I found a smarter way to search for flights
Plus: Apple’s latest Siri settlement, Google’s new Fitbit Air, and a scary new scam targeting seniors
Greetings and welcome to another edition of the Rich on Tech newsletter.
Hope you’re having a fantastic weekend!
It’s wild to think an AI-generated picture can give you the feels, but that’s exactly what happened when I saw this image of my current self looking directly into the eyes of my younger self.
This all started because ChatGPT recently upgraded its image generation tool. People immediately started testing out creative prompts, and one trend that took off was uploading two photos of yourself, one from childhood and one current, then having AI create an image of the two versions of you meeting face to face.
It makes you reflect on your life, the things you dreamed about when you were younger, the ambitions you had, and how that compares to where you are today. It’s nostalgia, personal growth, and reflection all wrapped into one image.
If you want to try it yourself, upload one current photo and one childhood photo into ChatGPT and use this prompt:
“Using the two uploaded photos, create a cinematic black-and-white birthday portrait: place the child (past) on the left facing right and the adult (present) on the right facing left, both clearly looking at each other, with a simple table and birthday cake in the center. Soft studio lighting, high contrast, clean background, ultra-realistic, editorial fashion style.”
Just be ready for all the feels.
My new favorite way to search for flights
I’m not ready to ditch Google Flights just yet, but I think I found my new favorite way to search for travel.
It’s a website called Mindtrip Flights, and instead of plugging in exact dates, airports, and airlines, you can search using natural language.
So instead of filling out a bunch of filters, you can type something like: “I’ve got a week off in March and want a direct flight from Los Angeles to somewhere with a beach.”
The site then uses AI and real-time flight data to sort through the options and explain why certain flights, dates, or destinations might work best for you.
What makes this different is that it’s not just matching dates and prices. It’s actually reasoning through your request and surfacing options based on what matters most to you, whether that’s cheaper fares, direct flights, lie-flat seats, shorter travel times, or simply the best overall value.
What I really like is that it expands your horizons a bit. Instead of forcing you to know exactly where and when you want to go, it helps you explore possibilities you may not have considered.
And for the record, Google Flights is still my go-to. Google acquired flight data company ITA Software years ago, which is a big reason its flight search tools are so good. Mindtrip Flights is powered by Sabre, another major travel technology company, so it also has access to deep, real-time airline information.
I’ve been testing this multiple times a day, and the extra context it provides is genuinely useful. There’s even a “Key Findings” section that explains trends, pricing insights, and why certain recommendations stand out.
Some fun searches to try: “Cheapest seven-day direct trips to Paris in October,” “Best lie-flat seat to London from LA area on a budget,” or “Best beach destinations with direct flights from Los Angeles for a four-day weekend in November”
Apple may owe some iPhone users money over delayed Siri features
If you bought an iPhone because you were excited about the more personalized Siri Apple showed off at WWDC 2024, you could soon be entitled to some cash.
Apple has agreed to a proposed $250 million settlement tied to claims that it misled customers about the rollout of its next-generation Siri features. If is approved, eligible users could receive somewhere between $25 and $95 per device, depending on how many people file claims.
The lawsuit centers around Apple heavily promoting a smarter, more personalized Siri experience that still hasn’t fully arrived.
The eligible devices reportedly include the iPhone 15 Pro, iPhone 15 Pro Max, and the entire iPhone 16 lineup purchased in the U.S. between June 10, 2024 and March 29, 2025.
I do think Apple jumped the gun here.
At the time, Google, Samsung, OpenAI, and practically every other tech company were racing to show off new AI capabilities. Apple clearly felt pressure to prove it had a serious AI strategy too, even if many of the headline features weren’t actually ready.
To Apple’s credit, I think the company probably believed these features would ship much sooner. But nearly two years later, we still haven’t seen the fully upgraded Siri Apple originally promised.
What Apple really marketed wasn’t just writing tools or AI image generation. The bigger vision was a Siri that could understand the rich personal context already stored on your iPhone, including your emails, messages, photos, calendar, and more, then use that information to answer questions and complete tasks in a genuinely useful way.
Instead, what we’ve gotten so far are smaller Apple Intelligence features like writing tools, summaries, image generation, and live translation.
Meanwhile, Apple has signed a deal with Google to use Gemini models to help power future Apple Intelligence features, including the more personalized Siri expected later this year, while it continues developing more of its own AI technology internally.
