E23: Radical DAs, breaking down FB/Google vs. Australia, sustained fear post-vaccine & fan questions

The Robinhood interview nearly fractured the podcast: David Friedberg tried to kill the episode and threatened to quit after concluding it had become a PR exercise. The group moved toward giving each host veto power over future episodes, while revealing that Vlad Tenev’s PR representative had sat in on the recording.

David Sacks openly acknowledged the conflict created when investors interview founders they financially support. He said he naturally gives portfolio founders the benefit of the doubt and could not authentically “trash” his own investment, even while concluding that Tenev’s strategy was largely to avoid saying anything damaging or quotable.

The sharpest media-policy distinction was between linking to journalism and reproducing enough of it to replace the publisher. Jason Calacanis argued that URLs and headlines should remain free while photos, abstracts and substantial snippets should require licenses; Sacks opposed Australia’s government-set payments and warned against effectively taxing hyperlinks.

Friedberg argued that America’s early vaccine bottleneck was administrative rather than primarily a shortage of doses. He cited production of roughly three to four million doses daily, criticized California’s eligibility and scheduling rules, and predicted that supply would overwhelm those restrictions by May, forcing broader access.

Their long-term investment theses were unusually specific: Friedberg chose biomanufacturing, Sacks bottom-up viral business software, and Chamath Palihapitiya inequality-reducing businesses and climate technology. Sacks said seeing PayPal reach roughly $200 billion and Slack achieve a $27 billion outcome convinced him that his bigger mistake was abandoning good ideas too early.

Calacanis disclosed that his investing syndicate had grown to 7,000 accredited investors and was running at roughly $60 million of annual capital deployment. He said the syndicate received access to about 60% of his deals, while his fund retained access to all of them, making the crowd vehicle several times larger than the fund.

Chamath said selling Bitcoin too early cost him “many tens of billions” in unrealized gains after he once controlled a low-to-mid-single-digit percentage of the available supply. He also spent 2,800 bitcoins on a $1.6 million Tahoe property in 2014—coins he estimated during the episode would then have been worth roughly $140–150 million.

Friedberg and Sacks also disclosed misses that illustrate the cost of underestimating compounding winners. Friedberg passed on investing $50,000 in Square at roughly a $10 million valuation, while Sacks said a failed early Twitter secondary transaction probably cost him “a couple hundred million” dollars.