The Diligent Observer Podcast

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 successes because he couldn't see the TAM evolution. This tension between betting on founders versus understanding how markets evolve is TOUGH.  
3. Cap table complexity kills deals - Hearing Larry describe VCs passing because unwinding angel side letters isn't worth the hassle was sobering. Angels often optimize for individual upside while inadvertently destroying company-wide value. 

Larry Warnock is the Founding Partner and current Partner Emeritus of Ring Ventures and a veteran investor with over 70 investments across early-stage technology companies. As a former CEO who led multiple successful startups to acquisition or IPO - including Gazzang (acquired by Cloudera) and Phurnace (acquired by BMC Software) - Larry brings rare operational perspective to venture investing. His experience spanning both sides of the table, from Silicon Valley to Texas, gives him unique insight into what separates winning investments from costly mistakes in the angel ecosystem.

During our conversation, Larry shares: 

• His 'Three T's' framework: TAM, Tech, and Team for evaluating investment opportunities 
• The importance of the team in the success of a venture 
• The stories of missed investment opportunities and lessons learned 
• Advises on the pitfalls of complicated cap tables and emphasizes the benefits of SAFE notes for angel investments 
• The conversation highlights the importance of building relationships with founders early 
• Current VC investment trends including the resurgence of hardware and AI applications 
• His insights on how angels can add value beyond financing 
• His advise for angel investors on leveraging research and trends to make informed investment decisions 
• The recounts of the more unusual pitches he's encountered, including one for recreating the woolly mammoth.

Connect with Larry 

LinkedIn

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• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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 advice that can flip defensive energy into offensive positioning.
3. Relevance as retention driver – Members of Golden Seeds stick around because the work keeps them intellectually current. The group’s 84% renewal rate suggests that learning, not just returns, is a powerful motivator for angel engagement. 

Loretta McCarthy is the Co-CEO and Managing Partner of Golden Seeds, the largest angel network in the United States investing exclusively in women-led companies - having deployed nearly $200 million across 260+ companies since 2004. Angela Allen is a Managing Director and Founding Member of Golden Seeds' newly launched Chicago Chapter, bringing 30+ years of operating experience including a 10x exit from an all-female executive team. Together, they bring both the macro perspective of building a national movement and the ground-level insight of launching a new local chapter. 

During our Conversation, Loretta and Angela share:

• The specific bias patterns that disadvantages women founders
• Why sector-specific training matters for angel confidence
• How a chapter-based geographic model enables national deal flow while maintaining local relationships 

Connect with Loretta McCarthy & Angela Allen

Golden Seeds' LinkedIn | Loretta's LinkedIn | Angela's LinkedIn

Stuff We Reference

• Golden Seeds
• OppenheimerFunds
• NanoPattern
• Every Body Eat
• Loyola University
• DePaul University
• mHUB
• ACA’s Angel Funders Report

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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 – John’s "where you stand depends on where you sit" framework for understanding global energy policy made geopolitical tensions seem much more obvious. 
3. Focused & capital-light > Mega infrastructure projects – Great perspective from John on why angels prioritize focused efficiency plays over major infrastructure initiatives. 

John Jeffers brings a rare combination of operational depth and investment acumen to clean energy, forged over a 32-year career tackling the energy sector's most critical challenges across ExxonMobil, Schlumberger, and Southwestern Energy. Since transitioning from corporate leadership in 2020, he has become a leading voice in the early-stage clean tech ecosystem - co-founding Revolution Turbine Technologies, serving on the board of SWAN Impact Network, and currently acting as Entrepreneur-in-Residence for Rice Alliance's Clean Energy Accelerator.  

During our conversation, John shares:  

• Why the rollback of IRA provisions has introduced more nuance, but NOT catastrophe   
• Why energy startups should consider seeking strategic partnerships earlier 
• The evolution of SWAN Impact Network's investment thesis

Connect with John 

LinkedIn 

Stuff We Reference 

• SWAN Impact Network
• Daniel Yergin’s The Prize
• Daniel Yergin’s The New Map
• Bob Bridge
• Rice Clean Energy Accelerator
• AtmoSpark
• Skyden Technologies
• Capwell Energy Service
• Variablegrid

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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 to me. 
3. Connection-making is a superpower - Catherine's emphasis on being a connector as free value creation made me realize how undervalued this skill is, yet how often I see it on display in some of the best people I’ve interacted with.  

Catherine Gray is the Executive Producer of Show Her The Money, a documentary that has screened in over 200 cities worldwide, and CEO of She Angel Investors, where she's hosted over 400 podcast interviews with female founders and funders. A veteran media entrepreneur, Catherine brings storytelling expertise with thoughtful venture capital strategy to help address the 2% funding gap facing women entrepreneurs.

