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

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 [https://www.thediligentobserver.com/]. 🗞️ 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 [https://www.linkedin.com/in/sdied/]Baylor Angel Network [https://www.linkedin.com/company/baylorangelnetwork/] Connect with Andrew: Newsletter [https://www.thediligentobserver.com/] | X [https://twitter.com/akazlow] | LinkedIn [https://www.linkedin.com/in/andrewkazlow] | Book [https://angelops.pitchfact.com/] | Website [https://pitchfact.com/] Stuff We Reference: Baylor Angel Network [https://www.linkedin.com/company/baylorangelnetwork/] Baylor Angel Network, Hankamer School of Business [https://hankamer.baylor.edu/]Baylor Angel Network Team [https://www.baylorangelnetwork.com/about/management/]Baylor Angel Network Student Practicum Team [https://hankamer.baylor.edu/angel-network/practicum/team]Baylor Prospective Analysts [https://hankamer.baylor.edu/angel-network/prospective-analysts]Baylor University [https://www.baylor.edu/]Baylor Entrepreneurship [https://hankamer.baylor.edu/entrepreneurship] Angel Capital Association [https://angelcapitalassociation.org/] ACA Summit [https://events.angelcapitalassociation.org/] https://www.cbo.gov/publication/61562 Want more?  * Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter [https://thediligentobserver.com/].  * Check out the entire show library [https://podcast.thediligentobserver.com/] and follow via Apple Podcasts [https://podcasts.apple.com/us/podcast/the-diligent-observer-podcast/id1759589362], Spotify [https://open.spotify.com/show/2c7mLtTDy3hdWMnCWh9a9l], and YouTube [https://www.youtube.com/playlist?list=PLLEI-yh8KE6MTx4PFYE3SVCCl5lmcojwO]. All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

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 [https://www.thediligentobserver.com/]. 🗞️ 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 [https://www.linkedin.com/in/mark-friedman-89a540/] RTP Angel Fund [https://www.rtpangelfund.com/]Dental Innovation Alliance [https://www.linkedin.com/company/diavc/] Connect with Andrew: Newsletter [https://www.thediligentobserver.com/] | X [https://twitter.com/akazlow] | LinkedIn [https://www.linkedin.com/in/andrewkazlow] | Book [https://angelops.pitchfact.com/] | Website [https://pitchfact.com/] Stuff We Reference: Angel Capital Association [https://angelcapitalassociation.org/] ACA Summit [https://events.angelcapitalassociation.org/]ACA Mission and Leadership [https://angelcapitalassociation.org/mission-and-leadership/] RTP Angel Fund [https://www.rtpangelfund.com/]Dental Innovation Alliance [https://www.dialliance.com/]QSBS Reform, ACA [https://angelcapitalassociation.org/blog/house-passes-key-legislative-priorities-for-angel-investors/] Qualified Small Business Stock, Section 1202 [https://www.law.cornell.edu/uscode/text/26/1202]INVEST Act overview, Carta [https://carta.com/policy/invest-act/]INVEST Act Congressional Research Service summary [https://www.everycrsreport.com/reports/R48885.html]Accredited Investor Definition, SEC [https://www.sec.gov/resources-small-businesses/capital-raising-building-blocks/accredited-investors]Equal Opportunity for All Investors Act, CBO [https://www.cbo.gov/publication/61562] Want more?  * Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter [https://thediligentobserver.com/].  * Check out the entire show library [https://podcast.thediligentobserver.com/] and follow via Apple Podcasts [https://podcasts.apple.com/us/podcast/the-diligent-observer-podcast/id1759589362], Spotify [https://open.spotify.com/show/2c7mLtTDy3hdWMnCWh9a9l], and YouTube [https://www.youtube.com/playlist?list=PLLEI-yh8KE6MTx4PFYE3SVCCl5lmcojwO]. All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

