hyperscalers' Earnings and $125 Billion in Quarterly AI Spending

10:47 - Why This AI Boom is Different

15:58 - Morgan Stanley Acquires EquityZen17:39 - Navan's Public Offering Performance

21:05 - Mercor Raises at a $10 Billion Valuation22:23 - Securitize Going Public via SPAC ($1.25B)

24:37 - Tether's $500B Valuation Rumor

28:05 - [ interview: blackbird vc / rick baker ]

28:49 - Rick Baker's Background and Founding the MLC Venture Program

35:56 - The Canva Story45:06 - The Australian Venture Capital Market

01:07:44 - How the Secondary Market Solves the Liquidity Problem

01:15:48 - [ valuation corner: tether]

01:13:30 - Tether's Aggressive vs. $CIRC’s Conservative Reserve Policy

01:16:32 - Calculating Tether's Valuation Based on P/E

01:24:00 - The Regulatory Uncertainty for Stablecoins

01:31:30 - Final Thoughts on Tether's $500B Valuation & Stablecoin Market

Episode 8 of the Trading Places Pod featuring Phil Haslett from EquityZen is out now. This week we dive deep into OpenAI's massive semiconductor partnership deals ($500B+ across AMD, Broadcom, Nvidia & Oracle), Goldman's billion-dollar acquisition of Industry Ventures, plus emerging IPO opportunities including Tempo's $5B series A and Anysphere's $27B valuation.

Our guest Phil Haslett breaks down the secondary market landscape, retail vs institutional strategies, and what Goldman's move means for the industry.

[ tech news + primary rounds ]

01:07 - OpenAI's chip kingmaker status 👑

01:45 - AMD deal: unusual equity stakes

03:17 - $500B in AI infrastructure deals

10:23 - Goldman acquires Industry Ventures 💰

16:49 - IPO market normalization signals

18:54 - Anysphere $27B coding AI valuation

20:30 - Tempo $5B blockchain payments series A

[ phil haslett, equityzen interview ]

24:00 - phil's journey from Lehman to EquityZen

28:17 - 500 Startups accelerator days

30:55 - customer segments: retail to institutional

35:41 - market concentration in top 30 names

40:12 - secondary market bargain hunting strategy 🎯

48:18 - Goldman acquisition impact analysis

53:24 - building without VC pressure

58:31 - ByteDance valuation insights

[ valuation corner: deel]

1:11:12 - Deel's $17.3B valuation deep dive

1:15:43 - Rippling vs Deel metrics comparison

1:18:29 - corporate espionage lawsuit drama

pod highlights this week:

-OpenAI flexing kingmaker status with unprecedented equity deals across AMD, Broadcom, Nvidia & Oracle worth $500B+ in AI infrastructure

-Goldman Sachs drops $965M to acquire Industry Ventures, signaling Wall Street's serious play for VC secondary market access

-Phil Haslett shares EquityZen's 12-year journey from 500 Startups to processing billions in secondary transactions

-retail investors driving 29% average discounts while top-tier names trade at premiums-corporate espionage drama between Deel and Rippling adds Silicon Valley spy thriller vibes to HR tech competition-Deel's $17.3B valuation looks reasonable at 15x revenue with 70% growth and 120%+ net revenue retention

**

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ phil haslett = https://www.linkedin.com/in/philhaslett/ | https://equityzen.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 ]

Episode 9 of the Trading Places Podcast featuring Seedcamp's Reshma Sohoni and Carlos Eduardo Espinal is out now. This week we cover a jam-packed news cycle (prediction markets 📈, Google-Anthropic deal, Oracle's $38B debt raise, Tether's 500M users 🌍) plus an in-depth interview with the legendary Seedcamp co-founders on their pioneering secondary fund sale strategy. And of course, Professor Verjee breaks down Anthropic's $183B valuation in [valuation corner].

