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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 • 51 episodes
The Diligent Observer Podcast
Latest Episodes
Episode 44: "Bridge Building, Not Wall Building" | Heartland Angel Network Lead Quinn Robertson on Connecting Local Founders to National Capital, the NW Arkansas Innovation Ecosystem, and Activating New Angel Investors
Today's episode explores three ideas that caught my attention:Capital proximity ≠ capital access - Quinn's take on the "access to capital problem" was a thoughtful take on perceived geographic disadvantages in fundraising.
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Season 1
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Episode 44
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41:02
Episode 43: "Campus-Born Ventures: An Underappreciated Asset Class" | Tom Duening on Democratizing Campus Capital, University Revenue Models, and Worldwide Deal Flow
Today's episode explores three ideas that caught my attention: The maturity evolution - His emphasis on campus ecosystems moving away from "every idea is good" to investor-ready reality checks highligh...
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Season 1
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Episode 43
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43:34
Episode 42: "Just Fix My Pitch Deck" | Power To Pitch Founder Kat Weaver on Why Communication Beats Perfect Decks, Creative Financing Options for Founders, and the “Founder-First” Investment Philosophy
Today's episode explores three ideas that caught my attention: Pitch deck ≠ the pitch. So many founders think their deck is the main thing standing between them and funding. It’s about so much more than the deck.&n...
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Season 1
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Episode 42
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40:17
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Special Episode: What Does the Big Beautiful Bill Mean for Angel Investors?
On July 4, 2025, Trump’s “Big Beautiful Bill” was signed into law. Here are the takeaways for angel investors. The Good News R&D expenses can now be deducted immediately instead of spre...
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11:22
Episode 41: "You Didn't Serve Alone, Don't Search Alone" | Owners in Honor Founder Patrick Flood on Why ETA Differs from Startup Investing, Post-WWII Entrepreneurship Patterns, and Risk Mitigation in Small Business Acquisition
Today's episode explores three ideas that caught my attention: "If these companies roll to zero, it's a big problem" – Understanding this fundamental difference between ETA and venture startup investing is critica...
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Season 1
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Episode 41
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53:01