During our conversation, Catherine shares: 

• The three-part funding structure for independent film projects
• A practical approach to film investment evaluation 
• The "connector superpower" methodology 

Connect with Catherine 

LinkedIn

Stuff We Reference 

• Ky Dickens
• Dr. Silvia Mah
• Marcia Dawood
• Mel Robbins
• Andrea Quinn
• From The Heart Productions
• Fund Women – Save The World
• Millennials Are Killing Musicals
• Emily Ventures
• Stella Foundation
• The Angel Next Door

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

 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 in the angel space that more deal flow equals more value.
3. The founder is everything - Amy's collaboration with clinical psychologist Marty Dubin to systematically assess founder DNA made me think about how tempting (at least, at the pre-seed and seed stage) it is to focus on evaluate a business when we really should be evaluating the person.

I explore these ideas and more with Amy Brandenburg, Co-Founder and Managing Partner of Denver Ventures Seed Fund, which has grown from an informal angel group to managing $65M+ AUM in just five years. Amy brings an iterative mindset thanks to her time at GitLab, as well as a distinctive focus on "founder DNA", collaborating with clinical psychologist and serial entrepreneur Marty Dubin to develop proprietary psychological evaluation methods that go beyond traditional due diligence in early-stage investing.

During our conversation, Amy shares:

• Member activation strategies that helped Denver Ventures grow from informal group to 850+ investors including why partner skin-in-the-game was crucial for credibility.
• Lessons from GitLab's asynchronous culture including the "no agenda, no meeting" rule and iteration-over-perfection mindset that shaped her leadership approach.
• Why Colorado's 20-year ecosystem building strategy succeeded where others failed and how coastal capital migration during COVID accelerated regional growth opportunities.

Connect with Amy

LinkedIn | X

Stuff We Reference 

• Brad Feld
• Chris Petersen
• Brian Leach
• Ibotta
• Dan Caruso
• Secrets of Sand Hill Road

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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 Findings

1. Texas dominates. 10 of the 72 networks were Texas-based, responsible for 22 investments. This likely reflects two things: Texas angels are more public about their deals, and my team is based here so we catch their activity more readily.
2. Angel groups regularly invest cross-border. Networks were based in 27 states and 12 countries, but funded companies in 30 states and 15 countries.
3. Healthcare is the runaway leader at 34% of deals. AI integration appeared in 64% of deals across all sectors - and that's probably understated. AI infrastructure is woven into everything.
4. Average angel network check: $329K (median $180K). This represents about 7% of the average $4.7M round size. That's meaningful capital, not just symbolic participation.

Behind the Scenes

Tracking 173 organizations (72 networks + 101 companies) was incredibly time-consuming. Multiple companies rebranded or pivoted between coverage and report publication. One shut down entirely. This underscores why we track activity weekly through the newsletter - these deals evolve fast.

Bottom Line

Organized angel investing is only 30 years old (Band of Angels formed in 1995), but it's rapidly maturing into a meaningful force. $330K checks representing 7% of funding rounds, combined with personal networks and hands-on support, deliver a different value proposition than institutional capital. This ecosystem is growing fast, crossing borders, and providing material support for early-stage innovation. 

Full report with infographics, company profiles, and sector breakdowns available at thediligentobserver.com/c/101. 

Stuff We Reference 

• LinkedIn
• ACA membership exclusive code

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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 angel investing in community? 
3. Scarcity really does drive urgency - Wade's amazing “fax machine story” illustrates how scarcity and momentum create investor FOMO.  

I explore these ideas and more with Wade Myers, Co-founder and General Partner at Eagle Venture Fund. Wade Myers brings a unique combination of military leadership, strategy consulting expertise, and 30 years of angel investing experience to early-stage capital allocation. As a former U.S. Army Airborne Ranger and Boston Consulting Group veteran with a Harvard MBA, he has invested in 150+ ventures while building systematic processes that filter through 20,000 annual pitches. Currently serving as chairman of a venture studio and partner in multiple investment funds, Wade has pioneered data-driven approaches to founder assessment that challenge the traditionally informal nature of the angel ecosystem. 

During our conversation, Wade shares: 

• Binary yes/no assessment questions that capture founder culture fit, perseverance, and business acumen without lengthy application essays. 
• Why 90% of angel network inefficiency stems from poor founder-investor matching and how marketplace mechanics can solve this problem. 
• The allocation strategy conversation every new angel needs - from calculating liquid net worth ratios to identifying where you can add immediate value beyond capital. 

