GTM in Flux - AI Changed Everything, and Nothing
What AI changed about trust in B2B SaaS go-to-market - and what it didn't.
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What AI changed about trust in B2B SaaS go-to-market - and what it didn't.
Keep readingProactive Family Finances is live, and the email quest reached its first inbox zero.
Keep readingOn a brand-new inbox. With almost no email. I classified and actioned 49 messages! It only took 14 hours and 8 minutes of active work, spread across 4 days, 21 hours, and 33 minutes, with 67 merged PRs. Oy.
Open in the Quest HubThe first four-email Slack brief got two action classifications right. Both the attention and FYI items should have been archived with no action, so the original brief remains unchanged and the 50% result becomes the baseline for calibration.
Open in the Quest HubRoundcube is live on the self-hosted mailbox, so the daily brief can link back to the copy that actually arrived on the server - from a phone or any browser.
Open in the Quest HubI keep finding the same thing: excellent outcomes from agent work require four basic characteristics.
Attention to detail and critical thought are the critical path. One catches the issue; the other makes sense of it. Curiosity helps me resolve it.
There are skills and best practices to working with AI. I still find that every one I’ve learned is mediated through these four characteristics.
If I hit a ceiling or get super frustrated with agentic work, I check which of the four is lagging and go self-resource it.
Working with agents creates a granular fragmentation of work. Each agent carries a small stream forward, but I still carry the map of all of them.
Cycling agent tabs in Claude Code or Codex requires rapid context switching: remembering what each agent is doing, what changed, which decision is waiting on me, and where to return next. The work includes directing agents and mentally tracking multiple concurrent streams without dropping one.
That’s a very particular skill set. It’s trainable, but it isn’t intuitive.
A serious pup scare, an unexpected staycation, and the agent-native email quest that brought me back to writing.
Keep readingThe July audit found a substantial build: 5,862 synthesized transactions and 160 categorization rules, but no trustworthy operating loop. A failed derived-layer repair proved that fixes must live in durable rules.
Open in the Quest HubIf my agents fail, first I need to check if I’ve set them up for success.
And when they do fail, I add new guardrails + evals to make sure it doesn’t happen again and I catch it if it does.
OpenAI's Sol sent my launch email before it was fully complete, making this the most ironic agent workflow possible. The achievement is not the mistake; it's turning the mistake into a traceable system improvement.
Open the receiptThriving with AI launched from the new agent-native stack - and OpenAI's Sol sent the launch email before it was fully complete. The most ironic agent workflow possible is now becoming a stricter dual-inbox test, explicit post-test approval gate, and permanent incident trail.
Open in the Quest HubMy first Thriving quest is to increase my capacity for connection with agent-native email.
Keep readingI need a better term for a grouping of agents.
Swarm feels like an undifferentiated mass. Team feels too corporate. I tried village for a while, but it never quite sat right. So I had a short brainstorming session with Claude and landed on cast: a cast of agents.
It works for an almost unreasonable number of reasons. A cast is a group of hawks or falcons, which fits because Hawkeye was my nickname for years. A cast of characters is already familiar. You cast a falcon, a spell, or an actor. You cast from a mold. You cast off and release.
It’s not a double entendre. It’s a multi-entendre.
So that’s the language I’m using from here on out: a cast of agents.
The quest hub went public - this page, the receipts, the real token costs, all of it. Two days after the mail server was born, the story of building it became the launch surface itself.
Open in the Quest HubThe hosting provider refused to open direct outbound - so the relay path designed on day one took over. Messages queued for 23 hours flushed in seconds, and the whole stack scored 10/10 on mail-tester. The foundation workstream is complete.
Open in the Quest HubThe launch surface went from route inventory to four reviewed page redesigns in one day - drafted as design cards, edited in a shared design pane, shipped as pull requests. 30 routes went dark; 13 pages remain, crawl-audited clean.
Open in the Quest HubMy thrivinghenry.com mailbox now receives on hardware I control: MX cutover done, first real message delivered in under a second, and an EA agent triaging at 100% on its golden-set eval.
Open in the Quest HubDesign spec approved before any building: a self-hosted OpenBSD mail server, a newsletter relaunch on owned rails, this quest hub, and a five-seat cast of agents - with success criteria declared up front.
Open in the Quest HubFinancial freedom, resilience, lifestyle boundaries, and redesign triggers were written down, then translated into goal tiers, income assumptions, budget thresholds, and allocation rules.
Open in the Quest HubStatements, Plaid, and Tiller became independent raw inputs feeding one synthesized ledger. Vendors could now be replaced without surrendering the family record or its provenance.
Open in the Quest HubGoals, watched spending, live metrics, balance snapshots, and commitments came together in one review surface. The breakthrough was treating family finance as a recurring decision ritual, not another dashboard.
Open in the Quest HubFive years ago I started writing about thriving without AI. The tools changed. The question didn't. My inaugural essay relaunching my website and newsletter to focus on Thriving with AI.
Keep readingThe long game: a Unified Theory of Thriving to understand and a Global Institute for Thriving to study and practice.
Keep readingNothing in that stream yet. A suspiciously tidy corner of the internet.