Shows
The Diligent Observer PodcastEpisode 45: Breaking Down the 2025 Angel Funders Report | ACA Board Member John Harbison on Valuation Compression, Board Seat Decline, and Follow-On PerformanceToday's episode explores three ideas that caught my attention: Angel board representation dropped from 34% to 26% - Despite consistently seeing better returns WITH board representation, fewer angel groups are securing board seats. Early-stage valuation compression - The gap between median pre-seed ($10M) and Series B ($19M) valuations has shrunk by 3x over the last few years. Hybrid angel group models write bigger checks - Groups combining both “pure networks” and funds tend to invest larger amounts than pure models. I explore these ideas and more with John Harbison, ACA Board Member, Chairman Emeritus o...
2025-08-2649 min
The Diligent Observer PodcastEpisode 44: "Bridge Building, Not Wall Building" | Heartland Angel Network Lead Quinn Robertson on Connecting Local Founders to National Capital, the NW Arkansas Innovation Ecosystem, and Activating New Angel InvestorsToday's episode explores three ideas that caught my attention:Capital proximity ≠ capital access - Quinn's take on the "access to capital problem" was a thoughtful take on perceived geographic disadvantages in fundraising.Non-investment motivations often attract angel participation - His insight that professional development and community often drive an angel’s first steps in the ecosystem was well said and aligns with my own experience.New investment categories being created in Micro-SaaS - The emergence of profitable but non-venture-scale businesses poses fascinating portfolio construction questions.I explore these ideas and more with...
2025-08-1241 min
The Diligent Observer PodcastEpisode 43: "Campus-Born Ventures: An Underappreciated Asset Class" | Tom Duening on Democratizing Campus Capital, University Revenue Models, and Worldwide Deal FlowToday's episode explores three ideas that caught my attention: The maturity evolution - His emphasis on campus ecosystems moving away from "every idea is good" to investor-ready reality checks highlights a necessary shift in the academic entrepreneurship model.The pledge-based investing model - Tom's concept of angels pledging a percentage of capital gains as a gift back to universities creates a virtuous funding loop I have seen deployed in some university entrepreneurship circles. Clever and effective way of giving back to an ecosystem.Business plans are not entrepreneurship - Tom's story about the...
2025-07-2943 min
The Diligent Observer PodcastEpisode 42: "Just Fix My Pitch Deck" | Power To Pitch Founder Kat Weaver on Why Communication Beats Perfect Decks, Creative Financing Options for Founders, and the “Founder-First” Investment PhilosophyToday'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 traum...
2025-07-1540 min
The Diligent Observer PodcastSpecial Episode: What Does the Big Beautiful Bill Mean for Angel Investors?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...
2025-07-1011 min
The Diligent Observer PodcastEpisode 41: "You Didn't Serve Alone, Don't Search Alone" | Owners in Honor Founder Patrick Flood on Why ETA Differs from Startup Investing, Post-WWII Entrepreneurship Patterns, and Risk Mitigation in Small Business AcquisitionToday'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 m...
2025-07-0153 min
The Diligent Observer PodcastEpisode 40: "Fuel for the Economic Engine" | Angel Capital Association CEO Patrick Gouhin on Professionalizing Angel Investing, Expanding Accreditation Pathways, and Cultivating Startup EcosystemsInsights 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....
2025-06-1722 min
The Diligent Observer PodcastEpisode 39: "The Devil is in the Details" | Seraf Investor CEO Alycia Doxon on Venture Market Corrections, Capital Consolidation Trends, and The Future of Angel NetworksInsights 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 ab...
2025-06-1039 min
The Diligent Observer PodcastEpisode 38: "Practice Your Thesis Until It’s Muscle Memory" | Stella Foundation Chairwoman Dr. Silvia Mah on Activating University Ecosystems, The Three C's of Capital, and Creating Proud Investment PortfoliosInsights 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 th...
2025-06-0336 min
The Diligent Observer PodcastEpisode 37: "Winners Emerge After the Five-Year Mark" | TCA Venture Group Chairman Emeritus John Harbison on Exit Timeline Expectations, Portfolio Diversification Strategies, and The Unexpected U-Curve of ReturnsInsights 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 year...