[ tech news + funding rounds ]

00:01:05 - Prediction Markets: Kalshi & Polymarket hit new valuations 🔥

00:10:44 - Google-Anthropic partnership deal 💰

00:14:54 - Oracle's $38B private credit raise 📊

00:17:26 - Tether hits 500M users globally 🌐

00:22:55 - Japan's Sakana AI raises $100M at $2.5B valuation

00:24:10 - AI productivity debate: Cathie Wood vs. reality check

[ seedcamp interview: reshma sohoni & carlos espinal ]

00:32:05 - Seedcamp's origin story & 500+ company portfolio

00:36:14 - Building the European VC ecosystem (2007-2014)

00:41:44 - Fund progression: from $2.5M to 100 investments

00:42:06 - Secondary sale strategy: selling funds 1 & 2 to Moulton

00:50:05 - LP secondary vs. direct secondary explained

00:57:12 - The 20% rule: when and how to sell positions

01:01:54 - Lessons from UiPath, TransferWise, Revolut exits

01:15:33 - European tech's future: demand-driven unicorns

[ valuation corner: anthropic ]

01:20:16 - Anthropic's $183B valuation breakdown 🤖

01:22:05 - OpenAI vs. Anthropic: who wins the AI race?

01:27:09 - The political divide: AI safety vs. acceleration

01:31:44 - David Sacks' critique & regulatory capture debate

01:37:45 - Final verdict: is Anthropic a good bet?

pod highlights this week:

-Prediction markets explode: Kalshi eyeing $10B valuation, Polymarket at $8B after sports betting approval from CFTC-Google deepens Anthropic partnership with $3B+ investment, securing cloud infrastructure with tensor chips

-Oracle raises massive $38B debt round to finance AI data center expansion in Texas & WisconsinTether reaches 500M users (vs. 340M Americans!) with $13B in annual profit—twice Blackrock's earnings

-Seedcamp's Reshma & Carlos reveal how they sold funds 1 & 2 to Moulton for a 4X+ return, unlocking fund 4 raise

-The "20% rule": Seedcamp's approach to secondary liquidity without timing the market perfectlyProfessor Verjee dissects Anthropic's $183B valuation (7B ARR, 7X YoY growth) and compares to OpenAI's $500B

-The AI political divide: why David Sacks criticized Anthropic's "woke" safety-first approach

**

[ trading places podcast = www.linktr.ee/tradingplacespod]

[ seedcamp = https://seedcamp.com/ ]

[ reshma sohoni = https://www.linkedin.com/in/reshmasohoni/ | https://x.com/reshmasohoni ]

[ carlos eduardo espinal = https://www.linkedin.com/in/carlosespinal/ | https://x.com/carlosespinal ]

[ 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 ]

#davemcclure #tradingplacespod #tradingplacespodcast #venturecapital #secondaries #seedcamp #anthropic #predictionmarkets #technews #AIvaluation

Episode 7 of  the Trading Places Podcast  featuring  Turner Novak from  The Peel Pod  and Banana Capital is out now.

This week we cover a range of news highlights from a very boisterous week in tech and fundings (Polymarket, Kalshi, Navan IPO, Bitcoin shorts, gold price boom) plus a jam packed [valuation corner] hosted by Practical Venture Capital's GPs Dave McClure and Aman Verjee on OpenAI's latest $500B valuation.

[ tech news + IPOs ]

00:44 - Navan IPO

03:38 - ⁠Reflection AI, Base Power

04:33 - ⁠prediction markets on fire

08:18 - China / Trump crypto crash

11:36 - Gold: gonna be gonna be Golden

[ turner novak, banana capital interview ]

15:09 - turner novak's background

27:10 - VC-posting

39:29 - “going viral” / distribution channels

53:41 - secondary strategies for DPI

[ valuation corner: openAI ]

1:11:42 - ⁠$500B secondary: AI bubble?

