the #1 podcast about all the #2 in VC

episode 16 — adrien gautier: employee stock option secondaries, oracle’s debt problem & waymo @ $45b

in this episode of trading places, dave mcclure & aman verjee welcome adrien gautier (bridgespan vc) to break down one of the most misunderstood corners of venture secondaries: employee stock option financing. adrien explains how bridgespan consistently buys common shares at 30–70% discounts to preferred, why non-recourse structures matter, and how tender offers have become a core exit path for late-stage private companies.

this week’s agenda:
– oracle’s bad week: leverage fears, cds spikes, and why debt matters again
– the 2026 ipo pipeline heats up: spacex, openai, and anthropic eye historic exits
– wealthfront stalls, medline prices at $55b, boom supersonic raises $300m
– goldman backs harness at $5.5b as ai infra funding keeps rolling
– fed uncertainty, rate cut math, and china blocks nvidia h200 exports
– adrien on bridgespan’s employee stock option strategy and equitybee partnership
– how tender offers became the default liquidity path for $10b+ companies
– why bridgespan generated dpi fast — including a 10x exit from firefly aerospace in 60 days
– valuation corner: waymo @ $45b — software vs hardware, tesla comps, and why legacy oems can’t catch up

employee liquidity used to be a perk — now it’s a strategy.
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episode 15 — ben black: secondary secrets, lp management truth bombs & vercel @ $9b

in this episode of trading places, dave mcclure & aman verjee sit down with ben black — founder of akkadian ventures and creator of the legendary raise conference — to unpack the real mechanics behind venture secondaries, lp management, fund discipline, and what it actually takes to build a durable vc firm. from losing his biggest lp during the 2008 crisis to running one of the most successful secondary funds in venture, ben shares hard-earned lessons, wild stories (including a green ferrari), and the philosophy behind saying “no” to 200+ lps a year.

this week’s agenda:
– spacex leaps to an $800b valuation, beating openai’s $500b sprint
– anthropic hires ipo counsel as rumors swirl around a potential $300b raise
– openai enters “code red,” netflix bids $83b for warner brothers, and prediction markets keep climbing
– kalshi @ $11b and polymarket @ $15b challenge traditional sportsbooks
– harvey ai skyrockets from $3b → $5b → $8b
– databricks hits $134b while meta’s vr spend goes up in flames
– ben on becoming a secondary pioneer and building akkadian from crisis to category leadership
– why lp management is more important than deal picking — quarterly letters, in-person meetings, and radical honesty
– raise conference origins: from 140 people to 1,000+ applications and global emerging manager dominance
– valuation corner: vercel @ $9b — 200m+ arr, 70–100% yoy growth, and how their ai cloud platform stacks up against digital ocean and replit

secondary liquidity used to be a workaround — now it’s the strategy. subscribe for more pod pain.

episode 14 — michael burry vs big tech, luma ai’s mega-raise & the grayscale ipo disaster watch

in this thanksgiving episode of trading places, dave mcclure & aman verjee dig into michael burry’s latest firestorm — accusing nvidia and the hyperscalers of accounting “fraud,” comparing today’s ai boom to worldcom, and warning that big tech is hiding billions through depreciation tricks. is burry the modern cassandra or just shouting into the wind? we break down the numbers, the history, and the hype.

this week’s agenda:
– burry vs nvidia: fraud claims, depreciation math, and the return of doomsday energy
– cassandra unchained: why burry keeps being early… and often wrong
– hyperscaler accounting deep dive: extending server life 3 → 6 years and what it does to earnings
– worldcom flashbacks: what maps to 2025 ai spending and what absolutely doesn’t
– luma ai rockets to an $8b valuation with saudi pif backing — a new geopolitical chapter in ai funding
– india’s ipo moment: meesho’s $600m debut signals real global alternatives to u.s. public markets
– revolut completes a $75b secondary sale amid questions about business mix
– valuation corner: grayscale @ $33b — 60x revenue, 88% product concentration, shrinking market share, and fee structures from another century

burry may be yelling “fraud,” but grayscale’s the one giving off real smoke.