2025-05-2734 min
The Diligent Observer PodcastEpisode 36: "Don't Panic" | Angel Capital Association Chair Dr. Ron Weissman on Navigating Market Volatility, Surging Investment in First-Time CEOs, and Why Downturns Are Great Investment WindowsInsights 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 disci...
2025-05-2007 min
The Diligent Observer PodcastEpisode 35: "108,000 Startups and Counting" | Dealum CEO Seren Rumjancevs on Angel Group Efficiency, AI-Powered Portfolio Tracking, and Bridging Global Angel NetworksInsights 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 appli...
2025-05-1328 min
The Diligent Observer PodcastEpisode 34: "Angels Are Always Hopeful" | Incoming ACA Chair Kristina Montague on Growing Women's Capital Networks, Expanding the Investor Tent, and Finding Arbitrage in Overlooked InnovatorsInsights 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 decis...
2025-05-0631 min
The Diligent Observer PodcastEpisode 33: "Angel Investing Isn't a Trending Topic" | ACA Chair Emeritus Marcia Dawood on Angel Investment Cycles, Using Philanthropic Capital for For-Profit Ventures, and Making Fundraising Easier for EntrepreneursInsights from an award-winning author and podcast host whose advocacy work is reshaping how angels invest and entrepreneurs access capital across ecosystems Today's episode explores three ideas that caught my attention: Clarity is kindness - Marcia highlighted how the most requested entrepreneur feedback is for angels to simply say "no" faster. Angel investing is still a mystery for many - It struck me how she still encounters people unaware they can participate in angel investing. There exists a massive pool of "latent” angels. The golden gut - 30 years of industry experie...
2025-04-2943 min
The Diligent Observer PodcastEpisode 32: "The Founder is Everything" | Super Angel Katie Dunn on Effective Due Diligence, How Relationship-Building Drives Returns, and Why Clarity is KindnessInsights from a commercial real estate veteran who's now funding underrepresented founders while challenging traditional angel investing assumptions Today's episode explores three ideas that caught my attention: Financial models are founder due diligence too - Katie evaluates financial projections not for accuracy but to understand how founders think. If it’s not a heck yes it’s a heck no - When she can't quickly decide, she defaults to "no." This candid approach respects founder time more than stringing them along.Angels tend to overvalue their money, undervalue their networks - The re...
2025-04-2244 min
The Diligent Observer PodcastEpisode 31: "Less Than 2% of VC Funding" | SWITCH CEO Kate Brodock on Untapped Founder Talent, The Arbitrage Opportunity in Women-Led Ventures, and Equipping New Angel InvestorsInsights from a twenty-year tech ecosystem veteran creating pathways for women angel investorsToday's episode explores 3 ideas that caught my attention: Capital distribution defies logic - Kate highlighted that less than 2% of VC funding goes to women-led teams, yet data shows they're 3x better at capital efficiency. Wild. Education activates capital - Confidence gaps, not capability gaps, often prevent qualified individuals from angel investing. Her focus on education first, then group formation, flips the traditional model brilliantly as this is something I’ve seen many investor communities struggle with. Unconscious bias has m...
2025-04-1541 min
The Diligent Observer PodcastEpisode 30: "You Need 500 Site Walks" | B2B Sales Leader Henry Talamantes on The Competitive Advantage of Ridiculous Customer Discovery, Post-Mall America, and the Next Chapter for Urban Office SpaceInsights from a PropTech growth veteran who's scaled multiple startups to $175M+ in venture funding while driving innovation in commercial real estate Today's episode explores 3 ideas that caught my attention: Ridiculous customer discovery is what it takes – The “in” doesn’t matter. What matters is being ready to make the most of that “in”. His first enterprise pitch came about because the buyer liked his logo. But the capacity to close was predicated on a stupid deep understanding of the problem. Entertainment could save retail – The anchor mall tenant is changing. The TopGolf compariso...
