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The Diligent Observer Podcast

Andrew Kazlow

58 episodes

5 days ago

We just released Angel Network Pulse: The First 101 - an analysis of 101 angel network investments tracked over nine months through The Diligent Observer newsletter. Here's what I learned: The Big Picture 101 deals across 72 angel networks in 15 countries. $288M in announced funding (likely closer to $500M total funding, since only 53% disclosed round sizes). This represents roughly 8-10% of total annual angel network activity based on ACA's tracking of 1,200-1,500 deals per year. Key Finding...

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Entrepreneurship

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We just released Angel Network Pulse: The First 101 - an analysis of 101 angel network investments tracked over nine months through The Diligent Observer newsletter. Here's what I learned: The Big Picture 101 deals across 72 angel networks in 15 countries. $288M in announced funding (likely closer to $500M total funding, since only 53% disclosed round sizes). This represents roughly 8-10% of total annual angel network activity based on ACA's tracking of 1,200-1,500 deals per year. Key Finding...

Show more...

Entrepreneurship

Episodes (20/58)

The Diligent Observer Podcast

Special Episode: Breaking Down "Angel Network Pulse: The First 101"

We just released Angel Network Pulse: The First 101 - an analysis of 101 angel network investments tracked over nine months through The Diligent Observer newsletter. Here's what I learned: The Big Picture 101 deals across 72 angel networks in 15 countries. $288M in announced funding (likely closer to $500M total funding, since only 53% disclosed round sizes). This represents roughly 8-10% of total annual angel network activity based on ACA's tracking of 1,200-1,500 deals per year. Key Finding...

5 days ago

15 minutes

The Diligent Observer Podcast

Episode 50: "Crush the Cost of Diligence" | Serial Entrepreneur Wade Myers on Systematic Founder Scoring, 30 Years of Investment Lessons, and The Future of Angel Investing

Today's episode explores three ideas that caught my attention: Binary scoring reduce bias - Wade's yes/no questions (vs typical “tell me a story” questions) help address the "I like every founder" problem. Transaction fees align incentives - Wade's preference for paying only when deals close checks out with many other conversations I’ve had in recent years. Perhaps the next evolution for angel investing in community? Scarcity really does drive urgency - Wade's amazing ...

2 weeks ago

50 minutes

The Diligent Observer Podcast

Episode 49: "It's a Volume Game" | Redbud VC's Brett Calhoun on Generalist Investing Philosophy, the Missouri Startup Ecosystem, and Why Gritty Industry Veterans Make Compelling Founders

Today's episode explores three ideas that caught my attention: The Missouri ecosystem is wild - I’ve 100% been sleeping on it. Names like Zapier, Equipment Share, Veterans United, and so many more all started there. It’s so easy to miss entire innovation hubs outside the usual suspects.Volume as competitive advantage - 300 LinkedIn messages weekly for five years straight. Sustaining this hustle is simple but NOT easy, and inevitably becomes a sourcing moat through sheer persistence.VCs pivot ...

1 month ago

33 minutes

The Diligent Observer Podcast

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

Today'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 silver bullets, just relentless coffee meetings and authentic relationship building.Community impact scales investment success - His ecosystem-building a...

1 month ago

42 minutes

The Diligent Observer Podcast

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

Today'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 recognition are meetings NOT moving deals forward crystallized why ego management matters so much in building thriving ecosyst...

1 month ago

19 minutes

The Diligent Observer Podcast

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 Champions are Everything

Today'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 noted healthcare found often lost loved ones or had bad experiences, resulting in higher-than-average grit. Rela...

2 months ago

32 minutes

The Diligent Observer Podcast

Episode 45: Breaking Down the 2025 Angel Funders Report | ACA Board Member John Harbison on Valuation Compression, Board Seat Decline, and Follow-On Performance

Today'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” a...

2 months ago

49 minutes

The Diligent Observer Podcast

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 Angel Investors

Today'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 -...

2 months ago

41 minutes

The Diligent Observer Podcast

Episode 43: "Campus-Born Ventures: An Underappreciated Asset Class" | Tom Duening on Democratizing Campus Capital, University Revenue Models, and Worldwide Deal Flow

Today'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 entreprene...

