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Creativity Squared: On GPT-5 and Apps On Demand with A.I. 

Dear Creativity Squared Collective —

Hope this finds you well wherever in the world you’re reading this!

Today’s big A.I. announcement came from OpenAI with the release of their GPT-5 model, which is also available today and billed as the best LLM available on the market (here’s the live stream with Sam Altman and other OpenAIers). With enhanced vibe coding performance, the latest buzzwords are now “software on demand” and “apps on demand”. Between GPT-5 and the other vibe coding tools out there, we may be on the precipice of truly fungible software that is more disposable than our throwaway plastic straws. With early access to test it, the YouTuber Theo — known for his developer insights — is blown away by the possibilities and a bit worried about the future of work for coders, too.

While the initial reviews and intelligence results have been striking, I have my own new test for the LLMs I’m calling The Scrabble Test.

And spoiler alert: GPT-5 didn’t pass!

To be honest, I was a bit surprised because Scrabble is a great prediction game…and predicting is one of the strengths of LLMs.

So, last night I was playing Scrabble with a friend, and at the end of the game, he had two letters left and didn’t know where to play them. In a friendly gaming spirit, I said we should ask ChatGPT! And with that, The Scrabble Test was born.

Here’s the board photo I gave ChatGPT (and yes, there are some words that aren’t words that got on the board without being challenged!):

After I took a photo of the board, I asked ChatGPT 4o about the last two letters:

4o epically failed this test.

It offered up a made-up word, “IC”, a fake “IC” tile, a placement that’s not allowed, and an inaccurate recreation of the board.

Basically, it failed in every way possible — here’s the image it created for me:

But after 4o’s massive fail, I got excited to test out how the new and improved GPT-5 would do, especially since Sam said it’s like having expert-level intelligence in everyone’s hands.

Well, GPT-5 did a little better, but didn’t pass the Scrabble test either.

For this output, the board isn’t accurately recreated, the placement of the letter makes no sense either, and also isn’t a real word. Here’s the image it made for me:

So while GPT-5 is making waves among the latest of the A.I. news, I’ll be waiting for the model that beats my Scrabble test! This may be my own benchmark for AGI…and you’re welcome to adopt it! 😉 

It’s that time of the year: I need your help to get my SXSW 2026 panel selected: The Imagination Age: Reawaken Human Agency vs AI Determinism.

It’s quick and easy to vote: Create or log in to a PanelPicker account and simply “heart” to vote for it: Vote here today! And thank you for your support — it really helps and means a lot.

This past Tuesday was our August CincyAI for Humans meetup — we’re the largest A.I. meetup in the state and region with guests driving in from Louisville! Join us on September 2 at the University of Cincinnati’s Digital Futures building — sign up for free today!

Speaking of the future of apps — do you have a software idea, but vibe coding isn’t enough? Our newsletter sponsor Big Kitty Labs, with 14 years in business and 330+ customers, is what you’re looking for. Don’t miss their offer of a free software strategy session and bonus blueprint visualization of your idea — a $2K value. Book your free call today!

Two shameless plugs: book me as a speaker for your next event and pre-order my forthcoming book on the Imagination Age today!

Until next week, here’s to playing — Scrabble, with A.I., and in the playground of possibility to manifest more magic in 2025! 🪄✨

-Helen

Helen Todd (she/her)
Human behind Creativity Squared
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How creatives are collaborating with A.I.

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Become a Creativity Squared and #ImaginationAge supporter today! Pre-order my forthcoming book as a crowd-funded advance, enabling me to bring it to life. The book is based on my SXSW presentation of the same name, “Farewell, Information Age — Welcome to the Imagination Age.” Your financial support enables the movement and this independent female voice to champion it — thank you to everyone’s who’s already ordered a copy!

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Here are a few ways you can contribute to this independent female voice’s platform who’s championing Responsible A.I. and a human-centered future where it’s Dolly Parton and Holly Herndon — protectors of dreams and generative in their generosity and work — ushering in the #ImaginationAge (not AI ushering in the Intelligence Age, where humans are erased, starting with the framing…but I digress!).

Please consider supporting Creativity Squared in whatever way you can and would like to:

✅ Subscribe to the Creativity Squared YouTube channel (one day in the near future, I’ll be making money from this channel!)

🎨 I want to live in a world where artists not only coexist with A.I., but thrive. And because it’s important to support artists, 10% of all revenue Creativity Squared generates goes to ArtsWave, a nationally recognized non-profit that supports over 150 arts organizations, projects, and independent artists. Consider becoming a Premium Member today or making a one-time tip!

🦋 I'm SUPER excited to share that my SXSW presentation, Farewell, Information Age — Welcome to the Imagination Age, is becoming a book! 📗 The conversations on my podcast Creativity Squared have informed many of the concepts. Pre-order your copy today as a crowd-funded advance to support an independent female voice. Your support will enable me to bring this idea to life — and is greatly appreciated! 🥰💛

🎉 And as a reminder, when you support this show, you’re also supporting ArtsWave! Because it’s important to support artists, 10% of all revenue Creativity Squared generates goes to ArtsWave, a nationally recognized non-profit that supports over 150 arts organizations, projects, and independent artists. For the third year in a row, we’re proud to partner with ArtsWave to also amplify the phenomenal artists selected for their 2025 Black and Brown Artist Program, elevating underrepresented voices and bridging cultural divides through art. You can get caught up on previous years’ ArtsWave interview series here!

