The Diligent Observer Podcast

Today's episode explores three ideas that caught my attention:    Pitch deck ≠ the pitch. So many founders think their deck is the main thing standing between them and funding. It’s about so much more than the deck. Corporate grants are legit. I think often about government grants, but have minimized the importance of corporate programs. But these organizations regularly write $10K-$50K checks with no equity dilution – and that is massive for a young business. Plus, the process of applying forms the founder in a powerful way. Ghosting sucks – we must be better about this. #1 way to create founder trauma is to never respond. I explore these ideas and more with Kat Weaver, serial entrepreneur and Founder of Power To Pitch. She built her first company straight out of her college dorm room and successfully exited after scaling with six figures in pitch competition winnings. Her systematic approach to winning 22 out of 23 pitch competitions revealed that most founders fail not due to bad ideas, but poor communication - insights that led her to launch Power To Pitch, where she's now helped founders raise over $50 million in capital. As both an active angel investor and fundraising coach, Kat brings a rare dual perspective on what works (and what fails) on both sides of the investment table. During our conversation, Kat shares: A systematic approach to corporate grants that delivers $10K-$50K in non-dilutive funding within months - including the exact questions these applications ask and why they're a great alternative to government grants for early-stage founders.Why grant applications are actually founder communication bootcamp - explaining how the constraint of answering core business questions in 100-character limits forces clarity that transforms how founders pitch to all stakeholders.Red flag investor behaviors that signal poor partnership potential - from inappropriate questions to female founders to strong-arming business model changes without collaborative discussion.Connect with KatWebsite | LinkedIn | Instagram | YouTube Stuff We Reference Y CombinatorForbesFounder InstituteTechCrunchKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

On July 4, 2025, Trump’s “Big Beautiful Bill” was signed into law. Here are the takeaways for angel investors. The Good News R&D expenses can now be deducted immediately instead of spreading over five years. Example: portfolio company spends $1M on research, they get the full tax benefit upfront rather than spreading out $200K annually. This is huge cash flow impact for software, deep tech, and biotech companies.Qualified Small Business Stock (QSBS) exclusion got a serious upgrade. Shareholders can now exclude up to $15M in gains per company (up from $10M), and don't need to wait the standard five years to receive benefit. Holding for three years now yields a 50% tax exclusion, and four years gets 75%. More companies qualify too - the asset limit jumped from $50M to $75M.The Concerning Stuff International talent just got significantly more expensive to bring to the US. If founders are planning to relocate overseas hires, budget a few extra percentage points per head. Clean tech investors are facing a rough 6-48 months as credits for EVs, solar, wind, and clean hydrogen etc get phased out. If you're invested in this space, consider giving your founders some TLC because they’re definitely not getting it from this administration. University endowments are getting hit with additional taxes, which may choke VC capital flow. Since angels often co-invest alongside VCs, I expect a tighter funding environment for follow-on rounds.Bottom Line This is generally positive for most angels, the major exception being clean tech investors. The QSBS changes alone could save hundreds of thousands on exits, and the R&D benefits could make deep tech more attractive. Just be ready for a potentially tougher institutional funding environment ahead.Know someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Today's episode explores three ideas that caught my attention:   "If these companies roll to zero, it's a big problem" – Understanding this fundamental difference between ETA and venture startup investing is critical for angel investor portfolio construction and risk management. The "peace dividend" creating veteran entrepreneurs - Patrick's observation about post-combat veterans seeking meaningful civilian engagement revealed how macro geopolitical shifts can create unexpected entrepreneurial waves. Military handoffs - Patrick's description of asking previous commanders about unfulfilled goals mirrors exactly what successful business buyers should ask sellers, which is one of the things that make veterans so successful in the ETA world.  