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PODCAST

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/https://feeds.buzzsprout.com/2459970.rss

business entrepreneurship

All Episodes

39:20

Episode 52: "Film Changes Culture" | Show Her The...

The Diligent Observer Podcast ·

2025/11/25

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. Fundraising is a community-driven exercise - "You're not asking for yourself" reframes the entire process as mission-driven rather than personal. This is a powerful shift in perspective that stood out to me. Connection-making is a superpower - Catherine's emphasis o...

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38:48

Episode 51: "Obsess Over Founder DNA" | Denver...

The Diligent Observer Podcast ·

2025/11/11

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 can be applied effectively in the angel investing world.Curation creates commitment - Amy's insight that showing fewer, highly-vetted deals can increase member engagement challenges a common assumption I see in the angel space that more deal flow equals more value.The fou...

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15:04

Special Episode: Breaking Down "Angel Network Pulse:...

The Diligent Observer Podcast ·

2025/10/29

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 Picture 101 deals across 72 angel networks in 15 countries. $288M in announced funding (likely closer to $500M total funding, since only 53% disclosed round sizes). This represents roughly 8-10% of total annual angel network activity based on ACA's tracking of 1,200-1,500 deals per year. Key Finding...

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50:33

Episode 50: "Crush the Cost of Diligence" | Serial...

The Diligent Observer Podcast ·

2025/10/14

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. Transaction fees align incentives - Wade's preference for paying only when deals close checks out with many other conversations I’ve had in recent years. Perhaps the next evolution for angel investing in community? Scarcity really does drive urgency - Wade's amazing ...

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33:40

Episode 49: "It's a Volume Game" | Redbud VC's Brett...

The Diligent Observer Podcast ·

2025/09/30

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’s so easy to miss entire innovation hubs outside the usual suspects.Volume as competitive advantage - 300 LinkedIn messages weekly for five years straight. Sustaining this hustle is simple but NOT easy, and inevitably becomes a sourcing moat through sheer persistence.VCs pivot ...

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42:57

Episode 48: "A Mile Deep" | North Texas Angel Network...

The Diligent Observer Podcast ·

2025/09/16

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 can dominate markets.Angel networks fail without grassroots hustle - Growing NTAN from 15 to 70 members required zero silver bullets, just relentless coffee meetings and authentic relationship building.Community impact scales investment success - His ecosystem-building a...

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19:42

Episode 47: "Friendly Competition" | The DEC...

The Diligent Observer Podcast ·

2025/09/09

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 external competition is a wonderful thing. “Who gets the credit” politics can kill momentum - Bill's observation that meetings about who gets recognition are meetings NOT moving deals forward crystallized why ego management matters so much in building thriving ecosyst...

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32:30

Episode 46: From "Anything But Healthcare" to "All-In...

The Diligent Observer Podcast ·

2025/09/03

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 key distinctives that allowed him to learn and grow so quickly. Personal pain often drives conviction in healthcare entrepreneurship - Trey noted healthcare found often lost loved ones or had bad experiences, resulting in higher-than-average grit. Rela...

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49:16

Episode 45: Breaking Down the 2025 Angel Funders...

The Diligent Observer Podcast ·

2025/08/26

Today's episode explores three ideas that caught my attention: Angel board representation dropped from 34% to 26% - Despite consistently seeing better returns WITH board representation, fewer angel groups are securing board seats. Early-stage valuation compression - The gap between median pre-seed ($10M) and Series B ($19M) valuations has shrunk by 3x over the last few years. Hybrid angel group models write bigger checks - Groups combining both “pure networks” a...

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41:02

Episode 44: "Bridge Building, Not Wall Building" |...

The Diligent Observer Podcast ·

2025/08/12

Today's episode explores three ideas that caught my attention: Capital proximity ≠ capital access - Quinn's take on the "access to capital problem" was a thoughtful take on perceived geographic disadvantages in fundraising.Non-investment motivations often attract angel participation - His insight that professional development and community often drive an angel’s first steps in the ecosystem was well said and aligns with my own experience.New investment categories being created in Micro-SaaS -...

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43:34

Episode 43: "Campus-Born Ventures: An...

