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
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|
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://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 ]