2025-04-0840 min
The Diligent Observer PodcastEpisode 29: "Values on Our Sleeve" | Liberty Ventures Founder Alexander McCobin on Values-Forward Capital Allocation, Building Authentic Communities, and Why Great Events are 100% Worth the EffortInsights from a former philosophy student who's built a 15,000+ member network of principled business leaders and facilitated values-aligned investmentsToday's episode explores 3 ideas that caught my attention:The power of a radically transparent thesis - Alexander's approach of explicitly stating values upfront both attracts aligned founders and repels mismatches. Patient capital as competitive advantage - His willingness to build relationships over months/years before investing challenges the all-too-common "FOMO" mindset. Slowing down can lead to better decisions. Events as ecosystem catalyst - Liberty Ventures uses gatherings to enhance their thesis an...
2025-04-0143 min
The Diligent Observer PodcastEpisode 28: "Patents Won't Save a Bad Business" | Patent Expert Russ Krajec on IP-Backed Lending, Why Patents Create the Most Value at Year 15, and Common Angel Due Diligence MistakesInsights from a patent strategist who's authored 1,000+ patents and is revolutionizing IP finance through patent insurance and IP-backed lending at BlueIronToday's episode explores three ideas that caught my attention: Provisionals are never a good idea - Founders who file provisional patents are explicitly saying they don't value their IP enough to spend an extra $600. Insurance vs litigation reality - Patent lawsuits are 10x more common than D&O claims, yet investors often push for D&O coverage while ignoring patent insurance.Trade secrets are so...
2025-03-2537 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 6: "Science Projects Masquerading as Commercial Products" | Dr. Chris Keefer on the SMR Hype Cycle & Energy Independence ImperativesToday's episode explores 3 ideas that caught my attention: Some Patience Required: Nuclear's rise from 50–60% to 93% capacity factors took decades, not years. Expecting quick returns on new nuclear tech ignores the industry’s inherently long development cycles. Infrastructure Economics Favor State Capital: Like railroads, nuclear requires high upfront investment with long-term benefits, making it better suited to state-backed efforts. That’s why countries like China build reactors faster and cheaper than the West, where costs and timelines balloon without national coordination. Fusion is a Long Way Away: Fusion, despite major investment, remains far more comple...
2025-03-1849 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 5 - "The Math Doesn't Work Without Nuclear" | Nuclear Supply Chain Leader Tighe Smith on the Evolving Market, Factory Style Manufacturing, & Fuel SupplyToday's episode explores three ideas that caught my attention: Commonality is the Way - Variance in design increases cost. Consistency in design reduces it. Tighe shared helpful parallels with other industries to highlight the point that the industry is beginning to benefit from some economies of repetition, and this pattern is increasing the speed and cost efficiencies afforded. The fusion funding paradox - Tighe pointed out fusion attracts outsized investment compared to fission, yet has never demonstrated ability to build actual power plants. Hmm. Forever chemicals vs. manageable radiation - Tighe's contrast bet...
2025-03-1136 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 4 - "The Secret Ingredient Is Demand Growth" | Nuclear Industry Writer Emmet Penney on Market Demand, What's Over/Underhyped, and Geography's RoleToday's episode explores three ideas that caught my attention:Nuclear's renaissance hinges on electricity demand growth - More than any other guest I’ve spoken with, Emmet nailed the point that macro demand growth—not new tech or climate concerns—is what will truly drive growth in the nuclear sector. And similarly, falling demand is what killed momentum in the space in the 1970s. The “safety” problem has already been solved - Nuclear energy is ridiculously safe, and the incremental return on “more safe” designs is miniscule. As long as the technology is “as safe” as existing...
2025-03-0446 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 3 - "Digital is No Longer a Four-Letter Word" | Control Systems Expert Ryan Marcum on Advanced Reactors, The Digital Evolution, and AI's Role in NuclearToday's episode explores three ideas that caught my attention: Demonstration Reactors are MVPs for Nuclear Energy - These reactors are 1/100 - 1/10 the size of a commercial scale reactor, and enable advanced reactor designs to be proven out from a technical and regulatory perspective with substantially lower cost than a full-scale reactor. Genius. Timelines are Long, but (Maybe?) Getting Shorter - 10ish years is a good ballpark timeline from idea to commercial scale. That’s a long time, but it used to be 20. Pioneers like Nuscale are “taking the lumps” to help shorten that timeframe.Underh...
