Love AI? Not as much as these Colombian parents who named their newborn baby Chat Yipiti after you know who. 🤷‍♂️

In Today’s Open Letter

Retail-gamifying Chinese brands are giving locals a run for their money, but Checkers is taking a play from their book in the one place they can’t match them (in-store) – we can’t wait to give it a spin…

In late 2019, Checkers piloted a solution that would change the way South Africans shop: Checkers Sixty60. After a few tests, COVID-19 lockdowns hit early 2020, and the whole release was accelerated. 

Today, the service is offered at more than 600 locations, and, while not official numbers, guestimates are that it’s generating more than R10 billion in revenue for the Shoprite Group annually. 

Customer convenience, turnover + data = the modern retailer's trifecta

For the longest time, retailers have been trying all kinds of tech to figure out what people are looking at online and how to attribute purchases to individuals. (You know, so they can price better and bargain with suppliers with real data, while generating some extra cash.)

Easily done online. But how do you get the same marriage of data convenience and spend in-store? For Checkers, this could just be their new smart trolley (or as we like to call it, Checkers SkipstySkipsty).

It’s equipped with a scale, multiple cameras, a touchscreen interface and a computer to help you shop smarter and skip the checkout queue. 

To kick it off, log in with your Xtra Savings Plus card and then get to spin to win some freebies (right out of the Temu gamification playbook).

Win something? You can now go grab it off the shelf – an interesting mechanic, ‘cos we can imagine it being used to make shoppers aware of nearby higher-margin products to up net basket margin.

Once you're set, you can either hit the aisles or search for items and use smart navigation (yes, like GP on your trolley) to get to the products you want. 

(We can’t help but think this idea came from an April Fools joke from 10 years ago…👇)

Gamified groceries

As you add these products to your trolley, you have to scan them and, if you forget, it gets flagged with a picture – eliminating the ability to add something that wasn’t scanned.

Once done, a special checkout zone is where an employee will do final checks and see any exceptions raised during the buying process – like unscanned items and making sure you are over 18 if you added wine. Then you pay with your credit card details stored in the Sixty60 app.

All in all, pretty cool tech, and you can check out this video to see it in action.

However, there still is some friction that will either get sorted out or result in the project not being rolled out mainstream. As an example, the checkout process doesn’t seem faster than normal checkout.

That being said, even if it ends up being used by a small subset of users, the data it could generate for Checkers might just be worth all the effort.

We can’t wait to try Checkers SkipstySkipsty…

AI image editing? Google’s new Gemini 2.5 Flash (Nano-Banana) nails character consistency across scenes and lets you edit or merge images with simple text. Try it free on AI Studio.

Too much editing? AutoPod automates podcast editing with plug-ins for multicam cuts, jump edits and social crops inside Premiere. Huge time-saver for creators. See it in action.

Building value-adds? KwaKwa lets you build and sell mobile-first social courses from a prompt or PDF — no camera, no hassle. Ideal for fast info product launches. Give it a spin.

21 August was World Entrepreneurial Day (yeah, sorry we missed it!), and it makes sense that those creating value by building a business get celebrated.

That’s why when we saw local cloud accounting startup, stub, celebrate small businesses and side-hustlers, we had to throw our weight behind it.

More than 1’700 entrepreneurs entered Stub’s World Entrepreneurship Day Ultimate Biz Bundle. And up for grabs were:

Congratulations to the winner, Zanah Afrikan (aka Leigh Dimakatso Thegwani, on TikTok here) from Joburg.

If you’re a sidehustler or early team fighting for momentum, this is your reminder: the right tools compound.

Stub gives you accounting that just works so you can run with less admin and more hustle — invoices and quotes to statements, P&L and cash flow, VAT, a chart of accounts and a Genius ledger that keeps it all together.

📚 Going Non-Profit. South African billionaire Jannie Mouton has made an offer to buy Curro private schools for R7.2bn and turn it into a non-profit. This will allow it to reinvest profits into new schools (without being taxed) and potentially other benefits like tax rebates for fees and donations from companies (all tax write-offs). Mega.

🚀 Crunch Time. TechCrunch has unveiled its Startup Battlefield 200 list, showcasing this year's most promising innovators ready to disrupt every major sector, and stand to win a spotlight at Disrupt 2025, $100k, and the iconic Disrupt Cup. Anyone catch your eye?

😎 Sassa’s Biometrics Play. Sassa will soon require beneficiaries to provide fingerprints and facial scans directly at their offices in an attempt to fight fraud. Cue Weekend at Bernie's vaabs in the coming months…

💳 Hey Big Spender. Ladies are double-tapping mobile wallets, with a stunning 99% surge in virtual card use last year, leaving men trailing at a mere 77%, with the ladies' virtual spending hitting a whopping R36.2 billion. Mega.

🚗 Ticket to Ride. Uber is offering 100’000 free rides to job seekers heading to interviews and partnering with Harambee to help 5’000 youth get driver's licenses. Nice one.

✅ The Stack. Founders need reliable tools and suppliers. That’s why our Founder’s Stack gives you your own CFO for a fraction of the cost with OCFO, WhatsApp marketing with 2'000% ROI powered by Chat Inc, and loads more vital startup tools & services.

Yesterday, we showed you how Kohort’s helping game developers better understand their users to lower CAC, asking about your favourite game to play. And most here aren’t gamers…

🟨⬜️⬜️⬜️⬜️⬜️ 🔫 Fortnite (6%)

🟨🟨🟨⬜️⬜️⬜️ 🎲 Board/card games (25%)

🟩🟩🟩🟩🟩🟩 🙄 Not a gamer (53%)

🟨⬜️⬜️⬜️⬜️⬜️ 🍬 I’m Crushing that Candy (3%)

🟨⬜️⬜️⬜️⬜️⬜️ 🚗 Waiting for GTA VI (13%)

Your 2 cents…

Ha ha, ja we rage quit after like 5 minutes, Rob (30 seconds longer than Dark Souls). 🕹

Nice, Andrew. Should we have a couple of those in The Open Letter, you think? 🧩

AI might not steal your job — but it’s already being asked how to do it.

Microsoft Research analysed 200k Copilot chats to see which jobs people are most often using AI to assist with:

💡 Interpreters, writers and customer service reps top the “high-risk” list — tasks in these jobs are most easily replaced by AI.

💡 Jobs involving physical labour or a human touch — like surgeons, housekeepers or tyre fitters — scored close to zero.

It’s not a full picture — but it does show what people are already outsourcing to AI.

🛠 Tool to Try: Acquirezy lets you explore 30k+ real acquisitions and query an AI to spot buyer trends, hot niches and exit patterns.

🤔 That’s Interesting: Poker pros call a starting hand with an Ace and a King of different suits an Anna Kournikova — because it looks great but rarely wins.

🔥 Next Level: Watch behind the scenes of a single TV shot that compresses years into minutes.

🍔 Hack: Want to break your phone addiction? Here’s a lengthy-but-worth-it visual playbook.

🌐 Wow Site: Need to look busy? BusySimulator plays stacks of app notification sounds so you can fake busyness.

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