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Bridge rounds halve Series A odds, No-code automation scores $3.9M, and the slow-cooker portfolio strategy
🔥 Angel Deals of the Week | May 29, 2025


Happy Thursday.
Here are your angel deals of the week, some bookmarks I think you’ll enjoy, and the best nugget from my conversation with John Harbison, Chairman Emeritus of TCA Venture Group.
🔥 Angel Deals of the Week
🤝 Recent funding rounds from angel networks. I have not personally vetted these deals and am sharing for informational purposes only. Have one to announce? Reply to this email.
🤖 Deal summaries generated using dealmemo.ai.
🧾 Check out every deal we’ve tracked here.

TeamCentral | Enterprise automation platform
Participating Group: Queen City Angels
TeamCentral operates a no-code data integration and workflow automation platform serving enterprises across manufacturing, construction, foodservice, transportation logistics, and property management industries. Founded in 2022, the company addresses data management challenges through its Central iPaaS platform, which enables integration across enterprise systems without coding requirements. The company recently secured $3.875 million in Seed funding to expand enterprise automation capabilities and launch AI Agent "Corbi," designed to integrate with over 60 ERP, CRM, HRIS and eCommerce platforms.
Marc Johnson | $3.9M Seed Round | Cincinnati, OH | May 2025 | Source

Iteright | AI-powered growth navigation
Participating Group: New World Angels
Iteright is developing an AI-powered Growth Navigation Platform for C-suite executives and strategy leaders, automating data collection and analysis to replace traditional spreadsheet-based approaches and expensive consulting services. The Tampa-based startup, a member of Embarc Collective, provides real-time insights for tracking and optimizing product and technology investments across mid-market and enterprise companies. New World Angels Innovation Fund-I led the investment round to accelerate the company's mission to transform how teams build and scale products, positioning Iteright within the broader professional services transformation market.
Alex Brodsky | Tampa, FL | April 2025 | Source

Luna Robotics | Defense tech night vision systems
Participating Group: Lithuanian Business Angel Network (LitBAN)
Luna Robotics is developing night vision technology for drones and unmanned vehicles, targeting defense and security markets with affordable, high-efficiency infrared systems designed for battlefield conditions. The Lithuanian company secured up to €250,000 through a syndicated investment led by LitBAN, with participation from Estonian and Latvian angel networks, after winning the Latitude59 Pitch Competition. The cross-border collaboration represents the first joint investment initiative between the three Baltic angel networks, positioning Luna Robotics within the growing defense technology sector focused on unmanned vehicle capabilities.
Elvinas Kukys | Up to €250,000 | Lithuania | May 2025 | Source
🔖 Bookmarks
🎙️ The Diligent Observer Hitlist: Forbes just dropped the latest “Midas List” of the best VCs in 2025. If you’re on the list, open invite to come on the pod 🙂
📉 Bridge Round? I’ll pass: Data from Peter Walker shows bridged companies make it to Series A half as often as non-bridged ones.
🪦 RIP Entry Level Tech Jobs: Research from SignalFire shows New grad hiring drops 50% compared to pre-pandemic levels.
In partnership with the Angel Capital Association

If you want to connect with experienced angel investors, stay ahead of trends, and tap into a wealth of resources, the Angel Capital Association (ACA) is the place to be. With 15,000+ members and $650M+ invested annually, ACA brings together the best minds in angel investing.
From Angel University’s practical education to the annual ACA Summit and exclusive reports, ACA equips members with the tools and connections to make smarter decisions. I’ve really enjoyed being part of this community, and I highly recommend it to anyone serious about angel investing.
🥇 The Nugget: My Top Takeaway from This Week’s Conversation with John Harbison
We’re in the slow cooker business: winners tend to emerge after 5+ years 🍲
Even if a portfolio is destined to return 5-6x, odds are it will barely be above 1x after the first five years. The winners take longer to cook, while losers tend to flash fry and shut down or exit at low multiples in less than 5 years.
From John: "Even if you'd invested in all 300 of those companies and eventually you got the 5.8x return, after five years, you just barely got above 1x... you would think you're terrible because after five years it was only a one multiple and there's a time value of money, and my IRR is terrible."
Takeaway: Be patient.
Don't trust portfolio performance metrics until at least year 7-8
Build an investment strategy around 10+ year hold periods, not 3-5 year expectations
When mentoring new angels, emphasize that early portfolio performance is meaningless and potentially misleading
Want more? Check out my full conversation with John 👇
🧰 Toolkit
🦾 There’s an AI for That: Check out one of my favorite newsletters for discovering new AI tools.
📍 Attend: Cool stuff is happening in Indy - check out RALLY 2025, where 297 VC firms with $27.6B AUM gathered last year. Keynotes by Mr. Wonderful & Molly Bloom, plus a gigantic $5M pitch competition. Get early-bird tickets now, and sign up using code "THEDILIGENTOBSERVER" by 5/31 for an extra $35 off.
⏰ Reclaim Your Week: Stop spending 15+ hours on angel group admin. The managed angel ops service from PitchFact handles deal flow processing, member comms, meeting coordination and more so you can get back to what matters most. Schedule a Call.*
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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? |