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trading places
Practical Venture Capital
17 episodes
2 days ago
a very bad 💩podcast about VC secondaries broken unicorns ❤️‍🩹🦄 & busted carry 📉🙈
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All content for trading places is the property of Practical Venture Capital and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
a very bad 💩podcast about VC secondaries broken unicorns ❤️‍🩹🦄 & busted carry 📉🙈
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Investing
Business
Episodes (17/17)
trading places
TP17: Caplight's Javier Avalos 📊 | Secondary Boom 🔥| Why Banks Need Private Mkts 🏦 | $230B xAI 🚀

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

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2 weeks ago
1 hour 28 minutes 32 seconds

trading places
TP16: Bridgespan VC 💰| Employee Stock Option Financing 🫴| Oracle Stock 📉 | Waymo Valuation 🏎️

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

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3 weeks ago
1 hour 29 minutes 14 seconds

trading places
TP15: Ben Black Akkadian Ventures🏆 | Secondaries Secrets 💎 | RAISE Conf 🎯 | Vercel $9B 🚀

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

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4 weeks ago
1 hour 19 minutes

trading places
TP14: Michael Burry vs Big Tech 🎯 | Grayscale IPO Disaster? 💥 | Thanksgiving Special 🦃

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



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1 month ago
32 minutes 28 seconds

trading places
TP13: Emily Zheng of Pitchbook 📊 | VC Secondaries Hit $95B 🔥 | Ramp $32B 💳

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

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1 month ago
1 hour 16 minutes 25 seconds

trading places
TP12: Top Tier's Sean Engel 🎯 | AI Bubble? 🎈 | Data Centers 🏗️ | Kraken 💰

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

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1 month ago
1 hour 23 minutes 4 seconds

trading places
TP11: Daniel Blake of UI Charitable 💰🎁 | Donor-Advised Funds 📊 | Polymarket vs Kalshi Showdown 🎲

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|

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1 month ago
1 hour 20 minutes 32 seconds

trading places
TP10: Blackbird VC + Canva 🎨 | OpenAI $1T IPO😱 | Tether $500B Val | EquityZen Acquisition

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

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1 month ago
1 hour 34 minutes 15 seconds

trading places
TP8: Phil Haslett EquityZen 🧘🏻‍♂️ | Goldman Acquires Industry Ventures 💰 | Deel at $17B 🤝

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 ]

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2 months ago
1 hour 22 minutes 34 seconds

trading places
TP9: Seedcamp Founders 🇪🇺 | Prediction Markets 📈 | Oracle $38B 💰 | Anthropic $183B 🤖

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

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2 months ago
1 hour 38 minutes 55 seconds

trading places
TP7: Turner Novak 🍌🧢 | Prediction Market 📈 | Gold Rush💰 | OpenAI's $500B Valuation 🙀

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 ]

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2 months ago
1 hour 27 minutes 1 second

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 months 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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3 months 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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3 months 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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3 months 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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4 months 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 ] 


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4 months ago
1 hour 2 minutes 34 seconds

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