2025-02-2539 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 2 - "We Need to Rebuild this Entire Industry" | Texas Nuclear Alliance Founder Reed Clay on Regulatory Reform, Rebuilding the Nuclear Workforce, & MomentumToday's episode explores three ideas that caught my attention: Perception is Reality - The discussion of nuclear waste politics surfaced how fear-based narratives can derail rational energy policy for decades.Nuclear = Massive Economic Development Opportunity - Reed drew a number of parallels between recent efforts to onshore the semiconductor industry – highlighting how massive industry investments create economic flourishing.Uri's Hidden Lesson - The revelation about cancelled expansions at Texas’ operating reactors Uri highlighted how different Texas's energy landscape might have been if some of these investments were made decades ago.I explo...
2025-02-1828 min
The Diligent Observer PodcastDeep Dive Season 1: Nuclear Energy | Episode 1 - "Fission is the New Fire" | Nuclear Investor Rod Adams on the Nuclear Renaissance, AI's Role in Nuclear Design, and Building Through Regulatory ChangeToday's episode explores three ideas that caught my attention: AI is Transforming Nuclear Too - The possibility of applying AI tools to parse 4,500-page regulatory documents represents a breakthrough in addressing one of nuclear's biggest bottlenecks - regulatory compliance. Falling Demand Drove Nuclear's Decline in the Late 1970s, Not 3 Mile Island - Rod's point about nuclear orders stopping in 1974—five years before Three Mile Island—due to falling electricity demand growth challenges the standard narrative. Reduced energy consumption, not safety concerns, actually killed the first nuclear boom.Don't Call It a Comeback - When...
2025-02-1157 min
Startup Stories from the TreehouseWhy Most Startups Shouldn't Seek Angel Investment: A Candid Look with Andrew Kazlow of PitchFact S03E03Should You Raise Angel Investment? A Contrarian ViewIn this eye-opening episode of Startup Stories from the Treehouse, Andrew Kazlow, CEO of PitchFact, challenges conventional wisdom about angel investing. Drawing from his extensive experience with angel networks and startups, Andrew boldly claims that most entrepreneurs shouldn't raise capital from angels.Through the lens of his 'Angel Ops' framework, Andrew breaks down the hidden mechanics of angel networks, revealing why many founders waste months pursuing the wrong funding strategy. He shares practical insights on due diligence red flags, relationship building, and valuation pitfalls that could make...
2025-02-0655 min
The Diligent Observer PodcastEpisode 27: "Water is Critically Underinvested" | Water Technology Expert Doug Lee on Why 0.2% is Not Enough, Barriers to Entry in Hard Tech, and Creating Win-Together ScenariosToday's episode explores three ideas that caught my attention: The “conjoined twin” - Water touches every form of energy generation. Doug’s laser focus on this point made me consider what other interdependencies we often overlook.Market signals can mislead on timing - It’s often said “It’ll take longer and cost more than you think.” Based on Doug’s comments, this saying applies even more in industrial applications - these things can take a long time to percolate, even when the market is responding positively. The future bill always comes due - Doug’s perspe...
2025-02-0443 min
The Diligent Observer PodcastEpisode 26: "Never Say Revenue" | Startup Economist Paul O'Brien on Seed-Stage Venture Philosophy, Building Domain-Specific Angel Portfolios, and Media-First InnovationToday's episode explores three ideas that caught my attention: The “angel investor party trick” - Paul highlighted how the rush to become an angel investor mirrors the increase in the appeal of the “celebrity entrepreneur” we’ve seen over the last couple of decades. He believes that to flourish, the investor community must consolidate (read: more of us become an LP in a fund vs doing our own thing) and the “average” angel must level up their value-add. His direct and aggressive stance on this aligns with commonly discussed themes here at the Diligent Observer, and correlates perf...
