OpenAI just closed a historic $110B funding round — the largest private raise ever.
At the same time:
• Stripe surged to a $159B valuation
• Anthropic is selling $6B of employee shares
• The Pentagon reportedly blocked Anthropic from defense work
• Sam Altman quickly picked up a DoD AI contract
• ByteDance hit a $550B valuation
• And Jack Dorsey laid off 4,000 employees citing AI productivity
Welcome to Episode 25 of Trading Places, where Dave McClure and Aman Verjee break down the biggest stories in venture capital, AI, and private markets.
In Valuation Corner, we analyze why Stripe now commands a $159B valuation — and whether PayPal could become an acquisition target.
Then we’re joined by Daniel Blake (UI Charitable) to explain a powerful strategy many founders and investors overlook:
How Donor-Advised Funds (DAFs) can turn illiquid startup equity, fund interests, or crypto into major tax deductions.
If you’re a founder, VC, or startup employee sitting on paper wealth, this episode is worth watching.
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00:00 - cold open
00:47 - [ tech & vc news ]
02:07 - OpenAI historic $110B raise 😲
06:14 - Anthropic $6B staff share sale 🕺
07:45 - Pentagon cancels Anthropic 🧨
11:08 - Sam Altman 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 - Robinhood $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
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[ links ]
[ invest = https://practicalvc.com ]
[ trading places socials = www.linktr.ee/tradingplacespod ]
[ daniel blake = https://www.linkedin.com/in/drblake/ ]
[ donor-advised fund info = https://www.uicharitable.org/ ]
[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 ]
*This content is for informational purposes only and should not be considered investment advice.
#VentureCapital #OpenAI #Stripe #Startups #AI #PrivateMarkets #TechNews