My First WWDC, 20 Years in the Making
WWDC25 Keynote at Apple Park
I didn't grow up with Apple. My family used Compaq Presarios and Dell PCs exclusively, with the latter being the desktop I took to college. But one day, I saw a computer that blew my mind.
I was a music major and in several ensembles throughout college. One day on the tour bus, I saw our acoustic guitarist pull out an object, which immediately had me smitten. I saw him using it on the ride and couldn't help but marvel at how a laptop could be that small and look that good.
Being naïve to this world, I didn't know why I needed it or what I would do with it, but I had to have it. During the summer after freshman year, I saved enough to buy my first Apple device, the 2005 12-inch G4 PowerBook.
While studying trumpet performance, I also began to teach myself Final Cut Express and GarageBand and fell in love with all things Mac. The iPhone came two years later, but I didn't have either the funds or the right carrier to get one. I settled for a Palm 755 on Sprint, an HTC Touch with Windows Mobile, and the HTC Hero with Android before finally getting the iPhone 4.
At the same time, I discovered the world of Engadget, Boy Genius Report, iMore, CNET, and Phone Arena, and I was hooked. I had a bookmark folder with all my favorite websites and would reload them several times a day, checking the latest news.
Long before events were live-streamed on YouTube, I fondly remember being engrossed in the Engadget live blogs during major events and then eagerly awaiting the podcast discussion to follow. It was then I realized not only do I love tech, but I want to cover it like all the websites I read every day.
I still remember one of my favorite episodes of the Engadget Podcast when Joshua Topolsky, Paul Miller, and Nilay Patel passionately discussed pixel density on iPhone 4 and IR blasters on the latest TV gadget. I was crushed when they announced their departure from Engadget, but I read every story on This is My Next, and later, The Verge became a daily read.
All the while, I wanted to do what they did: technology journalism for a new generation. But I had no background in that work; I had a music degree and was working several jobs to support my growing family. For years, I thought I missed my chance to do something I thought I'd love. It wasn't a begrudged thought, but something I learned to accept.
Over the next few years, I would try to have my own little blogs and solo podcasts for an audience of a few dozen. Mostly, friends and family want to know about the latest iPhone and how to use it. However, in 2015, I saw that AppleInsider had an open call for writers. I applied with some of my "tip" style blogs, and miraculously, they hired me to write for them.
I truly recognize that moment as a huge break, having no real experience in tech journalism or related work history. AppleInsider took a chance on me, and I'll be forever grateful. (Thank you, Jeff)
The team graciously assigned my first big review, the original Apple Watch. It was a huge moment for me to write a full review on a new product category for a tech news site. One dream had come true.
I still had full-time jobs and other responsibilities, so everything I did in the tech space was on the side. And while I enjoyed writing, what I truly wanted to do was host a podcast covering Apple. AppleInsider didn't have a podcast at the time, and they agreed to let me try it. You can still go back to the first 10 episodes of the show, and you'll hear me and the team.
Due to shifting jobs, I had to leave AppleInsider for a few years, and I figured that would be the end of my tech career. But in 2020, they asked me to return and host the podcast. I was ecstatic and hosted the show for four years. Plus, I began producing review videos on their YouTube channel and launched a second podcast with Andrew O'Hara, all about HomeKit.
It was an honor to host and produce these shows, but in the back of my mind, I wanted to know if I could make it for myself. Not attached to any other website or brand, just me, Stephen Robles.
In 2021, my family began building a house near Tampa, Florida, and for the first time, I was able to have a small dedicated office space. I was also changing careers at the time, trying to transition into full-time video creation, and landed a job with Riverside.fm in 2022.
That year, as I began to create YouTube content for Riverside, I also started putting a concerted effort into my own YouTube channel. Creating videos was easier for me than writing, and it seemed clear that if you want to make it as a solo creator, YouTube is the best path forward.
Growth was slow, but I stayed consistent. I learned more about YouTube through my own videos and with Riverside, and things really began to pick up. I remember my first big break was a HomePod 2 review video. John Voorhees embedded my video and even put my name in the headline of his article on MacStories.
I still cry thinking about it. Not because it was good exposure or spiked my subscribers but because it was validation. One of the sites I've read for years took notice of my video and thought it was good enough to embed on their site. Then, John Gruber linked my video on leather iPhone cases, The Verge linked my Action Button video, my now co-host on Inc.com, then 9to5Mac, MacRumors, ATP, and even Bloomberg.
It felt like something was happening.
Soon after, I landed an interview with Trisha Tierney, macOS Product Marketing at Apple. Another huge moment, as it was the first time I was able to interview someone at Apple for my platform. Who knew a couple of years later, I would be interviewing Apple's SVP of Retail, Dierdre O'Brien?
My YouTube channel had momentum, views were growing, and it finally felt possible. Maybe, just maybe, I would be invited in person to an Apple event. After all those times I followed via live blogs and then watched on live streams, it felt just within reach.
As my channel approached 100K subscribers in the summer of 2024, I hoped I would receive the mysterious invite email for WWDC, an iPad event, or anything else. Events would come and go; I would see other creators invited to New York or other special events, but nothing hit my inbox.