I explore these ideas and more with Patrick Flood who is the Founder and CEO of Owners in Honor, a nonprofit organization that has guided over 190 veterans toward business ownership through acquisition. A decorated Special Forces veteran who served for 26 years, Patrick brings a unique perspective on how military leadership skills translate to business operations. After earning his MBA from Duke's Fuqua School of Business, he identified the gap between veteran capabilities and traditional entrepreneurship paths, leading him to create a structured approach to business acquisition that leverages the collaborative, mission-driven mindset inherent in military culture.During our conversation, Patrick shares: The historical context of veteran entrepreneurship from WWII to today - explaining why current geopolitical conditions are creating a new wave of military-to-business transitions with unprecedented opportunity. Why the "smallest unit is two" principle creates natural advantages for veterans in business acquisition scenarios - contrasting this with the isolation challenges that traditional startup entrepreneurs face. A framework for understanding why ETA investments require different risk profiles than traditional startup investing - and how family offices and angel investors can benefit from this emerging asset class. Connect with PatrickLinkedIn | WebsiteStuff We ReferenceTexas A&MDuke UniversityPost-9/11 GI BillKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from an aerospace engineer turned association leader who's working to transform angel investing from "black art" to science while representing 15,000+ members deploying approximately $1 billion in private capital annuallyToday's episode explores three ideas that caught my attention:The path from art to science - Pat drew a fascinating parallel between angel investing and project management's evolution over 50 years. I wonder what 3 letter certification name we’ll land on!Accreditation through education - Pat's vision of certification as an alternative path to accredited investor status could democratize access to the asset class.Qualitative vs. quantitative tension - Pat's engineering background initially drove him toward standardization, but his board pushed back, emphasizing "gut feel." This reminds me how the subjective, “gut-feel” elements remain central to the angel investment process.I explore these ideas and more with Patrick Gouhin, CEO of Angel Capital Association. With 35+ years of experience leading professional societies - including the International Society of Automation and the American Institute of Aeronautics and Astronautics - Patrick combines his technical background with extensive community-building expertise to create educational pathways, knowledge infrastructure, and standards for the angel investing ecosystem.During our conversation, Patrick shares:How an estimated 20 million Americans qualify financially as accredited investors but most don't participate - representing a massive untapped resource for funding innovation across the country.His perspective that angel investors need a minimum of 10 investments (preferably 30) and must approach the asset class with patience, as failures typically appear in the first five years while winners emerge later.The ACA's strategy of providing low-barrier entry points to angel education (annual membership of $310) as an onramp before prospective angels commit to larger group membership fees and investment minimums.Connect with Patrick LinkedInStuff We Reference Bill PayneJohn HarbisonAngel UniversityFINRA ExamsKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from a portfolio management software CEO who sees the venture market's "healthy shakeup" forcing overdue conversations about profitability and angel group sustainabilityToday's episode explores three ideas that caught my attention:The venture market reset is healthy - Alycia embraces the current volatility as necessary medicine. It challenges the trope that stability is always preferable - perhaps occasional chaos forces better investment discipline.Angel group models are evolving - After 20+ years in existence, Alycia questions if the traditional angel group structure still works. I’ve had a lot of conversations recently about the model, and this one definitely got me thinking.Data tracking is hard – Hearing Alycia’s commentary on how even professional fund managers often struggle to locate basic investment documentation was a shock, and reminds me that the venture industry is still, in many ways, in its adolescence.I explore these ideas and more with Alycia Doxon, CEO of Seraf, a deal flow and portfolio management platform serving angel groups, VCs, and family offices. After raising $27 million as a tech company COO, she acquired Seraf in 2023 through her holding company Harriet Ventures. Alycia brings a unique dual perspective - combining operating experience with deep insight into private market mechanics - giving her a practical view of what's working and broken in early-stage investing.During our conversation, Alycia shares:Data-driven insights on geographic investment trends that challenge the post-COVID narrative about distributed entrepreneurship and explain why physical proximity to innovation hubs still dramatically impacts returns.A primer on "safe stacking" where founders can potentially raise multiple rounds without ever converting to equity—highlighting a critical vulnerability in one of the startup ecosystem's most popular investment vehicles.Critical due diligence questions most LPs never ask including how fund managers handle administration, accounting, and the surprising number who manage these functions internally despite the operational strain.Connect with Alycia LinkedInStuff We Reference Ron WeissmanChristopher Mirabile & Ham LordKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from the Chairwoman of Stella Foundation and founding member of Stella Angels who has invested in 160+ women-led