Summary
Bi-weekly deal review session with Andrew. Megaphone acquisition: add-backs being calculated, deadline end of July; if no deal by August 1st, all writers cut and Blake fulfills via AI. Reviewed four HF0 deals: Daily.fun (live in-context betting), Block Run (AI agent payment rails), Riffle (AI-native DAW), and Co-frame (AI-powered personalized interfaces, ~$4M ARR). Andrew pursuing venture partner conversations at Thrive and Coatue. Both agreeing to hold this bi-weekly slot more consistently.
Decisions
- Hold bi-weekly deal review slot more consistently going forward
- Target reviewing ~5 deals/week each, then syncing on perspectives
- Check size discipline: $5-20K angel checks preferred given upcoming land purchase and construction
- Venture partner targets: Thrive and Coatue as top targets; Next Wave too slow/part-time
- Rebrand underway: newsletter + personal brand, content resuming in ~2 weeks; business split into separate LLCs
Action Items
- Michael: send final classification to acquirer today (last outstanding M&A item)
- Michael: re-ping Daily.fun founder to book joint call (calendar link broken)
- Andrew/Michael: research why Stripe (and PayPal) won payments; apply lessons to evaluate Block Run
- Andrew: call Riffle tomorrow and share read afterward; confirm whether wedge is casual-to-pro or “everyone makes music”
- Michael: loop Jesse Middleton (Next Wave, led Splice) into Riffle discussion
- Andrew: get Co-frame valuation read from founder (existing relationship makes it easy)
- Both: sync next week after Riffle and Block Run calls
Notable Details
- Daily.fun: live in-context betting (will Trump say X in next 30 seconds); regulatory pressure may help carve a wedge
- Block Run: 700K transactions/day, ~$20M total volume; two market risks (crypto + AI agent adoption)
- Riffle: strong UX, good retention (weekly usage); existing DAWs (Logic, Ableton) are archaic; Atlantic CEO / Warner Music Chief Officer may invest
- Co-frame: ~$4M ARR, founder previously co-founded Autograph (unicorn w/ Tom Brady); reportedly working with Apple; valuation likely $100M+, probably angel-only
- Fall fundraising window: Labor Day to just after Thanksgiving for potential first close
- “Agentic back-end + personalized front-end” category worth watching
Transcript
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