The Diligent Observer Podcast

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.

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

Today's episode explores three ideas that caught my attention: 1. “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. 2. 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. 3. 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 [https://www.lagosangelnetwork.net/]. 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  LinkedIn [https://www.linkedin.com/in/solomon-king] Stuff We Reference  * Ideas, Cheques & Capital [https://share.google/hZRqQ87XUnAQnXvsg] * New York Angels [https://www.newyorkangels.com/] * Seraf Investor [https://www.seraf.io/] 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.