Sponsored: Take your personal info off the internet
One of the easiest ways to cut down on spam calls, scam texts, junk mail, and creepy targeted ads is to stop your personal information from being sold online in the first place.
That’s where Incogni comes in.
People search sites and data brokers collect and sell your personal details, including your phone number, home address, email, age, relatives, and even past addresses. Incogni automatically contacts these companies on your behalf and demands they remove your information, then keeps checking back to make sure it stays gone.
I’ve used Incogni myself and it’s eye-opening to see how much of your information is floating around online. In my case, Incogni has sent hundreds of removal requests and saved me a ton of time compared to doing this manually.
The setup takes just a few minutes, then it runs quietly in the background and sends regular progress reports showing which sites removed your data and which requests are still pending.
If you want to try it, Incogni is offering Rich on Tech readers 60% off annual plans with the code RICHONTECH.
🔗 Protect your privacy with Incogni
Google’s new Fitbit Air ditches the screen
Google is launching a potentially compelling new wearable.
There’s a growing trend toward screenless fitness trackers. Whoop is probably the best-known example. It looks more like a simple band than a smartwatch, but it can still track things like heart rate, blood oxygen, workouts, sleep, recovery, and other health metrics.
Google’s new version is called the Fitbit Air, and while I haven’t gone hands-on with it yet, the concept makes a lot of sense. It’s designed to be lightweight and comfortable enough to wear all day and all night. There’s no screen constantly demanding your attention, and battery life is up to a week.
At the same time, Google is rebranding the Fitbit app as Google Health, which feels like a smart move. It lines up more directly with Apple Health and positions the app as a hub for wellness data, not just Fitbit devices. It will pull in information from multiple compatible wearables and use AI to help make sense of it all.
I’ve been testing some of the new AI-powered coaching features inside the Fitbit app, and they’re actually useful. After a workout, it will generate a summary explaining how your body is responding overall, whether you’re recovering well, pushing too hard, or building cardio fitness over time. It’s much more conversational and insightful than simply closing rings on a smartwatch.
What’s interesting is that you can actually chat with the system about your health data almost like you would with an AI assistant. There are already a few iPhone apps experimenting with this style of personalized health coaching. One of the better-known examples is Bevel.
For what it’s worth, I’ve been wearing the Pixel Watch for the past week or so. While I still think the Apple Watch is the better overall smartwatch because of its app ecosystem and extra features, I’ve realized something about myself: I do not sleep well when I’m wearing a sleep tracker.
Every time I wear one overnight, I start thinking about the score I’m going to get the next morning. If I wake up, toss and turn, or get restless, I feel like I’m somehow going to fail my sleep. That mindset just doesn’t work for me.
I’m curious whether the Fitbit Air changes that. Since it’s smaller, lighter, and screenless, maybe it fades into the background a bit more. We’ll see.
The Fitbit Air is available for pre-order now starting at $99.99 and launches May 26. It works with both iPhone and Android.
This student turned a personal struggle into an invention
I love doing TV segments involving students because they remind me how young people are ready to take on the world. It’s always so inspiring.
This week we profiled a 14-year-old Orange County student named Aaryan Balani who created a DIY device to help people with intermittent strabismus, an eye condition that can cause one eye to drift without the person even realizing it.
The idea came from his own experience. His parents said he was bullied because of the condition and teachers sometimes thought he was looking elsewhere or even cheating on tests. So instead of just accepting it, he built something.
His invention uses infrared cameras and AI to detect when the eyes drift apart, then alerts the wearer so they can bring them back into alignment. It’s still an early prototype, but it already won top honors at a local science fair and he’s now headed to nationals.
Anytime I do a story with young adults or teens, I’m reminded how easy it is for the rest of us to get set in our ways as we get older.
I read a quote this week that really stuck with me:
“The secret of change is to focus all of your energy, not on fighting the old, but on building the new.” — Socrates
And it’s true. So many times in life we instinctively resist anything unfamiliar simply because it’s different from what we’re used to. But if you stay open to new ideas and new ways of thinking, sometimes they really do make life better.
A spoofed call leads to a $25,000 scam
Here’s another reminder that the tech world can be tough to navigate.
An Orange County man in his 80s recently lost $25,000 in an elaborate scam involving a spoofed phone call that appeared to come from the Irvine Police Department.