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episode 13 — emily zheng: $95b secondaries, ramp @ $32b & the new exit era

in this episode of trading places, dave mcclure & aman verjee (with amber sitting in) welcome emily zheng (pitchbook) to break down why vc secondaries have officially gone mainstream — hitting $95b annually and now sitting shoulder-to-shoulder with ipos and m&a as a real exit path.

this week’s agenda:
– market turbulence: bitcoin crashes, fed uncertainty, nvidia panic, and the jobs recession vibes
– ai wars: google’s gemini 3 comeback and anthropic raises $15b from microsoft & nvidia
– prediction markets escalate — kalshi ($11b) vs polymarket ($15b) in a regulatory arms race
– fintech momentum: ramp raises $300m @ $32b, kraken hits $20b with citadel stepping in
– platform consolidation: schwab acquires forge for $660m, secondary platforms go big-bank
– emily on pitchbook’s q3 report: $95b secondary volume, 682% spv explosion, and top 5 companies driving 54.7% of all trading
– discount math: recent rounds trade near par (0–8.5%) while 2020–22 vintages take 33–61% haircuts
– valuation corner: ramp @ $32b — $1b arr, 133% growth, profitable, and a brex showdown brewing

ipos used to be the finish line — now they’re just one option on the menu.
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episode 12 — sean engel: ai bubble talk, secondary strategies & the data center crunch

in this episode of trading places, dave mcclure & aman verjee sit down with sean engel (top tier capital partners) to unpack the new math of venture liquidity — from gp-led secondaries to fund-of-funds velocity. they also dive into whether we’re back in bubble territory as ai valuations go vertical and data center capacity hits the wall.

this week’s agenda:
– are we in another ai bubble? multi-billion seed rounds meet 300% growth curves
– data centers hit capacity limits — hyperscalers plan $100b+ in builds but energy & permitting lag behind
– softbank sells nvidia (again) to bet on openai — the world’s most expensive fomo
– goldman, schwab, and morgan stanley consolidate the secondary market — exits are the new entries
– sean engel on top tier’s velocity fund: 2x base case, 3x good days, 1.5x bad days — dpi in half the time
– lp/ gp secondaries, continuation vehicles, and how liquidity is finally coming to venture
– valuation corner: kraken @ $15b — crypto exchanges grow up as citadel steps in

when the smartest people in venture start selling early, maybe the bubble’s already here.
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episode 11 — daniel blake: the irs as your secondary buyer, dafs, & prediction market wars

in this episode of trading places, dave mcclure & aman verjee sit down with daniel blake (ui charitable) to explore how donor-advised funds (dafs) are becoming the stealth liquidity tool of 2025 — turning illiquid venture assets, crypto, and even carried interest into powerful tax deductions.

this week’s agenda:
– the irs as your secret secondary buyer — dafs, fmvs, and 2021-era valuations that still pay
– schwab acquires forge at a 75% premium, joining goldman and morgan stanley in the secondary land grab
– polymarket ($9b) vs kalshi ($5b) — prediction markets move in on draftkings and fanduel’s $45b turf
– ripple raises $500m @ $40b, metropolis at $1.6b — capital markets still alive (barely)
– donating crypto, s-corps, and illiquid vc positions — daniel’s guide to tax-efficient philanthropy
– valuation corner: the prediction market bubble or the future of truth?
– pvc spv spotlight: helm.ai — democratizing autonomous driving beyond tesla and waymo

tax breaks, liquidity hacks, and speculative truth markets — it’s a different kind of capitalism.
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episode 10 — rick baker: the canva bet, openai’s $1t ipo & tether @ $500b

in this episode of trading places, dave mcclure & aman verjee sit down with rick baker (blackbird ventures) to unpack how a $250k seed check in canva became a $40b success — and how blackbird built australia’s venture ecosystem from the ground up.

this week’s agenda:
– openai eyes a $1t ipo as microsoft trims to 27% and california greenlights its for-profit pivot
– big tech’s $125b quarterly ai spending spree across microsoft, amazon, alphabet & meta
– secondary shake-up: morgan stanley buys equityzen, goldman absorbs industry ventures
– ipo & funding watch: navan, mer, securitize, and the latest valuation rollercoasters
– rick on canva’s rise, fund i’s $120m secondary at 93% nav, and managing lp pressure
– the australian vc ecosystem: from super funds to the atlassian-canva alumni wave
– valuation corner: tether @ $500b — $13b in profits, 75% market share, and murky reserves

founder grit, secondary liquidity, and stablecoin delusion — it’s all here.
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episode 9 — reshma sohoni & carlos espinal: seedcamp’s secondary play, ai politics & tether’s trillion-dollar moment

in this episode of trading places, dave mcclure & aman verjee welcome reshma sohoni and carlos espinal of seedcamp to unpack europe’s secondary revolution and the new global liquidity race.

this week’s agenda:
– prediction markets explode as kalshi and polymarket hit unicorn status
– google deepens its $3b partnership with anthropic while oracle raises $38b in private credit to fuel ai datacenters
– tether passes 500m users and $13b annual profit — double blackrock’s earnings
– seedcamp reveals how selling funds 1 & 2 to molten unlocked a 4x+ return and powered fund 4
– the 20% rule: why selling early isn’t timing, it’s discipline
– valuation corner: professor verjee dissects anthropic’s $183b valuation and ai’s ideological divide

founders, lps, and ai maximalists alike — this one hits every market nerve.
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episode 8 — phil haslett: goldman’s secondary grab, ai chip wars & deel @ $17b

in this episode of trading places, dave mcclure & aman verjee sit down with phil haslett (equityzen) to decode wall street’s big move into venture secondaries — and how openai’s $500b chip empire is reshaping everything from nvidia to oracle.

