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All Episodes

The Diligent Observer Podcast — 69 episodes

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Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation

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Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)

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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

4

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

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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

6

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

7

Replay: The 3 T’s of Early Stage Investing | Larry Warnock, Partner Emeritus at Ring Ventures (Episode 16)

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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

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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

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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

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Episode 51: "Obsess Over Founder DNA" | Denver Ventures Co-Founder Amy Brandenburg on Founder Assessment Methods, Angel Community Scaling Strategies, and Portfolio Discipline

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Special Episode: Breaking Down "Angel Network Pulse: The First 101"

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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

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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

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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

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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

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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

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Episode 45: Breaking Down the 2025 Angel Funders Report | ACA Board Member John Harbison on Valuation Compression, Board Seat Decline, and Follow-On Performance

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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

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Episode 43: "Campus-Born Ventures: An Underappreciated Asset Class" | Tom Duening on Democratizing Campus Capital, University Revenue Models, and Worldwide Deal Flow

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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

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Special Episode: What Does the Big Beautiful Bill Mean for Angel Investors?

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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

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Episode 40: "Fuel for the Economic Engine" | Angel Capital Association CEO Patrick Gouhin on Professionalizing Angel Investing, Expanding Accreditation Pathways, and Cultivating Startup Ecosystems

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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

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Episode 38: "Practice Your Thesis Until It’s Muscle Memory" | Stella Foundation Chairwoman Dr. Silvia Mah on Activating University Ecosystems, The Three C's of Capital, and Creating Proud Investment Portfolios

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Episode 37: "Winners Emerge After the Five-Year Mark" | TCA Venture Group Chairman Emeritus John Harbison on Exit Timeline Expectations, Portfolio Diversification Strategies, and The Unexpected U-Curve of Returns

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Episode 36: "Don't Panic" | Angel Capital Association Chair Dr. Ron Weissman on Navigating Market Volatility, Surging Investment in First-Time CEOs, and Why Downturns Are Great Investment Windows

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Episode 35: "108,000 Startups and Counting" | Dealum CEO Seren Rumjancevs on Angel Group Efficiency, AI-Powered Portfolio Tracking, and Bridging Global Angel Networks

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Episode 34: "Angels Are Always Hopeful" | Incoming ACA Chair Kristina Montague on Growing Women's Capital Networks, Expanding the Investor Tent, and Finding Arbitrage in Overlooked Innovators

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Episode 33: "Angel Investing Isn't a Trending Topic" | ACA Chair Emeritus Marcia Dawood on Angel Investment Cycles, Using Philanthropic Capital for For-Profit Ventures, and Making Fundraising Easier for Entrepreneurs

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Episode 32: "The Founder is Everything" | Super Angel Katie Dunn on Effective Due Diligence, How Relationship-Building Drives Returns, and Why Clarity is Kindness

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Episode 31: "Less Than 2% of VC Funding" | SWITCH CEO Kate Brodock on Untapped Founder Talent, The Arbitrage Opportunity in Women-Led Ventures, and Equipping New Angel Investors

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Episode 30: "You Need 500 Site Walks" | B2B Sales Leader Henry Talamantes on The Competitive Advantage of Ridiculous Customer Discovery, Post-Mall America, and the Next Chapter for Urban Office Space

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Episode 29: "Values on Our Sleeve" | Liberty Ventures Founder Alexander McCobin on Values-Forward Capital Allocation, Building Authentic Communities, and Why Great Events are 100% Worth the Effort

36

Episode 28: "Patents Won't Save a Bad Business" | Patent Expert Russ Krajec on IP-Backed Lending, Why Patents Create the Most Value at Year 15, and Common Angel Due Diligence Mistakes

37

Deep Dive Season 1: Nuclear Energy | Episode 6: "Science Projects Masquerading as Commercial Products" | Dr. Chris Keefer on the SMR Hype Cycle & Energy Independence Imperatives

38

Deep Dive Season 1: Nuclear Energy | Episode 5 - "The Math Doesn't Work Without Nuclear" | Nuclear Supply Chain Leader Tighe Smith on the Evolving Market, Factory Style Manufacturing, & Fuel Supply

