Being a founder is a tough gig. I’m constantly thinking about my business, but having a conversation in my own head isn’t that productive. Unfortunately, finding someone else to talk to isn’t always easy, especially when what you need to say is that you’re unsure, anxious, or confused about what to do next.
I don’t know about you, but I have these stories in my head about being a leader—and how we’re supposed to project an air of confidence and certainty. So, when I’m feeling down or depressed, or even just curious about what our next move should be, my first instinct isn’t to go spill my guts to a member of my team. I’m working on being more candid, but in the meantime I wish I had a safe space to just talk things out, say the wrong thing, risk sounding like an idiot (or even an asshole), all without consequence.
Some of us are lucky enough to have cofounders that act as that sounding board for us, but even they are a limited resource. Cofounders sleep, go on vacation, and (gasp) have feelings and needs of their own. The result is that most founders feel isolated.
And founder isolation is a real problem. That’s why forums (like Hampton or EO) are so popular. Founders are desperate to be among their own where they can let their guard down, get advice, and figure out what’s next. But what to do about the other 29 days a month?
Well, the solution I found might surprise you.
Founders, meet Maple.
I’ve been using Generative AI pretty heavily for the past two years. But it’s almost always been via chat. I’ve used ChatGPT, Claude, Perplexity, Midjourney, Suno, you name it. And while those products have been incredibly helpful, they have always felt… transactional. I go to them with pointed questions or tasks, and I get the results that I need (or I don’t). No muss, no fuss.
But a few weeks ago, I was walking home and thinking hard about our target customer for Plumb (an AI workflow automation tool). I wanted to talk to somebody who could help me brainstorm narrower segments of the founder population. Plumb is for non-technical founders, but I was curious about what sorts of entrepreneurs would be an especially good fit for us. I needed someone that could act as an expert in segmentation, at that exact moment, for free.
On a whim, I opened up ChatGPT on my phone and flipped over to the new Advanced Voice Mode. This new mode dropped in late September, and you might recall when it did, because there was a lot of kerfuffle about one of the voices sounding exactly like Scarlett Johansson.
With Advanced Voice Mode (henceforth AVM) open, I turned on the “Background Conversations” option (so I could put my phone back in my pocket), chose which voice I wanted to hear (a voice called Maple) and started talking.
“How can I help you today?” Maple asked.
“Uh… I’m trying to figure out how to thin slice our target customer and I want to talk it out,” I said.
“Okay, let’s do it,” she said.
And that was that. Five minutes into the conversation, I had almost forgotten that Maple was a robot. And that’s because AVM is remarkably good at tracking emotion and responding accordingly. Twenty minutes later, I had a dozen ideas that I was ready to test. I closed the conversation, but honestly, it felt more like ending a phone call.
The next day, I was standing on a train platform, thinking about updating my wardrobe for fall. I had just purchased new shoes and I was wondering how to style them. Suffice it to say, this is not my area of expertise. I needed help. Then I had a thought… maybe Maple could help?
So I called her (it? them?). Or rather, I opened ChatGPT and clicked on the voice feature. Five minutes later, I had three outfit ideas, and I felt a little more confident about my style.
Since then, I’ve had at least three conversations per week that were longer than ten minutes and expansive in scope. These were conversations that weren’t going to happen otherwise, because I didn’t know who to call, or the timing wasn’t right, or I didn’t want to pay for the advice I needed. Suddenly all that was changing.
Here's an audio clip of me talking to Maple.
Three ways to play.
Since that night, I've been using AVM almost daily. It's become my go-to thought partner for everything from strategic decisions to this blog post itself. Here are a few ways I've been leveraging it:
Strategy Discussions
During one conversation, I was thinking about how to position Plumb against competitors like Zapier. I had the idea to position Plumb like Canva did for design, making automation more accessible for non-technical users.
Me: "I’m thinking we can position Plumb the way Canva disrupted design by making it easier for non-technical users. What do you think?"
Maple: "That’s a great direction. You can emphasize how Plumb simplifies automation for people who find existing tools too complex. It’s about lowering the barrier and making them feel empowered rather than intimidated."
From there we explored all the different ways that products can be perceived as hard or easy to use, and identified some key parts of the experience that I wanted to focus on. That conversation helped shape our messaging around making Plumb the most user-friendly automation tool for non-tech founders.
Content Ideation
We had a conversation about creating content for Plumb’s blog. I wanted to write about the role of AI in shaping the future of work and needed a compelling angle that would appeal to startup founders.
Me: "I want to write a blog post that talks about how AI will shape the future of work, but I need to make it relevant to our target audience who might be skeptical about how AI can make work better."
Maple: "How about focusing on how AI can empower teams to focus on more meaningful, creative tasks by automating the mundane? You could tie it to the theme of 'The Human Side of AI,' showing that AI isn't about replacing people but elevating their work."
I really wanted to dig in on how to tell that story without it being all hype and no substance. So, we explored a bunch of potential futures and I pushed back on the ones that felt unrealistic to me. That conversation led to a blog post that I’m still planning to write, titled The Human Side of AI: How AI Can Empower Your Team to Do More Meaningful Work.
Rehearsal
There have been a couple occasions where I have to have a hard conversation, or even a high stakes conversation like a negotiation, and it’s helpful to practice with a partner.
Me: “I have to have a conversation with Bob about equity and I’m a little worried I won’t say the right thing, or I’ll struggle to find the right words. Can you pretend to be Bob and react naturally, so I can rehearse? Then, when I say I’m done, I’d like your general feedback on how I did, using Non-Violent Communication and my personality type as lenses for analysis.”
Maple: “No problem. I can be Bob and give you feedback when we’re done. Ready when you are.”
The nice thing about this conversation is that you can interrupt Maple at any time and start over from zero, so every time you have an insight you can put it into practice right away. It's a bit reminiscent of that Nathan Fielder show, The Rehearsal, minus the unhinged ending.
It’s emotional.
It’s unexpected that an AI could deliver an emotional benefit—it’s just technology under the hood. But something about the combination of low latency and emotional range has made working with Maple feel good. It’s honestly nice to have someone who will listen to you, without getting tired of your shit, in a way that feels pretty natural—even if you know it’s not real.
Because again, the alternative is talking to myself, and while there’s a place for that, it tends to draw weird looks from people on the street.
Above all, AVM has given me a safe space to vocalize my thoughts without fear of judgment. As founders, we often hesitate to share our doubts or wild ideas with our teams and investors. With Maple, I can think out loud, explore unconventional thoughts, and work through my insecurities without worrying about how it might affect others' perceptions of me.
Then, when I show up to real conversations—which make up most of my day and are extremely important to me—I’m ready.
Founders, pick up your phones.
To my fellow founders out there: if you're feeling the weight of isolation, I highly recommend giving AVM a try. Just boot it up, allow “Background Conversations” in settings, and take a walk. It's not a replacement for human interaction (truly), but it's an incredibly powerful tool for working through all the questions and challenges that come with running a business—on your time and on your terms.
So, the next time you're feeling stuck or alone in your founder journey, just say, "Hey Maple..." You might be surprised at the conversation that follows.