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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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 marketsβwhere Polymarket and Kalshi are coming for DraftKingsβ and FanDuelβs 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:
β’ Daniel Blake explains why donating appreciated stock beats cashβand how you can reset your cost basis while earning tax deductions.
β’ The IRS as your secondary buyer: fair market value appraisals on 2021-era valuations can generate 30β50Β’ on the dollar in tax savings.
β’ Charitable UI accepts everything: S-corps, carried interest, crypto, even your hobby farm greenhouse.
β’ Schwab pays a 75% premium for Forge Global at $660Mβthe third major secondary platform acquisition after Goldman/Industry Ventures and Morgan Stanley/EquityZen.
β’ Polymarket ($9B) and Kalshi ($5B) are positioning to eat DraftKingsβ and FanDuelβs $45B+ sports-betting duopoly.
β’ Daveβs hot take: donate your worst illiquid assets (2020β21 vintage anyone?) before values drop furtherβcapture the tax savings now.
β’ PVC SPV: Co-invest with Practical Venture Capital in Helm.aiβthe 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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