save $$ on your 2026 taxes by donating startup stock or VC fund interests into your own #DAF (Donor Advised Fund) -- for more info check out: PracticalVC.com/DAF more info on our upcoming DAF education webinars below and on our website. cc @UI_Charitable

If you want to save money on your 2026 taxes, signup for one of our free #DAF education webinars this Thu 9/24 or Mon 9/28 — info: PracticalVC.com/DAF ✅ Learn how to donate #startup stock or #VC funds to your own DAF (Donor Advised Fund), and save $25K-100K or more on your taxes every year💰 This can be *very* useful if you’ve had a big #secondary sale or #IPO in 2026, a large #capital gain, or just ordinary #income to offset🧾 You can also use your DAF to #invest tax-free in #startups & VC funds, or give to #charitable groups #nonprofits that have positive impact on the world📈💪🏽🕊️ DAF education webinars are hosted by @PracticalVC + @UI_Charitable

OMG this podcast is SO BAD.💩 wild speculation, inaccurate tech & financial analysis, clueless hot takes, and the hosts are a couple of tier 3 entitled VC jackasses. 🫏🫏 complete & total waste of time. 🙈

Dave and Aman break down a packed week in VC and tech in ep28 of @TradingVCs: OpenAI cancels sidequests, Kraken pulls its IPO, PayPal finally launches stablecoins in 70 countries, and a $55M prop bet on @iamcardib turns into a legal mess. The Private Mag7 gets a full ranking debate: SpaceX is comfortably #1 at over a trillion, but @anduriltech's surprise $20B DoD contract has it punching into the top three. Valuation Corner goes deep on the prediction market arms race: Kalshi vs Polymarket. @davemcclure and @AmanVerjee stack them up against DraftKings and FanDuel — and make their call. [ tech and vc news ] 0:33 — "you shall not pass" straits of hormuz ✋ 2:58 — private mag7 rankings 🏆 6:04 — @elonmusk terafab in austin 🔋 7:21 — @Tesla x @SpaceX super merger? 🤝 10:26 — @OpenAI abandons sidequests 🫳 11:41 — who will take no. 7 🔔 14:57 — @krakenfx freezes IPO plan 🥶 16:25 — @PayPal expands stablecoin 🌏 [ valuation corner: prediction markets ] 18:07 — @Kalshi vs. @Polymarket 🥊 20:15 — the incumbents: @DraftKings & @FanDuel 👴🏻 27:42 — which is best bet? 💰 28:40 — the tale of cardi b 💃 30:45 — second takes 😂

Practical VC founder Dave McClure joins UI Charitable CEO Daniel Blake for a session on giving like an investor: why donating cash is usually the wrong choice, how Donor-Advised Funds (DAFs) actually work, and how to donate illiquid or complex assets. nitter.net/i/broadcasts/1RJjpzbqA…

Runnin’ Down a Dream: How to Succeed and Thrive in a Career You Love by @bgurley has been one of the most valuable talks l've ever heard. For years I’ve been using ideas from that talk to build *this* podcast. Bill wrote a new book based on that talk. This episode explores the most valuable ideas from the book and talk.

As David notes, he was an early fan of the “beta” version of my new book. His support, alongside many others, gave me the confidence to invest five more years to deliver a richer, deeper, and hopefully more impactful piece of work. Much appreciation @FoundersPodcast.

OpenAI just closed a $110B funding round — the largest private raise in history. Meanwhile Stripe is now worth $159B, ByteDance hit $550B, and Jack Dorsey just laid off 4,000 employees citing AI productivity. In Episode 25 of Trading Places, @davemcclure and @AmanVerjee break down the biggest stories in AI, venture capital, and private markets. Then Daniel Blake (@UI_Charitable) joins us to explain the donor-advised fund strategy founders and investors use to turn illiquid assets into major tax deductions. 00:00 - cold open 00:47 - [ tech & vc news ] 02:07 -⁠ ⁠@OpenAI historic $110B raise 😲 06:14 - @AnthropicAI $6B staff share sale 🕺 07:45 -⁠ ⁠Pentagon cancels Anthropic 🧨 11:08 -⁠ @sama grabs DoD AI bag💥 14:26 -⁠ ⁠SaaSpocalypse update 📉 18:20 -⁠ ⁠@jack Dorsey lays off 4,000 🚶‍➡️ 21:37 -⁠ ⁠ByteDance @ $550B 💃 24:11 - ⁠@Plaid tender offer @ $8B 🔒 25:49 -⁠ ⁠@RobinhoodApp $1B private fund 🤺 27:24 - [ val corner: @stripe @ $159B ] 29:58 -⁠ ⁠Competitive analysis 💪 32:40 -⁠ ⁠@PayPal acquisition target 🎯 39:23 - [ intvw: Daniel Blake - UI Charitable ] 40:09 - introducing Daniel Blake and UI Charitable 👋 40:43 - the problem with selling privately held complex assets 🧐 42:39 - intro to Donor-Advised Funds 🤲 49:03 - DAFs for founders + employees 1️⃣ 52:10 - DAFs for investors 2️⃣ 1:01:54 - donate your crypto holdings 💛 1:03:43 - not all DAFs are created equal ≠ 1:05:07 - case studies 📖 1:10:20 - get in touch with UI Charitable 📞 1:10:43 - second takes Thanks for watching and sharing this horrible, no-good podcast with a friend.

