Helping angel investors see what most miss. Want more? Get essential angel intel in 5 min with The Diligent Observer Newsletter: your weekly shortcut to vetted deals and expert takes. https://www.thediligentobserver.com/ https://feeds.buzzsprout.com/2459970.rss
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Andrew Kazlow Podcasts

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Episode 48: "A Mile Deep" | North Texas Angel Network Co-Chairman Ichan Stall on Assessing Founder Psychology, Building Angel Communities, and Why Pulling the Lawnmower Behind Your Bicycle is the Way
42:57
42:57
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42:57Today's episode explores three ideas that caught my attention: Small operational advantages compound infinitely - His lawnmower efficiency tracking and strategic positioning showed me how founders who obsess over tiny details can dominate markets. Angel networks fail without grassroots hustle - Growing NTAN from 15 to 70 members required zero silve…
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Episode 47: "Friendly Competition" | The DEC Network's Bill Chinn on the Role of Angel Investors in North Texas, Healthy Ecosystem Rivalry, and Managing Type-A Personalities
19:42
19:42
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19:42Today's episode explores three ideas that caught my attention: Ecosystem competition breeds innovation – The friendly rivalry between DFW Startup Week and Brad Feld's Denver Startup Week shows how healthy external competition is a wonderful thing. “Who gets the credit” politics can kill momentum - Bill's observation that meetings about who gets rec…
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Episode 46: From "Anything But Healthcare" to "All-In on Healthcare" | Serial Healthcare Investor Trey Bowles on the Rise of Venture Studios, The Art of Problem-Focused Selling in Healthcare, and Why Internal ...
32:30
32:30
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32:30Today's episode explores three ideas that caught my attention: The courage to admit ignorance can be a competitive advantage - Trey's willingness to ask "dumb" questions in healthcare settings was one of the key distinctives that allowed him to learn and grow so quickly. Personal pain often drives conviction in healthcare entrepreneurship - Trey no…
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Episode 45: Breaking Down the 2025 Angel Funders Report | ACA Board Member John Harbison on Valuation Compression, Board Seat Decline, and Follow-On Performance
49:16
49:16
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49:16Today'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…
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Episode 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 ...
41:02
41:02
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41:02Today'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 d…
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Episode 43: "Campus-Born Ventures: An Underappreciated Asset Class" | Tom Duening on Democratizing Campus Capital, University Revenue Models, and Worldwide Deal Flow
43:34
43:34
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43:34Today'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 capi…
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Episode 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 Philosophy ...
40:17
40:17
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40:17Today'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 org…
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Special Episode: What Does the Big Beautiful Bill Mean for Angel Investors?
11:22
11:22
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11:22On 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 hug…
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Episode 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 ...
53:01
53:01
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53:01Today'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 observat…
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Episode 40: "Fuel for the Economic Engine" | Angel Capital Association CEO Patrick Gouhin on Professionalizing Angel Investing, Expanding Accreditation Pathways, and Cultivating Startup Ecosystems
22:19
22:19
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22:19Insights 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 annually Today's episode explores three ideas that caught my attention: The path from art to science - Pat drew a fascinating pa…
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Episode 39: "The Devil is in the Details" | Seraf Investor CEO Alycia Doxon on Venture Market Corrections, Capital Consolidation Trends, and The Future of Angel Networks
39:40
39:40
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39:40Insights from a portfolio management software CEO who sees the venture market's "healthy shakeup" forcing overdue conversations about profitability and angel group sustainability Today's episode explores three ideas that caught my attention: The venture market reset is healthy - Alycia embraces the current volatility as necessary medicine. It chall…
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Episode 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 Portfolios ...
36:11
36:11
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36:11Insights 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 capital Today's episode explores three ideas that caught my attention: Creativity is the gateway to better investing - Sil…
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Episode 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 ...
34:48
34:48
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34:48Insights from a 20-year angel investing veteran who created data-driven tools used by hundreds of angel groups Today'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 >> crowd…
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Episode 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 Windows
7:36
7:36
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7:36Insights 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 pa…
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Episode 35: "108,000 Startups and Counting" | Dealum CEO Seren Rumjancevs on Angel Group Efficiency, AI-Powered Portfolio Tracking, and Bridging Global Angel Networks
28:40
28:40
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28:40Insights 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 f…
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Episode 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 Innovators
31:45
31:45
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31:45Insights 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 Chair Today'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 invest…
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Episode 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 ...