2025-01-2845 min
The Diligent Observer PodcastEpisode 25: "Intestinal Fortitude" | Startup Sales Veteran Rob Balena on Vetting Enterprise Sales Strategy, Hiring a Great Sales Force, and Where Most Founders Get it WrongToday's episode explores three ideas that caught my attention: Long ball is the name of the game - Can this company survive long enough to close a deal? Maybe they’ve closed some VC funding, but the risk-seeking VC buyer is VERY different from the risk-averse enterprise buyer. Proof in one does not serve as proof in another. How is this company going to get great sellers to come sell for them? - This is not a guarantee. Can this founder convince the best salespeople that their thing is worth selling? The founder’s vision...
2025-01-2147 min
The Diligent Observer PodcastEpisode 24: "Build the Rainforest in the Desert" | New Mexico Angels President Drew Tulchin on Defense Tech Innovation, Ecosystem Building, and Investing Alongside Government GrantsToday's episode explores three ideas that caught my attention: The Double-edged Sword of Government Grants - Fascinating perspective on how SBIR grants can either validate or misdirect founders. The pattern of companies becoming "SBIR shops" highlights a key risk when coinvesting with the US Government.The Silent Technical Founder - Counter to my expectation, Drew argues that technical founders who can't communicate well may signal team-building challenges rather than an alpha-generating opportunity.The Advantages of a Rural Ecosystem - The "frontier mentality" displayed by the New Mexico Angels illustrates that r...
2025-01-1425 min
The Diligent Observer PodcastEpisode 23: "Patents Are Just One Piece" | University Innovation Leader Pete ONeill on the Opportunity in Highly Regulated Markets, Founder Credibility, and Strategic SpecializationToday's episode explores three ideas that caught my attention: The paradox of regulatory rigor - Many investors simply screen out opportunities in highly regulated spaces like medical, deep tech, and defense. “I only look at post-revenue software deals",” for example. But Pete's insight that difficult regulatory requirements actually create competitive advantages suggests this approach completely misses a huge opportunity to back highly defensible businesses. Yes, heavy regulation increases risk, but it also increases possible return. Faculty are rarely suited to be entrepreneurs - Pete’s observation that tenured faculty rarely make ideal startup CEOs highligh...
2025-01-0738 min
The Diligent Observer PodcastEpisode 22: "50% of Corporate Payments are Still Paper Checks" | Payments Veteran Blair Jeffery on The Evolution of B2B Payments, Cross-Border Innovation, and Building Through Market TurbulenceToday's episode explores three ideas that caught my attention: The persistence of paper checks reveals deeper truths about business incentives - It totally blew my mind that half of B2B payments are issued by check. Blair’s comments immediately brought to mind the classic Charlie Munger quote: “Show me the incentive and I’ll show you the outcome.”Regulatory shifts can derail even the best execution - Blair's story of how unexpectedly being forced into “regulated entity” status highlights how unexpected external forces can completely shove a company “off into a ditch,” regardless of how strong pro...
2024-12-1745 min
The Diligent Observer PodcastEpisode 21: "95% Business, 5% Technical" | AI CONNEX Founder Dan Sinawat on Vertical AI Strategy, The Evolution of Machine Intelligence, and Why World Cup 2026 is a Massive OpportunityToday's episode explores three ideas that caught my attention: * It’s like 6yr too late for horizontal AI - Dan's commentary about how startups trying to “develop a new LLM” are wasting their time competing with billion-dollar foundational models reinforced how many founders are setting themselves up for failure by not laser focusing on vertical applications. Don’t be everything. Be one thing. * Global events as AI catalysts - PSA: The world is bigger than just the USA. Dan’s perspective on major world events (such as World Cup 2026) as unique opportunities for AI technology reframed h...
2024-12-1038 min
The Diligent Observer PodcastEpisode 20: "Part Art, Part Process" | Elevate Ventures' Patrick Sweeney on Startup Success Predictors, Recent Evolutions in VC Hiring, and the Criticality of Founder EmpathyToday's episode explores three ideas that caught my attention: * Immigrant founders outperform statistically - Patrick's research shows a strong correlation between immigrant status and startup success. Makes me wonder how much untapped potential exists in commonly overlooked founder demographics.* The empathy imperative - Treating every "no" with respect is SO important because you never know where founders will be in a few years. * Sometimes revolution starts with regulation - A single 1968 ruling unleashed institutional capital into VC, which Patrick mentioned has enabled roughly 75% of public company value today. Got me wondering what current...