How does OpenAI's projected $100B burn rate stack up historically? "Meta ... burned to date something between 73 and $76 billion. ... OpenAI will jump that shark. ... OpenAI over three years will outspend the Great Wall of China. ... The point is a lot, a lot of money in a very short amount of time." — @amanverjee with @davemcclure on @TradingVCs Ep.24

The AI funding race just hit a historic milestone. "It is going to be the biggest round of all time, and I mean, not just the biggest private round, but it dwarfs the biggest IPO of all time... It's over a hundred billion. Nvidia is now locked in for 30 billion. Amazon has already said they're in for as much as 50 billion and SoftBank and Microsoft and others are entered as well." — @Amanverjee on @TradingVCs Podcast Ep.24

6) another strategy that can be used in SPVs is to manage liquidity (aka #DPI) within the SPV by gradually shifting ownership in progressing winners from the original fund position to other members of the SPV. while this strategy may be complex and may limit some upside in the originating fund in exchange for (partial) liquidity, it allows for more predictable DPI in years 5-10 that isn’t dependent on exits or tenders or partial secondary sales to a 3rd party, and may avoid ROFRs and transfer restrictions by CEOs and boards that occur in an attempted secondary sale to a 3rd party. more on this topic later… it also raises issues around RIA vs VC exemption, QSBS treatment, and potential tax consequences for LPs, but overall it still gives the GP more control over liquidity and DPI.

5) lastly, whether you recycle or not, it’s become pretty clear to me that a strategy like Everywhere / Hustle that uses SPVs to double-down is highly preferable to a big reserve budget in the originating fund. 5a) if you win with your SPVs, it leverages the additional capital for extra carry. 5b) if you LOSE with your SPV bets, they don’t affect the results of your original fund, and you’re not recycling $ into your losers or tweeners and delaying DPI 5c) in a mix of SPV wins & losses, the GP gets carry from the wins but does NOT subtract losses like they would in a normal fund with reserves. (note: arguably this is bad for SPV LPs, however the market has spoken and doesn’t seem to care about this issue)

some thoughts on #reserves, #follow-on investing, #recycling, and #SPVs for emerging managers (h/t to @credistick @JoinOdin and @pmoe for starting the convo) + credit to @fredwilson @joshk @bfeld @msuster @pmarca on these topics for excellent advice when starting 500 way back when, even if i didn’t always listen ;)

Stripe CEO Patrick Collison: "Software should be like pizza… cooked right then and there at the moment of use." "You don’t want mass-produced industrial scale software. You want bespoke custom software made for you, that moment." "Up until now, the economics of software have been conceived as fixed cost and then infinitely monetized." "Once there are inference costs and custom creation involved, it really shifts. It’s kind of the non-Walrasian software regime." @patrickc with @collision on @tbpn

🥊 $830B vs $380B 🥊 Welcome to Episode 24 of @tradingvcs This week, @davemcclure & @AmanVerjee debate @OpenAI vs @Anthropic and make bets on who will ultimately win. Plus: guest @thetyson on pricing transparency, broker networks, and what’s really happening in secondaries. Watch below: 00:53 - [ tech & vc news ] 02:09 - ⁠OpenAI @ $830B🥇 02:56 - ⁠ Anthropic @ $380B🥈 04:02 -⁠ ⁠@stripe tender @ $140B 💸 06:38 -⁠ ⁠@databricks @ $134B 🧱 08:39 - ⁠@harvey @ $11B👨🏽‍⚖️ 11:07 -⁠ ⁠SCOTUS rejects Trump Tariffs 🙅‍♂️ 22:30 - [ intvw: Tyson Hendricksen / @noticedotco ] 23:17 - ⁠olympic training to 🍍 farmer 26:21 -⁠ ⁠founding Notice 💼 33:48 -⁠ ⁠product walkthrough 🚶‍➡️ 37:58 -⁠ why people need transparent pricing 👀 55:50 - prediction markets 🎰 [ val corner: OpenAI vs Anthropic ] 1:03:20 -⁠ ⁠OpenAI raise history 🚀 1:08:04 -⁠ ⁠OpenAI vs. Anthropic 🥊 1:13:43 - ⁠who wins Gold 🥇 1:18:07 - second takes Bonus - Don't miss the webinar on Donor-Advised Funds with Dave and Daniel Blake of UI Charitable. This Thursday, Feb 26th and Wed, Mar 4th, 11 a.m. PT. Sign up online via practicalvc website.

