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Hi Playmakers,
I could have my baby literally any day between now and the end of the month (and trying to get my life sorted before he arrives.)
As I lay here writing this newsletter, struggling to get out of bed, I’ve been wondering what kind of world he’s going to grow up into. My husband and I talk about it almost everyday. The topic that comes up most often is AI.
The other night, my husband and I were having dinner when I threw out, “Do you think our baby will go to college?”
“No.”
It didn’t take long for us to conclude that AI was changing everything, with education being at or near the top of the list. Both of us agreed we were learning more today than four years ago, and that’s largely thanks to understanding how to use AI tools effectively.
In fact, it’s abundantly clear from OpenAI’s own data that most people are using it to learn.
Here are three key things that stood out to me from the data:
Tutoring and how-to is dominating: People are looking to learn with their AI tools. This is an obvious use case for a massive edtech boom — especially given the lucrative B2G contracts offered in the space. This could also be a huge opportunity for the re-skilling economy. This is quite timely given the announcement about Ivy Leagues now investing into vocational training.
Specific search is still a big space: though Google’s dominance as the main search engine on the planet (in some regions, such as Nigeria, they account for a whopping 98% of search queries) remains in place, it is obvious from ChatGPT’s data that Google will need to lean much more into their AI summaries.
Image and content creation is a niche opportunity for the right tool: With the advent of Google’s Veo, OpusClips, and other tools specifically designed for content and image/video creation, this is still a big market for tools. Operators don’t want generic images — they are looking for quality.
So, bringing it back to the dinner table…
Why would our child go to college and use AI to write essays, when we can pay $30/month for AI tools that are exponentially getting better? As parents, we’ll guide him on how to leverage these technologies properly, and we’ll help him learn about anything and everything.
Plus, let’s face it, the ROI on a four-year degree is rapidly deteriorating. That expensive piece of paper doesn’t carry the weight that it used to.
What do you think? Are we moving into a post-college world thanks to AI? Is AI making you smarter?
Jenny
P.S. One AI tool in particular that I’ve been obsessed with is Lovable. It’s unlocking my ability to make apps and websites, something I was never good at before. It’s comically easy.
The Play of the Week: Mira Murati, CEO of Thinking Machines Labs
This 36 year old CEO built OpenAI, then walked away from the $80 billion company to build her own AI competitor — now worth $12 billion.
The Execution Plan: Your Play for the Week
This week’s challenge: Do a deep dive on a topic you’ve been interested in (and do it with AI.)
The best way I’ve found to learn with AI is to keep it structured and conversational. Don’t just say “teach me about X.”
Instead, try the following:
1️⃣ Tell your favorite AI tool that you want to learn about a specific topic. Have the AI draft an outline of the topic that allows you to build on the knowledge.
2️⃣ Ask the AI to teach you based on that outline.
3️⃣ Keep it conversational, as if you had your own, private tutor. (Pro tip: Explain what you’ve learned back in your own words to have the AI measure your understanding.)
This simple approach has helped me learn and retain new knowledge better than ever. When you’re done, ask for a cheat sheet you can reference anytime you want to dive back into the topic.
Got a method for learning that works for you? Tell me all about it!
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Playmaker’s Spotlight: Real People, Real Wins
Every week, I spotlight somebody from the community who is making a big play in their career or industry. This week’s play comes Ben Mann, co-founder of Anthropic.
As we re-think the future of work, Ben’s thoughts on the future of school and how he thinks of his toddler’s future opens up a fascinating vision for what is to come.
Anthropic co-founder Ben Mann on why he chose Montessori for his daughter:
"If this were 10-20 years ago, I'd be lining her up for top-tier schools and extracurriculars. But now I don't think any of it's going to matter. Learning facts is going to fade into the background. What
— #Lenny Rachitsky (#@lennysan)
12:04 AM • Jul 23, 2025
Want to be featured next?
Make sure to tag @Jenny Stojkovic on your post for a chance to be featured.
The Extra Edge: AI Edition
👉🏼 With how fast AI is changing, I’m revisiting Ray Kurzweil’s work. The Singularity is Near, and the recent add-on, The Singularity is Nearer, are must reads for anyone interested in technology’s acceleration.
👉🏼 I’ve been using HighLevel to build my business, website, and CRM. It’s been a game changer for me.
👉🏼 Trying to create content while super pregnant is easier when I can use AI tools like Opus Clip to edit quickly.
☕️ Want to have virtual coffee with me?
I’d love your help spreading the word about The Wednesday Play. Refer other people to the newsletter and get free time with me for a video call.
How to Get Involved:
The Wednesday Play isn’t just a newsletter — it’s a community. I’ll be announcing much more in coming weeks and months! For now, let’s connect across social.