The scammers convinced him he was involved in a money laundering investigation and needed to withdraw cash to “clear things up.” He ended up taking money out of two banks, putting it in a box, and handing it to a courier in a Kohl’s parking lot.
If you’re wondering how anyone could fall for this, remember: these scammers are experts at creating panic and isolation. They keep people on the phone, make everything sound urgent, and try to stop them from checking with anyone else.
My advice is always the same: slow down, hang up, verify independently, and never hand over cash to anyone… unless you’re actually buying something. ;)
And please share these stories with parents and grandparents.
🔗 Learn the signs of a scam at ScamSpotter.org
🔗 KTLA: Elderly man loses $25K in scam involving call from fake police chief
RIP Ask Jeeves
It’s the end of an era for one of the internet’s oldest search engines. Ask.com, also known as Ask Jeeves, shut down this week after nearly 30 years online.
I’m old enough to remember when Ask Jeeves launched, and at the time, it was hyped as revolutionary. Most search engines relied on keywords. Sites like AltaVista and Excite basically made you guess the right terms to type in.
Ask Jeeves was different because you could type in an actual question and get an answer back.
Of course, this was right before Google arrived and completely changed search forever.
The funny thing is, Ask Jeeves was probably ahead of its time. The results were never very good, but the core idea was.
Because now, this is exactly how we interact with technology. We ask questions in natural language. We talk to ChatGPT, Claude, and Gemini the same way we once (tried to) talk to Jeeves.
The difference is that the technology finally caught up to the vision.
I don’t think many people are mourning the loss of Ask Jeeves, but it was a good run.
Tech Tidbits
Google Photos is shutting down a feature inside the Google Drive desktop app that automatically uploads new pictures from watched folders on your computer. You can still set up folder watching through the Google Photos website by clicking the plus sign and selecting “Back up folders,” but uploads will only happen when the Google Photos site is open in your browser, not continuously in the background.
Amazon Photos now lets you search your pictures using natural language instead of just keywords. For example, you can search things like “sunset at the beach” or “dog in the snow.” Also, if you’re a Prime member, Amazon Photos still includes unlimited full-resolution photo storage. Video storage is limited to 5 GB unless you pay for more, so if you’re using it as a secondary backup, it may be smart to disable video uploads in the app.
Spectrum Mobile now lets customers add a second phone number to the same smartphone for $10 a month. The extra line supports separate calling and texting while sharing data from your primary Spectrum Mobile line.
Q&A: Why your connected car won’t switch carriers
Fred in Lompoc, CA listening on KSMA Santa Maria asks:
“I bought a 2020 VW Golf that came with a Verizon connected car plan. I recently switched my phone service to Xfinity Mobile because of a great deal with unlimited data, and now I’m trying to move the car’s connection over too. The Xfinity store couldn’t figure it out. Since Xfinity uses Verizon’s network, I thought maybe I could just transfer the modem like another phone line. Is there any way to do this so I’m not still paying Verizon separately for the car?”
Connected car systems are often tied to a specific carrier partnership set up by the automaker, so even though Xfinity uses Verizon’s network, that doesn’t mean the car’s built-in modem can transfer over.
Your best bet is finding the IMEI for the car’s modem and asking Xfinity whether it’s compatible, but chances are slim.
A lot of these systems are designed to only work through the original carrier relationship with the automaker. It’s a good reminder that “same towers” does not always mean devices are interchangeable.
Eyelo & Bumpy
Feedbag
Dave W. writes…
“Hi Rich, I saw your report about Scamwise and used it to verify a suspicious email saying I was owed money. I uploaded a photo and it told me it was likely legitimate, and it was. I ended up getting some money back on a digital Visa card and used it to help pay for groceries this month.
Really appreciate what you do, not just highlighting cool gadgets but tools that can actually save people money.”
Dave P. writes…
“Hey Rich, I wanted to thank you for your info on Fubo carrying Dodgers games alongside Spectrum and DirecTV. You basically saved me $150 a month and I really appreciate it. Big fan…!”
As always, I love hearing from you. You can use this page to get in touch with me.
And be sure to listen to my radio show Saturdays on KFI AM 640 from 11 a.m. to 2 p.m. Pacific. If you have a question or need tech advice, give me a call at 888-RICH-101.
You can also listen to the replay Sunday nights from 8 p.m. to 11 p.m. Eastern on 710 WOR or subscribe to the podcast and listen anytime.
Have a great weekend,
Rich