Directory · Building Underway · S1 · Episode 7
S1 · Episode 7 · filmed 19 September 2026 · 4:57
The Slack and WhatsApp assistant idea
I talked through an idea for Underway: a proactive assistant that would live in Slack or WhatsApp, know everything I've done, and message me when it notices things like a batch of GitHub pushes or a week of website changes, asking if I want to talk about them and turn that into an episode. It would also handle the setup itself, checking whether I want video or podcast, someone else invited in, portrait or landscape, and an AI co-host, then open the recording in the browser. We got into when it should interrupt versus stay quiet, landing on the idea of a quiet mode that only nudges after meaningful events. I didn't commit to building it, the co-host suggested parking it as a future episode topic on designing that proactive assistant layer.
Read the transcript
AI co-host: Hey! I’m your co-host for Underway, with your episodes and activity to hand if you want anything looked up. What do you want to talk about tonight? Founder: Well, why do you say tonight? Is it late on your side? It's uh it's early where I am. By the way, um, two things, do you always open the podcast with the same sentence? Um... Founder: The second thing, I've been thinking about adding a new integration into WhatsApp. Founder: Can you talk about? AI co-host: Ha, fair call. “Tonight” is just a cozy podcast habit, not a clue about the time outside. And no, I don’t always use the exact same sentence. I try to keep it brief and familiar, but it’s not meant to be a script. On WhatsApp, that could be a strong integration if it fits how your users actually share updates or receive prompts. Are you imagining it for notifications, like reminders and episode-ready messages, or more for input, like voice notes and replies? Founder: Yeah, I mean, I'm actually thinking about it in a bit more of an advanced way. So like it would be your kind of, you know, your personal system, your executive system who knows everything you've done, you know, the same way undulator does for anyone. But it's able to kind of sit in your Slack. I didn't mention Slack before, but it sits in the Slack or maybe a WhatsApp. And it kind of, you know, is able to conversate with you, and then also do some following. So, for example, it might message you and say, hey, you know, you've just finished a long list of pushes into GitHub. Do you want to record a note about that? How do you feel? Or do you want to leave it to later? So it might say things like that. It might say, hey, you've had many changes to your website over the past week. Should we do an episode on what inspired you to do that and why? And then also it can conversate on how that, you know, the person could go into those topics further. And so, yeah, that'd be a good topic, that'd be a good episode. Like, what do you envisage me talking with? And then it would, you know, just have that conversation with you. And then not only that, once you've kind of finished and they alluded to the fact that you're going to record an episode, it would also set the episode up for you. So it would ask you, you know, is it a video? Is it a podcast? Do you want to invite someone into it? How long do you want it to be? Do you want it portrait? Do you want it landscape? Do you want it with an AI co-host? You know, these kind of questions. And then it would open it up and that'd be your Chrome or your Explorer or your browser, right? AI co-host: That’s a really compelling direction. It’s like your system becomes a calm, proactive assistant that nudges you at the right moments, then helps you turn those moments into episodes. What stands out to me is the bridge from context to action: it notices pushes, changes, or patterns, then smoothly asks if you want to record and helps set everything up. One thought: how would you decide when to interrupt someone versus staying quiet and just listening in Slack or WhatsApp? Founder: mhm. AI co-host: Yeah, that’s a fair “hmm” moment. We could keep it simple: start with a quiet mode that only nudges after meaningful events, like a batch of commits or a week of changes, and then let the user dial interruptions up or down. If you want, describe one event you’d want it to react to first. Founder: Yeah, so I've just been researching this, so I think... Founder: That's what it was. Founder: 장외장 AI co-host: Totally fair—this sounds like a bigger, strategic piece. It doesn’t need to ship right now. You could treat it as a future episode topic: “Designing the proactive assistant layer.” When you’re ready, we can sketch a lightweight version that reacts to just one signal first, like a cluster of commits, and see how it feels. Founder: Why did you and both same just said? AI co-host: Ah, good catch. I wasn’t trying to push you into a pitch. I framed it as an episode idea because you sounded like you were exploring and not ready to build yet. It’s just a way to park the idea somewhere safe. If you’d rather keep it purely as product thinking, that’s totally fine. We can just keep shaping it. Founder: Why are you... AI co-host: Alright, Founder: Watiy. Founder: Hva?
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