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. Episode 66: “Build vs Buy” | Black Prism Capital Partners Founder Steven Miller on Dual-Use Investing, Government Sales, and Deep Tech Diligence

    vor 4 Tagen ·  Video

    Episode 66: “Build vs Buy” | Black Prism Capital Partners Founder Steven Miller on Dual-Use Investing, Government Sales, and Deep Tech Diligence

    🗞️ 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 Government demand is not the same as government revenue: Steven explains why “the government needs this” is not enough for an investor. A real dual-use thesis requires evidence of a buyer, a budget, a contracting path, and people inside the government who can execute. ② Commercial-first companies need a distinct government strategy: Selling to the federal government is a completely different sales motion. Steven shares why companies should not let a speculative government opportunity distract from their commercial growth, and why the right specialist can help build a separate federal pathway. ③ Investor diligence has to go beyond the pitch deck: From SBIR awards to high-profile advisory boards, Steven explains why surface-level signals can mislead investors who do not understand the government market. Steven spent two decades building a government contracting company before launching Black Prism, a venture firm focused on commercial-first deep tech companies with credible dual-use potential. In this conversation, he shares how he thinks about government buying behavior, federal sales, AI security, early-stage diligence, and the signals investors should look for before backing a dual-use company. During our conversation, he shares: • Why the government is increasingly looking to buy commercial technology rather than build it internally. • How to distinguish a real government customer from a vague government-market claim. • Why a Phase I SBIR award does not automatically create lasting revenue. • How Hardshell is approaching data security in the age of AI. • Why stacked advisory boards should be reference-checked, not simply admired. • Why selling to the federal government requires a separate sales motion. • The questions every angel investor should ask before underwriting a dual-use opportunity. Connect with Steven: LinkedIn Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Black Prism Capital Partners Hardshell Certus Core America’s Seed Fund, SBIR/STTR Defense Innovation Unit Commercial Solutions Openings DFARS Subpart 212.70 Know someone who would enjoy this episode? Share it with them!   All opinions expressed are personal and may not reflect the views of the individual’s organization or of The Diligent Observer. Not investment advice. 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.

    54 Min.
  2. Episode 65: Faith Driven Angel Investing | Will Thomas, Co-Founder of Ambassadors Impact Network

    23. Juni ·  Video

    Episode 65: Faith Driven Angel Investing | Will Thomas, Co-Founder of Ambassadors Impact Network

    🗞️ 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 Faith-driven investing is growing: Will shares how the ecosystem has expanded from a small number of early players into a much broader community of investors, funds, founders, and networks thinking seriously about faith and private markets. ② Return and impact should be measured separately: Ambassadors Impact Network evaluates companies with two distinct scorecards: one for financial return and one for spiritual integration. Will explains why keeping those categories separate helps serve both founders and members well. ③ Christian investing is not charity: Will is clear that Ambassadors wants to bless founders, fund managers, employees, and communities. But the group is still underwriting real investments, reviewing deal terms, and looking for companies that can produce meaningful returns. Will is an Air Force veteran, Harvard MBA, and co-founder of Ambassadors Impact Network, a Dallas-based investor group that has deployed more than $27 million into gospel-advancing companies and funds since 2018. During our conversation, he shares: • Why faith-driven investing has grown so quickly. • How Ambassadors Impact Network got started. • Why the group moved from only funding operating companies to also investing in fund structures. • How Ambassadors evaluates financial returns and spiritual integration separately. • Why the group focuses on post-revenue companies. • What founders should understand before approaching faith-driven investors. • How Christian investors can pursue impact without creating unhealthy workplace dynamics. Connect with Will: LinkedIn Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Ambassadors Impact Network Sovereign’s Capital Praxis Faith Driven Investor The Lion’s Den C12 Group Marketplace Chaplains Abide Startup Garage Redemptive Real Estate Know someone who would enjoy this episode? Share it with them!   All opinions expressed are personal and may not reflect the views of the individual’s organization or of The Diligent Observer. Not investment advice. 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.

    41 Min.
  3. Episode 64: “We Pass on 98.5%” | Bio Angels Yaniv Sneor and Alex Pederson on Life Science Angel Investing, Screening Criteria, and Exit Discipline

    16. Juni ·  Video

    Episode 64: “We Pass on 98.5%” | Bio Angels Yaniv Sneor and Alex Pederson on Life Science Angel Investing, Screening Criteria, and Exit Discipline