startups and co-managed six consecutive San Diego Angel Conference funds totaling millions in early-stage capitalToday's episode explores three ideas that caught my attention:   Creativity is the gateway to better investing - Silvia's classroom exercises aren't just for students. Her approach to opening minds through creative prompts parallels exactly how angels need to spot outliers that don't fit conventional patterns.Relationships endure beyond failure - Her experience supporting founders through bankruptcy reminded me how the most valuable connections aren't defined by financial returns but by integrity during difficult moments. Muscle memory in pitching your thesis - Just as Silvia has her students pitch daily to build confidence, angels need the same repetitive practice to clarify and refine what truly matters in their investment approach.I explore these ideas and more with Dr. Silvia Mah, Director of Innovation at Biola University and Chairwoman of Stella Foundation. She brings a rare combination of scientific rigor and investment acumen as both a biochemistry PhD and seasoned angel investor who's backed over 160 startups with diverse founding teams. She bridges academic entrepreneurship with practical investment strategies while pioneering gender lens investing through multiple funds and angel groups. Her perspective is particularly valuable for understanding how university ecosystems can better connect with angel investors to create sustainable startup growth channels. During our conversation, Silvia shares: A "Three Cs of Capital" framework that helps angels understand their full value beyond just writing checks: financial capital, experiential capital, and network capital. A practical AI implementation technique for angel groups that transforms entrepreneur information into streamlined due diligence memos and project plans for volunteer teams. The "Angel Conference" model that universities are adopting nationwide to activate alumni networks, educate new angels, and fund campus-connected startups through mini-funds.Connect with Silvia LinkedInStuff We ReferenceIlya StrebulaevJohn HarbisonNext WaveKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from a 20-year angel investing veteran who created data-driven tools used by hundreds of angel groupsToday's episode explores three ideas that caught my attention:Simple beats complex every time - John's URL clicking method to track outcomes is brilliantly basic. Sometimes the best solutions are staring us in the face.Expertise >> crowds - John's analysis revealed a U-shaped return curve where heavily-invested deals performed well, but surprisingly, some smaller deals with just a few deep-industry experts also outperformed. Fresh perspective on the “wisdom of the crowds.”The first five years deceive us - Learning that early outcomes skew negative while big returns happen 5-15 years later explains why many angels quit too soon. Vital for inclusion in any angel education.I explore these ideas and more with John Harbison, Chairman Emeritus of TCA Venture Group. With over 20 years of angel investing experience, John has led the ACA's data initiatives and helped develop the Angel Funders Report. His blend of management consulting and hands-on investing makes him a highly insightful, data-driven leader in the industry.During our conversation, John shares:A practical approach to data collection that simplifies complex cap table analysis by focusing on the key ratio between investment amount and return amount, making portfolio tracking manageable for groups of any size.Detailed data analysis showing that early investment outcomes are misleading – the first five years are dominated by shutdowns while significant exits typically happen between years 5-15, fundamentally reshaping how angels should set expectations.A forward-looking vision for how AI can transform angel investing, from automating member expertise matching to guiding diligence questions, potentially improving both efficiency and decision quality. Connect with John LinkedIn | BlogStuff We ReferenceSerafAlycia DoxonRon WeissmanCTANLaunchpad VenturesKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from a 25-year veteran angel who advises investors and governments across four continents while chairing Silicon Valley's oldest angel network and the ACA Board of Directors Today's episode explores three ideas that caught my attention:   Angels are insulated from market turbulence - Ron's data shows angels maintaining pre-2021 investment patterns despite market volatility in recent months.  First-time CEOs are getting MORE funding - Contrary to what you'd expect in uncertain times, angels are backing more first-timers than ever. This challenges the conventional "flight to safety" narrative. Long-view investing as emotional discipline - Ron's emphasis on the reality of 5-8 year time horizons for angel investments is a psychological framework that helps investors avoid reactive decisions to monthly or quarterly fluctuations.  I explore these ideas and more with Ron Weissman, Chair of the Board of Directors at the ACA. He brings over 25 years in global venture capital and nearly two decades as an angel investor to his role. As Chairman of the Software Industry Group at Band of Angels, Silicon Valley's oldest angel network, Ron combines deep technical knowledge with historical perspective, having previously served as a CMO and Director under Steve Jobs at NeXT. His unique background as both a former Professor of History and technology executive made this a fascinating lesson in navigating uncertainty.  