The Diligent Observer Podcast ·

2025/07/29

Today's episode explores three ideas that caught my attention: The maturity evolution - His emphasis on campus ecosystems moving away from "every idea is good" to investor-ready reality checks highlights a necessary shift in the academic entrepreneurship model.The pledge-based investing model - Tom's concept of angels pledging a percentage of capital gains as a gift back to universities creates a virtuous funding loop I have seen deployed in some university entreprene...

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40:17

Episode 42: "Just Fix My Pitch Deck" | Power To Pitch...

The Diligent Observer Podcast ·

2025/07/15

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. Corporate grants are legit. I think often about government grants, but have minimized the importance of corporate programs. But these organizations regularly write $10K-$50K checks with no equity dilution – and that is massive for a young business. Plus, the p...

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11:22

Special Episode: What Does the Big Beautiful Bill...

The Diligent Observer Podcast ·

2025/07/10

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 spreading over five years. Example: portfolio company spends $1M on research, they get the full tax benefit upfront rather than spreading out $200K annually. This is huge cash flow impact for software, deep tech, and biotech companies.Qualified Small Business Stock (QSBS) exclusion got a serio...

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53:01

Episode 41: "You Didn't Serve Alone, Don't Search...

The Diligent Observer Podcast ·

2025/07/01

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 critical for angel investor portfolio construction and risk management. The "peace dividend" creating veteran entrepreneurs - Patrick's observation about post-combat veterans seeking meaningful civilian engagement revealed how macro geopolitical shifts can create unexpecte...

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22:19

Episode 40: "Fuel for the Economic Engine" | Angel...

The Diligent Observer Podcast ·

2025/06/17

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 annually Today's episode explores three ideas that caught my attention: The path from art to science - Pat drew a fascinating parallel between angel investing and project management's evolution over 50 years. I wonder what 3 letter certification name we’ll land on!Accreditat...

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39:40

Episode 39: "The Devil is in the Details" | Seraf...

The Diligent Observer Podcast ·

2025/06/10

Insights from a portfolio management software CEO who sees the venture market's "healthy shakeup" forcing overdue conversations about profitability and angel group sustainability Today's episode explores three ideas that caught my attention: The venture market reset is healthy - Alycia embraces the current volatility as necessary medicine. It challenges the trope that stability is always preferable - perhaps occasional chaos forces better investment discipline.Angel group models are evolving ...

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36:11

Episode 38: "Practice Your Thesis Until It’s Muscle...

The Diligent Observer Podcast ·

2025/06/03

Insights from the Chairwoman of Stella Foundation and founding member of Stella Angels who has invested in 160+ women-led startups and co-managed six consecutive San Diego Angel Conference funds totaling millions in early-stage capital Today's episode explores three ideas that caught my attention: Creativity is the gateway to better investing - Silvia's classroom exercises aren't just for students. Her approach to opening minds through creative prompts parallels exactly how angel...

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34:48

Episode 37: "Winners Emerge After the Five-Year Mark"...

The Diligent Observer Podcast ·

2025/05/27

Insights from a 20-year angel investing veteran who created data-driven tools used by hundreds of angel groups Today's episode explores three ideas that caught my attention: The zombie portfolio problem - John created a simple "Lost Cause Fund" solution that lets angels harvest tax losses from walking dead companies. Genius. How many other innovations remain undershared across angel networks?Expertise >> crowds - John's analysis revealed a U-shaped return curve where heavily-invested de...

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7:36

Episode 36: "Don't Panic" | Angel Capital Association...

The Diligent Observer Podcast ·

2025/05/20

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 my attention: Angels are insulated from market turbulence - Ron's data shows angels maintaining pre-2021 investment patterns despite market volatility in recent months. First-time CEOs are getting MORE funding - Contrary to what you'd expec...

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28:40

Episode 35: "108,000 Startups and Counting" | Dealum...

The Diligent Observer Podcast ·

2025/05/13

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 that sign up for the AI Portfolio Monitoring waitlist a pair of Dealum’s signature red socks. What better way to impress your fellow angels at the next pitch event?! Today's episode explores three ideas that caught my attention: A 30% spike in angel fundr...

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