Meeting
2026-06-29 - Andy Milligan - 1:1
Gist
Chris LaFay and Andy Milligan caught up on their weekly 1:1, mostly comparing conference experiences: Andy debriefed his awkward time at a heavy-drinking healthcare conference in Put-in-Bay with mixed networking results, while Chris shared observations from manning a booth at a dental conference for New York Ave, a company that spent $60k on a three-booth sponsorship and landed several $5k retainer leads. They swapped notes on sales closing techniques, unconventional marketing ideas (snail mail, 'cold caking'), and a podcast recording mishap Andy had. Chris also mentioned exploring a low-cost website/hosting subscription model idea and reviewed his current project mix using Claude Code analysis of Classic City's financials.
Distilled from the transcript by claude-sonnet-5 · Jul 25
What came out of it
Risks and blockers2
- Andy struggles with direct sales conversations and closing at ICP-heavy conferences
- Podcast recording with a healthcare go-to-market host failed to save, wasting a 45-minute session
Open questions2
- Will Andy respond to the podcast host's request to re-record?
- Will Chris pursue the low-cost recurring website/hosting subscription model idea?
Next steps3
- ClientAndy to decide how to respond to the podcast host asking to re-record the interview
- MeChris to prep the site kicking off and finish two landing pages launching this week
- MeChris to attend a meeting about a buddy's potential convention hosting idea
A record of what was agreed, not a task list — nothing here was scheduled.
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