The Diligent Observer Podcast

Today'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 and mission is important, but it can’t be something to “over rotate” on, as it won’t get the sellers paid. “Tell me the story of this logo.” - Details are gold. Generalities? Red flag. Sellers taking quick wins and shortcuts will not land enduring partnerships. Sellers taking the long, thoughtful, strategic route? Maybe they’ve got a shot. I explore these ideas and more with Rob Balena, Strategic Accounts at TeamSense. He brings extensive expertise in enterprise software sales, having successfully guided multiple venture-backed startups in selling to Fortune 500 companies. Currently leading sales at TeamSense, he combines deep experience in technical enterprise sales with a unique perspective on manufacturing technology adoption. His journey from founding a sales coaching practice to driving enterprise deals gives him valuable perspective into both the strategic and tactical elements of complex B2B sales.During our conversation, Rob shares:A framework for evaluating startup-to-enterprise fit that challenges founders to think beyond their VC pitch and focus on risk mitigation for corporate buyers.Practical strategies for building credibility as a small company selling to large enterprises, including specific examples of leveraging customer success stories.Critical considerations for sales leadership roles at startups, including the balance between process creation and customer engagement.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: 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 resource constraints can seriously strengthen community bonds. I explore these ideas and more with Drew Tulchin, President of New Mexico Angels and former CFO of Meow Wolf. He brings unique insight as a bridge-builder between impact investing and high-growth startups, demonstrated through his role in scaling Meow Wolf from 50 to 400 employees as CFO. Now as the leader of New Mexico Angels and General Partner at the New Mexico Vintage Fund, he's pioneering approaches to angel investing that blend government partnership, regional development, and frontier innovation. His experience spans Native American nations, 40+ countries, and transformative work with organizations like the Grameen Foundation, giving him a distinctive lens on building sustainable startup ecosystems in resource-constrained environments.During our conversation, Drew shares:Practical guidance for angels working with government-funded startups including key red flags and validation signals.A nuanced perspective on supporting university innovators that challenges the standard commercialization playbook.Real examples of successful technical founders like Adam Stepanovich who demonstrated leadership through action rather than charisma.Connect with DrewLinkedIn | Facebook | WebsiteStuff We ReferenceAdam Stepanovich: https://www.linkedin.com/in/asteps/Angel Capital Association: https://angelcapitalassociation.org/ Solstar Space: https://solstarspace.com/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: 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 highlights a critical gap in university innovation ecosystem: business leadership. If I was an energetic entrepreneur looking for a new project, I’d hang out around a university ecosystem and dig for a project worth scaling. The “evolutionary” versus “revolutionary” investment - Pete’s distinction between the “evolutionary” and “revolutionary” opportunity stood out to me. He highlights that angel investors can still profit nicely from evolutionary investments, unlike most VCs who depend on revolutionary, portfolio-returning deals. I explore these ideas and more with Pete ONeill, Chief Innovation Officer for Texas A&M Innovation. He oversees intellectual property management across 11 universities and 8 state agencies, building on his experience as Executive Director of Cleveland Clinic Innovations and leadership of multiple successful healthcare startups. His unique journey from investment casting for jet engines to launching medical device companies gives him a distinctive perspective on transforming technical innovations into real-world opportunities.During our conversation, Pete shares:A framework for spotting regulatory readiness that evaluates how knowledgeable founders are and how they view regulatory relationships. Why market understanding must precede technical validation - demonstrated through his experience evaluating healthcare innovations at Cleveland Clinic.A practical approach to university technology transfer that emphasizes matching external expertise with internal intellectual property.Connect with PeteLinkedInStuff We Reference Plug and PlayKnow 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: 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 product-market fit might be.Risk-taking has different dimensions - I LOVED Blair’s interview questions about "what’s the biggest professional risk you’ve taken?” and “What’s the biggest disaster you’ve been a part of?” These are 100% going into my investing (and interviewing) toolbox. I explore these ideas and more with Blair Jeffery, President & COO at