New episode of Trading Places Podcast with @davemcclure and @AmanVerjee out now! 🚨 This week is a full-spectrum market tour: the latest rumors swirling around Elon’s empire, the mega-rounds and IPO chess games of Anthropic + OpenAI, & the reality check hitting public SaaS multiples reported by @jaminball. We’re joined by Anurag Chandra (trustee of San Jose Pension Fund) for a rare look inside how real capital allocators think: risk budgets, time horizons, pension constraints, and why governance + incentives matter more than “manager genius.” Then we head to Valuation Corner LATAM with Karin Tenenbaum @LadyChutzpa from the @PracticalVC team for a breakdown of Latin America unicorns, the IPO window reopening, and what could be next after PicPay’s IPO. Timestamps: 0:00 – cold open 00:53 – [ news ] 1:13 – Elon Inc: xAI + SpaceX + Tesla 🚀 6:06 – @AnthropicAI doubles to $350B 💰 8:16 – @OpenAI Q4 IPO 🏁 12:25 – @get_Ethos $200M US IPO 🔔 13:55 – AI eats SaaS 🍽️ @jaminball inspired 16:00 – Kevin Warsh Fed chair nod 🪑 19:04 – @Waymo $110B valuation 🚕 21:37 – social media goes on trial 👩🏽‍⚖️ 24:11 – moltbot viral swarm AI 🦞 30:31 – [ intvw: Anurag Chandra ] 32:05 – $2B VC money managed 💪 33:12 – Family office fundamentals 💼 37:40 – San Jose Pension Fund success 🙌 38:17 – Future of San Jose 🔮 1:01:32 – [ val corner: @picpay $2.5B IPO ] 1:02:07 – Analysis: LatAm exit market & liquidity history 1:03:43 – top LatAm unicorns 🦄 1:11:44 – PicPay & fintech competition 1:17:46 – second takes

The center of gravity in venture has shifted from IPOs to secondaries. CEO @noelregrets & Co-Founder @adamcrawley1 joined @PracticalVC alongside our research partner, Sacra’s @ballve, to unpack the new mechanics of venture liquidity: 🤖 Capital concentration in AI infra & model platforms 🏛️ Companies staying private far longer 📉 Valuations vs. fundamentals in late-stage AI 📊 Data-driven coverage of private markets 🧱 Augment’s role vs. banks & brokers as infra 💸 Explosion of SPVs & structured secondaries Catch the full episode here: vist.ly/4nu78 #VC #Secondaries #AI #FinTech

Thanks @PracticalVC for having me on the pod, and to @ballve from Sacra for the research firepower. 🎙️ We got into: ⚙️ Capital concentration in AI infra & model platforms 🏦 Why companies are staying private way longer 📉 Valuations vs. fundamentals in late-stage 📊 AI Data-driven coverage of private markets 🧩 Augment’s role vs. banks/brokers in secondaries 💸 Explosion of SPVs & structured secondaries Catch the full episode here: piped.video/KD4PTYpOEg0?si=aVfk…

Episode 19 of [trading places] is here. @davemcclure and @AmanVerjee break down what’s actually happening in venture right now. we start with the reopening IPO market in 2026, @a16z raising another $15B, @bgurley's latest AI takes, and why everyone suddenly cares about private-market liquidity again. then we’re joined by @nathanlustig (@MagmaPartners) and @LadyChutzpa (@PracticalVC) for a deep dive on latin america — the exits, the capital cycles, Pix payments in brazil, verticalized plays like Mottu, and why LatAm may be the most misunderstood venture market of the last decade. we wrap with a valuation corner on @discord — its rejected Microsoft offer, the $15B 2021 valuation, and what it might actually be worth now in a very different market. 0:00 - cold open [ tech & vc news ] 1:24 - 2026 IPO market opens 🏁 4:31 - a16z raises $15B across several funds 🥇 6:38 - Top 10 VC firms in the world 12:36 - China blocks @ManusAI ✋ 16:16 - Bill Gurley on AI 24:15 - @AnthropicAI, @OpenAI, @xai valuations 💸 32:15 - Discord & @Strava IPOs 🔔 37:29 - G Squared + Nasdaq team up for private market liquidity 🤝 [ intvw: Nathan Lustig / Magma Partners ] 40:26 - Nathan Lustig background and moving to Chile 40:34 - Karin Tenenboim on PVC LatAm strategy 🌎 49:25 - Brazil Pix payments breakthrough 52:45 - Mottu vertical stack (Motorcycle leasing/logistics) 🏍️ 1:07:30 - Investing strategy in LatAm 1:08:56 - PVC + Magma LatAm 2ndry Fund partnership 🥳 [ val corner: Discord IPO ] 1:34:36 - What is Discord 🗣️ 1:42:07 - 2021 valued at $14.7B / $15B 📈 1:43:24 - Rejected $12B Microsoft offer 🚫 1:43:24 - Valuation today 🤔 1:44:19 - second takes thank you for watching our very bad podcast on VC secondary

#TradingPlaces Pod: Top 5 Reasons People Sell #Secondaries in VC piped.video/zUxf0y84gok?si=9gMR… via @TradingVCs cc #BenBlack #AkkadianVC @raiseconference