2024-12-0334 min
The Diligent Observer PodcastEpisode 19: "Smart Money Goes Beyond the Checkbook" | Seasoned Angel Investor Mitra Miller on the Importance of Founder "Relentlessness", Innovation in Houston, and "Poker" vs "Roulette"Today's episode explores three ideas that caught my attention: * The power of student innovation - The story of Ariana Williams turning a class paper into Prairie View A&M's first innovation center demonstrates how exposure to possibilities can catalyze institutional change.* Angel groups are getting younger - The shift from mostly retirees to 75% working professionals in the Houston Angel Network reflects a broader evolution of early-stage investing. This materially changes the dynamics of engagement.* Daily optimization >>> big pivots - Her insight about successful founders making micro-adjustments daily rather than dramatic strategy shifts challenges...
2024-11-2645 min
The Diligent Observer PodcastEpisode 18: "Government CAN Move Efficiently" | Innovation Fund Manager Mike Wilkes on Non-Dilutive Capital, Startup Support, and Local Job CreationToday's episode explores three ideas that caught my attention: * The Value of Intentional Silence - Mike’s approach to founder interviews, watching body language, and creating space for stories shows how sometimes what's NOT said reveals more than what is.* Government as Startup Catalyst - Mike explains how efficient government support can drive innovation. This challenges the stereotype of slow bureaucracy. McKinney EDC’s unique Innovation Fund model is making a crazy impact with nearly 50 companies funded so far. * Due Diligence Isn’t Just Analytical - The level of emotional connection to a proble...
2024-11-1935 min
The Diligent Observer PodcastEpisode 17: "Your Board Can Make or Break the Company" | Curtis Feeny on Governance, Market Cycles, and the "Say Yes" CareerToday'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...
2024-11-1244 min
The Diligent Observer PodcastEpisode 16: The 3 T’s of Early Stage Investing | Larry WarnockLarry Warnock is the Founding Partner of Ring Ventures (part of the Alumni Ventures Group), a Venture Capital Fund that deploys investment capital into tech and tech-enabled early-stage businesses. He continues consulting with the fund as a Partner Emeritus. He has made over 70 investments in his tenure as a VC. Larry is a seasoned venture-backed tech executive with multiple exits via acquisition or IPO. Prior to founding Ring Ventures he was the President and CEO of Olono, an AI platform for sales effectiveness (acquired by InsightSquared). Previously he was theCEO of Gazzang, a provider of big data...
2024-11-0551 min
The Diligent Observer PodcastEpisode 15: Diligence the Diligence: Unpacking the SideCar Angels Strategy | Alden ZechaAlden Zecha is the Managing Director at SideCar Angels and serves on the Board of the Angel Capital Association. He has invested in over 80 startups, two of which have become unicorns valued at over $1 billion. Alden has founded multiple enterprises and previously worked in various roles in government, academia, and private industry. He has spoken at the White House on entrepreneurship, serves as a Senior Fellow at Duke University's Fuqua School of Business, and is NACD Director Certified. Alden also serves on multiple corporate boards including chairing an audit committee and focuses on international expansion with an...
2024-10-2940 min
The Diligent Observer PodcastEpisode 14: Don't Throw Away $50K: Lessons from Startup CTO Expert | Igor BelagorudskyIgor Belagorudsky builds, advises and scales startups. From a germ of an idea through seed, VC rounds, strategic partnerships and anything that comes next. Sometimes, he invests in them too.He helps entrepreneurs make good decisions about product, team, processes and everything in between.As a CTO, Igor is a confident full stack enterprise architect in several technology ecosystems. As a leader, he is a champion of smart and transparent teams, open communication across the entire organization, repeatable processes and leadership by example. As a human, he is an ardent believer in equality, equity, fair...
2024-10-2243 min
The Diligent Observer PodcastEpisode 13: Growing the Alamo Angels from 30 to 130 Members in 4 Years | Sebastian GarzonJuan “Sebastian” Garzon serves as the Executive Director of Alamo Angels, the largest angel network in Texas. In his role, he facilitates access to capital via angel investing to companies across the U.S. and Latin America. Through his strategic guidance, Alamo Angels has invested in over 50 companies to date.Sebastian's exceptional acumen and dedication have been recognized by industry peers and publications alike. His notable accolades include being named to the prestigious Texas Top 100 for 2024, as well as being recognized as a recipient of "40 Under 40" in Corpus Christi. Moreover, his commitment to continuous growth and...