During our conversation, Ron shares: Evidence-based perspective on angel resilience backed by quantitative data showing investment patterns remain consistent despite economic turbulence. A counterintuitive insight that angels are funding more first-time CEOs than ever before, challenging the assumption that uncertain markets drive investors toward experienced founders. Historical patterns showing funds started after economic downturns "went higher, faster" and why this makes economic turbulence potentially advantageous for disciplined investors. Connect with Ron LinkedInStuff We Reference Denominator Effect by Ron WeissmanMary Todd LincolnACABand of AngelsKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from a global ecosystem builder who's processed data on 108,000 startups while helping 240 investor communities across six continents manage their deal flow. GET FREE SOCKS: Seren will send the first 100 listeners that sign up for the AI Portfolio Monitoring waitlist a pair of Dealum’s signature red socks. What better way to impress your fellow angels at the next pitch event?!Today's episode explores three ideas that caught my attention:   A 30% spike in angel fundraising activity in Q4 2024 - Seren shared data showing a remarkable uptick in companies submitting fundraising applications, which could have a wide range of implications.  2,000 new companies per month - That's 108,000 startups total with structured data! Such a value-add for the ecosystem.  The "pitch deck black hole" - Seren's firsthand experience as a failed founder gives her empathy for entrepreneurs who send applications “into the void.” This perspective is so important for investors to consider as we design and implement our processes.I explore these ideas and more with Seren Rumjancevs, CEO of Dealum. Having sat on every side of the cap table as founder, accelerator manager, and innovation consultant, She now leads the platform managing deal flow for over 240 investor communities worldwide with data on more than 108,000 startups. Her firsthand experience with the "pitch deck black hole" drives her mission to create transparency and efficiency in early-stage fundraising. During our conversation, Seren shares:How a perfect storm of platform failures created both opportunity and skepticism - revealing the challenges European startups face when trying to win trust from US angel communities during a crisis.Insights from tracking 108,000 startups globally, including recent data showing a 30% spike in fundraising activity starting in Q4 2023.Why portfolio tracking remains a major operational challenge for angel groups, detailing how Dealum’s newest AI solution will transform unstructured email updates into structured data visualizations.Connect with Seren LinkedIn | LinkedIn | XStuff We ReferenceTrends in Funding Rates Part 1Know someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Insights from a fund manager who has mobilized hundreds of women investors, championed gender-lens investing in the Southeast, and is now steering the ACA as its incoming ChairToday's episode explores 3 ideas that caught my attention:   Women angels grew 8x in 10 years - Kristina shared that female angels increased from 5% to 40% of all angel investors since 2014."Get out of your sandbox" - Her advice to deliberately step into unfamiliar networks struck me as the simplest yet most overlooked strategy for finding opportunities others miss.  Let’s be honest: we make investment decisions from the heart - When she quoted Bill Payne that investing ultimately comes from the heart, it validated what I’ve observed again and again. At the end of the day, most angel investment decisions, no matter how well researched or diligenced, are made with our gut. I explore these ideas and more with Kristina Montague, Managing Partner at JumpFund, which supports women-led ventures in the Southeast. As incoming Chair of the ACA and author of Jump In: Women Investing in Women, she brings over a decade of experience in gender-lens investing and building investor networks that drive returns and expand opportunities for overlooked founders. During our conversation, Kristina shares: Her account of launching the first micro-venture fund in the Southeast focused entirely on women-led ventures, illuminating the unique challenges and opportunities of pioneering a gender-lens investment approach in a traditionally underserved region. Tactical approaches for overcoming bias in investor due diligence questioning, including awareness of "prevention vs. promotion" questioning patterns that can disadvantage certain founders. An insider's view of the ACA's strategic initiatives, including new individual membership programs and advanced AI tools to leverage 20 years of investor data. Connect with KristinaLinkedIn | Website | XStuff We ReferenceAngel Funders ReportRon WeissmanMarcia DawoodKnow someone who would enjoy this episode? Share it with them! P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts. 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. Connect with Andrew LinkedIn | X | Angel Ops E-Book All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.