Trade Compliance AI Closes $2.5M Seed, Sequoia's 'Return Free Risk' Warning, and Why It Takes 1,000 Deals to Calibrate Angel Judgment

Happy Thursday.

PSA in case you’re like me and the holidays snuck up on you: Thanksgiving is 7 days away and Christmas will be here in just 35.

Wishing you and yours well during this holiday season.

In today’s issue:

• Angel Deals of the Week | 113 Deals, 83 Networks

• Bookmarks I think you’ll enjoy

• The best nugget from my conversation with Sovereigns Capital Venture Partner Phil Jung.

🔥 Angel Deals of the Week

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: 113 Deals, 83 Networks.

VBASE Oil Company | High-performance sustainable base oils

Participating Group: Charlotte Angel Fund

VBASE Oil Company produces sustainable base oils used in industrial lubricants for hydropower, food-grade processing, and high-efficiency gear and hydraulic systems. The company's biobased, biodegradable oils are certified USDA BioPreferred, EU Ecolabel, and NSF HX-1, delivering higher performance than traditional petroleum-based alternatives while reducing environmental impact. VBASE recently secured seed investment from Charlotte Angel Fund to accelerate deployment in critical industrial markets and position for global scaling.

Jeffrey DiMaio | Pendleton, SC | Sep 2025 | Source

BITE Data Corporation | AI-powered global trade compliance solutions

Participating Group: New Dominion Angels

BITE Data is developing AI-native SaaS tools for global trade compliance automation. Founded by former US customs enforcement personnel, including a senior ICE technical leader, the company recently secured $2.5 million in Series Seed funding led by Las Olas Venture Capital, with participation from New Dominion Angels and Blue Impact Venture Capital. Funds will be used to expand the company’s engineering team and build out sales capabilities.

Thariq Kara | $2.5M Seed | Leesburg, VA | Nov 2025 | Source

Rebookify | AI-powered hotel rebooking for agencies

Participating Group: Latvian Business Angel Network

Rebookify is developing an AI platform that monitors refundable hotel reservations for travel agencies, automatically identifying when cheaper rates become available and enabling rebooking to capture higher margins. The company serves a market where 30-40% of bookings are refundable but rarely optimized for price drops. Rebookify recently secured €200,000 ($232,000) from Latvian Business Angel Network and 500 Global. The funding will expand the team, automate onboarding, and scale sales operations in UK and European markets.

Matīss Reinis Puriņš | ~$232K Pre-seed | Vilnius, Lithuania | Oct 2025 | Source

📣 Have an Angel Deal to Announce?

🔖 Bookmarks

1. 💡 Venture is not an Asset Class: Sequoia’s Roelof Botha on the state of venture. Fav quote: “Venture is a return free risk.” Oof.

2. 🏗️ Manufacturing Startups: Kyle Harrison argues YC has evolved from helping founders solve problems to simply manufacturing consensus-driven startups.

3. 🌤️ When ARR Drops from the Sky: Carta's latest report shows AI startups captured 44% of all VC dollars in 2025, up from 39% in 2024.

🥇 The Nugget: My Top Takeaway from A Conversation with Phil Jung

It takes 1,000 deals to calibrate angel judgment, not 10 📊

This theme has shown up again and again in both my interviews and lived experience running angel groups for the last four years:

As a new angel, everything looks amazing.

But over time, the “quality” radar gets more and more refined.

Humans are exceptional at pattern recognition, and without sufficient time for that skill to develop, new angels are at risk of making otherwise “easily” avoidable mistakes.

Takeaway: 

New investors: Get reps. Look at a ton of deals - not just 10.

Angel operators & experienced investors: Gut-check the new investors around you.

Want more? Check out my full conversation with Phil 👇

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

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