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|