The Diligent Observer Podcast
By Andrew Kazlow
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Category: Entrepreneurship
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Episodes: 94
Description
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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| Episode | Date |
|---|---|
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Episode 80: The Penn State Pipeline with Executive Director of Nittany Angels Joe Herbst
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Nov 03, 2026 |
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Replay: 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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Oct 27, 2026 |
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Episode 79: Angel Investing Is Poker, Not Chess with RevUp Capital Managing Partner Melissa Withers
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Oct 20, 2026 |
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Replay: 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
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Oct 13, 2026 |
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Episode 78: The ETA Financing Angel Group | Frontier Angels Managing Director Graham Conran
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Oct 06, 2026 |
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Episode 77: Why Great Products Still Lose with AngelsRound founder Ashher Syed
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Sep 29, 2026 |
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Episode 76: NuFund Executive Director and Co-Fund Manager Ashok Kamal on A Faster Angel Model
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Sep 22, 2026 |
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Episode 75: Tourist Town → Tech Hub with Bridge Angel Investors Linda Jellison and Peter Offringa
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Sep 15, 2026 |
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Episode 74: SaaS Isn’t Dead | Lighter Capital CEO Melissa Widner
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Sep 08, 2026 |
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Episode 73: Why Food Tech Is So Hard to Fund with New York Angels Executive Director Peter Bodenheimer
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Sep 01, 2026 |
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Episode 72: When the Deal Goes Sideways | TEN Capital Network Founder and CEO Hall Martin on Angel Investing’s Next Era
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Aug 25, 2026 |
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Episode 71: Nebraska Angels Executive Director Josh Bartels on Building a High-Trust Angel Network
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Aug 18, 2026 |
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Replay: Episode 20: Part Art, Part Process | Elevate Ventures Principal Patrick Sweeney on Data-Driven Startup Investing
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Aug 11, 2026 |
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Episode 70: "The Story Is the Asset" | Courtside Ventures Founding Partner Vasu Kulkarni on Collectibles, Community, and Angel Investing
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Aug 04, 2026 |
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Episode 69: "Roll Up Your Sleeves or Go Home" | Israel365 Media's Ben Woolf on Israel's Prove It First Investment Culture, Founder Grit, and Why Ideas Alone Don't Get Funded
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Jul 28, 2026 |
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Episode 68: "Dual Use Isn’t a Distraction" | 757 Collab President & CEO Paul Nolde on Dual-Use Startups
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Jul 21, 2026 |
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Episode 67: Charlotte Angel Fund Administrator Greg Brown On Why a $50M Exit Might Not Be Enough
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Jul 14, 2026 |
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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"
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Jul 07, 2026 |
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Episode 66: “Build vs Buy” | Black Prism Capital Partners Founder Steven Miller on Dual-Use Investing, Government Sales, and Deep Tech Diligence
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Jun 30, 2026 |
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Episode 65: Faith Driven Angel Investing | Will Thomas, Co-Founder of Ambassadors Impact Network
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Jun 23, 2026 |
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Episode 64: “We Pass on 98.5%” | Bio Angels Yaniv Sneor and Alex Pederson on Life Science Angel Investing, Screening Criteria, and Exit Discipline
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Jun 16, 2026 |
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Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel Investing
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Jun 09, 2026 |
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Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors
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Jun 02, 2026 |
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Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act
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May 26, 2026 |
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Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing
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May 19, 2026 |
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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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May 12, 2026 |
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Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)
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Apr 14, 2026 |
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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
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Mar 31, 2026 |
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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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Mar 17, 2026 |
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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
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Mar 03, 2026 |
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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
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Feb 17, 2026 |
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Replay: The 3 T’s of Early Stage Investing | Larry Warnock, Partner Emeritus at Ring Ventures (Episode 16)
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Feb 05, 2026 |
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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
|
Jan 13, 2026 |
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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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Dec 09, 2025 |
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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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Nov 25, 2025 |
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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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Nov 11, 2025 |
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Special Episode: Breaking Down "Angel Network Pulse: The First 101"
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Oct 29, 2025 |
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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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Oct 14, 2025 |
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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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Sep 30, 2025 |
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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
|
Sep 16, 2025 |
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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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Sep 09, 2025 |
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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
|
Sep 03, 2025 |
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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
|
Aug 26, 2025 |
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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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Aug 12, 2025 |
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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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Jul 29, 2025 |
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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
|
Jul 15, 2025 |
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Special Episode: What Does the Big Beautiful Bill Mean for Angel Investors?