    🗞️ 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 Disciplined screening can be tested: Yaniv and Alex explain how Mid Atlantic Bio Angels reviewed more than a decade of life science startup applications to ask whether the group’s screening criteria were helping or causing them to miss the winners. ② Life science angel investing has different economics: In therapeutics, medical devices, diagnostics, and digital health, the capital path matters. A company may be promising, but if it needs too much money before reaching an exit, it may be a better fit for venture capital than angel capital. ③ Angel-scale life science exits are about being acquired early: Alex explains why time, capital intensity, clinical risk, and later-stage dilution can make “growing big” less attractive for early angel investors than reaching a strategic acquisition sooner. Yaniv is a co-founder of Mid Atlantic Bio Angels and a biotech CEO. Alex is an oncology commercialization professional who helped lead a detailed analysis of BioAngels’ screening criteria, applicant outcomes, missed deals, and exit patterns. During our conversation, he shares: • Why BioAngels invests in fewer than 1.5% of companies that apply. • What they learned by analyzing nearly 1,100 life science startup applications. • Why only a small percentage of passed companies reached an exit. • How life science angels think about dilution, time to exit, and capital requirements. • Why one of their first screening questions is: how much money do you need to reach an exit? • Why some companies are better VC opportunities than angel investment opportunities. Connect with Yaniv: Yaniv's LinkedIn Connect with Alex: Alex's LinkedIn Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Mid Atlantic Bio Angels BioAngels Investment Criteria BioAngels Investment Process ACA Data Insight: “What Do Outcomes Teach Us About Screening Criteria?” ACA Data Insight: “IPOs as Outcomes for Life Science Angels: What Changes, and When?” Angel Capital Association PitchBook ClinicalTrials.gov MedTech Strategist BioSpace Denatured episode with Yaniv Sneor and Alex Pederson Know someone who would enjoy this episode? Share it with them!   All opinions expressed are personal and may not reflect the views of the individual’s organization or of The Diligent Observer. Not investment advice. 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.

    41 Min.
  4. Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel Investing

    9. Juni ·  Video

    Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel Investing

    🗞️ 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 how board involvement, written diligence, follow-on investing, and industry diversification have all shown up in CTAN’s data as meaningful drivers of better angel investing outcomes. ③Many angel groups are still operating like supper clubs: Rick argues that too many groups gather, hear pitches, write checks, and fail to track what happens next. His challenge is simple: angel investing is an asset class, and it requires process. Rick spent decades in finance leadership at Motorola and Cisco, where he helped apply Six Sigma principles to financial operations. In this conversation, recorded live at the Angel Capital Association Annual Summit, Rick explains how that same data-driven mindset shaped his approach to angel investing, portfolio tracking, member education, due diligence, and post-investment involvement. During our conversation, he shares: • How Cisco moved from a three-week monthly close to a one-day close. • Why CTAN tracks 78 metrics across its angel investment portfolio. • Why Rick believes many angel groups still operate more like supper clubs than professional investor groups. • How board involvement and formal due diligence have affected CTAN’s investment outcomes. • Why successful angel investing often takes five to eight years. • Why Rick is concerned about secondary markets, SaaS liquidity, and the concentration of capital flowing into AI. Connect with Rick: Rick's LinkedIn Central Texas Angel Network Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: CTAN Investment Data CTAN Entrepreneurs CTAN Membership ACA Data Insights ACA Data Insight by Rick Timmins ACA Angel Funders Report Cisco Investor Relations Six Sigma Tech Coast Angels / TCA Venture Group Angel Capital Association Summit Austin Technology Incubator Angel Capital Association ACA Summit Know someone who would enjoy this episode? Share it with them!   All opinions expressed are personal and may not reflect the views of the individual’s organization or of The Diligent Observer. Not investment advice. 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.

    37 Min.
  5. Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors

    2. Juni ·  Video

    Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors

    🗞️ 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 analyst model changes the student experience: Baylor’s program is not a short internship. Students move through coursework, shadowing, deal analysis, peer training, and hands-on responsibility over multiple semesters. ③ Angel investors need diversification: Steven shares how Baylor’s data showed the network’s overall returns were in line with angel investing benchmarks, but many individual members had not seen returns because they were in too few deals. Steven brings a unique perspective as both a former student analyst in the program and its current executive director. In this conversation, recorded live at the Angel Capital Association Annual Summit, Steven breaks down how Baylor Angel Network built a university-affiliated angel group that serves students, investors, and founders through a structured two-year analyst program. During our conversation, he shares: • How Baylor Angel Network’s two-year student analyst program works. • Why university angel programs need to serve students, investors, and founders at the same time. • How Baylor’s analyst alumni have become investors, founders, fund managers, and members of the network. • Why a fund structure can help angel investors get diversified exposure while still allowing direct investing. • What other universities should consider before trying to build their own angel network. Connect with Steven: Steven's LinkedIn Baylor Angel Network Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Baylor Angel Network Baylor Angel Network, Hankamer School of Business Baylor Angel Network Team Baylor Angel Network Student Practicum Team Baylor Prospective Analysts Baylor University Baylor Entrepreneurship Angel Capital Association ACA Summit 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.

