Learn to ask AI smarter questions

Today, I’m diving into Apple’s quiet moves around Perplexity AI, Meta’s new AI glasses that are way more than a gimmick, and the surprising lessons an MIT researcher learned after running 100+ AI prompt-a-thons.

In today’s post:

• Apple might be eyeing Perplexity AI

• Meta’s AI glasses are actually impressive

• MIT’s prompt-a-thons reveal how we really think

• Trending AI tools + Would you pay $50 for a Linkedin Mastery course?

What’s Trending Today

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Acquisition talks

Apple might buy Perplexity for all the good reasons

Apple didn’t say much about AI at WWDC 2025. But its latest move suggests something bigger is brewing.

Apple is reportedly exploring an acquisition of Perplexity AI, the fast-growing AI search startup.

Here’s everything you need to know:

• Talks are still early, no bids, no offers, just internal discussions. A full acquisition could give Apple a serious boost in AI powered search, an area it’s long lagged in.

• Another option: partner with Perplexity to bake its tech directly into iOS or Siri. This could give Apple a backup plan if its deal with Google gets dismantled in court.

• Apple’s own AI tools, including the promised Siri upgrade, still don’t have a release date.

• Buying Perplexity would help Apple catch up to rivals like Google and Meta; fast.

Here’s what I think about this:

Apple has a history of quiet, calculated moves and this feels like one. If it buys Perplexity, it won’t just be a tech deal. It’ll be a statement: Apple wants to shape how we search, not just how we scroll. I think something is coming…but don’t know if its Perplexity + Apple or something else.

Launch

 Meta’s new AI glasses talk, record, and coach you!

Meta is getting more serious about wearables and it's not just another pair of smart glasses. This time, the company is teaming up with Oakley to launch AI-powered eyewear aimed at athletes and sports fans.

Here’s everything you need to know:

• Meta's latest wearable, the Oakley Meta HSTN, launches this summer starting at $399.

• Designed with athletes in mind, the glasses combine Oakley’s look with Meta’s AI tech.

• You can take hands-free videos, listen to music, send texts, and make calls. The glasses include a voice-activated AI assistant that answers real-time questions.

• Meta showcased the glasses with J.R. Smith using them mid-golf to check wind speed.

• This follows Meta’s earlier collaboration with Ray-Ban and EssilorLuxottica.

• Big names like Kylian Mbappé and Patrick Mahomes are fronting the launch campaign.

I think Meta isn’t just trying to win at AI, it’s trying to win the real world. Glasses like these are a bet that AI belongs not in a lab, but in motion, on fields, and in daily life. Whether people buy into that vision will depend less on the tech, and more on how useful it actually feels day-to-day.

Lessons

What 100+ AI prompt-a-thons reveal about how teams really think

MIT’s Michael Schrage has run over 100 “prompt-a-thons” across companies and classrooms. His takeaway? Prompting isn’t just an AI skill it’s a mirror.

Here’s all the lessons + info:

• Prompt-a-thons are structured, team-based sprints to design and test AI prompts—aimed at improving real business decisions.

• In finance especially, these sessions uncover flawed logic, buried assumptions, and outdated habits baked into daily work.

• Rather than treating prompting as a tech hack, Schrage frames it as a diagnostic tool for culture, clarity, and collaboration.

• He argues the best prompts don’t automate—they provoke. They challenge how teams think and expose what they avoid.

• Small, cross-functional teams spark better prompts by debating, testing, and evolving ideas in real time.

• In FP&A and forecasting, this method routinely surfaces strategic blind spots that simple dashboards miss.

• Schrage’s golden rule: iterative prompts evolve thinking. One-shot asks just reinforce what you already believe.

Here’s what I think:

Prompting isn’t about mastering AI but it’s about surfacing how teams think, decide, and resist change. As AI becomes table stakes, decision quality will set winners apart. Start with better questions.

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