Wilkinson predicts AI agent 'iPhone moment' within next five years
Andrew Wilkinson · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson · Jul 3, 2025 · at 56:14
Andrew Wilkinson, co-founder of Tiny, discusses AI agent adoption and compares current agent tools to the early Palm Treo smartphone era.
0:00 / 0:40exact quote · 40.6s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“And so I think that if it was accessible to everybody in terms of, if you could just open chat GPT and say, Hey, ChatGPT, I run a business. Can you help me? And it started asking you questions and it said, oh, well, you know, you do sales. Do you want me to set up a sales agent? Okay, great. Plug in your HubSpot API. Now tell me a few things and then give me access to all your data. And then before you know it, it's just a digital employee that's on the other end of the phone on ChatGPT. Just like in the movie Her that you can talk to and it can go do stuff. I think that is kind of the iPhone moment that we're going to have in some time in the next five years.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Andrew Wilkinson
Wilkinson: Things creator has 'won' more than Asana founder Dustin Moskovitz
“I am generally much more in the camp of the things guy has won, not Dustin Moskovitz. Dustin Moskovitz is just playing a different game than the things guy.”
Wilkinson: Leaders should fire an employee immediately upon first considering it
“And the kind of heuristic I have is if I ever think, should I fire this person even once I should fire them immediately. It has always been a signal, at least for me, that when someone's a superstar, I can't imagine firing them.”
Wilkinson: Hire fully formed talent for current needs rather than potential
“So I'd say like the lesson really is hire for what you need. Don't hire just for potential, which is counter to what a lot of people say. A lot of people say hire for potential and coach them into being whatever you need. I just haven't found that. I think you…”
Wilkinson: Teaching children how to code is becoming obsolete
“So now teaching kids how to code is like teaching kids basic and we have a GUI, right? You don't need to learn punch cards and basic programming because, or MS DOS, because we all have keyboards and mice. We don't have to do that. And I feel like coding has re…”
Wilkinson: Prompt engineering will become obsolete as AI elicits intent
“And I think now people are saying people need to learn how to prompt, which I think is very true for the tool set right now, but I don't know how relevant that is in the future because I think we're still, again, in the palm trio phase. I think that the AIs wi…”
Wilkinson: First-time founders should start small instead of building complex AI or banking startups
“I don't necessarily think it has to be something that is small forever, but it has to be something that like, I think about if you're a first time entrepreneur or a student or something, you don't want to walk into the gym on day one and try and deadlift 300 p…”