    37 Min.
  6. Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act

    26. Mai ·  Video

    Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act

    🗞️ 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 rethink: If old thresholds were simply indexed to inflation, Mark says it could remove 40 to 60% of current angel investors from the market. His argument is that sophistication and education should matter, not just net worth. ③ Regulation should evolve with the market: From QSBS reform to the INVEST Act, Mark shows how small technical changes can have major consequences for founders, funds, pitch competitions, and angel groups. Mark brings a rare perspective from the intersection of angel investing, venture capital, public policy, and startup ecosystem building. In this conversation, recorded live at the Angel Capital Association Annual Summit, he pulls back the curtain on how the ACA supports policy improvements for early-stage investors and founders, including recent QSBS changes and proposed updates to the accredited investor definition. During our conversation, he shares: • Why the ACA’s policy work matters for founders, angel investors, and the broader early-stage ecosystem. • How recent QSBS improvements could lead to more rational exit decisions for startups and their investors. • Why simply indexing accredited investor thresholds could have major unintended consequences for startup capital formation. • How a sophistication test could allow more knowledgeable investors to participate in private markets. • What the INVEST Act could change for angel funds, pitch competitions, accredited investor rules, and early-stage capital access. Connect with Mark: Mark's LinkedIn RTP Angel Fund Dental Innovation Alliance Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Angel Capital Association ACA Summit ACA Mission and Leadership RTP Angel Fund Dental Innovation Alliance QSBS Reform, ACA Qualified Small Business Stock, Section 1202 INVEST Act overview, Carta INVEST Act Congressional Research Service summary Accredited Investor Definition, SEC Equal Opportunity for All Investors Act, CBO 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.

    40 Min.
  7. Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing

    19. Mai ·  Video

    Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing

    🗞️ 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’s data suggests angels who ignore them are ignoring a major part of today’s early-stage market. ③ Distribution is becoming a moat: As AI makes product advantages easier to copy, Peter believes trust, audience, and personal distribution will matter more for founders, operators, and investors. Peter leads the team that turns Carta’s private market data into some of the most widely cited research in the venture ecosystem. In this conversation, recorded immediately after his keynote at the Angel Capital Association Annual Summit, Peter shares what Carta’s data reveals about angel investing, SAFEs, exit strategy, secondaries, AI, geography, and the changing role of early-stage investors.  During our conversation, he shares: • Why angels and small funds should think more clearly about how portfolio companies actually exit. • A practical way to ask founders about potential acquirers, industry structure, and strategic relationships. • Why SAFEs are now a default instrument in much of the startup market, and how angels can make them more investor-friendly. • How AI is changing startup formation, product development, and the expectations angels should bring into software diligence. • Why the role of angels may become more relational, advisory, and trust-based as sourcing becomes increasingly automated. Connect with Peter: Peter's LinkedIn Carta's Website Carta's LinkedIn Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: Carta Data Angel Capital Association SAFE Financing Documents Angel Funders Report Rockies Venture Club Datadog 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.

    45 Min.
  8. Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation

    12. Mai

    Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation

    🗞️ 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 QCA can’t be a board observer or sit on the board, they’re not interested. ③ AI is changing angel networks: QCA is already using AI to match deals with member expertise, and Scott is thinking even bigger about how angel groups could learn from decades of shared deal data. Scott brings a rare operational perspective from leading one of the country’s longest-running angel investor groups. Originally founded as Queen City Angels in 2000, QCA Ventures has spent more than two decades refining its hybrid fund plus network model, due diligence process, member engagement systems, and founder education programs. His experience offers a practical look at what professional angel investing looks like when process, governance, and continuous improvement are treated as core advantages. During our conversation, he shares: • A look inside QCA’s Standards and Practices Guide, including how the group uses 28 diligence variables to create more consistent deal evaluation. • Lessons from a difficult investment that reinforced the importance of board governance, financial verification, and post-check oversight. • Practical examples of how QCA is using AI to match deals with member expertise and explore new ways for angel groups to learn from their own data. Connect with Scott: Scott's LinkedIn QCA Ventures QCA Ventures LinkedIn Connect with Andrew: Newsletter | X | LinkedIn | Book | Website Stuff We Reference: QCA Ventures Queen City Angels Angel Capital Association ACA Summit QCA Standards and Practices Guide At-A-Glance QCA Entrepreneur Boot Camp 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.

    46 Min.
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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 

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  • Erstellt von
    Andrew Kazlow
  • Jahre aktiv
    2024 - 2026
  • Folgen
    76
  • Bewertung
    Anstößig
  • Copyright
    © 2026 The Diligent Observer Podcast
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