1:17:06 - OpenAI / Oracle / Nvidia deal

***

pod highlights this week:

-prediction markets are having a moment: Kalshi and Polymarket both announce huge funding rounds

-gold prices skyrocket; bitcoin crashes

-turner novak of banana capital on the art of 💩posting and how being a social media vc-fluencer helps him support his port co's and get better access to deal flow

-turner drops wisdom from his years working as an intern at AFORE to launching his own fund during quarantine and his investment thesis these days ("you need to fix something for someone")

-professor verjee walks us through the insane latest $500B OpenAI valuation at $500B (up from $300B in March 2025)

**

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ turner novak = https://x.com/turnernovak ]

[ 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 ]

episode 6 of @+[trading places] feat. our dear friend / VC’s chief graph officer, peter walker of carta—is out now!

00:00 — cold open

[ news ]

00:38 — this week’s news

01:34 — triple triple double double = ded ded DED

03:36 — state of the software 2025 report

07:42 — openAI completes tender offer… what now?

09:43 — IPOs Q3 update

11:43 — get ur IPO on: wealthfront

12:32 — cerebras don’t need no stinkin’ IPO!

14:20 — AI dev tools SO HOT RN[ interview: peter walker, carta ]

17:24 — introducing the head DATA NERD @carta

18:23 — peter walker’s journey

20:33 — are we out of the nuclear winter???

22:02 — what’s wrong with the AI bubble

26:13 — post-covid ZIRP29:28 — why companies stay private 10–12 years

40:31 — secondary buyers: do they know what they’re buying?

43:37 — are we in an AI bubble?47:02 — seed stage madness & too much money in venture

57:28 — wrap-up & peter’s 6-month prediction

[ valuation corner: revolut ]

01:00:59 — intro: revolut at $75B

01:04:30 — the BIG question for revolut investors***

pod highlights this week: dave mcclure and aman verjee react to controversial VC takes of the week heard on harry stebbings' 20VC and whether the golden rules of VC math are now ancient texts (is “triple triple double double” dead or does everyone just need to calm down amidst the AI fundraise hype?) -OpenAI’s tender offer: **only** $6 billion of the $10 billion of shares sold and what does this mean?-Wealthfront files for IPO; @+Cerebras’ unfiles for IPO-peter’s journey to becoming a LinkedInfluencer and VC’s data viz darling -peter’s takes on the AI bubble plus a first of firsts: series a startups x secondary sales per the data-professor verjee takes us through the $75 BILLION price tag on OG fintech revolut in this week’s [valuation corner]

[ trading places podcast = www.linktr.ee/tradingplacespod ]

[ peter walker = https://x.com/PeterJ_Walker ]

[ 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 ]

episode 5 of @+[trading places], a very bad 💩podcast about VC #secondary 2️⃣, broken unicorns 🦄💔& busted carry 😱, is out NOW!

this week, we sit down with Joe Schorge and Omolade Idebisi of EU fund of funds (FoF) Isomer Capital about secondary fund strategy, GP-led vs. LP-led and how they navigate a world of weird discounts when they go to trade in the secondary market.

plus Dave Mcclure shares his criteria on how he evaluates deals these days and Aman Verjee is BACK with another [valuation corner] feat. a breakdown of SpaceX’s latest price tag at $400B.

[news]

00:00 — cold open: “i love your fund… at a 47% discount”

00:42 — mega-deals mania (nvidia + openai $100b, oracle $300b, tether $500b)

06:17 — tiktok handoff: bytedance, oracle & trump’s blessing[interview: isomer capital]

22:45 — joe & omolade intro + isomer’s 10-yr journey into secondaries28:57 — vc secondaries ≠ pe secondaries (pricing, competition, access to data)

43:01 — gp-led vs lp-led, weird discounts & how deals actually get done

52:00 — case study: 24 lps sell, gp + co-lp + isomer buy in:

02:29 — revolut @ $75b: buy, sell, or hold?

