The Diligent Observer Podcast

Alden 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 eye toward social impact.During our conversation, he discusses: * Aligning perspectives when reviewing diligence materials* His extensive experience in entrepreneurship and angel investing* Evolution of investment strategy towards smaller, diversified bets* SideCar Angels' model for aggregating investments and member participation* Benefits of SideCar's approach including low legal fees and fast decision-making* Challenges such as potential missed opportunities due to deal lead barriers* Importance of thorough evaluation of investment memos and diligence reports* Key factors in evaluating investment opportunities and VCs’ diligence* Highlights of successful investments in ezCater and Wasabi* Trends in AI investments and the need for educating new angel investorsListen now on Spotify, Apple Podcasts, and YouTube. What We Cover:* 00:00 Introduction* 02:51 Alden's Journey into Angel Investing * 03:51 Building a Diverse Portfolio * 06:09 Evolving Investment Strategies * 08:23 The SideCar Angels Model * 23:26 Key Elements of Written Materials * 24:59 Evaluating Team and Competitors * 27:04 Questions for Angel Investors * 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.

Igor 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 pay, science and continuous pursuit of knowledge.During our conversation, he discusses: * The emotional and financial impact of failed investments on bootstrapped founders* His mission to redeem the staffing industry from exploitative practices* The creation of FastCTO to help non-technical founders find reliable talent* Ethical engagement and collaboration with accelerators like TechStars* Advising founders on careful validation of ideas and efficient budget use* The importance of user traction and code quality for investment decisions* Understanding and managing tech debt for startup sustainability* The role of AI in helping non-technical founders create MVPs* His career reflections and notable missed opportunitiesListen now on Spotify, Apple Podcasts, and YouTube. What We Cover:* 00:00 Introduction * 02:17 Challenges in the Staffing Industry * 04:24 The Impact of Financial Situations on Startups * 10:54 The Birth of FastCTO * 21:43 The Importance of Due Diligence in Angel Investing * 24:15 Understanding Traction and Investment Strategies * 27:42 Assessing Tech Stacks and Development Strategies * 34:13 The Role of Tech Debt in Startups * 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.

Juan “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 excellence led him to complete the rigorous VC Unlocked program, a collaborative initiative between Stanford University and 500 Global, designed to empower emerging venture capital leaders from around the world with cutting-edge insights and strategies.Beyond his career in investment, Sebastian is also the visionary behind Passport2Fluency, a company aimed at empowering individuals to enhance their Spanish language skills. Through Passport2Fluency, he embodies his passion for education and cultural exchange, making a tangible impact on the lives of countless learners seeking linguistic proficiency and global connectivity.During our conversation, he discusses: The importance of curating high-quality companies and connecting with the right investorsGrowing Alamo Angels and their focus on Latin American startupsCultural differences between U.S. and Latin American business interactionsLeveraging community-driven approaches and simplifying the investment processThe role of strategic partnerships and cultural intelligence in building trustIntegration with Velocity Texas and shared resource benefitsCreating a sense of community and facilitating organic learning through eventsExpanding investment opportunities in South Texas and cross-border activitiesLong-term potential of startup activity and nearshoring trendsConnect with Sebastian: LinkedIn | InstagramStuff We Reference  DisneyStanford VC Unlocked South Coast Angel NetworkKnow 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.

Brook 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 and an MBA in Finance from the University of Texas McCombs School of Business, where he was awarded the McCombs Entrepreneur Summer Fellowship. He is particularly passionate about working with bold founders, leveraging his entrepreneurial and investing background to focus on founder psychology, early-stage data inefficiencies, and identifying high growth opportunities across various sectors.During our conversation, he discusses: The evolution of entry barriers in software and the advent of AI.Brook’s entrepreneurial journey and learnings from running a fashion brand and a beverage company.The significance of founder-market fit and having a deep passion for a space.Strategies for evaluating consumer retail and SaaS investment opportunities.The importance of diversification in angel investing to manage risk.Navigating the noise in SaaS investments amidst technological advancements.The role of resourcefulness in angel investing when direct access to founders is limited.Connect with BrookLinkedInStuff We ReferenceNikeAlex StroudRalph LaurenRalph Lauren RRL Brand Texas A&M UniversityFunding CircleLondon Stock ExchangeUniversity of TexasRockstar EnergyMonster EnergyLaCroixKnow 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.

Patrick 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 part of the founding executive team at Nehemiah Security, Patrick was responsible for evaluating acquisition and funding opportunities to grow and eventually exit the business. Patrick was also responsible for Operations at Nehemiah, where he functioned as an executive leader in legal, recruiting, compliance, security, procurement, and cross departmental projects.Patrick is a graduate of Vanderbilt University with a double major in Human & Organizational Development and Economics, where he attended on a full-tuition Dean’s Academic Scholarship.During our conversation, he discusses: The benefits of investing together versus investing aloneChallenges in running and operating angel networksThe importance of the founder's spiritual and emotional healthEvaluating founders based on specific traits such as openness and boldnessStarting PAC and the expansion to AustinEmphasis on relationships and community within the investment processBalancing impact with potential profitability in investmentsNavigating the macroeconomic factors affecting early-stage investmentsLessons learned and the potential pitfalls in sticking to core valuesConnect with PatrickLinkedIn | WebsiteStuff We Reference Semester at SeaManaus BrazilDEETPlease Assist MeStephanie CummingsRashad CummingsPrinciples by Ray DalioGrant Van CleveKnow 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.

