49: Why we're being so transparent

49: Why we're being so transparent

Feb 03, 2026
In this episode, we unpack why we’ve chosen to be so transparent on the podcast - the upside for listeners, the potential risks with customers and competitors, and where we draw the line on sharing sensitive details. We also share a stack of updates as AIME approaches, including meeting bookings, a new client trial, analytics learnings from Heroly, multi-agent AI workflows, and a big strategic planning prompt from Inductive. Plus, wedding prep and fitness check-ins to round things out.

Chapters
  • (00:00) - Intro
  • (00:46) - AIME meeting bookings update (Gavin on 11+, Mitch on 3)
  • (03:20) - Banner logistics and prep for Melbourne
  • (06:07) - The secret AI breakthrough teaser for AIM
  • (09:28) - Why we’re being so transparent (and the downsides)
  • (16:34) - Being “small” vs getting on people’s radar
  • (18:40) - New client trial and shifting to community-based pricing
  • (20:43) - Why short events don’t suit “tagging” features
  • (22:10) - Catching up with Heroly: analytics, AI and advice
  • (24:35) - Using multiple AI agents in parallel (what worked, what didn’t)
  • (29:00) - Claude Code vs Cursor experiments
  • (30:02) - Project Hammer update and deadlines
  • (30:40) - Inductive session: backcasting to $10M-$20M
  • (32:45) - Wedding planning update (catering, dogs, MC/DJ, photo booth, bus)
  • (37:41) - Fitness check-in (weight, habits, 5k walks, Apple Watch, Strava)
  • (46:24) - Episode 50 coming up and outro

In this episode, we cover:
  • Why we’re choosing transparency, and what could go wrong
  • The trade-offs between “looking big” vs being honest about being small
  • AIME prep: meeting bookings, banners, and how we’re pitching the stand
  • A new client trial and testing a community-based, ongoing pricing model
  • Why “tagging” style features don’t suit short events and meetups
  • Learning from Heroly's analytics setup (and what we’re missing)
  • Using multiple AI agents in parallel without melting your brain
  • Cursor vs Claude Code, and what we’re experimenting with next
  • Project Hammer update and timelines for event setup
  • Backcasting with Inductive to plan for a $10M-$20M future
  • Wedding planning progress and suit decisions
  • Fitness habits: daily 5k walks, early gym sessions, and staying consistent
  • Episode 50 coming up

Got questions or topics you want us to cover? Email us at journey@sixsides.co

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