this week’s agenda:
– openai’s chip kingmaker moment: $500b+ in equity deals with amd, broadcom, nvidia & oracle
– goldman sachs acquires industry ventures for $965m — the secondary market goes institutional
– tempo’s $5b series a & anysphere’s $27b valuation — bubble or breakout?
– phil on equityzen’s 12-year ride from 500 startups to billions in secondary trades
– retail vs institutional: why 29% discounts still move markets
– valuation corner: deel @ $17.3b — solid fundamentals or hr-tech espionage theater?

ai deals, wall street money, and spy-level hr drama — just another week in venture purgatory.
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episode 7 — turner novak: shitposting, prediction markets & openai @ $500b

in this episode of trading places, dave mcclure & aman verjee welcome turner novak (banana capital) to unpack the new reality where memes move markets and prediction markets go mainstream.

this week’s agenda:
– kalshi & polymarket raise big — are prediction markets the next gold rush or just expensive gambling?
– gold hits highs, bitcoin tanks — flight to safety or flight to prophecy?
– turner on shitposting as a venture strategy, social media clout as dealflow, and building banana capital post-quarantine
– investing thesis: “you need to fix something for someone” — no ai fairy dust allowed
– valuation corner: aman breaks down openai’s jump to $500b (yes, again)

if twitter is the new bloomberg terminal, turner is already trading. subscribe for more pod pain.

episode 6 — peter walker: carta charts, openai tender & the death of triple-triple-double-double

in this episode of trading places, dave mcclure & aman verjee invite peter walker (carta) to unpack whether vc’s sacred growth mantra — 3x 3x 2x 2x — is officially dead, or just drowning in ai delusion.

this week’s chaos includes:
– openai’s tender: only $6b of $10b actually sold — should founders worry?
– wealthfront files, cerebras un-files — ipo windows or revolving doors?
– peter’s rise as carta’s chart whisperer & reluctant linkedfluencer
– ai bubble talk: panic or paradigm shift?
– new data drop: series a founders selling secondaries — already?
– valuation corner: aman dissects revolut’s $75b fintech fever

vc math used to be religion. now it’s vibes and liquidity.
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episode 5 — isomer capital: secondary science, spacex @ $400b & eu discount hunting

in this episode of trading places, dave mcclure & aman verjee sit down with joe schorge and omolade idebisi of isomer capital — europe’s fund-of-funds dissecting the secondary market with surgical precision. they break down gp-led vs lp-led deals, weird eu discounts, and why pricing risk in 2025 feels like quantum physics.

meanwhile:
– dave reveals his current deal filters (aka why he says no)
– aman’s valuation corner returns with spacex at $400b
– debate of the week: revolut — buy, sell, or hold?

this one is for the allocators, the spreadsheet monks, and anyone who thinks fof capital is “boring money.”
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episode 4 — nik talreja: spvs, tiktok diplomacy & stripe’s $91b hangover

in this episode of trading places, dave mcclure & aman verjee dive into the messy middle of venture — where spvs meet kyc, and liquidity dreams go to die. joined by nik talreja (sydecar), they break down why anyone with a docu-sign can launch an spv… and why that might be a problem.

they get into:
– klarna, netskope & stubhub teasing an ipo window
– tiktok: oracle, xi, trump — one app, three egos
– fed cuts & tech hopium
– “you can buy a barge in alaska with an spv” (yes, really)
– continuation vehicles & lp migraines
– stripe @ $91b vs adyen — bubble math revisited

plus: sushant sharma (omni ventures) drops niche alpha and unicorn delusions via corp m&a.

no inspiration. just cap tables and regret.
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episode 3 — sim desai, emily zheng & vlad voroninski: the secondary swarm

in this third episode of trading places, dave mcclure & aman verjee accidentally assemble a liquidity brain trust to talk why ipos are overrated and secondaries are the real game.

guests include:
– emily zheng (pitchbook) — breaking down $61b in vc secondaries, step-ups, discounts, and why ai is the only thing propping up your carry.
– sim desai (hiive) — on transparency vs liquidity, kraken vs coinbase, spvs breeding like rabbits, and why today’s market = ai + crypto or nothing.
– vlad voroninski (helm.ai) — on why honda & vw are betting on his adas-to-l4 stack, why oems can’t build it, and whether robo-cars land before the singularity.
– vitaly golomb — translating helm into vc so the rest of us can pretend we get it.

if you still believe in ipo fairy tales, this episode will hurt.
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