The Diligent Observer Podcast

Andrew Kazlow
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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 

  1. Replay: The 3 T’s of Early Stage Investing | Larry Warnock, Partner Emeritus at Ring Ventures (Episode 16)

    FEB 5

    Replay: The 3 T’s of Early Stage Investing | Larry Warnock, Partner Emeritus at Ring Ventures (Episode 16)

    Today's episode explores three ideas that caught my attention:     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. 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.  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 Know someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    59 min
  2. 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

    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

    Today's episode explores three ideas that caught my attention: 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.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.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 foundersWhy sector-specific training matters for angel confidenceHow 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 SeedsOppenheimerFundsNanoPatternEvery Body EatLoyola UniversityDePaul UniversitymHUBACA’s Angel Funders ReportKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    49 min
  3. 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

    12/09/2025

    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

    Today's episode explores three ideas that caught my attention:      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. 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. 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 thesisConnect with John  LinkedIn  Stuff We Reference  SWAN Impact NetworkDaniel Yergin’s The PrizeDaniel Yergin’s The New MapBob BridgeRice Clean Energy AcceleratorAtmoSparkSkyden TechnologiesCapwell Energy ServiceVariablegridKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    48 min
  4. 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

    11/25/2025

    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

    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 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 projectsA practical approach to film investment evaluation The "connector superpower" methodology Connect with Catherine  LinkedIn Stuff We Reference  Ky DickensDr. Silvia MahMarcia DawoodMel RobbinsAndrea QuinnFrom The Heart ProductionsFund Women – Save The WorldMillennials Are Killing MusicalsEmily VenturesStella FoundationThe Angel Next DoorKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    39 min
  5. Episode 51: "Obsess Over Founder DNA" | Denver Ventures Co-Founder Amy Brandenburg on Founder Assessment Methods, Angel Community Scaling Strategies, and Portfolio Discipline

    11/11/2025

    Episode 51: "Obsess Over Founder DNA" | Denver Ventures Co-Founder Amy Brandenburg on Founder Assessment Methods, Angel Community Scaling Strategies, and Portfolio Discipline

    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 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 FeldChris PetersenBrian LeachIbottaDan CarusoSecrets of Sand Hill RoadKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    39 min
  6. Special Episode: Breaking Down "Angel Network Pulse: The First 101"

    10/29/2025

    Special Episode: Breaking Down "Angel Network Pulse: The First 101"

    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 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.Angel groups regularly invest cross-border. Networks were based in 27 states and 12 countries, but funded companies in 30 states and 15 countries.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.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  LinkedInACA membership exclusive codeKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    15 min
  7. 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

    10/14/2025

    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

    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 “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 MorganBoston Consulting GroupTechstars Plug and PlayGoldman SachsStartup Grind  Know someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    51 min
  8. 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

    09/30/2025

    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

    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 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 VCForbes 30 Under 30SynvectScale AcceleratorEquipmentShareVeterans United Home LoansCarfaxKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

    34 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

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 

Information

  • Creator
    Andrew Kazlow
  • Years Active
    2024 - 2026
  • Episodes
    63
  • Rating
    Clean
  • Copyright
    © 2026 The Diligent Observer Podcast
  • Show Website
    The Diligent Observer Podcast