ConnexPay. He brings 25 years of payments industry expertise as President & COO of ConnexPay, where he's pioneering virtual payment solutions for travel and B2B companies. His journey includes leading Noventis through its WEX acquisition and serving as CEO at Vertical, where he transformed construction payment processes. With executive roles at industry leaders like First Data and successful exits through Paymetric (WorldPay) and Textura (Oracle), Blair combines deep operational knowledge with financial acumen from his CFA background. Beyond his operational impact, he actively shapes the next generation of fintech entrepreneurs through his board role with the Aggie Angel Network, bringing both capital and industry wisdom to early-stage startups.During our conversation, Blair shares:Why the seemingly simple goal of digitizing B2B payments remains elusive, including a discussion about float economics, relationship dynamics, and reconciliation challenges.A practical methodology for evaluating African fintech opportunities that focuses on team differentiation and product evolution potential beyond initial use cases.Insights into geographic expansion challenges demonstrated through ConnexPay's European market entry and the necessary pivots in operational approach.Connect with BlairLinkedInStuff We ReferenceBitcoinJerry SeinfeldKnow 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: * 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 how I think about major events’ potential for driving innovation. * The evolution of AI reasoning - Dan's breakdown of the next frontiers in AI tech highlighted how, despite the ridiculous stuff we can now do with AI, we're still just scratching the surface. His timeline for AGI development feels both exciting and sobering. And ASI… all at once wonderful and terrifying to think about. I explore these ideas and more with Dan Sinawat, Founder at AI CONNEX.Dan Sinawat brings a truly global perspective to AI innovation, shaped by his experiences across New York, Thailand, Japan, Singapore, and Texas. As the founder of AI CONNEX, he's addressing a critical gap in the market: the business application of AI technology. His unique vision of making Texas the AI capital of the world by 2026 is backed by strategic partnerships with respected venture firms and a deep understanding of both technical and business aspects of AI implementation. Dan's work has earned recognition from Dallas Innovates and the Dallas Regional Chamber as one of the most innovative AI leaders in DFW.During our conversation, Dan shares:* A framework for evaluating AI startups beyond the tech that emphasizes vertical focus, domain expertise, and scalability potential.* A clear timeline for AI evolution spanning from current applications through agentic AI (2025), machine reasoning, and eventual AGI (2026-2027).* A strategic approach to global expansion leveraging government programs and international partnerships for AI startups.What We Cover:* 00:00 Introduction * 01:57 Dan's Global Journey and AI Connex * 03:02 Bridging the AI Business Gap * 05:24 The Importance of Vertical AI * 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: * 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 rules limit tomorrow's breakthroughs.I explore these ideas and more with Patrick Sweeney, Principal at Elevate Ventures.Patrick Sweeney brings a unique blend of quantitative rigor and founder empathy to venture investing, informed by his time as a Harvard Business School researcher studying the economic impact of venture capital. Now as Principal at Elevate Ventures, he leads investments for Indiana's $225M evergreen fund while championing the transformative power of innovation. His journey from energy trading to academic research to venture capital gives him a distinctive perspective on how capital allocation can drive both financial returns and societal progress.During our conversation, Patrick shares:* A practical approach to balancing quantitative and qualitative factors in early-stage due diligence, particularly around customer value propositions.* Insights on the microchip industry's strategic importance and why maintaining manufacturing capabilities is critical for economic stability.* A framework for thinking about product-market fit through three key indicators: positive unit economics, demonstrated demand, and scalability potential.What We Cover:* 00:00 Introduction * 01:02 Meet Patrick Sweeney * 04:02 Patrick's Venture Capital Journey * 06:16 Ellen Pao vs. Kleiner Perkins Case * 08:55 Diversity in Venture Capital * 10:45 The Art and Science of Investing * 13:07 Patrick's Mission and Motivation * 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: * 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 the popular narrative about “pivots.” I explore these ideas and more with Mitra Miller, Vice President & President-Elect of the Houston Angel Network.Mitra Miller brings 25 years of venture development and innovation expertise to her role as Vice President & President-Elect of the Houston Angel Network. As managing member of Mill River Advisors, she works directly with investors and founders to optimize early-stage ventures, bringing deep expertise in strategic planning, due diligence, and commercialization. Beyond her commercial work, Mitra demonstrates her commitment to expanding innovation access through Eagle Investors, her non-profit focused on connecting under-resourced high school students with startup opportunities and business communities.During our conversation, Mitra shares:* Deep insights into building a sustainable innovation ecosystem in Houston through intentional collaboration between investors, entrepreneurs, and community organizations.