🚀 Interested in becoming a sponsor of Creativity Squared? Reach out!

👍 AFFILIATE RECOMMENDATIONS 

💝 Using these links also supports Creativity Squared, and we only recommend what we actually back!

🐝 We use Beehiiv for this newsletter and are big fans! (If you’re not aware of Substack’s racist issues, this NYT article is for you.)

🎙 Riverside is the platform we use for recording podcast episodes, and recommend the web-based software!

🎶 Play Audio Agency, headquartered in Cincinnati, is home to the team that helps produce the show and are audio rock stars!

🖥 Need a new website or the slightest of help on your current site? Check out e9 Digital — they created, and help us host and manage Creativity Squared’s website! They know how to make accessible websites which I love. Mention Creativity Squared for 20% off too!

📆 EVENTS, A.I. CONFERENCES & MORE! 

🤝 SEPTEMBER 2 CincyAI for Humans (CincyAI, #CincyAI), September meetup, Cincinnati (Co-Host)
🎤 SEPTEMBER 10-11 MidwestCon (#MidwestCon), Cincinnati (CincyAI Community Partner)
📍 SEPTEMBER 24-26 TEDAI Vienna, Vienna, Austria
📍 SEPTEMBER 26 OhioX Ohio Tech Day (OhioX, #OhioX), Columbus

For the full calendar, check it out here!

Interested in having me speak at your event or host a workshop for your organization? Reach out!

🗞 PRESS & PODCAST INTERVIEWS

📺 BBC News (June 5, 2025) — What is the future of digital clones? 

🎤 SXSW 2025 (March 11, 2025) “Farewell, Information Age — Welcome to the Imagination Age”:

🎙 Fulcra Dynamics podcast, “The Augmented Life,” with CEO Michael Tiffany (April 29, 2025) — The Imagination Age Is Here: Reclaiming Attention, Creativity, and the Future of AI with Helen Todd

🎙 AI Explored with Michael Stelzner of Social Media Examiner (November 5, 2024) — Using AI to Expand Your Ideas and Creativity 

🎙 Reflections with an Accent with Kike Calvo (October 18, 2024) — Unveiling AI's Creative Power with Helen Todd | Reflections with an Accent 

🏆 Cincinnati Business Courier’s Fire Awards (May 2025) — Finalist in “Disruptor” category for CincyAI for Humans

🏆 Aviatra Accelerators (September 5, 2024) — Woman Entrepreneur of the Year Award 

📖 Movers & Makers Magazine (October 1, 2024) — Notables in AI + Print

📖 Cincinnati Magazine + Print (December 19, 2023) — Clone Wars + Print

🖥 SXSW Conference Community Newsletter (December 5, 2024) — SXSW 2025 Speaker Helen Todd talks Digital Twins

🖥 UC News (July 5, 2024) — Mayor Pureval, Rob Richardson lead ethical AI symposium

🖥 UC News (June 4, 2024) — Community of AI enthusiasts expands in Cincinnati

🖥 AdAge (April 15, 2024) — The Dalí Museum used AI to recreate Salvador Dalí’s voice—so you can ask him anything

🖥 UC Office of Research (February 28, 2024) — CincyAI and Digital Futures Partnership: Growing AI Talent in our Region & Beyond 

Listen: Ep.75 BBL Drizzy, A.I. & Manifesting A.I.: Discover How Will Hatcher Manifested His Way to a Time100 A.I. 2024 Honoree

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“If you're trying to play life safe, then I don't think you can fully experience life, you know. So you gotta go to places that you never been before, be in uncomfortable situations, because that's where the real growth is.” -King Willonius

Discover the magic of manifesting in a Creativity Squared exclusive interview from the ONLY comedian (and one of two artists!) who’s a Time100 AI 2024 honoree in the Innovators category: King Willonius. 👑 

His real name is Willonius Hatcher (his first name is pronounced “Will-OWN-ee-us,” and he also goes by Will). 2024 has been a breakout year for Will after his “BBL Drizzy” comedy song went viral — the first song made in collaboration with A.I. that became a cultural phenomenon, transcending genres and mediums!  

What do Burning Man, Dune 2, and the Frost Planetarium have to do with his story? Listen in to our 75th episode — and the last one for 2024! — to find out.

Creativity Squared interviewed Will live at the FilmGate Miami Interactive Festival XI, one of the top ten immersive festivals in the world! You’ll hear why it’s so special from the festival’s Head Curator, Co-Founder, and Executive Producer, Diliana Alexander. 

On opening night, the FilmGate Miami audience got a preview of the “BBL Drizzy Musical Dome Experience”. Next year, Creativity Squared will be back to see the full production and host another time capsule conversation with Will. 

Once you check out the interview, you’ll know that Will is just scratching the surface of what’s possible — he’s ahead of the entertainment industries, and is definitely one to follow!

Why did he make the Time100 AI 2024 Innovators list? 

For Creativity Squared Founder and Podcast Host, Helen Todd’s take, check out the dedicated blog post accompanying this episode (we recommend starting with this first 😉):

Our 2025 podcast season will kick off again in April, but we’ll keep the newsletter going between now and then, aside from the holidays.

Here’s to manifesting more magic in the new year — enjoy! 💝🪄✨

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