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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 • 49 episodes
The Diligent Observer Podcast
Latest Episodes
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
Episode 40: "Fuel for the Economic Engine" | Angel Capital Association CEO Patrick Gouhin on Professionalizing Angel Investing, Expanding Accreditation Pathways, and Cultivating Startup Ecosystems
Insights from an aerospace engineer turned association leader who's working to transform angel investing from "black art" to science while representing 15,000+ members deploying approximately $1 billion in private capital annuallyToday's...
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Season 1
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Episode 40
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22:19
Episode 39: "The Devil is in the Details" | Seraf Investor CEO Alycia Doxon on Venture Market Corrections, Capital Consolidation Trends, and The Future of Angel Networks
Insights from a portfolio management software CEO who sees the venture market's "healthy shakeup" forcing overdue conversations about profitability and angel group sustainabilityToday's episode explores three ideas that caught my attenti...
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Season 1
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Episode 39
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39:40
