Happy Friday Reader!

At SXSW last weekend, I picked up a new icebreaker question that I think might be my new go-to at networking events:

👉 What is your latest failure?

​Anne-Laure Le Cunff, PhD, dropped this gem while launching her new book, Tiny Experiments, at SXSW EDU (which, by the way, is brilliant—I just finished it):

Imagine a world where it’s totally normal to ask this.

No awkward silences.

No pressure to sound impressive.

Just honest conversations about what didn’t work and what we learned from it.

So, here’s mine:

Every time I go to a conference (especially when the ticket costs over $1,000), I swear I’ll be better prepared. Yet, every single time, I find myself scrambling—sometimes on the plane, sometimes just hours before it starts.

This year? Same mistake.

Almost.

The night before, with a glass of wine in hand, I sat down to curate my SXSW schedule using the app. But after scrolling through what felt like thousands of sessions, activations, workshops, ice cream pop-ups, comedy shows, and book signings—each one screaming "Don’t miss me!"—the FOMO hit me hard.

90 minutes in, I gave up.

You know that feeling when you’ve already spent so much time on something that you should finish, but instead, you start thinking…

Wouldn’t watching the latest Netflix episode be a better use of my time?

Yep, that happened.

ChatGPT (but not my ChatGPT…)

On the way to SXSW, I told my husband I was "kind of prepared," secretly thinking he was probably less prepared.

Turns out… he had done his homework.

"How?" I asked, completely shocked.

His answer: ChatGPT.

Wait, what?

I tried ChatGPT too, and my results were meh. Despite my best prompt, I assumed it just wasn’t smart enough to curate a schedule tailored to my interests.

Then, in our Austin hotel, he casually showed me how he used the "deep research mode" to generate a full schedule in under ten minutes. 🤯

So, I tried again.

This time, I gave it proper context—topics I care about, speakers I admire, and the insights I hoped to get.

And guess what? It nailed it.

How did I know?

After spending 90 minutes manually picking sessions, ChatGPT gave me the same ones—plus more I would’ve overlooked- with explanations on why they fit my interests. It even factored in logistics, helping me prioritize sessions without having to sprint across Austin (although hitting my 10,000-step goal was a nice bonus).

So, in the spirit of sharing wins (and failures), here’s my AI-curated list—plus recommendations from friends I met along the way.

If you couldn’t make it to SXSW, you can now catch some of the best sessions online.

My Curated SXSW 2025 Top Highlights

✅ Amy Webb’s 2025 Tech Trends Report – Because it wouldn’t be SXSW without her annual crystal ball moment.
🎥 Watch the session (Warning: the report is 1,000 pages long. The video plus executive summary might be enough!)

✅ Scott Galloway’s "Prof G Predictions: 2025" – The best session of the conference. A brutally honest critique of politics, tech leadership, and AI’s economic impact. It was so controversial that they removed the video from YouTube after just a few hours. (The only thing left is his live podcast with Kara Swisher—he is so over the top how he enters the stage and speaks, but the talk is OK.)

✅ Anne-Laure Le Cunff’s "Tiny Experiments" Keynote – The future of learning is all about curiosity, adaptability, and embracing failure. I missed it live but watched it online.
🎥 Watch here​

✅ Best Startups from SXSW Pitch 2025 – If you love discovering the next big thing, check out Claus Schuster’s recap on LinkedIn (yes, it’s in German, but you’ll get it!)

✅ The State of Online Security & AI Privacy – A must-watch keynote featuring Meredith Whittaker & Guy Kawasaki. Makes me think of switching from WhatsApp to Signal because I think Meredith is so cool.
🎥 Watch here​

Speaking of privacy, I also joined a fantastic AI & Privacy session at The German Haus, covering AI regulation from a transatlantic perspective. No recording, but worth mentioning because, well… I had the best Brezel and sausages (and beer) in Austin. 🍻

✅ AI & The Future of Education at SXSW EDU (Sinead Bovell & Natalie Monbiot) – If AI is changing work, how do we prepare students for jobs that don’t exist yet? A must-see for lifelong learners (aka all of us, right?).
🎥 Watch here​

✅ SXSW Bookstore Browsing – Always a goldmine for fresh ideas and must-read books.

My Lesson Learned at SXSW:

"I tried, and it didn’t work" is no longer a valid excuse in the age of AI.

Not just for curating a conference schedule but for everything.

At the SXSW EDU recap session, one panel participant said at the end:

And here’s what struck me the most: Most people expect to talk about their wins—a big project success, a promotion, a major milestone.

But what if we flipped the script and normalized sharing failures instead?

Because failure isn’t the opposite of success—it’s the foundation of it.

When we talk about what didn’t work, we get real.

We learn.

We grow.

And we connect on a much deeper level.

So, tell me—what’s a recent failure you’ve learned from?

Hit reply. I’d love to hear it.

❤️ from Venice Beach

Simone

P.S. I'll be in Munich for the M.STORIES Female Business Festival on March 28th, co-hosting the "ReAImagine Female Talent" masterclass from 10:00 to 10:50 AM with Miriam Kugel from Microsoft's SkillHer initiative. DM me if you'd like to join; I can offer a 20% discount to my community.