- The Diligent Observer
- Posts
- AI Maternity Care Secures $8M, a16z's Prediction Economy Thesis, and why Guardrails are a Good Thing
AI Maternity Care Secures $8M, a16z's Prediction Economy Thesis, and why Guardrails are a Good Thing
🔥 Angel Deals of the Week | October 16, 2025

Happy Thursday.
In today’s issue:
Angel Deals of the Week | 98 Deals, 70 Networks
Bookmarks I think you’ll enjoy
The best nugget from my conversation with Serial Entrepreneur, Army Ranger, and co-founder of Eagle Venture Fund Wade Myers
🔥 Angel Deals of the Week

NEXT WEEK we’ll cross 100 angel deals tracked. To celebrate, on Thursday 10/23 at 12pm CT I’m dropping a HUGE subscriber-only report. Mark your calendar.
Angel funding rounds announced in recent weeks, compiled from public sources. These deals represent the elite few that survived an angel network’s vetting process. Note: I have not personally analyzed these companies and am sharing for informational purposes only.
🤖 Deal summaries generated using dealmemo.ai.
📊 Angel Network Investment Tracker: 98 Deals, 70 Networks.

Waveful | Creator-fan community and monetization platform
Participating Groups: Italian Angels for Growth
Waveful is developing a creator-fan community platform where users connect through content and challenges. The company surpassed three million downloads in under six months with over 200% monthly growth, 40 million posts, and $1 million in B2C sales. Waveful recently raised $2.08 million from Italian Angels for Growth, a16z Speedrun, and other investors to expand to the US, enhance AI features, and grow the team, targeting 500,000 American users within twelve months.
Steven Motta | $2.08M Seed | Milan, Italy | September 2025 | Source
Empirical Security | Custom cybersecurity AI models
Participating Group: Hyde Park Angels
Empirical Security is developing custom AI models that help companies prioritize which cybersecurity threats to address first. The platform monitors 17,000+ actively exploited vulnerabilities and combines this real-time attack data with each customer's specific infrastructure to predict their most critical risks. Empirical recently secured $12 million in seed funding led by Costanoa, with participation from Hyde Park Angels, DNX Ventures, and Sixty Degree Capital.

Lōvu Health | AI-powered maternal health platform
Participating Group: Sand Hill Angels
Lōvu Health is developing an AI-powered digital platform that monitors mothers from conception through postpartum with real-time patient monitoring and curated specialty care marketplace. The platform identified depression in 30% of clinical populations and enabled earlier preeclampsia intervention for 6% of mothers. Lōvu recently secured $8 million in Series A funding led by SJF Ventures, with participation from Sand Hill Angels. Funds will support AI agent development and scaling operations.
📣 Have an Angel Deal to Announce?
🔖 Bookmarks
🔒 Why VCs Can't Touch Hardware: Great tweet from Hadrien Thieblot explaining how LP agreements often ban hardware/defense sectors for a fund's lifetime.
🎯 Why Prediction Markets are a Huge Deal: a16z co-leads Kalshi's Series D and explains why prediction is the “atomic unit of value creation” in an AI economy.
🏠 Unexpected AI Power Users: Parents. New data from Menlo Ventures shows 29% of parents use AI daily, nearly 2x the rate of non-parents.
🥇 The Nugget: My Top Takeaway from A Conversation with Wade Myers
Systems provide guardrails for enthusiasm 🛡️
As Wade Myers has scaled up to processing 20,000 pitches a year, he's been forced to systematize.
He admitted something many of us resonate with: he tends to like every founder he meets. The passion, the vision, the energy - it’s all pretty infectious.
And without a systematic approach to serve as a guardrail, that natural optimism can become a liability. Wade admitted to writing checks based on enthusiasm, then regretting those decisions later.
The solution isn't to eliminate emotion, but to build thoughtful boundaries within which that emotion can thrive.
From Wade (emphasis mine): "I tend to like every founder I meet, you know what I mean? I tend to like, oh yeah, yeah, great idea. And you kind of want to cheer them on. You wanna lean into it, you know? And so I would find that if I didn't have a way to quantify and score, I would tend to like every deal and then later regret going, oh man, why did I rush into that?"
Takeaway: Put up some guardrails.
What will you NOT invest in?
What are your immediate “red flags”?
Defining and respecting these guardrails will provide language and structure to help “pass” on a deal that otherwise might be very tempting.
Want more? Check out my full conversation with Wade 👇
Listen now on Apple Podcasts, Spotify, YouTube, and more.
🕵️ Looking for an Angel Group?
Finding the right angel community can be tough.
Answer 12 quick questions and I’ll curate 3 groups you might enjoy.
Even better - if one of them feels like a fit, I’ll personally make the intro.
Until Next Week 👋
Thanks for reading - have a great week.
-Andrew
P.S. If you enjoyed this post, could you do me a quick favor? Hit the "like" button or leave a comment with your thoughts. It may not seem like much, but it really helps me out a ton.
How did I do this week? |