2024-10-1544 min
The Diligent Observer PodcastEpisode 12: From CPG Founder to B2B SaaS Investor | Brook StroudBrook Stroud is a Senior Principal at Alumni Ventures, where he applies his passion for early-stage investing, drawing from his experience as both an entrepreneur and investor. He founded and successfully exited two consumer startups: La Matera, a fashion brand, and Somerset, a beverage company.Prior to Alumni Ventures, Brook worked at Brand Foundry Ventures, focusing on early-stage investments, due diligence, and portfolio management. He also gained valuable fintech experience at Funding Circle during its expansion phase leading up to its IPO.Brook earned a BA in History from the University of Richmond...
2024-10-0840 min
The Diligent Observer PodcastEpisode 11: The Power of Relationship-Driven Angel Investing | Patrick FarrellPatrick Farrell founded Potomac Angel Capital in early 2022 to bring like-minded angel investors together in the D.C. area to invest in mission-driven, early-stage entrepreneurs for mutual financial benefit, lasting impact, and meaningful relationship. As the Executive Director, Patrick is intimately involved in sourcing deals, hosting events, leading diligence, and serving as a trusted advisor to investors/portfolio companies. In late 2023, he moved to Austin, TX to expand PAC and plant a second angel network as part of a vision to enable flourishing entrepreneurial ecosystems in cities across the U.S.Prior to PAC, as...
2024-10-0136 min
The Diligent Observer PodcastEpisode 10: Investing in Venture Capital for Human Flourishing | Phil JungPhil Jung is a Partner at Sovereign’s Capital where he invests in Seed and Series A stage technology companies led by faith-driven entrepreneurs across the U.S. and Southeast Asia. He was previously the CFO and CPO at Mindoula, a healthtech company that serves populations with complex behavioral health, medical, and social challenges. Prior, he was with the Maryland Venture Fund, Foundation Capital, and TDF Ventures, leading investments in early and growth stage technology companies. He began his career at KPMG’s Risk Consulting practice in Silicon Valley and co-founded the Jeremy Lin Foundation, a non-profit whos...
2024-09-2436 min
The Diligent Observer PodcastEpisode 9: Bouldering & Biomedical Entrepreneurship | John CriscioneDr. John Criscione is a professor of Biomedical Engineering at Texas A&M University who trains medical device engineers while simultaneously inventing, testing, and commercializing medical technologies. Dr. Criscione has been serving in this capacity for over 20 years and also serves as the CTO for CorInnova, a biomedical technology company focused on addressing Acute Heart Failure. During our conversation, he discusses: * The importance of disagreement for innovation* Translating inventions into marketable products* The challenges of new technologies and indications in medical devices* The pivotal role of angel in...
2024-09-1743 min
The Diligent Observer PodcastEpisode 8: The Art & Science of Angel Investor Education | Dr. Margaret BachelerDr. Margaret Bacheler is the Director of Educational Initiatives for the Angel Capital Association, where she oversees the Ann and Bill Payne ACA Angel University program. Dr. Bacheler is passionate about inclusive economic development, facilitating opportunities for multigenerational wealth creation, and diversifying the ranks of angel investors and the founders they support. She has also been awarded a National Science Foundation grant to elevate Early Stage Investing in the Deep Tech Space. She holds an Ed.d in Educational Leadership from Widener University, an MBA from Saint Joseph’s University, and a BA in World Politics from Ha...
2024-09-1040 min
The Diligent Observer PodcastEpisode 7: Evaluating Startup Marketing Strategy | Matt BellMatt Bell was born and raised in the UK, has lived on 4 continents, worked in, or visited, over 50 countries, and now calls Houston, Texas, home. His career journey has taken him from field operations to company leadership and corporate venture capital, from startup to growth stage, and on to strategy consulting, marketing, and angel investing.As co-founder of MessageUp and Strategic Piece, Matt works with B2B companies to make messaging and content more effective without overburdening their teams. This reflects his belief that content marketing has become mission-critical and will differentiate successful B2B...