43:10
43:10
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43:10Insights 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. Ang…
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Episode 32: "The Founder is Everything" | Super Angel Katie Dunn on Effective Due Diligence, How Relationship-Building Drives Returns, and Why Clarity is Kindness
44:02
44:02
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44:02Insights 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 thi…
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Episode 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 Investors
41:36
41:36
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41:36Insights from a twenty-year tech ecosystem veteran creating pathways for women angel investors Today'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 capi…
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Episode 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 Space
40:40
40:40
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40:40Insights 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 fir…
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Episode 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 Effort
43:21
43:21
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43:21Insights from a former philosophy student who's built a 15,000+ member network of principled business leaders and facilitated values-aligned investments Today'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…
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Episode 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 Mistakes
37:51
37:51
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37:51Insights from a patent strategist who's authored 1,000+ patents and is revolutionizing IP finance through patent insurance and IP-backed lending at BlueIron Today'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 …
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Deep Dive Season 1: Nuclear Energy | Episode 6: "Science Projects Masquerading as Commercial Products" | Dr. Chris Keefer on the SMR Hype Cycle & Energy Independence Imperatives
49:59
49:59
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49:59Today'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 upfr…
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Deep 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 Supply
36:48
36:48
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36:48Today'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…
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Deep 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 Role
46:39
46:39
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46:39Today'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 mo…
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Deep 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 Nuclear
39:53
39:53
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39:53Today'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. …
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Deep 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, & Momentum
28:53
28:53
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28:53Today'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 ind…
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Deep 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 Change
57:25
57:25
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57:25Today'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 Islan…
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Episode 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 Scenarios
43:37
43:37
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43:37Today'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’…
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Episode 26: "Never Say Revenue" | Startup Economist Paul O'Brien on Seed-Stage Venture Philosophy, Building Domain-Specific Angel Portfolios, and Media-First Innovation
45:08
45:08
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45:08Today'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 o…
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Episode 25: "Intestinal Fortitude" | Startup Sales Veteran Rob Balena on Vetting Enterprise Sales Strategy, Hiring a Great Sales Force, and Where Most Founders Get it Wrong
47:37
47:37
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47:37Today'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 goi…
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Episode 24: "Build the Rainforest in the Desert" | New Mexico Angels President Drew Tulchin on Defense Tech Innovation, Ecosystem Building, and Investing Alongside Government Grants
25:18
25:18
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25:18Today'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 …
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Episode 23: "Patents Are Just One Piece" | University Innovation Leader Pete ONeill on the Opportunity in Highly Regulated Markets, Founder Credibility, and Strategic Specialization
38:13
38:13
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38:13Today'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 competi…
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Episode 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 Turbulence
45:19
45:19
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45:19Today'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.” …
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Episode 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 Opportunity
38:06
38:06
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38:06Today'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 ap…
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Episode 20: "Part Art, Part Process" | Elevate Ventures' Patrick Sweeney on Startup Success Predictors, Recent Evolutions in VC Hiring, and the Criticality of Founder Empathy
34:13
34:13
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34:13Today'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…
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Episode 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"
45:02
45:02
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45:02Today'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%…
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Episode 18: "Government CAN Move Efficiently" | Innovation Fund Manager Mike Wilkes on Non-Dilutive Capital, Startup Support, and Local Job Creation
35:46
35:46
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35:46Today'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 i…
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Episode 17: "Your Board Can Make or Break the Company" | Curtis Feeny on Governance, Market Cycles, and the "Say Yes" Career
44:05
44:05
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44:05Today'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…
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Episode 16: The 3 T’s of Early Stage Investing | Larry Warnock
51:31
51:31
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51:31Larry 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 t…
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Episode 15: Diligence the Diligence: Unpacking the SideCar Angels Strategy | Alden Zecha
40:22
40:22
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40:22Alden 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 …
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Episode 14: Don't Throw Away $50K: Lessons from Startup CTO Expert | Igor Belagorudsky
43:05
43:05
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43:05Igor 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 archit…
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Episode 13: Growing the Alamo Angels from 30 to 130 Members in 4 Years | Sebastian Garzon
44:38
44:38
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44:38Juan “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 ded…
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Episode 12: From CPG Founder to B2B SaaS Investor | Brook Stroud
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40:05
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40:05Brook 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 Found…
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Episode 11: The Power of Relationship-Driven Angel Investing | Patrick Farrell
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36:55
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36:55Patrick 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, lead…
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Episode 10: Investing in Venture Capital for Human Flourishing | Phil Jung
36:03
36:03
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36:03Phil 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…
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Episode 9: Bouldering & Biomedical Entrepreneurship | John Criscione
43:34
43:34
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43:34Dr. 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…
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Episode 8: The Art & Science of Angel Investor Education | Dr. Margaret Bacheler
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40:02Dr. 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 a…
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Episode 7: Evaluating Startup Marketing Strategy | Matt Bell
51:16
51:16
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51:16Matt 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 …
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Episode 6: Lessons in WealthTech Investing | Marshall Smith
39:50
39:50
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39:50Marshall 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 M…
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