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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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Episodes
42 episodes
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
Insights from a 25-year veteran angel who advises investors and governments across four continents while chairing Silicon Valley's oldest angel network and the ACA Board of Directors Today's episode explores three ideas that caught ...
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Season 1
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Episode 36
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7:36
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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
Insights from a global ecosystem builder who's processed data on 108,000 startups while helping 240 investor communities across six continents manage their deal flow. GET FREE SOCKS: Seren will send the first 100 listeners th...
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Season 1
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Episode 35
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28:40
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
Insights from a fund manager who has mobilized hundreds of women investors, championed gender-lens investing in the Southeast, and is now steering the ACA as its incoming ChairToday's e...
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Season 1
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Episode 34
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31:45
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
Insights from an award-winning author and podcast host whose advocacy work is reshaping how angels invest and entrepreneurs access capital across ecosystems Today's episode explores three ideas that caught my attention: ...
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Season 1
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Episode 33
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43:10
Episode 32: "The Founder is Everything" | Super Angel Katie Dunn on Effective Due Diligence, How Relationship-Building Drives Returns, and Why Clarity is Kindness
Insights from a commercial real estate veteran who's now funding underrepresented founders while challenging traditional angel investing assumptions Today's episode explores three ideas that caught my attention: ...
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Season 1
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Episode 32
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44:02
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
Insights from a twenty-year tech ecosystem veteran creating pathways for women angel investorsToday's episode explores 3 ideas that caught my attention: Capital distribution defies logic - Kate highlighted that le...
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Season 1
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Episode 31
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41:36
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
Insights from a PropTech growth veteran who's scaled multiple startups to $175M+ in venture funding while driving innovation in commercial real estate Today's episode explores 3 ideas that caught my attention: R...
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Season 1
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Episode 30
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40:40
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
Insights from a former philosophy student who's built a 15,000+ member network of principled business leaders and facilitated values-aligned investmentsToday's episode explores 3 ideas that caught my attention:The power of...
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Season 1
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Episode 29
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43:21
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
Insights from a patent strategist who's authored 1,000+ patents and is revolutionizing IP finance through patent insurance and IP-backed lending at BlueIronToday's episode explores three ideas that caught my attention: ...
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Episode 28
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37:51
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
Today's episode explores 3 ideas that caught my attention: Some Patience Required: Nuclear's rise from 50–60% to 93% capacity factors took decades, not years. Expecting quick returns on new nuclear tech ignores the indus...
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Season 1
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Episode 6
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49:59
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
Today's episode explores three ideas that caught my attention: * Commonality is the Way - Variance in design increases cost. Consistency in design reduces it. Tighe shared helpful parallels with other industries to highlight ...
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Season 1
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Episode 5
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36:48
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
Today's episode explores three ideas that caught my attention:* Nuclear's renaissance hinges on electricity demand growth - More than any other guest I’ve spoken with, Emmet nailed the point that macro demand growth—not ...
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Season 1
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Episode 4
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46:39
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
Today's episode explores three ideas that caught my attention: * Demonstration Reactors are MVPs for Nuclear Energy - These reactors are 1/100 - 1/10 the size of a commercial scale reactor, and enable advanced reactor de...
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Season 1
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Episode 3
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39:53
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
Today's episode explores three ideas that caught my attention: Perception is Reality - The discussion of nuclear waste politics surfaced how fear-based narratives can derail rational energy policy for decades.
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Season 1
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Episode 2
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28:53
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
Today's episode explores three ideas that caught my attention: * AI is Transforming Nuclear Too - The possibility of applying AI tools to parse 4,500-page regulatory documents represents a breakthrough in addressing one ...
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Season 1
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Episode 1
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57:25
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
Today's episode explores three ideas that caught my attention: * The “conjoined twin” - Water touches every form of energy generation. Doug’s laser focus on this point made me consider what other interdependencies we oft...
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Episode 27
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43:37
Episode 26: "Never Say Revenue" | Startup Economist Paul O'Brien on Seed-Stage Venture Philosophy, Building Domain-Specific Angel Portfolios, and Media-First Innovation
Today's episode explores three ideas that caught my attention: * The “angel investor party trick” - Paul highlighted how the rush to become an angel investor mirrors the increase in the appeal of the “celebrity entrepren...
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Episode 26
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45:08
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
Today's episode explores three ideas that caught my attention: * Long ball is the name of the game - Can this company survive long enough to close a deal? Maybe they’ve closed some VC funding, but the risk-seeking VC buy...
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Episode 25
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47:37
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
Today's episode explores three ideas that caught my attention: * The Double-edged Sword of Government Grants - Fascinating perspective on how SBIR grants can either validate or misdirect founders. The pattern of companie...
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Episode 24
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25:18
Episode 23: "Patents Are Just One Piece" | University Innovation Leader Pete ONeill on the Opportunity in Highly Regulated Markets, Founder Credibility, and Strategic Specialization
Today's episode explores three ideas that caught my attention: * The paradox of regulatory rigor - Many investors simply screen out opportunities in highly regulated spaces like medical, deep tech, and defense. “I only l...
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Episode 23
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38:13
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
Today's episode explores three ideas that caught my attention: * The persistence of paper checks reveals deeper truths about business incentives - It totally blew my mind that half of B2B payments are issued by check. Bl...
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Episode 22
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45:19
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
Today's episode explores three ideas that caught my attention: * It’s like 6yr too late for horizontal AI - Dan's commentary about how startups trying to “develop a new LLM” are wasting their time competing with billion-...
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38:06
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
Today's episode explores three ideas that caught my attention: * Immigrant founders outperform statistically - Patrick's research shows a strong correlation between immigrant status and startup success. Makes me wonder h...
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34:13
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"
Today's episode explores three ideas that caught my attention: * The power of student innovation - The story of Ariana Williams turning a class paper into Prairie View A&M's first innovation center demonstrates how expos...
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45:02
Episode 18: "Government CAN Move Efficiently" | Innovation Fund Manager Mike Wilkes on Non-Dilutive Capital, Startup Support, and Local Job Creation
Today's episode explores three ideas that caught my attention: * The Value of Intentional Silence - Mike’s approach to founder interviews, watching body language, and creating space for stories shows how sometimes what's...
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35:46
