Podcast
The Diligent Observer Podcast
Hosted by Andrew Kazlow · EN
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.
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11episodes
Episodes
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Episode 63: Central Texas Angel Network's Rick Timmins on Data-Driven Angel Investing
1w ago00:37:25Tap to summarize🗞️ 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 LinkedInCentral Texas Angel NetworkConnect with Andrew:Newsletter | X | LinkedIn | Book | WebsiteStuff We Reference:CTAN Investment DataCTAN EntrepreneursCTAN MembershipACA Data InsightsACA Data Insight by Rick TimminsACA Angel Funders ReportCisco Investor RelationsSix SigmaTech Coast Angels / TCA Venture GroupAngel Capital Association SummitAustin Technology IncubatorAngel Capital AssociationACA SummitKnow 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.
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Episode 62: Baylor Angel Network's Steven Diedrich on Training Students to Think Like Angel Investors
2w ago00:36:56Tap to summarize🗞️ 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 LinkedInBaylor Angel NetworkConnect with Andrew:Newsletter | X | LinkedIn | Book | WebsiteStuff We Reference:Baylor Angel NetworkBaylor Angel Network, Hankamer School of BusinessBaylor Angel Network TeamBaylor Angel Network Student Practicum TeamBaylor Prospective AnalystsBaylor UniversityBaylor EntrepreneurshipAngel Capital AssociationACA SummitWant 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.
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Episode 61: “40 to 60% of Angel Investors Gone?” | ACA Board Member Mark Friedman on Startup Policy, QSBS, and the INVEST Act
3w ago00:40:22Tap to summarize🗞️ 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 LinkedInRTP Angel FundDental Innovation AllianceConnect with Andrew:Newsletter | X | LinkedIn | Book | WebsiteStuff We Reference:Angel Capital AssociationACA SummitACA Mission and LeadershipRTP Angel FundDental Innovation AllianceQSBS Reform, ACAQualified Small Business Stock, Section 1202INVEST Act overview, CartaINVEST Act Congressional Research Service summaryAccredited Investor Definition, SECEqual Opportunity for All Investors Act, CBOWant 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.
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Episode 60: “Startups Are Hype Machines” | Carta’s Peter Walker on Angel Exits, SAFEs, and AI-Age Investing
4w ago00:44:44Tap to summarize🗞️ 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 LinkedInCarta's WebsiteCarta's LinkedInConnect with Andrew:Newsletter | X | LinkedIn | Book | WebsiteStuff We Reference:Carta DataAngel Capital AssociationSAFE Financing DocumentsAngel Funders ReportRockies Venture ClubDatadogWant 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.
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Episode 59: QCA Ventures Director Scott Jacobs on Angel Due Diligence, Board Governance, and AI-Powered Deal Evaluation
May 1200:46:01Tap to summarize🗞️ 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 LinkedInQCA VenturesQCA Ventures LinkedInConnect with Andrew:Newsletter | X | LinkedIn | Book | WebsiteStuff We Reference:QCA VenturesQueen City AngelsAngel Capital AssociationACA SummitQCA Standards and Practices Guide At-A-GlanceQCA Entrepreneur Boot CampWant 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.
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Replay: "Your Board Can Make or Break the Company" | Curtis Feeny (Episode 17)
Apr 1400:56:58Tap to summarizeToday'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 LinkedInCurtis’ 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 HorowitzWant 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.
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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 3100:52:01Tap to summarizeToday'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 | WebsiteStuff We ReferenceQualified 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.
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Episode 57: "Old Money To New Money" | Lagos Angel Network Executive Director Dr. Solomon King on Mobilizing Legacy Nigerian Wealth into Venture, Building Angel Culture from Scratch, and Correcting African Founders' Biggest Misconceptions
Mar 1700:40:53Tap to summarizeToday's episode explores three ideas that caught my attention:“Old money” sitting on the sidelines – Solomon aims to convert Nigeria's legacy industrialists into venture investors. It made me wonder how much capital is waiting to be “activated” into the venture space, particularly in emerging capital markets.Community norms shape investment behavior – Solomon noted Africa's communal culture affects how accountability around angel capital is understood. Great reminder that investment frameworks can't necessarily be copy-pasted across cultures.A six-hour boat ride for a magazine – Solomon's early hustle to access business knowledge from remote Nigeria puts founder "resourcefulness" on a whole new level.I explore these ideas and more with Dr. Solomon King, Executive Director of the Lagos Angel Network. Dr. King brings over 18 years of experience spanning behavioral finance, alternative investments, and fundraising – a combination that uniquely positions him to bridge the gap between capital and the founders who need it most. As Executive Director of the Lagos Angel Network, he has led the organization's growth from a small community of 12 to over 120 active angel investors, while pioneering structured education programs that are reshaping how Africa's next generation of investors learns to deploy capital. With a background across banking, consulting, academia, and impact finance, Solomon offers a ground-level yet globally-informed perspective on what it truly takes to build an early-stage investment ecosystem from the ground up.During our conversation, Dr. King Shares:Why Africa's communal culture requires a fundamentally different accountability conversation with founders around angel capital, and how LAN has adapted Western angel frameworks to reflect that reality.His thesis that climate tech in Africa is poised to follow a similar trajectory FinTech did a decade ago – driven by infrastructure buildout, democratizing access, and investor attention finally catching up to the opportunity.How Lagos Angel Network grew from 12 to 120 members in two years by positioning angel investing as a portfolio strategy accessible to anyone with disposable investable income – not just institutional players.Connect with Dr. Solomon King LinkedInStuff We Reference Ideas, Cheques & CapitalNew York AngelsSeraf InvestorWant 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.
