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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.
https://www.thediligentobserver.com/
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Podcasting since 2024 • 59 episodes
The Diligent Observer Podcast
Latest Episodes
Episode 51: "Obsess Over Founder DNA" | Denver Ventures Co-Founder Amy Brandenburg on Founder Assessment Methods, Angel Community Scaling Strategies, and Portfolio Discipline
Today's episode explores three ideas that caught my attention: Angel investment dollar-cost averaging - The vintage year matters, and Amy's comments got me thinking about how traditional finance concepts like DCA c...
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Season 1
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Episode 51
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38:48
Special Episode: Breaking Down "Angel Network Pulse: The First 101"
We just released Angel Network Pulse: The First 101 - an analysis of 101 angel network investments tracked over nine months through The Diligent Observer newsletter. Here's what I learned:The Big Picture101 deals acr...
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Season 1
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15:04
Episode 50: "Crush the Cost of Diligence" | Serial Entrepreneur Wade Myers on Systematic Founder Scoring, 30 Years of Investment Lessons, and The Future of Angel Investing
Today's episode explores three ideas that caught my attention: Binary scoring reduce bias - Wade's yes/no questions (vs typical “tell me a story” questions) help address the "I like every founder" problem. <...
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Season 1
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Episode 50
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50:33
Episode 49: "It's a Volume Game" | Redbud VC's Brett Calhoun on Generalist Investing Philosophy, the Missouri Startup Ecosystem, and Why Gritty Industry Veterans Make Compelling Founders
Today's episode explores three ideas that caught my attention:The Missouri ecosystem is wild - I’ve 100% been sleeping on it. Names like Zapier, Equipment Share, Veterans United, and so many more all started there. It’...
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Season 1
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Episode 49
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33:40
Episode 48: "A Mile Deep" | North Texas Angel Network Co-Chairman Ichan Stall on Assessing Founder Psychology, Building Angel Communities, and Why Pulling the Lawnmower Behind Your Bicycle is the Way
Today's episode explores three ideas that caught my attention:Small operational advantages compound infinitely - His lawnmower efficiency tracking and strategic positioning showed me how founders who obsess over tiny details ...
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Season 1
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Episode 48
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42:57
