The Road to UNBOUND - Season 2, Fourth Stop: Is This Cheating? A Lullaby, Guilt, and Where You Put the Effort
- Rob JonesHost
- Chris CarolanHost
- Casey HawkinsHost
- George B. ThomasHost
- Kyle JepsonHost
October 28, 2026
Rob Jones drove the fourth stop of the second season with Chris Carolan, Casey Hawkins, George B. Thomas and Kyle Jepson, and he left to get a prop while Chris set the context. Rob had shared a post about the satisfaction of doing it yourself, with a chart that tied AI doing the thing to decreased satisfaction. Chris challenged it a little, "especially when it comes to having AI do things that you never wanted to be doing like in the first place." The exchange moved from LinkedIn to text messages, and Rob brought it here.
The prop was his guitar. Before his daughter was born, Rob wrote her a lullaby, and he always heard it as something that would play out of a music box. He plays from tablature ("I still don't know how to write music let alone read it"), so for years the song only lived in his head. When he learned that you can now play or sing straight into Suno, "immediately I grabbed the guitar and I opened up Suno and I played into Suno that lullaby." On air he played it on guitar and then played what Suno made of it. "This was the first sensory overload AI moment," he said. Then came the question that ran through the whole hour: "the whole did I cheat is this cheating conversation." There was a little guilt, and he came down on collaboration: "This was help, like help me. Here is the melody. Here is one line of a prompt, like should sound like a music box. That's it."
George went straight at the guilt: "guilt shouldn't rob the joy of the moment … that was the right time and the time that that was supposed to happen." Rob asked whether it is "more okay to do it personally than professionally." Chris read back Rob's own words about a weird guilt that he never figured out how to make it happen or put in the effort himself, and gave the answer he had sent Rob: "but you did do it yourself. Just not with the planned toolbox." The tools came together, he said, "but that outcome does not exist without Rob Jones." Rob picked out effort as the key word: "where do you put the effort?"
Chris took it to outcomes. Before the show he asked his assistant what it would take for him not to have to ask for the show prep command at all, and the answer was simple: "we have to put it in the definition of done for the morning prep." He realized he had only to change "the bar of what success looks like." His questions for everyone: "What kind of outcome do you want, or do you even know exists? And is that outcome going to be valuable for you or the audience?"
Casey had been honored to get a song Rob made for her with AI, and it didn't bother her at all that he had used it. Guilt is one of her own strongest feelings, though: "while I think it's okay for you, Rob, … would it be okay for me is where I keep kind of getting stuck." She has friends who are firmly against AI and posts of theirs she doesn't entirely disagree with, and she is still asking "where do I draw that line … maybe that's different for everyone and maybe that's different for each audience too."
Kyle said he had no settled opinion and would work it out in front of everyone. His big question: "is this additive or is this... I don't know if subtractive is a word." Suno jingles on the section slides of his year-end deck were "purely additive." An animated musical he has spent four years trying to get made is different. He is very close to a world where a few lengthy prompts could probably produce one, but generating it and calling the job done would mean "Yeah, I would have cheated," because "That effort was always the point. I wanted to go on an adventure, and I'm still on it." He told the story of a mathematician who invented graph theory because he couldn't just look up the answer: "there is a world in which we jump to the answer and we lose something." His conclusion was that "we're going to have to get better at understanding what we want and what a good outcome is for us."
Chris pulled on a phrase of Kyle's ("There was no world. … I literally wrote that down"): once Rob heard his song, "the whole path becomes visible. You still have to choose to take the path." Kyle answered that "it is okay to get lost in administrative friction and your vision to never come to light," and named what he worries we will lose: "just building for the sake of building with your hands in the mud." "What if we liked it when it took a year?" he asked, and in the same breath said he is excited about "the things I'm going to be able to build that I never could have before these tools existed." That is why he wants it to be additive: "If it's bringing things into your life that were never going to be in your life any other way, that's good. Celebrate that." If it is only speed, "I'm not sure we solve for the best things when we solve solely for speed."
George called it the reason he wrote his article "trajectory over speed." He said he doesn't struggle with the guilt because "I don't go to work, I go to play. And it's really hard to feel guilty about playing." He once said from stage that he felt like he was cheating, and "I feel like I'm cheating more today … Trust me, but it's not cheating." He puts the time into "the system that allows me to ask the system to do the things that I once used to do," and the speed it gives him goes to other people: "yes, I'm getting speed out of it, but the thing is the speed equals value to another human." His daily question is "how do I create this ecosystem that is value first human powered AI assisted content driven," and he closed on the line his website has always carried, "A catalyst for growth": "If I can use this technology to be a catalyst for growth and unlock or unbound people, sign me up and put me in, coach."
Rob has a riddle for next time, "a short story but I can't tell you now or you will go and find the answer." He also left two triggers for the week. One was growth for its own sake: "something else that grows for the sake of growth itself is … called metastasis." The other was a comparison: "The AI usage is like micro billionarism. You know who else is unbound by almost anything? People with infinite money."
Moments from this stop
13 short cuts from this conversation.
Key takeaways
Using AI can be collaboration rather than delegation.
Rob Jones: "This was help, like help me. Here is the melody. Here is one line of a prompt, like should sound like a music box. That's it."
Don't let guilt take the moment.
George B. Thomas: "guilt shouldn't rob the joy of the moment … that was the right time and the time that that was supposed to happen."
The tool doesn't make it any less yours.
Chris Carolan, to Rob: "but you did do it yourself. Just not with the planned toolbox."
Change the bar before you change the tool.
Chris Carolan: "What kind of outcome do you want, or do you even know exists? And is that outcome going to be valuable for you or the audience?"
Where the line sits can be different for each person.
Casey Hawkins: "while I think it's okay for you, Rob, … would it be okay for me is where I keep kind of getting stuck."
Sometimes the effort is the point.
Kyle Jepson: "That effort was always the point. I wanted to go on an adventure, and I'm still on it."
Know which kind of question you are asking.
Kyle Jepson: "There is a world in which getting the answer, getting the result is not the point. The point is to learn something or gain some skills or transform ourselves along the way."
Additive beats faster.
Kyle Jepson: "If it's bringing things into your life that were never going to be in your life any other way, that's good. Celebrate that."
Speed counts when it reaches someone.
George B. Thomas: "yes, I'm getting speed out of it, but the thing is the speed equals value to another human."
Transcript
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