* A perspective on value creation beyond check size that emphasizes strategic introductions, industry knowledge, and active engagement with portfolio companies.* How the cap table composition tells a story about an entrepreneur’s existing investor base. If it’s all dumb money - that’s a yellow flag. What We Cover:* 00:00 Introduction * 01:02 Meet Mitra Miller: Mentor of the Year * 06:44 Impactful Mentorship Stories * 11:13 Defining Innovation and Houston's Ecosystem * 17:37 Houston Angel Network: Vision and Trends * 23:50 Lessons LeKnow 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: * 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 problem affects investment decisions. This realization transformed Mike's approach from purely analytical to understanding founder passion as risk mitigation.I explore these ideas and much more with Mike Wilkes, Project Manager for the McKinney EDC Innovation Fund.Mike Wilkes is a Marine Corps veteran who now serves as Project Manager of the McKinney EDC Innovation Fund, where he oversees non-dilutive capital investments ranging from $50,000 to $500,000 for tech companies that headquarter in McKinney and create local jobs. After serving as a Marine Corps squad leader, he dove into entrepreneurship at Texas A&M and managed deal flow for North Texas Angel Network while still in college. He now applies this combined military and angel community management experience to drive innovative models for government-backed startup funding.During our conversation, Mike shares:* The 12-point McKinney EDC due diligence framework covering founder assessment to market analysis, showing how government entities can adopt venture-grade evaluation processes.* The critical role of corporate partnerships in ecosystem building as illustrated through a recent Plug and Play collaboration driving global connections and improved entrepreneur support services.* A perspective on DFW's funding gap at Series B and C stages, highlighting the opportunity for later-stage capital to round out the ecosystem.What We Cover:* 00:00 Introduction * 02:43 Challenges and Realizations in the Primer Industry * 06:53 Mentorship and Early Entrepreneurial Experiences * 07:37 Involvement with the Dallas Entrepreneurship Center * 08:45 Learning from the North Texas AnKnow 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.

Curtis Feeney, Senior Advisor at Peterson Partners, shares his remarkable journey from managing Stanford's endowment to serving on numerous boards. He discusses the shift in mindset required in long-term investing versus short-term profits. Curtis emphasizes that downturns can enhance decision-making and prevent bad habits. He also reveals how advisory board positions are often earned through genuine contributions, showcasing the importance of a 'give first' mentality for professional growth.

Larry 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 security software (acquired by Cloudera), andPhurnace, a provider of DevOps software (acquired by BMC Software). Earlier in his career he was a VP of Marketing for a company in California that went public on the NASDAQ exchange. After moving back to Texas from Silicon Valley, Larry was a Venture Partner at AVLabs, the incubator fund of Austin Ventures. His career has allowed him to work with numerous VCs and companies across California, Colorado, and Texas. Lake LBJ in central Texas is now his home with his wife of 40 years. He has two adult children and 2 grandchildren. Larry graduated from Texas A&M in 1983 with a Degree in Marketing. He is a frequent speaker at Texas A&M’s Mays School of Business and sits on the Advisory Board of the McFerrin Center for Entrepreneurship at A&M.During our conversation, he discusses: * His 'Three T's' framework: TAM, Tech, and Team for evaluating investment opportunities* The importance of the team in the success of a venture* The stories of missed investment opportunities and lessons learned* Advises on the pitfalls of complicated cap tables and emphasizes the benefits of SAFE notes for angel investments* The conversation highlights the importance of building relationships with founders early* Current VC investment trends including the resurgence of hardware and AI applications* His insights on how angels can add value beyond financing* His advise for angel investors on leveraging research and trends to make informed investment decisions* The recounts of the more unusual pitches he's encountered, including one for recreating the woolly mammoth.Listen now on Spotify, Apple Podcasts, and YouTube. What We Cover:* 01:47 Larry Warnock's Three T'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.