[valuation corner: spacex]

1:06:12 — spacex @ $400b: is that cheap? starlink, cashflows & comps

1:21:00 — beyond starlink: mars colonies & east india company vibes

find us at:

[trading places podcast = www.linktr.ee/tradingplacespod]

[joe schorge = https://www.linkedin.com/in/joe-schorge-isomer/ | https://x.com/JSchorge ]

[rachel adebisi = https://www.linkedin.com/in/omolade-r-adebisi/]

[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 ]

[ trading places ] episode 4:a very bad 💩podcast about VC #secondary 2️⃣, broken unicorns 🦄💔& busted carry 😱

this week in 2ndry: we talk #SPVs #KYC and #liquidity w/ nik talreja CEO @ sydecar

timestamps:

[ tech + vc news ]

01:14 — ipo window creaks open (klarna, figma, netskope, stubhub)

07:00 — tiktok deal: oracle, xi, trump

10:16 — fed cuts 25bps → bullish for tech

[ nik talreja interview ]

13:30 — lawyer → lp → sydecar

19:55 — “you can buy a barge in alaska w/ an spv”

25:05 — continuation vehicles & liquidity headaches

[ valuation: stripe ]

58:23 — stripe vs adyen comps

01:03:04 — 2021’s $100b bubble outlier

[ OPP | omni ventures ]

01:06:14 — sushant sharma on omni venture labs

01:10:16 — exits via corp m&a → unicorn daydreams

01:11:43 — unlocking alpha: niche vc thesis

find us at:

[trading places podcast = www.linktr.ee/tradingplacespod]

[nik tarleja = https://x.com/niktalreja | https://www.linkedin.com/in/niktalreja/ ]

[shushant sharma = https://www.linkedin.com/in/sushantlnkd/ ]

[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 ]

IPOs are overrated. secondaries are where the bodies get buried.

in ep.3 of [trading places], dave mcclure & aman verjee get way too many smart people on one bad pod:

emily zheng (pitchbook) — the adult in the room with $61b in us vc secondaries, step-ups, discounts, rofrs, and why ai is the only thing saving your carry.

sim desai (hiive) — transparency = liquidity. kraken vs coinbase, spvs multiplying like rabbits, whales vs minnows, and how most of the market is just ai + crypto.

vlad voroninski (helm.ai) — why honda & vw are betting on his adas → l4 software, why oems can’t build it themselves, and whether robo-cars actually ship before the singularity.

vitaly golomb — the investor/friend translating helm.ai into vc-speak.

timestamps:

00:00 — [intro]

00:44 — [emily zheng, pitchbook]

11:24 — [interview: sim desai, hiive]

46:27 — [news + tech: revolut, klarna, affirm]

54:34 — [valuation corner: bytedance / tiktok]

01:05:07 — [deal spotlight: helm.ai ft. vlad voroninski + vitaly golomb]

find us at:

www.linktr.ee/tradingplacespod

[sim desai = https://x.com/SimDesai ]

[emily zheng = https://x.com/EMZheng47 ] | https://www.linkedin.com/in/emzheng/ | https://www.instagram.com/bycheznails ]

[vlad voroninski = https://x.com/VVoroninski]

[vitaly golomb = https://www.linkedin.com/in/vitalyg/]

[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 ]

subscribe for pod pain, regret, and the 137th best vc podcast.

a very bad podcast about broken unicorns & busted carry

in this ep of [trading places],

dave mcclure & aman verjee sit down with upfront ventures’ mark suster to talk:

* why he sold $600m+ in secondaries before the crash

* why vcs are emotionally bad at selling (spoiler: regret math)

* how funds fake “long-term conviction” while quietly cashing out

* the trillion-dollar tiktok problem & klarna’s rollercoaster ipo

* and why dpi is greater than tvpi (but most g(p)s don’t get it)

was that canva secondary a win or a loss? are vcs cowards for not taking chips off the table? is anthropic worth $170b or just another bubble?