That Fall, I did start getting my first Apple review units, and it felt like another milestone. AirPods 4, iPad mini, M4 iMac, I must be doing something right. In January 2025, I was invited to the Miami Worldcenter Apple Store opening and given early access. It may not have been an "Apple Event," but getting a special invite felt significant.
When Apple announced the dates for WWDC 2025, the anticipation skyrocketed. Could this be the year? I asked my friend and co-host Jason Aten when media invites would be sent out, and it seemed I would have to wait weeks before knowing whether I made the cut. I booked travel, even though my invite wasn't assured, and eagerly waited.
The day invite emails went out, it was surreal. This was it, I made it.
I screenshot the invite email several times, and then I would click the RSVP link over and over to confirm it was real.
Receiving an invite to WWDC meant way more than just "my YouTube channel was big enough" or my podcast had some traction. It was validation for the many years of trying to break into this world, and most importantly:
I wasn't too late.
As with any good or successful thing, we all wish we had started sooner. If I started my YouTube channel five or ten years earlier, it would be that much larger. If I had started my podcast earlier, it would have a much larger audience today.
Those thoughts still nag me at times, but I can usually quiet them by thinking, "Yeah, I may have started late, but it wasn't too late." And this invitation to WWDC was further proof that I hadn't missed my chance.
Fast forward to the morning of Monday, June 9th, WWDC Keynote Day. I didn't want anything to go wrong that morning. While it may have been a little superstitious, I took the stairs instead of the elevator in my hotel…just in case.
Even having the Apple Wallet pass on my iPhone felt surreal, but as I checked in that morning and was handed a media badge for the week, I realized this was actually happening. I was here at Apple Park for my first in-person WWDC Keynote.
I cherished every moment. From walking up to the rows of chairs in front of the large screens to eating breakfast at Caffè Macs like I had seen so many others post about. And yes, Apple Park is as stunning as everyone says.
Thankfully, throughout the week, I was able to set foot in Steve Jobs Theater, the Observatory building that's just a year old, and recorded twice in Apple Podcast Studios. Several times, as I walked the paths to meetings, I tried to take a moment and bask in the surroundings. I was really there.
I won't bore you with all the details about my experience at WWDC, although you can listen to the latest Primary Technology episode for more thoughts. Instead, I want to share the best part of WWDC - the people.
The saying goes, "Never meet your heroes," likely because they will disappoint you. From my experience this week, the opposite is true within our tech news and Apple bubble.
I knew many of my heroes would be at WWDC, so I was determined to meet (and take a selfie) with all of them. There are too many to name, and they were all wonderful, but I'd like to share just a few truly meaningful interactions.
At one dinner, as I awkwardly milled about, several recognized me and said hi, which was very nice, but Dan Moren and Jason Snell were especially kind. They let me third-wheel sit with them for dinner and shoot the breeze about Jeopardy!, tech blogging, and more.
I met my longtime co-host of HomeKit Insider, Andrew O'Hara, YouTuber Tyler Stalman, Brian Tong, whom I've followed since the Apple Byte, and so many others.
Later in the evening, I met Federico Viticci and John Voorhees. Federico said he liked my work and embraced me so quickly that the water in my hand spilled everywhere. It was terrific, and for the record, he is very handsome.
Faruk, known as iPhonedo on YouTube, was incredibly warm, and whenever our paths crossed, he would take time to chat. Tom from Byte Review is genuinely kind and friendly. KDigitalStudio was wonderful, and got to interview Craig Federighi! Meeting my longtime Shortcuts hero, Matthew Cassinelli, was the best. He even took me out to lunch one day so we could nerd out about new Shortcuts in iOS 26.
Plus, I got to meet Nilay Patel, Joanna Stern, Sebastiaan de With, Andru Edwards had me on his podcast, MKBHD, iJustine, Christian Selig, Chance Miller, Christopher Lawley, and many more. Vjeran Pavic from The Verge chatted with me for about 15 minutes before the keynote, and during the F1 screening, as I looked alone and wandering, Allison Johnson invited me to sit by her.
Not one person disappointed, they are all as wonderful as you'd imagine.
I don't know if this will be my only WWDC or in-person Apple event, but even if it is, I am forever grateful.
I want to thank my wife, Whitney, for supporting my efforts. I'm sure it sounded silly when a guy in his late 30s with three kids said, "I think I want to try and make YouTube videos for a living," but you trusted me anyway.
Thank you to the AppleInsider team for taking a chance on me and the many creators and tech sites who linked to my work along the way. Thank you to Riverside for allowing me to continue my personal YouTube journey while working to grow their channel as well.
Thank you, Jason Aten, for including me in several articles and then agreeing to do a podcast! And finally, thank you all. From those who listened to the AppleInsider podcast, followed my work on socials, subscribed to the newsletter I write once a year, joined my community, and subscribed on YouTube. Without an audience, these doors would not have opened.
This week has been a dream come true, and I can't wait to see what's next.