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Episode 56: "Hard Tech Is Hard, But So Is Software” | Industrial Sustainability VC Anthony Del Porto on Finding Step-Change Value in Hard Tech, Why the Valley of Death Is Shrinking, and Where he’s Seeing Alpha in 2026
Mar 300:46:53Tap to summarizeToday's episode explores three ideas that caught my attention:Green premium is a deal killer – Anthony won't touch deals where eco-friendliness costs more (end state). If the sustainable solution isn't also the economically superior one, it won't easily scale.Tech transfer done right – Hearing Anthony describe how he’s seen universities claim 50% equity and “blow up” a cap table from day 1 highlights how critical doing tech transfer “right” is for the industrial sustainability ecosystem.The “valley of death” is shrinking – Fascinating insight into where Anthony sees the next wave of hard tech financing coming from, including why the "valley of death" between VC and institutional debt is beginning to close.I explore these ideas and more with a mechanical engineer-turned-COO-turned VC, Anthony Del Porto. He began his career as a mechanical engineer doing industrial process automation – literally walking factory floors, building custom machines, and watching firsthand how the physical world gets made. After a pivot into fintech as COO of an early-stage startup, he developed a dual lens that's rare in early-stage investing: deep technical credibility in hard, physical systems combined with firsthand experience navigating the chaos of a high-growth software company. He now runs BetterWay, a pre-seed VC firm focused exclusively on industrial sustainability – funding startups that are both environmentally superior and economically compelling, a combination he argues is the only kind worth backing.During our conversation, Anthony shares:A framework for evaluating whether a sustainability startup can actually compete on price.Why circular economy startups are uniquely insulated from tariff risk and supply chain volatility.The specific reason he looks for startups that can be profitable at small scale before building a large plant.Connect with AnthonyLinkedIn | WebsiteStuff We ReferenceDexMatRavelThird SphereWant 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.
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Episode 55: "We Need to Disrupt Ourselves" | SWAN Impact Network Executive Director Suresh Sundarababu on Breaking the Angel Group Mold, Building Great Founder Support Ecosystems, and Takeaways from The 2026 World Economic Forum
Feb 1700:43:39Tap to summarizeToday's episode explores three ideas that caught my attention: The “angel investor” imposter syndrome – Suresh’s admission of feeling “unworthy” of the title despite being accredited made me reconsider how much terminology matters, and how many “angels” just consider themselves “investors”. Time and talent > treasure – Suresh mentioned SWAN's clever “associate” model that welcomes non-investors and challenges the exclusivity that can often limit network growth and pipeline development for future investors. A provocation that angel networks will be disrupted if they don't disrupt themselves - detailing specific antiquated processes that prioritize member comfort over founder success and mission impact. I explore these ideas and more with Suresh Sundarababu, Executive Director of SWAN Impact Network, where he's leading an ambitious reimagining of how angel groups can serve both founders and investors. With nearly three decades scaling global organizations and a master's in electrical engineering, Suresh brings an unconventional background to angel investing - one that prioritizes purpose over pedigree. His guiding principle, "not trying to change the world, but the world I touch," has shaped SWAN's recent evolution into an experimental platform for democratizing impact investment and building comprehensive founder support ecosystems. During our conversation, Suresh shares: A fascinating experiment in “fast-tracking” deals outside traditional angel group processes that tests whether trusted partner referrals can bypass more traditional committee-driven evaluation cycles. The “ecosystem partner” framework that saved a wind turbine founder thousands in legal fees by connecting startups with fractional services, executive coaches, and specialized firms aligned with early-stage constraints. A vision for “collective investment” structure where a hardened company pitches to multiple aligned angel groups simultaneously and closes their entire round in one coordinated effort rather than needing to hit 15-20 groups sequentially. Connect with Suresh LinkedIn | LinkedInStuff We Reference SWAN Impact NetworkBob BridgeWant 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.
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