2024-09-0351 min
The Diligent Observer PodcastEpisode 6: Lessons in WealthTech Investing | Marshall SmithMarshall Smith is a seasoned WealthTech investor and corporate development leader with over 18 years of experience in WealthTech, Fintech and SaaS. He is the Managing Director of First Rate Ventures, the corporate venture capital arm of First Rate Inc, the global leader in data aggregation, performance, and reporting solutions for over 500 Wealth Managers, Family Offices and Asset Managers across five continents.Marshall leads the strategy and execution of minority investments in early-stage WealthTech startups, as well as majority acquisitions of successful WealthTech platforms globally. He also co-founded and serves on the advisory board of WealthTech...
2024-08-2739 min
The Diligent Observer PodcastEpisode 5: Angel Investing in the Energy Transition | John Jeffers John Jeffers brings 32 years of energy industry expertise spanning leadership roles at ExxonMobil, Schlumberger, and Southwestern Energy to our conversation. Since 2020, he has channeled his extensive corporate experience into angel investing, startup mentorship, and co-founding Revolution Turbine Technologies, focusing on waste energy recovery and natural gas decarbonization solutions. During our conversation, he discusses: His transition from working in oil and gas to angel investingThe role of subsidies and unit economics in clean energyThe potential of waste heat recovery technologiesThe future of hydrogen as a fuel and potential methods of productionStrategies for evaluating investment opportunities in...
2024-08-2049 min
The Diligent Observer PodcastEpisode 4: Where the Magic Happens: Sports, Media, and Culture | Geoffrey ChengGeoffrey Cheng is the Investment Manager for Comcast SportsTech. Before working at Comcast SportsTech, he was lucky enough to work alongside entrepreneurs and management teams from seed stage to growth stage. He's been one of the first employees at a startup, worked at a media investment advisory firm (where he worked on deals impacting over $750M in total assets), and spent time with dozens of startups as investor, advisor, and ad-hoc fundraising guru.During our conversation, he discusses: The transition from computational biology to investment managementBuilding key partnerships and strategy at Comcast SportsTechThe essence o...
2024-08-1338 min
The Diligent Observer PodcastEpisode 3: Evaluating Startup Quality of Earnings | John Samore IIIJohn Samore III is a Certified Public Accountant and Certified Fraud Examiner with over 25 years of experience in forensic accounting, fraud investigations, and litigation. He has worked with Big 4 firms and other professional service firms, collaborating with companies across various industries.John specializes in financial, managerial, and operational due diligence for M&A transactions, including quality of earnings and working capital analysis. He has also performed internal audits, control testing, SOX compliance, and policy recommendations. His experience spans government entities, nonprofits, and public and private companies in industries such as banking, healthcare, media, retail, real...
2024-08-0633 min
The Diligent Observer PodcastEpisode 2: Thesis-Driven Investing | Eric AlfuthEric Alfuth is an investor and advisor with over 20 years of experience. He is the managing partner of the early-stage VC Caymont Ventures, and he serves as a board member and advisor to multiple emerging companies. He also serves as President of the Houston Angel Network, one of the largest and most active angel networks in the country.Prior to forming Caymont Eric helped launch and sell two energy companies, a public exit and a private sale. Before his entrepreneurial journey, Eric led a high yield credit hedge fund and managed a $4 billion international fund for AIG...
2024-07-3045 min
The Diligent Observer PodcastEpisode 1: Identifying a Great Pitch | Matt GoreMatt Gore was a BCG consultant and startup founder with the Saturn Five Venture Studio. Along the way, he got hooked on crafting stories that help founders raise money. Now he manages OPTIO, a firm that specializes in crafting pitch decks. OPTIO pitch decks have helped founders raise over $2 Billion dollars in capital from top firms like A16Z. He is a partner in several service businesses, an angel investor, and leads the Aggie Venture Fund, a student VC fund at Texas A&M. During our conversation, he talks about: • The story of his...
2024-07-2343 min