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PODCAST

The Diligent Observer Podcast

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

business entrepreneurship

All Episodes

31:45

Episode 34: "Angels Are Always Hopeful" | Incoming...

The Diligent Observer Podcast ·

2025/05/06

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 8x 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 unf...

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43:10

Episode 33: "Angel Investing Isn't a Trending Topic"...

The Diligent Observer Podcast ·

2025/04/29

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...

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44:02

Episode 32: "The Founder is Everything" | Super Angel...

The Diligent Observer Podcast ·

2025/04/22

Insights from a commercial real estate veteran who's now funding underrepresented founders while challenging traditional angel investing assumptions Today's episode explores three ideas that caught my attention: Financial models are founder due diligence too - Katie evaluates financial projections not for accuracy but to understand how founders think. If it’s not a heck yes it’s a heck no - When Katie can't quickly decide, she defaults to "no." This candid approach re...

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41:36

Episode 31: "Less Than 2% of VC Funding" | SWITCH CEO...

The Diligent Observer Podcast ·

2025/04/15

Insights from a twenty-year tech ecosystem veteran creating pathways for women angel investors Today's episode explores three ideas that caught my attention: Capital distribution defies logic - Kate highlighted that less than 2% of VC funding goes to women-led teams, yet data shows they're 3x better at capital efficiency. Wild. Education activates capital - Confidence gaps, not capability gaps, often prevent qualified individuals from angel investing. Kate's focus on education fir...

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40:40

Episode 30: "You Need 500 Site Walks" | B2B Sales...

The Diligent Observer Podcast ·

2025/04/08

Insights 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 three ideas that caught my attention: Ridiculous customer discovery is what it takes – The “in” doesn’t matter. What matters is being ready to make the most of that “in”. His first enterprise pitch came about because the buyer liked his logo. But the capacity to close was predicated on a stupid deep u...

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43:21

Episode 29: "Values on Our Sleeve" | Liberty Ventures...

The Diligent Observer Podcast ·

2025/04/01

Insights 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 three ideas that caught my attention: The power of a radically transparent thesis - Alexander's approach of explicitly stating values upfront both attracts aligned founders and repels mismatches. Patient capital as competitive advantage - His willingness to build relationships over months/years before inv...

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37:51

Episode 28: "Patents Won't Save a Bad Business" |...

The Diligent Observer Podcast ·

2025/03/25

Insights 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 to spend an extra $600. Insurance vs litigation reality - Patent lawsuits are 10x more common than D&O claims, yet investors often...

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46:40

Deep Dive Season 1: Nuclear Energy | Episode 4 - "The...

The Diligent Observer Podcast ·

2025/03/04

Today's episode explores three ideas that caught my attention:* Nuclear's renaissance hinges on electricity demand growth - More than any other guest I’ve spoken with, Emmet nailed the point that macro demand growth—not new tech or climate concerns—is what will truly drive growth in the nuclear sector. And similarly, falling demand is what killed momentum in the space in the 1970s. * The “safety” problem has already been solved - Nuclear energy is ridiculously safe, and the incremental return on

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39:54

Deep Dive Season 1: Nuclear Energy | Episode 3 -...

The Diligent Observer Podcast ·

2025/02/25

Today's episode explores three ideas that caught my attention: * Demonstration Reactors are MVPs for Nuclear Energy - These reactors are 1/100 - 1/10 the size of a commercial scale reactor, and enable advanced reactor designs to be proven out from a technical and regulatory perspective with substantially lower cost than a full-scale reactor. Genius. * Timelines are Long, but (Maybe?) Getting Shorter - 10ish years is a good ballpark timeline from idea to commercial scale. That’s a long time, but it

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28:53

Deep Dive Season 1: Nuclear Energy | Episode 2 - "We...

The Diligent Observer Podcast ·

2025/02/18

Today's episode explores three ideas that caught my attention: * Perception is Reality - The discussion of nuclear waste politics surfaced how fear-based narratives can derail rational energy policy for decades.* Nuclear = Massive Economic Development Opportunity - Reed drew a number of parallels between recent efforts to onshore the semiconductor industry – highlighting how massive industry investments create economic flourishing.* Uri's Hidden Lesson - The revelation about cancelled expansions at

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57:26

Deep Dive Season 1: Nuclear Energy | Episode 1 -...

The Diligent Observer Podcast ·

2025/02/11

Today's episode explores three ideas that caught my attention: * AI is Transforming Nuclear Too - The possibility of applying AI tools to parse 4,500-page regulatory documents represents a breakthrough in addressing one of nuclear's biggest bottlenecks - regulatory compliance. * Falling Demand Drove Nuclear's Decline in the Late 1970s, Not 3 Mile Island - Rod's point about nuclear orders stopping in 1974—five years before Three Mile Island—due to falling electricity demand growth challenges the

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43:37

Episode 27: "Water is Critically Underinvested" |...

The Diligent Observer Podcast ·

2025/02/04

Today's episode explores three ideas that caught my attention: * The “conjoined twin” - Water touches every form of energy generation. Doug’s laser focus on this point made me consider what other interdependencies we often overlook.* Market signals can mislead on timing - It’s often said “It’ll take longer and cost more than you think.” Based on Doug’s comments, this saying applies even more in industrial applications - these things can take a long time to percolate, even when the market is

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45:09

Episode 26: "Never Say Revenue" | Startup Economist...

The Diligent Observer Podcast ·

2025/01/28

Today's episode explores three ideas that caught my attention: * The “angel investor party trick” - Paul highlighted how the rush to become an angel investor mirrors the increase in the appeal of the “celebrity entrepreneur” we’ve seen over the last couple of decades. He believes that to flourish, the investor community must consolidate (read: more of us become an LP in a fund vs doing our own thing) and the “average” angel must level up their value-add. His direct and aggressive stance on this

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47:37

Episode 25: "Intestinal Fortitude" | Startup Sales...

The Diligent Observer Podcast ·

2025/01/21

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

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25:18

Episode 24: "Build the Rainforest in the Desert" |...

The Diligent Observer Podcast ·

2025/01/14

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

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38:14

Episode 23: "Patents Are Just One Piece" | University...

The Diligent Observer Podcast ·

2025/01/07

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,

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45:19

Episode 22: "50% of Corporate Payments are Still...

The Diligent Observer Podcast ·

2024/12/17

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

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38:07

Episode 21: "95% Business, 5% Technical" | AI CONNEX...

The Diligent Observer Podcast ·

2024/12/10

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

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34:14

Episode 20: "Part Art, Part Process" | Elevate...

The Diligent Observer Podcast ·

2024/12/03

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

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45:02

Episode 19: "Smart Money Goes Beyond the Checkbook" |...

The Diligent Observer Podcast ·

2024/11/26

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

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58 results

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