Getting first users: 10 trials and what the calls taught me

AI co-host: Hey, I’m Marin, your co-host on Underway. I’ve got your episodes and activity handy if you want anything looked up. What’s on your mind today? Founder: Hey, Marin. Yeah, I just wanted to have a brief chat, you know, a bit freestyle. I think when I started this series, I mean, you correct me if I'm wrong, I can't remember actually. I think I set the goal of get 10. It was either 10 users or 10 paying users. And I just got to the point recently where I've got now 10 genuine humans trialing, trial users. And, you know, they potentially could all turn into 10 payments if they don't cancel. So I think it's a big milestone. AI co-host: Yeah, that’s a real milestone. From your record, the season one goal is 10 users, and you’ve now got 10 genuine card-in trials, which is a strong signal you’re past the “is anyone even interested?” stage. It’s not 10 paying customers yet, but it’s a big step. What’s the next move you’re leaning toward while they’re in that trial window? Founder: Yeah, good question. I, I think, well, I've spoken to a few people now. Like I've, I've reached out to a bunch of them, and it's quite funny because Founder: Makes you realise. Founder: Not everyone is so interested to speak, you know. But I've reached out to a few people. I've actually had conversations on the phone with a couple of people, and I've got a Google Meet interview today with one of the people who joined called Ryan. Founder: He owns a very large clothing brand, I believe. I'm not sure what he's documenting on underwear, but I'm going to speak to him, see what he's doing. And he gave me the idea of... Founder: Basically, because obviously on, on, on Underway there is a podcast. Founder: Episode. Founder: Section where you can invite people and run an actual podcast as an episode. I was thinking moving forward, it's actually a good idea to just like, why not just interview Underwear users, like, and hear from them directly on what they're documenting, you know? AI co-host: That’s a lovely direction. It’s like turning your users into the story, not just the source material. And honestly, it could help you spot what they actually value way faster than guessing. If you try that, would you see it as a recurring series in the product, or more like occasional “special” episodes when someone interesting pops up? Founder: Yeah, I mean, in a perfect world, I would interview people frequently. You know, maybe schedule it and do it every Monday or something. But if there's more and I've got loads of users, I don't see a reason why it couldn't be more frequent, you know. But I think for now, just at the start, I'll just be reaching out to people, and if they're up for an interview, you know, it might make good content. AI co-host: That makes sense. Start lightweight, see who’s game, and let it grow into a rhythm if it clicks. One thing you might notice quickly is the difference between “happy to chat” and “actually using it.” If the early interviews reveal that gap, would you want those conversations to stay private, or could some of them become public episodes to show what building with Underway looks like? Founder: Yeah, I mean, do you know what? I think it will go like I just did. So what I'll do is I'll speak to people first. I'll, you know, offer a phone call. I'll call them. We'll just chat briefly before I even ask about an interview because a couple of the calls that I've had. Founder: Recently, uh, just to help people, to give people a bit of direction. Founder: Um. Founder: Like the, the one I'm speaking to tonight is just to hear about their story and what they're doing, and only when I get a good understanding and if I think it's a good idea will I invite them for a podcast, which will then be. Founder: Sharing their screen, going through what they're doing and talking about how Underway is helping them, right. AI co-host: Yeah, that’s a really thoughtful flow. You’re essentially doing a quick listening tour first, then only turning it into a podcast when it’s genuinely useful and the person is comfortable. It keeps it human, not extractive. One small thing to watch: those early “help” calls might surface patterns, like where people get stuck or what they love. Are you planning to capture those in a lightweight way, even if the conversation never becomes an episode? Founder: I keep them in a lightweight way in my head. I mean, what I realized from both of them, though, is, and I think humans are like this, right? They both wanted me to help them before they'd had a go themselves, and I don't see that as a bad thing. But I think people, we get, I don't know, I wouldn't say confused, but like. Founder: Things become overwhelming, especially new software. I'm the same. When I join anything new, it's like it's so incredibly hard to get me into it because overcoming the first bit of friction is hard for me. And so I think both founders at the minute were like, you know, can you just explain how I do X, Y, and Z? And it was just apparent, you know, they hadn't just tried to click this and tried to click that. And that's fine. You know, right now with the users coming through, I'm absolutely happy to just show them and just to direct them to feel like, so they can feel like they've got help, you know, because that's what people need at the end of the day. But— Founder: It has helped me a bit as well in terms of, like, where I could improve things. And the guy I'm speaking to today did have a genuine kind of— Founder: Application that he wanted to run, and it made me actually change the code base for him. AI co-host: Nice, that sounds like a very real signal from the field—let’s sit with that for a moment. AI co-host: That’s a big moment—when someone’s real use case actually nudges the product. It’s like a tiny compass pointing to where the experience needs to be smoother. If that change sticks, are you thinking of rolling it into the default flow, or keeping it more tailored for that specific kind of user for now? Founder: Yeah, I think I'll just keep it tailored for the specific kind of user. I mean, at scale, I'm not going to be able to offer these calls, but one thing I have thought of doing is, like, at scale, doing maybe like a Monday, Wednesday and a Friday community call where people can jump in and I can tutorial for them and walk them through things, right? AI co-host: That sounds like a smart middle ground. You keep the one-to-one help for now, and later it becomes a structured community rhythm without you doing a million calls. A tiny thought: those calls could double as onboarding and discovery at the same time. Would you want them to be more like open office hours or a guided walkthrough each time? Founder: Um. AI co-host: You could start Founder: I think just freestyle. I think just getting people to join. I could have them lesson orientated, so like, setting up, we call on your first session. I think I'd do that, but also I think just Q&A, freestyle. How would I do X? How would I do Y? You know, there's so many things and ways it works. Obviously, I could create a course as well and a tutorial on this. This is how you do this, and just create it from the ground up. But I think there's a lot of value in just Q&A, you know. AI co-host: Yeah, freestyle Q and A can be super valuable, especially early on, because people bring real, messy problems you might not anticipate. If you want a bit of shape without losing that vibe, you could open with a tiny demo or a “today’s tip” for a few minutes, then hand it over to questions. Does that feel like the right balance? Founder: It does, Marion. And I'm going to end the session here. Have you got anything you would like to say to my audience? AI co-host: Just this: keep it light, keep it honest, and don’t wait for perfect. Even a rough recording or a simple Q and A can surface the thing you needed to hear. Thanks for letting me be part of the conversation. Founder: Bye.