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 [https://www.thediligentobserver.com/]. 🗞️ 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 [https://www.linkedin.com/in/peterjameswalker/] Carta's Website [https://carta.com/] Carta's LinkedIn [https://www.linkedin.com/company/carta--/] Connect with Andrew: Newsletter [https://www.thediligentobserver.com/] | X [https://twitter.com/akazlow] | LinkedIn [https://www.linkedin.com/in/andrewkazlow] | Book [https://angelops.pitchfact.com/] | Website [https://pitchfact.com/] Stuff We Reference: Carta Data [https://carta.com/data/] Angel Capital Association [https://angelcapitalassociation.org/] SAFE Financing Documents [https://www.ycombinator.com/documents] Angel Funders Report [https://angelcapitalassociation.org/angel-funders-report/] Rockies Venture Club [https://www.rockiesventureclub.org/] Datadog [https://www.datadoghq.com/] Want more?  * Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter [https://thediligentobserver.com/].  * Check out the entire show library [https://podcast.thediligentobserver.com/] and follow via Apple Podcasts [https://podcasts.apple.com/us/podcast/the-diligent-observer-podcast/id1759589362], Spotify [https://open.spotify.com/show/2c7mLtTDy3hdWMnCWh9a9l], and YouTube [https://www.youtube.com/playlist?list=PLLEI-yh8KE6MTx4PFYE3SVCCl5lmcojwO]. All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

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 [https://www.thediligentobserver.com/]. 🗞️ 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 [https://www.linkedin.com/in/sc0ttjac0bs/] QCA Ventures [https://www.qca.com/] QCA Ventures LinkedIn [https://www.linkedin.com/company/qca-ventures] Connect with Andrew: Newsletter [https://www.thediligentobserver.com/] | X [https://twitter.com/akazlow] | LinkedIn [https://www.linkedin.com/in/andrewkazlow] | Book [https://angelops.pitchfact.com/] | Website [https://pitchfact.com/] Stuff We Reference: QCA Ventures [https://www.qca.com/] Queen City Angels [https://www.qca.com/] Angel Capital Association [https://angelcapitalassociation.org/] ACA Summit [https://events.angelcapitalassociation.org/] QCA Standards and Practices Guide At-A-Glance [https://www.qca.com/wp-content/uploads/2025/02/QCA-Standards-and-Practices-Guide-At-A-Glance_2025.pdf] QCA Entrepreneur Boot Camp [https://www.qcabootcamp.com/] Want more?  * Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter [https://thediligentobserver.com/].  * Check out the entire show library [https://podcast.thediligentobserver.com/] and follow via Apple Podcasts [https://podcasts.apple.com/us/podcast/the-diligent-observer-podcast/id1759589362], Spotify [https://open.spotify.com/show/2c7mLtTDy3hdWMnCWh9a9l], and YouTube [https://www.youtube.com/playlist?list=PLLEI-yh8KE6MTx4PFYE3SVCCl5lmcojwO]. All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

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

Today's episode explores three ideas that caught my attention: 1. 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.  2. 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.  3. 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 [https://www.khanacademy.org/], 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 [https://www.linkedin.com/in/curtisfeeny/] Curtis’ Bookshelf: • Crossing the Chasm | Geoffrey Moore [https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream-dp-0062292986/dp/0062292986/ref=dp_ob_title_bk] • This is How They Tell Me the World Ends | Nicole Perlroth [https://www.amazon.com/This-They-Tell-World-Ends/dp/1635576059 ] • The End of the World is Just the Beginning | Peter Zeihan [https://www.amazon.com/End-World-Just-Beginning-Globalization/dp/006323047X] • Nuclear War | Annie Jacobsen [https://www.amazon.com/Nuclear-War-Scenario-Annie-Jacobsen/dp/0593476093] • Zero to One | Peter Thiel [https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296] • The Hard Thing about Hard Things | Ben Horowitz [https://a.co/d/b3bhcbU] Want more?  * Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter [https://thediligentobserver.com/].  * Check out the entire show library [https://podcast.thediligentobserver.com/] and follow via Apple Podcasts [https://podcasts.apple.com/us/podcast/the-diligent-observer-podcast/id1759589362], Spotify [https://open.spotify.com/show/2c7mLtTDy3hdWMnCWh9a9l], and YouTube [https://www.youtube.com/playlist?list=PLLEI-yh8KE6MTx4PFYE3SVCCl5lmcojwO]. All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.