Transparent VC Podcast · Tribe Talkin'

Ep 123: Never Waste A Good Crisis. We'll Need More Than "I Don't Want To Pay Tax". Your Business Is Not Your Baby. Sharts.

15 May 2026 · 55:39

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Don, Aaron and Jack unpack a big week in venture, AI and building companies.

  • The week after CGT week: a suspiciously frank 'Albo' clip on negative gearing ('I said no 50 times, then changed it'), auction clearances plummet, and LPs shift into wait-and-see mode. Don's take: with the right structures the hit is roughly 23% to 30% tax, which is a very expensive reason to miss the venture bus.
  • Tim Doyle's fix for the CGT mess: make ESOPs exempt so startups win the global talent war and more operators join great teams instead of founding average ones. The hosts stress test it and predict every founder (and investor) would suddenly demand a spot on the ESOP.
  • Christopher Joye's charts show Australia sliding toward the least competitive CGT regime among its peers, but Capital Brief nails the real problem: 'I don't want to pay more tax' is not an argument, the industry has to sell jobs, super returns and sovereign capability.
  • Don's 'bureaucrat nation' post (DAs blowing out from 3 months to 12, publicly funded workers up 45% since 2007) triggers a comment-section brawl, and a bigger worry about whether rational public debate is still possible.
  • AI note-takers are making lawyers nervous: bring a bot into the wrong meeting and you can wave goodbye to legal privilege, while every offhand comment becomes searchable across the whole organisation.
  • Ken Griffin says Citadel is watching work that took finance PhDs weeks get done by AI agents in hours. Don backs it up by building a childcare rostering compliance tool in 10 minutes that found 101 hours of excess float.
  • The bus has left for non-AI-native executives: a senior HR exec who 'chose to sit back' is still job hunting a year later, while a college kid's fully AI OnlyFans girl clears $43K in 30 days from 1,247 paying subscribers.
  • Take-Two's Strauss Zelnick on why AI is great at asset creation but hit creation is another thing entirely, and Jack asks whether a million free vibe-coded games drags down the price of GTA VI.
  • Jason Lemkin declares firesides and keynote speakers dead because podcasts do it better, so what should events become? Plus philosophy corner via Dave Letterman: make sure you fail doing exactly what you wanted to do.

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