The Diligent Observer Podcast

🗞️ 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:
① Angel investing needs better data: Rick explains how his Six Sigma background shaped the way he thinks about angel investing, including why CTAN tracks dozens of metrics across its investment portfolio.
② Due diligence changes outcomes: Rick shares h...

🗞️ 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:
① University angel networks need clear priorities: Steven explains why Baylor Angel Network works because it knows its primary purpose: experiential student education. But the model only succeeds because it also serves investors and founders well.
② A two-year...

🗞️ 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:
① Startup policy is capital formation policy: Mark explains why the ACA’s public policy work is not just about helping investors. It is about helping early-stage companies access the capital they need to grow.
② Accredited investor rules may need a rethi...

🗞️ 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:

① Angels need clearer exit logic: Peter argues that angels and small funds do not spend enough time asking how a company actually exits, especially when a $1B IPO is not the likely path.

② SAFEs are not going away: Peter is not saying SAFEs are perfect, but Carta&rsqu...

🗞️ 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:
① Process compounds: QCA Ventures was founded by engineers, and that mindset still shows up in their playbook, 28-point diligence scoring, and constant process improvement.
② Governance matters: Scott’s lesson from a difficult investment was simple: if Q...

Today's episode explores three ideas that caught my attention:

1. The university endowment mindset shift - Transition from the for-profit real estate world to Stanford's endowment revealed how different time horizons (centuries vs quarters) fundamentally change decision-making. 
2. Weak markets force better habits - Launching a career in Oklahoma during the energy crash of the 80s and jumping into Silicon Valley post-internet-bubb...

Today's episode explores three ideas that caught my attention:

1. 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 ordinary income deductions on losses than from capital gains exclusions on wins.
2. “We’re QSBS-eligible” is nice but not everything. Founders advertising QSBS eligibility can subtly distort...

Today's episode explores three ideas that caught my attention:

1. “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 waiting to be “activated” into the venture space, particularly in emerging capital markets.
2. Community norms shape investment behavior – Solomon noted Africa's communal culture a...

Today's episode explores three ideas that caught my attention:

1. 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 superior one, it won't easily scale.
2. Tech transfer done right – Hearing Anthony describe how he’s seen universities claim 50% equity and “blow up” a cap table from day 1 highligh...

Today's episode explores three ideas that caught my attention:     

1. The “angel investor” imposter syndrome – Suresh’s admission of feeling “unworthy” of the title despite being accredited made me reconsider how much terminology matters, and how many “angels” just consider themselves “investors”. 
2. Time and talent > treasure – Suresh mentioned ...

Today's episode explores three ideas that caught my attention:    

1. Execution defines greatness - Larry's conviction that the "best tech doesn't always win" challenges a LOT of assumptions we commonly hold – for example the Mars Rover example made me reconsider how often we confuse technical superiority with market dominance. 
2. The pivot paradox - Larry nearly passed on companies that became massive succes...

Today's episode explores three ideas that caught my attention:

1. 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.
2. The promotional pivot – Loretta & Angela often coach female entrepreneurs to treat negative questions (which are more commonly asked of women due to unintentional bias) as promotional opportunities. It's ...

Today's episode explores three ideas that caught my attention:     

1. It’s weird we measure data centers measured in gigawatts – John’s observation that we tend to discuss data centers based on their power consumption vs their computational output was fascinating – it’s like buying a car based on annual fuel consumption instead of its true utility. 
2. Geography drives energy politics ...

Today's episode explores three ideas that caught my attention:    

1. Film investment isn't always about ROI maximization – Many of Catherine's investors measure success by impact and community, not returns.  
2. 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...

 Today's episode explores three ideas that caught my attention: 

1. 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.
2. Curation creates commitment - Amy's insight that showing fewer, highly-vetted deals can increase member engagement challenges a common assumption I see...

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 ...

Today's episode explores three ideas that caught my attention:   

1. Binary scoring reduce bias - Wade's yes/no questions (vs typical “tell me a story” questions) help address the "I like every founder" problem.  
2. 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 ange...

Today's episode explores three ideas that caught my attention:

1. 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.
2. Volume as competitive advantage - 300 LinkedIn messages weekly for five years straight. Sustaining this hustle is simple but NOT easy...

Today's episode explores three ideas that caught my attention:

1. Small operational advantages compound infinitely - His lawnmower efficiency tracking and strategic positioning showed me how founders who obsess over tiny details can dominate markets.
2. 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.
3. Comm...