#85: Revisiting Relentlessly Curious Predictions
Keeping myself honest on my hot takes
Happy first Relentlessly Curious edition of Q2 to those keeping track!
*Crickets*
Well, anyway, it seems like a good time to reflect on some of the predictions I’ve made since the inception of Relentlessly Curious. For this week, I pulled out some of the hottest takes from articles that I wrote at least six months ago and am grading myself on whether I was on the right track. If you’ve been a longtime subscriber, I’m sure some of these pieces will ring a bell. If you’re new here, you get a recap of the content to date.
Let’s get going.
Prediction #01: Apple will acquire Perplexity
Article: AI + Acquisitions
Date: July 25th, 2025
Score: Wrong 🔴
This one was way off. At the time I made this prediction, Apple did not have a clear AI strategy while their peers were seeing blistering progress. Despite not being particularly acquisitive (is that a word?) over the years (Beats by Dre is their largest acquisition to date), Perplexity was an appealing fit for the tech giant. Perplexity’s strong user growth in July 2025, recent launch of the Comet agentic browser, early adoption of advertising and affiliate channels, and relatively low valuation compared to their peers (i.e. OpenAI, Anthropic) put it in a prime position for acquisition discussions.
Spoiler alert: Apple did not acquire Perplexity. Since I wrote this article, Perplexity tried to acquire Google Chrome, even though Chrome was valued more than Perplexity at the time of their bid. Additionally, they ditched their advertising business and launched Perplexity Computer, their AI agent platform. Simply put, I have no idea what Perplexity’s longer-term strategy is, and I’m going to pause on making predictions about them. However, what I do feel confident about is that they need to choose a niche sooner rather than later, as they do not have the capital to compete with OpenAI, Anthropic, or Google on either mass-market consumer or enterprise AI adoption.
Maybe they reach down and try to own a portion of the vertical layer. I’ve always found Perplexity helpful for deep research. Maybe with their Perplexity Computer platform, they can build de facto software for researching anything. Yes, I know that’s vague, but for a company that has a $20 billion valuation, they still need to tackle vague problems.
Prediction #02: ChatGPT will launch in-prompt purchases
Article: AI + Brand (Part I)
Date: May 2nd, 2025
Score: Correct 🟢
I was early on this take, but I don’t want to take too much of a victory lap as the writing was on the wall. There were Shopify code leaks referring to ChatGPT as a shopping channel that surfaced as early as April 2025. Thus, it was a matter of when, not if.
OpenAI needs to take on trillion-dollar industries, and commerce is certainly one of them. Given their “spray and pray” approach to new product development in 2025, it was a natural fit. They began rolling out in-prompt shopping experiments by October 2025.
How did that go? See below.
Prediction #03: OpenAI’s Instant Checkout will struggle upon launch.
Article: The Case Against Instant Checkout
Date: October 14th, 2025
Score: Correct 🟢
As a follow-up to the previous prediction, I bet that shopping within ChatGPT would struggle upon launch. Which it did, so I’m marking this one as green.
Yet, I didn’t predict that OpenAI would shut down Instant Checkout as quickly as they did. Instant Checkout first became available in October 2025 and OpenAI pulled the plug in March 2026. The quick takeaway is that OpenAI spread itself across too many initiatives, Instant Checkout did not drive the level of user engagement and checkout volume they predicted, and the operational challenges with integrating commerce into AI proved to be quite challenging. The AI goliath retreated from commerce, as well as from their video generation app Sora, in a prioritization push to capturing the enterprise segment (although they are still introducing advertising into ChatGPT).
My take was that Instant Checkout would struggle because the sheer amount of sales needed to make their investment worth it was unlikely to be achieved. Just because shopping is available within an AI prompt does not mean consumers suddenly have more purchasing power. The bulk of sales volume was likely to be a share shift from existing e-commerce platforms like Shopify and Walmart. Not net new consumer spending.
But Walmart didn’t need to worry about their website losing volume to ChatGPT. They saw conversion rates roughly three times worse within Instant Checkout than on Walmart.com. No share shift of volume there.
I’m still marking this as green as I did call out that people were unlikely to immediately associate ChatGPT with “shopping”, which was observed in the lack of shopping intent among ChatGPT users, according to OpenAI.
Prediction #04: Strava will IPO in 2026 and become the next major social media platform.
Article: Hot Takes on Consumer Brands
Date: August 19th, 2025
Score: In progress 🟡
Looking to diversify away from AI in your portfolio? Try out Strava*, potentially heading to public markets soon. In February, Strava submitted an S-1 form with the SEC, a legal precursor to a public stock offering.
I marked this take as yellow, as the groundwork appears to be laid for the take to be at least partially correct. When it comes to “the next major social media platform”, that remains to be seen. As of a few weeks ago, Strava claims to have over 195 million users, with 50 million monthly active users. The key statistic to anchor when comparing social media giants is monthly active users (MAU).
Now, the 50 million MAU figure is a far cry from the likes of mid-tier social media players like Pinterest (619 million) and Snap (946 million). If we draw the line of major platforms at Pinterest, then Strava is unlikely to hit the milestone even in five years.
But Strava certainly has tailwinds in its sails, with running more popular than ever. Also, Strava recently announced a substantial global expansion with localization in ten additional countries, along with new sports for activity tracking. I believe Strava is looking to be the social media platform for exercise.
*Not financial advice