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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 • 56 episodes
The Diligent Observer Podcast
Latest Episodes
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

Episode 47: "Friendly Competition" | The DEC Network's Bill Chinn on the Role of Angel Investors in North Texas, Healthy Ecosystem Rivalry, and Managing Type-A Personalities
Today's episode explores three ideas that caught my attention: Ecosystem competition breeds innovation – The friendly rivalry between DFW Startup Week and Brad Feld's Denver Startup Week shows how healthy ex...
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Season 1
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Episode 47
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19:42

Episode 46: From "Anything But Healthcare" to "All-In on Healthcare" | Serial Healthcare Investor Trey Bowles on the Rise of Venture Studios, The Art of Problem-Focused Selling in Healthcare, and Why Internal Champions are Everything
Today's episode explores three ideas that caught my attention: The courage to admit ignorance can be a competitive advantage - Trey's willingness to ask "dumb" questions in healthcare settings was one of the...
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Season 1
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Episode 46
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32:30

Episode 45: Breaking Down the 2025 Angel Funders Report | ACA Board Member John Harbison on Valuation Compression, Board Seat Decline, and Follow-On Performance
Today's episode explores three ideas that caught my attention: Angel board representation dropped from 34% to 26% - Despite consistently seeing better returns WITH board representation, fewer angel groups ar...
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Season 1
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Episode 45
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49:16