tune in for regret, rage, and bad lp math.

subscribe for more pod pain.

timestamps:00:00 — cold open: the 137th best vc podcast00:52 — tech + news bytedance @ $330b — still cheap or still risky?03:38 — klarna ipo hangover: softbank’s fantasy, sequoia’s deal07:09 — is vertical saas dead? bessemer says nope10:16 — anthropic at $170b — bubble or rocket fuel?14:29 — the ipo bar is now $831m revenue15:09 — guest intro: mark suster of upfront ventures15:53 — founder → salesforce → vc: the suster origin story20:30 — how la became the new space-tech hub 🚀24:38 — “lines not dots” still haunting seed decks28:24 — why founder liquidity isn’t a sin (“feed the family money”)31:23 — selling discipline: house money vs regret math35:17 — lp reality check: they want dpi, not vibes43:09 — top quartile vc = 2.5x net (sorry, not 10x)45:40 — selling in 2021, buying in 2023 — suster’s playbook47:48 — who actually sells in secondaries (hint: not just losers)54:27 — valuation corner: canva vs figma — who’s cheap?01:07:28 — opp spotlight: humanrace capital

find us at: 

www.linktr.ee/tradingplacespod 

[mark suster = https://www.linkedin.com/in/marksuster/ | https://x.com/msuster ]  

[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 ]  

in this inaugural ep of [trading places], dave mcclure & aman verjee welcome david zhou (super clusters) to talk secondary markets, ai bubbles, and why your DPI might be total bs

we go deep on:

– openai’s $500B tender

– canvas vs databricks valuations

– LP/GP dynamics

– when to sell in secondaries

– spv food fights

– and the ghost of rap battles past

also: mean VC, VC trading cards, and the most painful vc math lesson you’ll hear this year.

subscribe for more pod pain.

Timestamps:

00:00 — cold open

43:10 — welcome to a very bad podcast about vc secondaries

00:01:00 — what is a secondary? (not just pre-ipo shares)

00:04:05 — how to think about valuation: revenue vs hype

00:06:07 —  openai at $500B — overpriced or fair?

00:10:48 — canva vs databricks — who’s actually worth it?

00:12:58 — is AI in a bubble? we argue both sides

00:15:33 — the SPV food fight begins

00:18:00 — why companies hate multi-layered SPVs

00:19:40 — guest intro: david zhou of super clusters

00:21:58 — how david became an LP by accident

00:23:46 — the rap origin story of erik torenberg

00:27:05 — what is DPI and when should GPs sell?

00:32:47 — the tradeoffs of selling winners too early

00:37:00 — are we living in an “overmarked” AI cycle?

00:40:56 — why pricing efficiency matters in secondaries

00:44:00 — the myth of public-like liquidity in secondaries

00:48:33 — valuation corner: databricks vs snowflake

00:54:12 — OPP spotlight: yohei nakajima & the rise of mean VC

01:01:09 — mark suster ep2 teaser

01:01:41 — bloopers

referenced links:

https://cupofzhou.com/the-non-obvious-emerging-lp-playbook/

https://cupofzhou.com/the-science-of-selling/https://www.nytimes.com/2025/08/19/technology/openai-chatgpt-stock-sale-valuation.html

https://www.reuters.com/technology/artificial-intelligence/what-is-deepseek-why-is-it-disrupting-ai-sector-2025-01-27/

https://africa.businessinsider.com/news/anthropic-seeing-voracious-demand-for-shares-is-clamping-down-on-a-certain-kind-of/4g25zyw

https://openai.com/policies/unauthorized-openai-equity-transactions/

https://www.investopedia.com/terms/1/2000-investor-limit.asp

find us at: www.linktr.ee/tradingplacespod 

[david zhou > https://www.linkedin.com/in/davidjzhou | https://x.com/cupazhou ] 

[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 ]