3 months ago

43 minutes

The Diligent Observer Podcast

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

Today's episode explores three ideas that caught my attention: Pitch deck ≠ the pitch. So many founders think their deck is the main thing standing between them and funding. It’s about so much more than the deck. Corporate grants are legit. I think often about government grants, but have minimized the importance of corporate programs. But these organizations regularly write $10K-$50K checks with no equity dilution – and that is massive for a young business. Plus, the p...

3 months ago

40 minutes

The Diligent Observer Podcast

Special 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 serio...

3 months ago

11 minutes

The Diligent Observer Podcast

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 Business Acquisition

Today's episode explores three ideas that caught my attention: "If these companies roll to zero, it's a big problem" – Understanding this fundamental difference between ETA and venture startup investing is critical for angel investor portfolio construction and risk management. The "peace dividend" creating veteran entrepreneurs - Patrick's observation about post-combat veterans seeking meaningful civilian engagement revealed how macro geopolitical shifts can create unexpecte...

4 months ago

53 minutes

The Diligent Observer Podcast

Episode 40: "Fuel for the Economic Engine" | Angel Capital Association CEO Patrick Gouhin on Professionalizing Angel Investing, Expanding Accreditation Pathways, and Cultivating Startup Ecosystems

Insights from an aerospace engineer turned association leader who's working to transform angel investing from "black art" to science while representing 15,000+ members deploying approximately $1 billion in private capital annually Today'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!Accreditat...

4 months ago

22 minutes

The Diligent Observer Podcast

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

Insights 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 challenges the trope that stability is always preferable - perhaps occasional chaos forces better investment discipline.Angel group models are evolving ...

4 months ago

39 minutes

The Diligent Observer Podcast

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

Insights from the Chairwoman of Stella Foundation and founding member of Stella Angels who has invested in 160+ women-led startups and co-managed six consecutive San Diego Angel Conference funds totaling millions in early-stage capital Today'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 angel...

5 months ago

36 minutes

The Diligent Observer Podcast

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 of Returns

Insights 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: The zombie portfolio problem - John created a simple "Lost Cause Fund" solution that lets angels harvest tax losses from walking dead companies. Genius. How many other innovations remain undershared across angel networks?Expertise >> crowds - John's analysis revealed a U-shaped return curve where heavily-invested de...

5 months ago

34 minutes

The Diligent Observer Podcast

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

Insights from a 25-year veteran angel who advises investors and governments across four continents while chairing Silicon Valley's oldest angel network and the ACA Board of Directors Today's episode explores three ideas that caught my attention: Angels are insulated from market turbulence - Ron's data shows angels maintaining pre-2021 investment patterns despite market volatility in recent months. First-time CEOs are getting MORE funding - Contrary to what you'd expec...

5 months ago

7 minutes

The Diligent Observer Podcast

Episode 35: "108,000 Startups and Counting" | Dealum CEO Seren Rumjancevs on Angel Group Efficiency, AI-Powered Portfolio Tracking, and Bridging Global Angel Networks

Insights from a global ecosystem builder who's processed data on 108,000 startups while helping 240 investor communities across six continents manage their deal flow GET FREE SOCKS: Seren will send the first 100 listeners that sign up for the AI Portfolio Monitoring waitlist a pair of Dealum’s signature red socks. What better way to impress your fellow angels at the next pitch event?! Today's episode explores three ideas that caught my attention: A 30% spike in angel fundraising ...

5 months ago

28 minutes

The Diligent Observer Podcast

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

Insights from a fund manager who has mobilized hundreds of women investors, championed gender-lens investing in the Southeast, and is now steering the Angel Capital Association as its incoming chair Today's episode explores three ideas that caught my attention: Women angels grew 10x in 10 years - Kristina shared that female angels increased from 5% to 40% of all angel investors since 2014. Wow. "Get out of your sandbox" - Kristina's advice to deliberately step into un...

6 months ago

31 minutes

The Diligent Observer Podcast

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 Entrepreneurs

Insights 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 Marcia still encounters people unaware they can participate in...

6 months ago

43 minutes