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

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.

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: 1. 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. 2. “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. 3. 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 [https://www.modernfp.com/], 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 [https://www.linkedin.com/in/bryanhasling] | Website [https://www.modernfp.com/] Stuff We Reference * Qualified Small Business Stock (QSBS) – Section 1202 [https://www.irs.gov/instructions/i1040sd] * One Big Beautiful Bill Act (OBBBA) [https://www.irs.gov/newsroom/one-big-beautiful-bill-act-tax-deductions-for-working-americans-and-seniors] * John Harbison [https://www.buzzsprout.com/2459970/episodes/17689098] * What does the Big Beautiful Bill Mean for Angel Investors? [https://youtu.be/OhlX2PnTWSo] –A special podcast episode  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.