39

Deep Dive Season 1: Nuclear Energy | Episode 4 - "The Secret Ingredient Is Demand Growth" | Nuclear Industry Writer Emmet Penney on Market Demand, What's Over/Underhyped, and Geography's Role

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Deep Dive Season 1: Nuclear Energy | Episode 3 - "Digital is No Longer a Four-Letter Word" | Control Systems Expert Ryan Marcum on Advanced Reactors, The Digital Evolution, and AI's Role in Nuclear

41

Deep Dive Season 1: Nuclear Energy | Episode 2 - "We Need to Rebuild this Entire Industry" | Texas Nuclear Alliance Founder Reed Clay on Regulatory Reform, Rebuilding the Nuclear Workforce, & Momentum

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Deep Dive Season 1: Nuclear Energy | Episode 1 - "Fission is the New Fire" | Nuclear Investor Rod Adams on the Nuclear Renaissance, AI's Role in Nuclear Design, and Building Through Regulatory Change

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Episode 27: "Water is Critically Underinvested" | Water Technology Expert Doug Lee on Why 0.2% is Not Enough, Barriers to Entry in Hard Tech, and Creating Win-Together Scenarios

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Episode 26: "Never Say Revenue" | Startup Economist Paul O'Brien on Seed-Stage Venture Philosophy, Building Domain-Specific Angel Portfolios, and Media-First Innovation

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Episode 25: "Intestinal Fortitude" | Startup Sales Veteran Rob Balena on Vetting Enterprise Sales Strategy, Hiring a Great Sales Force, and Where Most Founders Get it Wrong

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Episode 24: "Build the Rainforest in the Desert" | New Mexico Angels President Drew Tulchin on Defense Tech Innovation, Ecosystem Building, and Investing Alongside Government Grants

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Episode 23: "Patents Are Just One Piece" | University Innovation Leader Pete ONeill on the Opportunity in Highly Regulated Markets, Founder Credibility, and Strategic Specialization

48

Episode 22: "50% of Corporate Payments are Still Paper Checks" | Payments Veteran Blair Jeffery on The Evolution of B2B Payments, Cross-Border Innovation, and Building Through Market Turbulence

49

Episode 21: "95% Business, 5% Technical" | AI CONNEX Founder Dan Sinawat on Vertical AI Strategy, The Evolution of Machine Intelligence, and Why World Cup 2026 is a Massive Opportunity

50

Episode 20: "Part Art, Part Process" | Elevate Ventures' Patrick Sweeney on Startup Success Predictors, Recent Evolutions in VC Hiring, and the Criticality of Founder Empathy

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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"

52

Episode 18: "Government CAN Move Efficiently" | Innovation Fund Manager Mike Wilkes on Non-Dilutive Capital, Startup Support, and Local Job Creation

53

Episode 17: "Your Board Can Make or Break the Company" | Curtis Feeny on Governance, Market Cycles, and the "Say Yes" Career

54

Episode 16: The 3 T’s of Early Stage Investing | Larry Warnock

55

Episode 15: Diligence the Diligence: Unpacking the SideCar Angels Strategy | Alden Zecha

56

Episode 14: Don't Throw Away $50K: Lessons from Startup CTO Expert | Igor Belagorudsky

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Episode 13: Growing the Alamo Angels from 30 to 130 Members in 4 Years | Sebastian Garzon

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Episode 12: From CPG Founder to B2B SaaS Investor | Brook Stroud

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Episode 11: The Power of Relationship-Driven Angel Investing | Patrick Farrell

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Episode 10: Investing in Venture Capital for Human Flourishing | Phil Jung

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Episode 9: Bouldering & Biomedical Entrepreneurship | John Criscione

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Episode 8: The Art & Science of Angel Investor Education | Dr. Margaret Bacheler

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Episode 7: Evaluating Startup Marketing Strategy | Matt Bell

64

Episode 6: Lessons in WealthTech Investing | Marshall Smith

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Episode 5: Angel Investing in the Energy Transition | John Jeffers

66

Episode 4: Where the Magic Happens: Sports, Media, and Culture | Geoffrey Cheng

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Episode 3: Evaluating Startup Quality of Earnings | John Samore III

68

Episode 2: Thesis-Driven Investing | Eric Alfuth

69

Episode 1: Identifying a Great Pitch | Matt Gore