Happy Friday everyone! Welcome back to Ship Happens, your weekly product manager newsletter.
I'm using this newsletter to share at least three things l've come across this week to help you build better product. Subscribe so you don't miss these when they come out:
On to this week's thoughts and updates:
At the top: I've created a podcast and video version of these newsletters! I hope you take advantage of these experiences. I hope they're helpful. Hopefully you can listen to this stuff if it's useful on your run, on your commute. Or watching in your side panel while you're doing PRDs.
1. Do things that make your palms sweaty
I've been going through orientation this week and meeting a lot of my new coworkers, and one of the things that came up was an icebreaker: "What was some of the best career advice you've ever gotten?"
I had two. One we can talk about another time. But the other one was that you should do things in your career that make your palms a little sweaty.
You should do things in your career that make you uncomfortable. And I have to be honest, some of what I've been doing lately is a little bit uncomfortable. It's making my palms a little sweaty — working in AI and working in a new space.
I feel like I am living out that advice right now. And it's good advice. You should be thinking about how you can move forward in your career and make yourself feel a little uncomfortable — that means you're learning and growing.
Now, some might interpret that advice as: make sure you're doing things that you don't want to do, or that you have to go into management, or do something specific. You don't.
I think it's really more about personal growth and doing things that you find challenging and interesting and that really light your fire. I feel like that's the journey that I'm on right now and I'm really excited about it!
2. Apple should just give up on Siri
Unpopular opinion alert! But I'm really starting to believe that Apple should just capitulate in the voice assistant race — and capitulate to something like ChatGPT.
You could consider me your tech grandpa because I've been doing this since 2007. 👴🏼 One of the advantages of doing that is that you have a long lens into history. Like, you can remember a lot of stuff that sometimes gets lost in the sands of time.
A lot of people forget that Apple bought Siri in 2010. I had to look this up to get the info right…they bought Siri in 2010 — it wasn't even a homegrown product. And they've been trying to make it great since then, FOREVER ago.
This latest iteration of Siri that's supposed to be coming out is supposed to be incredible. It's supposed to have all of these AI features. And… it hasn't happened.
At some point you have to accept that Apple is, at best, a little behind on the AI side of things. At worst, just not able to deliver the kind of AI experience that users expect now, especially with the advent of ChatGPT, Gemini, DeepSeek, Perplexity… all these new products that are frankly amazing.
You have to lean into the things you're good at. And potentially outsource or yield ground in places you're not. This was all spurred by me doing some research recently on iOS and ChatGPT integration.
One thing I learned is that ChatGPT’s integration in iOS goes beyond just being a release valve for Siri. Previously I thought you’d initiate Siri, and if Siri can’t do something, it punts to ChatGPT.
But if you use the hotword "ChatGPT" before your voice command, you can go straight into ChatGPT. I’ve made advanced voice mode a hot button on my home screen. And it is just so much better than Siri. I don’t know if Siri will ever be that good.
Marques Brownlee did a video on this too, talking about something similar.
Apple has been working on this for 15 years. That’s a long time to be committed to something and not have it work. I don’t know anything about what’s going on inside of Apple, of course, but if I was there, I’d ask: is this ever going to happen or not?
Not to stoke the fires here. I’m just a guy. I work in tech. But ChatGPT as an acquisition target for Apple would make a lot of sense.
Google’s got Gemini. OpenAI’s tech is valuable — not just the model, but the experience. Maybe Apple should go after ChatGPT and OpenAI. Maybe that’s the end game…
3. Why OpenAI is probably raising money on ChatGPT the app — not the models
It’s making more and more sense to me why OpenAI would raise money based on ChatGPT and not the models themselves.
For years there’s been this assumption that whoever figures out AI at scale is sitting on a gold mine. And I think that’s true — but not in the way we expected.
We thought the LLMs would be the gold mine. That they’d generate billions or trillions in value. But turns out… they’re enabling tech. And that value is eroding because the cost of running LLMs is dropping quickly.
Now there are great free models — DeepSeek, Gemini, Meta's new Llama 4 models.
So what is actually valuable then? The ChatGPT experience.
You can see OpenAI separating OpenAI the company from ChatGPT the product. It makes sense. Because the value is not just the model — it’s the app.
And this ties into what we’ve been reading in AI Powered Search as part of the book club (around page 70). Good search experiences parse the query. They don’t just take it at face value. And the processing layer? That’s not happening in the LLM itself. It’s happening in ChatGPT.
Same thing with Perplexity — their secret sauce is in that query processing and ranking layer. ChatGPT is in the same space.
But it’s more than that. ChatGPT is becoming my life assistant. I use it as a daily driver.
Canvas is a great step for documents and notes, but there’s more potential. Tasks doesn’t really work the way I want it to. Projects doesn’t support the full feature set. You can’t use Tasks or Deep Research in Projects right now.
I’m sure they’re working on it. But it just shows you: ChatGPT needs more love. The value is there. And it makes sense they’d raise money on ChatGPT — not the models.
Because model costs are dropping to near zero. But ChatGPT’s value is climbing.
Remember when image generation melted their servers? That’s a sign of real demand. And a reminder that good product takes effort — to help users understand how new tech fits into their lives.
If they just announced "we have image generation," people would’ve been like meh. But they let it go viral — anime, art types, model training — it hit.
That’s what makes ChatGPT so valuable.
4. iOS is getting really complex
This might just be because I’m getting older. (Tech grandpa strikes again.)
But I found myself watching an explainer video just to understand ChatGPT’s new features in iOS. And it really made me realize: iOS is getting complicated.
There are so many features now. Apple does a good job pruning what doesn’t work, but it’s time for a cleanup. Hopefully that’s coming in iOS 19.
5. Heart health update
If you’ve been reading, you know I’ve been on this health journey during my break. Trying to reduce stress and put good habits in place before heading back to work.
I posted a thread about stress on LinkedIn (thanks for all the replies!) — and Tom Hale, CEO of Oura and my former boss, left a comment that stuck with me.
He reminded me that stress is a canary in the coal mine for heart health. VO2 max and cardiovascular age matter just as much.
Mine is about five years older than where it should be…
And I was like DAMN IT!!! I keep trying to fix this. Last time I made progress I was running regularly — six weeks of solid running — and it worked.
But I injured my back. (Tech grandpa strikes again! 👴🏼) So I went back to cycling and weightlifting, and it didn’t help. My cardio age climbed, and stress took over.
I was also doing saunas, but not consistently. Now I’m trying a new routine:
Zone 2 cycling on off-days
Weight training once a week
Daily walks with the dog
Sauna almost every night
It’s starting to work again!!!
My cardio age is dropping, largely due to a change in my VO2 Max.
Still a ways to go, but it’s trending right. More to come…
That's it for this week! Thanks everyone for tuning in.
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