Less Miserable Tech

LMT Backchannel 01 | 42:14

My AI assistant is doing a daily news brief, but it keeps missing things I actually care about. That gets Lucas, Nat, and me talking about what it takes to make these tools useful beyond the first impressive demo.

Nat walks us through the system she uses to organize projects, turn meeting notes into next steps, and keep track of what her agents have done. We compare notes on coding tools, subscriptions that don't actually save us money, and why capturing a task isn't much help if we never look at it again. Lucas describes a legal-document workbench where the user can request an evidence packet without writing a prompt.

It's a conversation about the things we're building, the parts that still frustrate us, and the small changes worth trying next. The common thread: the technology should fit the way people work, not give them another system to babysit.

Recorded August 13, 2026, with Kelly Hodsdon, Nat Walstead, and Lucas Whelan. Tool names, prices, and model comparisons reflect the conversation at the time of recording.

00:00 Opening

00:39 Why the AI news brief keeps missing things

05:08 Coding agents, rabbit holes, and staying in the loop

06:47 More coding tools, more subscriptions

11:08 The PDF prototype and the hard last mile

12:51 Capturing tasks and bringing them back

15:17 Nat's project system and agent instructions

18:56 POP: Progress, Obstacles, and Priorities

21:54 Trello, daily sweeps, and agent receipts

25:34 Building for people who won't use your system

26:54 A tour of the TechHive

31:27 An always-on personal assistant, and who maintains it

34:18 Meet people where they are and hide the plumbing

39:18 A legal-document workbench without a prompt box

41:56 Goodbyes

• Fix the process behind an AI's recurring mistakes.
• Compare the cost of the whole workflow, including extra subscriptions and learning time.
• Plan for integration and everyday use after the first working demo.
• Capture needs a review habit that brings information back when it matters.
• Keep meetings connected to project work. Nat's POP structure means Progress, Obstacles, and Priorities: what changed, what's blocked, and who does what before the next meeting.
• Give unattended agent work clear permission boundaries and a linked record of what changed.
• Meet people in the channels they already use. Hide the plumbing behind the task they are trying to complete.
• Combine fixed rules, AI interpretation, and human review.

Music: "Gimme that Groove!" by Michael Ramir C., via Mixkit.

Watch this conversation: https://www.youtube.com/watch?v=SnP9V1cL7Is

Website: https://lessmiserabletech.com/

Watch, listen and read the transcript: https://podcast.lessmiserabletech.com/the-last-mile-of-making-ai-useful-backchannel-01/

My AI agent could do useful work. The little things that made it frustrating to use kept getting in the way.

While setting up Milo, my Hermes agent, I kept running into friction: long silences, progress updates that just said “Python,” and no easy way to stop a long answer or get the agent into a conversation.

Each annoyance became one small fix: more useful progress updates, a Stop button, a Join button. The interaction got smooth enough that I wanted to use it regularly.

In this episode:

• Finding the little things that make you avoid using a tool
• Turning vague status messages into useful, sometimes funny updates
• Solving one friction point at a time
• Why your simplest useful fix may look different from mine

Try this with your own agent: “Here's the problem I'm trying to solve. What's the simplest fix?”

Less Miserable Tech is a podcast and field journal about real workflows: where they get stuck, what small fixes actually help, and how to make systems fit the people doing the work.

Website: https://lessmiserabletech.com/

Watch, listen and read transcripts: https://podcast.lessmiserabletech.com/make-your-ai-agent-less-miserable/

I almost didn’t make this episode because I was trying to make it too perfect.

The problem was not that I lacked equipment. I own four tripods. The problem was that I needed to record Episode 01, and all the equipment was packed somewhere in the middle of a move.

The smallest useful fix turned out to be an outdoor table, a toolbox, and a cardboard box.

In this episode:

- Why naming the problem matters before choosing a tool

- How chasing the perfect setup can become the problem

- Why the simplest working solution is sometimes the right one

Principle 01: Name the problem before picking the tool.

Less Miserable Tech is a podcast and field journal about real workflows: where they get stuck, what small fixes actually help, and how to make systems fit the people doing the work.

Website: https://lessmiserabletech.com

Episode page: https://podcast.lessmiserabletech.com/the-right-tool-was-a-cardboard-box/