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Jul 10, 2025 |
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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
|
Jul 01, 2025 |
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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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Jun 17, 2025 |
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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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Jun 10, 2025 |
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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
|
Jun 03, 2025 |
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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
|
May 27, 2025 |
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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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May 20, 2025 |
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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
|
May 13, 2025 |
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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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May 06, 2025 |
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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
|
Apr 29, 2025 |
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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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Apr 22, 2025 |
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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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Apr 15, 2025 |
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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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Apr 08, 2025 |
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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
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Apr 01, 2025 |
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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
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Mar 25, 2025 |
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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
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Mar 18, 2025 |
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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
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Mar 11, 2025 |
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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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Mar 04, 2025 |
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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
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Feb 25, 2025 |
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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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Feb 18, 2025 |
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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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Feb 11, 2025 |
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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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Feb 04, 2025 |
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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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Jan 28, 2025 |
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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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Jan 21, 2025 |
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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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Jan 14, 2025 |
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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
|
Jan 07, 2025 |
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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
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Dec 17, 2024 |
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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
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Dec 10, 2024 |
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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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Dec 03, 2024 |
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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"
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Nov 26, 2024 |
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Episode 18: "Government CAN Move Efficiently" | Innovation Fund Manager Mike Wilkes on Non-Dilutive Capital, Startup Support, and Local Job Creation
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Nov 19, 2024 |
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Episode 17: "Your Board Can Make or Break the Company" | Curtis Feeny on Governance, Market Cycles, and the "Say Yes" Career
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Nov 12, 2024 |
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Episode 16: The 3 T’s of Early Stage Investing | Larry Warnock
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Nov 05, 2024 |
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Episode 15: Diligence the Diligence: Unpacking the SideCar Angels Strategy | Alden Zecha
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Oct 29, 2024 |
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Episode 14: Don't Throw Away $50K: Lessons from Startup CTO Expert | Igor Belagorudsky
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Oct 22, 2024 |
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Episode 13: Growing the Alamo Angels from 30 to 130 Members in 4 Years | Sebastian Garzon
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Oct 15, 2024 |
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Episode 12: From CPG Founder to B2B SaaS Investor | Brook Stroud
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Oct 08, 2024 |
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Episode 11: The Power of Relationship-Driven Angel Investing | Patrick Farrell
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Oct 01, 2024 |
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Episode 10: Investing in Venture Capital for Human Flourishing | Phil Jung
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Sep 24, 2024 |
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Episode 9: Bouldering & Biomedical Entrepreneurship | John Criscione
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Sep 17, 2024 |
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Episode 8: The Art & Science of Angel Investor Education | Dr. Margaret Bacheler
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Sep 10, 2024 |
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Episode 7: Evaluating Startup Marketing Strategy | Matt Bell
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Sep 03, 2024 |
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Episode 6: Lessons in WealthTech Investing | Marshall Smith
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Aug 27, 2024 |
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Episode 5: Angel Investing in the Energy Transition | John Jeffers
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Aug 20, 2024 |
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Episode 4: Where the Magic Happens: Sports, Media, and Culture | Geoffrey Cheng
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Aug 13, 2024 |
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Episode 3: Evaluating Startup Quality of Earnings | John Samore III
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Aug 06, 2024 |
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Episode 2: Thesis-Driven Investing | Eric Alfuth
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Jul 30, 2024 |
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Episode 1: Identifying a Great Pitch | Matt Gore
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Jul 23, 2024 |