The Diligent Observer Podcast

Andrew Kazlow
  • 5.0 (3)
  • Entrepreneurship
  • Updated Weekly

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

    1d ago ·  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
  2. Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel Investing

    Jun 9 ·  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
  3. Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors

    Jun 2 ·  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
  4. Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act

    May 26 ·  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
  5. Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing

    May 19 ·  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
  6. Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation

    May 12

    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
  7. Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)

    Apr 14

    Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)

    Today's episode explores three ideas that caught my attention: 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. Weak markets force better habits - Launching a career in Oklahoma during the energy crash of the 80s and jumping into Silicon Valley post-internet-bubble taught Curtis that downturns force rigor and prevent the development of bad habits. A counterintuitive advantage in the face of a “tough” market. Advisory board seats are earned - The Khan Academy progression from “informal advisor” to board member showed how the best board seats develop organically through proven value. The “give first” mentality seems to pay off. Curtis brings rare perspective from helping grow Stanford University's endowment from $1.5B to $10.5B, serving on over 35 corporate boards (including CBRE, Staples, Khan Academy, and more) and spending two decades as a venture investor at Voyager Capital. His unique journey from real estate operations to endowment management to venture capital provides him with an uncommonly broad view of how companies succeed and fail across multiple market cycles.  During our conversation, Curtis shares:  Insights on the evolution of university endowment investing, including cautionary tales of concentration risk from NYU and Emory's experiences.Clear warnings about premature scaling, demonstrated through the story of Verari, a high-performance computing data center startup that reached $100M in revenue & raised growth capital at exactly the wrong time.Perspectives on emerging opportunities in nuclear power, cybersecurity, and deglobalization that suggest where future innovation may be needed.  Connect with Curtis LinkedIn Curtis’ Bookshelf: • Crossing the Chasm | Geoffrey Moore • This is How They Tell Me the World Ends | Nicole Perlroth • The End of the World is Just the Beginning | Peter Zeihan • Nuclear War | Annie Jacobsen • Zero to One | Peter Thiel • The Hard Thing about Hard Things | Ben Horowitz 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.

    57 min
  8. Episode 58: "$15 Million in Capital Gains: Gone" Startup Wealth Strategist Bryan Hasling on What Angel Investors Need to Know About QSBS, Maximizing the Tax Benefits of a Losing Investment, and the Limits of Tax-Driven Deal Selection

    Mar 31

    Episode 58: "$15 Million in Capital Gains: Gone" Startup Wealth Strategist Bryan Hasling on What Angel Investors Need to Know About QSBS, Maximizing the Tax Benefits of a Losing Investment, and the Limits of Tax-Driven Deal Selection

    Today's episode explores three ideas that caught my attention: 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.“We’re QSBS-eligible” is nice but not everything. Founders advertising QSBS eligibility can subtly distort investor judgment. Don’t let the tail wag the dog.QSBS claims are low-hanging fruit for IRS audits. Claiming a zero-tax outcome on a big winner almost guarantees scrutiny. Make sure your documentation is in order.I explore these ideas and more with Startup Wealth Strategist Bryan Hasling. Bryan Hasling is a Partner at Modern Financial Planning, a firm specializing in advanced tax and wealth management for families navigating the complexities of tech careers and startup equity. As both a practicing wealth advisor and an active angel investor with roots in Silicon Valley, Bryan brings a rare perspective: he lives on both sides of the table, helping clients extract maximum after-tax value from their investments while making those same bets himself. His work sits at the intersection of early-stage portfolio strategy and tax code fluency, giving him a uniquely practical lens on the tools many angels leave on the table.  During our conversation, Bryan shares: A breakdown of the five qualifying criteria a startup must meet to be considered a Qualified Small Business, including why the $75 million gross asset threshold matters more than most investors realize and how easy it is to accidentally miss it.The case for why 1244 ordinary income losses are arguably the more relevant tax tool for most angel portfolios, offering up to $100,000 in deductions for married filers against regular income when a startup shuts down.A practical documentation protocol for angel groups, including which records to collect at the time of investment to build an audit-ready file long before a liquidity event forces the issue.Connect with Bryan:  LinkedIn | Website Stuff We Reference Qualified Small Business Stock (QSBS) – Section 1202One Big Beautiful Bill Act (OBBBA)John HarbisonWhat does the Big Beautiful Bill Mean for Angel Investors? –A special podcast episode 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.

    52 min
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Ratings & Reviews

5
out of 5
3 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
    74
  • Rating
    Explicit
  • Copyright
    © 2026 The Diligent Observer Podcast
  • Show Website
    The Diligent Observer Podcast

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