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The Diligent Observer Podcast
Helping angel investors see what most miss.
Want more? Get essential angel intel in 5 min with The Diligent Observer Newsletter: your weekly shortcut to vetted deals and expert takes.
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The Diligent Observer Podcast
Latest Episodes
Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act
🗞️ Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 🗞️Today's episode explores three ideas that caught my attention:① Star...
Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing
🗞️ Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 🗞️Today's episode explores three ideas that caught my attention:①
Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation
🗞️ Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 🗞️Today's episode explores three ideas that caught my attention:① Process...
Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)
Today's episode explores three ideas that caught my attention:The university endowment mindset shift - Transition from the for-profit real estate world to Stanford's endowment revealed how different time horizons (centuries v...
Episode 58: "$15 Million in Capital Gains: Gone" Startup Wealth Strategist Bryan Hasling on What Angel Investors Need to Know About QSBS, Maximizing the Tax Benefits of a Losing Investment, and the Limits of Tax-Driven Deal Selection
Today's episode explores three ideas that caught my attention:The most important tax provision you’ve never heard of: 1244 losses. Bryan made the case (and I agree 100%) that most angels will benefit as much or more from ordi...
