Ahead for iOS

2.0 is… less

I released Ahead 2.0 in October 2026, and the biggest change is what I took out. I’d been adding features that each made sense on their own, and I noticed I was using the app less. So I rebuilt it around one idea: what you need at 8 in the morning is different from what you need at 8 at night.

Ahead now checks in three times a day. Each check-in reads your calendar, your reminders and how you slept, and puts what matters at the top in a sentence or two. Swipe a card right and more of that comes first. Swipe left and less of it does. It’s yours to shape: more ownership, not more magic.

Three bigger decisions came with it:

• Apple’s model instead of Claude. Ahead used to send your day to Claude to be written. Calling an API and running it through several prompts took longer than anyone would wait to hear what’s next. Apple’s on-device model now writes it in a few seconds, online or not. The writing is a little less varied, and where the writing isn’t the point, the app builds the facts directly.
• Nothing leaves your phone. During TestFlight a friend who isn’t in tech asked how they’d know the app wouldn’t steal their data, and I realized I didn’t know. I’m one person and can’t handle it if something goes wrong, so the honest answer was to make sure nothing can. No account, no servers, nothing uploaded. Only your location goes to Apple, for the weather.
• Free. Ahead Plus is gone. I’d rather it be in as many hands as possible.

The full story is in the (re)introduction on aheadof.app.

What 1.0 taught me

I design Ahead, build it, ship it and support it by myself. At Daimler a hard call gets a meeting. On Ahead every hard call is mine, usually at night, usually with the App Store review clock running. These are the lessons from the first version I want to remember, laid out as a deck of cards because that’s how Ahead itself works.

platform1 / 7

Make the limitation feel intentional

iOS widgets can't call APIs. So Ahead's widget refresh button sets a flag the app can see, turns into a green “queued” check, and the app refreshes the next time you open it. The limit is still there. It just feels like a feature now.

onboarding2 / 7

The demo got more design time than the features

Where the demo button sits, what “press and hold” should say, what pops up when a tester taps the wrong thing. I moved that button four times. If the first two minutes lose people, they never see your features.

pricing3 / 7

A free tier is a design problem

Paying for the API forced the question of what should be free. Calendar plus reminders isn't much of a gift when Apple already combines them for you. Free had to be useful and paid had to be better, and the first people to pay got a founder deal. In 2.0 I removed the paid tier entirely.

honesty4 / 7

Kill the chart you can't stand behind

The health forecast looked impressive, and I couldn't vouch for how accurate it was. It shipped as plain, high-level numbers instead. I'd rather show less than promise something I can't back up.

Some of these cards are turning into full posts in a series called Shipping Ahead.