Phil 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 whose mission is to serve at-risk youth through education and leadership development in underserved communities.During our conversation, Phil discusses: His career transition from KPMG to Sovereign’s CapitalThe role of mentorship and relationship-building in venture capitalReflecting on the influence of his musical background on his professional lifeThe importance of a supportive investor-founders relationshipSovereign’s Capital’s missionExamples of impactful investments like Grab and PrevetaPhil's tips on transitioning from consulting to VC Insights into Sovereign’s early stage venture funding strategyConnect with PhilLinkedInStuff We Reference  Georgetown UniversityHeny KaestnerLuke RoushBandwidthGrabAnthony TanAmbassadors Impact NetworkPotomac Angel CapitalHarvard Business SchoolNASDAQPrevetaKnow 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.

Dr. 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 investors in technology development* Navigating the 'valley of death' in medical technology commercialization* The specific difficulties of pediatric medical devices* Partnering for commercialization versus solo invention* The role and impact of the Southwest Pediatric Device ConsortiumListen now on Spotify, Apple Podcasts, and YouTube. What We Cover:* 00:00 The Nature of Innovation * 04:08 John’s Journey into Biomedical Engineering * 06:09 Challenges in Medical Technology * 10:47 The Valley of Death in Medical Innovation * 13:57 Funding and Investment Challenges * 15:12 CorInnova's Inception and Early Years * 20:51 The Double Whammy of New Technologies * 25:59 The Role of Angel Investors * 28:33 The Burdens of Innovation * 35:52 Challenges in Pediatric Medical Devices * 40:20 Key Questions for Pediatric Device InvestmentConnect with Dr. Criscione:* LinkedIn: https://wKnow 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.

Dr. 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 Hamilton College, where she was elected to the Phi Beta Kappa honor society. She is an active angel investor with angel investments in angel funds designed to support female founders.During our conversation, she discusses: * Her journey into angel investing, sparked by a women's investing conference. * The importance of due diligence in mitigating investment risks. * Key factors to evaluate in founders and startups.* The broad scope and diversity of angel investment opportunities, from deep tech to clean tech to women's health.* Common misconceptions and learning challenges faced by new angel investors.* Strategies for potentially successful angel investments, and the importance of a diversified portfolio.* The growing educational tools and resources available for angel investors.Connect with Margaret & the ACALinkedIn | Website | Angel University Schedule | AngelBox ToolkitKnow 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.

Matt 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 companies from the rest in an increasingly digital-first world.As Vice President of the Imperial College Foundation, he helps enable tax-efficient giving from US-based alumni and friends that supports ground-breaking research and the highest quality education at Imperial College. During our conversation, he discusses: The concept and challenges of content marketing for early-stage B2B companiesThe importance of brand awareness and building a consistent audience earlyThe pitfalls of poorly executed marketing strategiesAligning corporate and marketing objectives to measure effectivenessThe impact of AI on content creation and the need for authenticityKey considerations for investors evaluating a startup's marketing strategyThe evolution of the CMO role and strategic marketing importanceThe future trends in marketing and buyer behaviorConnect with Matt BellGet access to expert coaching from Matt with the B2B Marketing Tune Up, an online cohort for B2B business leadersLinkedIn | Website | Newsletter | Books | Voice ActingStuff We ReferenceGeoDynamicsHAN Owl Spark at Rice UniversityRed Labs University of HoustonRice Business Plan CompetitionTo Sell is Human by Daniel PinkKnow 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.

Marshall 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 Strategy Partners, a boutique advisory firm that helps early-stage WealthTechs. Additionally, he is a co-founder, board director, and accelerator selection committee member of The Founders Arena, a unique and first-of-its-kind go-to-market accelerator for WealthTech companies. Marshall holds the CIPM credential from the CFA Institute and has published multiple white papers on risk management and performance measurement. He is passionate about fostering innovation, collaboration, and impact in the WealthTech ecosystem.Marshall lives in Southlake, Texas with his Wife Shannon and four kids. They are involved in Business as Mission, Adoption and Foster Care Ministry and serving their local church.During our conversation, he discusses: The definition of WealthTech and its relation to FinTechThe importance of progressive product market fitKey factors for evaluating investment opportunities in WealthTechHiring talent worldwideImportance of angel investors adding strategic value beyond capitalNavigating sales cycles and target markets within WealthTechConnect with MarshallLinkedIn | XStuff We ReferenceFirst Rate VenturesWealthTech Strategy PartnersBloomberg TerminalWall Street JournalFispokeFirst Rate Fispoke Press ReleaseOwl ESGKnow 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.