Connect with Wade 

LinkedIn

Stuff We Reference 

• JP Morgan
• Boston Consulting Group
• Techstars 
• Plug and Play
• Goldman Sachs
• Startup Grind
  
   

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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, and inevitably becomes a sourcing moat through sheer persistence.
3. VCs pivot too - After launching an accelerator, Brett discovered the most valuable thing they did was make introductions to customers and investors, not programming. So they pivoted their strategy.

I explore these ideas and more with Brett Calhoun, General Partner at Redbud VC,  a top-decile early-stage venture fund that has carved out a unique positioning in America's heartland. A former entrepreneur who co-founded three fintech startups and was named to Forbes 30 Under 30 in Venture Capital in 2024, Brett brings both operational experience and financial expertise to his role. His firm's counter-positioning strategy - focusing on gritty founders with industry experience rather than traditional pedigree - has begun to generate outsized returns while building a distinctive brand amidst Missouri's robust startup ecosystem.

During our conversation, Brett shares:

• The Missouri market inefficiency - explaining how 20% of Forbes 300 companies are concentrated in the region, but only 6% of venture-backed startups.
• The counterintuitive insight that “forcing your framework” might not be such a good idea - learned through experience that pushing a playbook onto entrepreneurs can actually kill their trajectory.
• Why volume trumps thesis - detailing how conducting 1,500 annual first calls and reviewing thousands of deals creates a sustainable competitive advantage over pure thematic approaches.

Connect with Brett 

LinkedIn | X

Stuff We Reference

• Redbud VC
• Forbes 30 Under 30
• Synvect
• Scale Accelerator
• EquipmentShare
• Veterans United Home Loans
• Carfax
• Club Car Wash
• Learfield

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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. Community impact scales investment success - His ecosystem-building approach generates better deal flow than having a “pure financial” focus.

I explore these ideas and more with Ichan Stall. He brings over 25 years of enterprise software and operations experience, having co-founded multiple companies including Crunch Data and CrunchBot AI (both acquired by QlikTech). During his tenure at the North Texas Angel Network, he's worked with the group’s leadership team to rapidly grow from 15 members to 70 members in just three years, which was recently celebrated as institutional investor of the year. His unique perspective combines Silicon Valley tech experience with grassroots community building, shaped by a multicultural upbringing across 70+ countries on military bases worldwide.

During our conversation, Ichan shares:

• A systematic framework for evaluating founder psychology through subtle testing and behavioral observation that reveals true grit beyond pitch presentations.
• Why going "a mile deep with founders versus a mile wide" creates better investment outcomes through authentic relationship building and vulnerability assessment.
• How his teenage military base landscaping business taught competitive advantage principles that he now uses to identify founders who will outwork their competition.

Connect with Ichan

LinkedIn

Stuff We Reference:

• The DEC Network
• CodeLaunch
• Houston Angel Network
• Alamo Angels
• Cowtown Angels
• SWAN
• Bill Chinn
• Trey Bowles
• Mike Wilkes

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice. 

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

1. 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. 
2. “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 ecosystems. 
3. Government pace requires some empathy - Bill's point about Type-A personalities wanting to "move off without" slow government partners really stuck with me. Go fast alone, go far together. 

I explore these ideas and more with Bill Chinn who leads the DEC Network, a 501(c)(3) nonprofit supporting entrepreneurs across the DFW area with particular focus on women founders and entrepreneurs of color. His career path spanning 20 years at GameStop, various entrepreneurial ventures, and nonprofit leadership, uniquely positions him to understand both the capitalist and collaborative sides of ecosystem building. As someone who witnessed Silicon Valley's collaborative culture firsthand during the 2000s boom, Bill brings a rare perspective on how healthy competition and nonprofit neutrality can accelerate regional startup growth. 

During our conversation, Bill shares: 

• The hidden role of nonprofits as ecosystem neutral conveners - demonstrating how 501(c)(3) status creates unique credibility to push competing groups toward cooperation. 
• Specific evidence of Fort Worth's rapid emergence as an entrepreneurship hub - backed by national rankings and mayor-level support that most investors are missing. 
• The Silicon Valley collaboration model that worked during the 2000s boom - and how selflessness during fast-moving periods prevented credit politics from slowing progress. 

Connect with Bill 

LinkedIn 

Stuff We Reference 

•  Brad Feld
• DFW Startup Week
• Cowtown Angels
• Texas Stock Exchange
• Pegasus Park

Want more? 

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter. 
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.