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trading places
Practical Venture Capital
6 episodes
4 hours ago
a very bad 💩podcast about VC secondaries broken unicorns ❤️‍🩹🦄 & busted carry 📉🙈
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a very bad 💩podcast about VC secondaries broken unicorns ❤️‍🩹🦄 & busted carry 📉🙈
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Investing
Business
Episodes (6/6)
trading places
TP6: Peter Walker of Carta 📊 | OpenAI Tender 🧾| Revolut $75B Valuation 💳 | Is 3X 3X 2X 2X 💀?

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 ]



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3 weeks ago
1 hour 7 minutes 22 seconds

trading places
TP5: Isomer Capital 🔬 | SpaceX $400B Valuation 🚀 | Nvidia 🤝 OpenAI | Revolut: Buy Sell or Hold? 🤔

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 ]

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1 month ago
1 hour 25 minutes 42 seconds

trading places
TP4: Sydecar 🛵 | TikTok deal 🇺🇸🤝🇨🇳 | Netskope Stubhub Figure IPOs 📈 | xAI @ 200B💰| Stripe @ 91B 💳 | Omni Ventures ⚙️

[ 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 ]


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1 month ago
1 hour 14 minutes 26 seconds

trading places
TP3: ⁠sim desai hiive🐝 •⁠ emily zheng pitchbook⁠⚾️📓 •⁠ vlad voroninski helm.ai 🤖🚙 •⁠ bytedance 🫦🕺🏻-- [trading places] ep.3

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.


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1 month ago
1 hour 15 minutes 59 seconds

trading places
TP2: why VCs panic sell 💸 & unicorns break 🦄 — mark suster — [trading places] 

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 ]  

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1 month ago
1 hour 17 minutes 1 second

trading places
TP1: a VERY BAD💩 podcast on VC 2️⃣NDRY, BROKEN❤️‍🩹 unicorns🦄 & BUSTED carry😱

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 ]  




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2 months ago
1 hour 2 minutes 34 seconds

trading places
a very bad 💩podcast about VC secondaries broken unicorns ❤️‍🩹🦄 & busted carry 📉🙈