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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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Episodes
77 episodes
Replay: Episode 19: "Smart Money Goes Beyond the Checkbook" | Seasoned Angel Investor Mitra Miller on the Importance of Founder "Relentlessness", Innovation in Houston, and "Poker" vs "Roulette"
🗞️ 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:①The power o...
Episode 66: “Build vs Buy” | Black Prism Capital Partners Founder Steven Miller on Dual-Use Investing, Government Sales, and Deep Tech Diligence
🗞️ 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:①Government ...
Episode 65: Faith Driven Angel Investing | Will Thomas, Co-Founder of Ambassadors Impact Network
🗞️ 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:①Faith-drive...
Episode 64: “We Pass on 98.5%” | Bio Angels Yaniv Sneor and Alex Pederson on Life Science Angel Investing, Screening Criteria, and Exit Discipline
🗞️ 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:①Disciplined...
Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel 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:①Ang...
Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors
🗞️ 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:①University ...
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:①Star...
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:â‘
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:①Process...
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...
Episode 57: "Old Money To New Money" | Lagos Angel Network Executive Director Dr. Solomon King on Mobilizing Legacy Nigerian Wealth into Venture, Building Angel Culture from Scratch, and Correcting African Founders' Biggest Misconceptions
Today's episode explores three ideas that caught my attention:“Old money” sitting on the sidelines – Solomon aims to convert Nigeria's legacy industrialists into venture investors. It made me wonder how much capital is waitin...
Episode 56: "Hard Tech Is Hard, But So Is Software” | Industrial Sustainability VC Anthony Del Porto on Finding Step-Change Value in Hard Tech, Why the Valley of Death Is Shrinking, and Where he’s Seeing Alpha in 2026
Today's episode explores three ideas that caught my attention:Green premium is a deal killer – Anthony won't touch deals where eco-friendliness costs more (end state). If the sustainable solution isn't also the economically s...
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Episode 55: "We Need to Disrupt Ourselves" | SWAN Impact Network Executive Director Suresh Sundarababu on Breaking the Angel Group Mold, Building Great Founder Support Ecosystems, and Takeaways from The 2026 World Economic Forum
Today's episode explores three ideas that caught my attention: The “angel investor” imposter syndrome – Suresh’s admission of feeling “unworthy” of the title despite being accredited made me reconsider how ...
Replay: The 3 T’s of Early Stage Investing | Larry Warnock, Partner Emeritus at Ring Ventures (Episode 16)
Today's episode explores three ideas that caught my attention: Execution defines greatness - Larry's conviction that the "best tech doesn't always win" challenges a LOT of assumptions we commonly hold – for ...
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Episode 54: Women at the Table | Golden Seeds' Loretta McCarthy & Angela Allen on Building America's Largest Women-Focused Angel Network, The 3% to 30% Transformation, and Why Angel Education is so Critical
Today's episode explores three ideas that caught my attention:The math of representation – Loretta shared that having just one woman in a VC decision room doubles or triples funding odds for women-led companies.Th...
Episode 53: “Where You Stand Depends on Where You Sit” | SWAN Impact Network Board Member John Jeffers on the State of CleanTech, Strategic Exit Models for Energy Startups, and Finding Opportunity Amidst Policy Upheaval
Today's episode explores three ideas that caught my attention: It’s weird we measure data centers measured in gigawatts – John’s observation that we tend to discuss data centers based on their power consump...
Episode 52: "Film Changes Culture" | Show Her The Money Executive Producer Catherine Gray on Film as Impact Investment, Vulnerability with Persistence, and the Power of Like-Minded Capital
Today's episode explores three ideas that caught my attention: Film investment isn't always about ROI maximization – Many of Catherine's investors measure success by impact and community, not returns. ...
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...
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...
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. <...
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’...
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 ...
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...
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...
