33. Howbout – a shared calendar that’s keeping Gen Z connected

Founders: Neil Tanna, Jake Jenner, and Duncan Cowan 
Year founded: 2019
Website: howbout.app

There are plenty of myths about ageing. One adage that isn’t false? The older you get, the harder it is to make plans. Coffee and a catch-up can take weeks to organise. And forget about that group holiday to Greece; it was doomed before you could spell ‘T-Z-A-T-Z-I-K-I’.

Howbout isn’t here to fix the trappings of modern life. But it does want to make it easier for friendship groups to spend time together between work, fitness, hobbies, and downtime.

It’s a basic idea; a shared calendar for mates to plug with their weekly plans. Within the app, you can see you and your friends’ schedules, share your availability, and create groups for easy planning with people you regularly hang out with.

But Howbout doesn’t want to be just another digital diary. It views social media apps, like Snapchat and Instagram, as its competitors. Its USP? Unlike curated images and posed interactions, the platform keeps things grounded in real-life plans and shared experiences.

It almost didn’t happen. Birthed just before the pandemic, Howbout’s launch was immediately curtailed by the start of lockdown — not great for an app for recording active lives. 

Like many businesses, however, Howbout pivoted by bringing in features like a video call link for staying social with friends over Zoom calls, and focusing marketing on making plans with friends when lockdown eased — tapping into a craving for IRL connection that has stuck around.

“Gen Z are seeking more ways to feel more connected,” say the founders. “The ultimate friendship badge of honour is being included in more intimate circles to stay connected.”

Howbout now has almost five million downloads in over 150 countries. By partnering with brands such as Tinder, and gaining the backing of YouTubers like The Sidemen, the app has built a loyal audience of young adults who are discovering how valuable their spare time is.

Last August, Howbout closed an $8m Series A funding round, which its founders describe as their biggest achievement so far. Then, investor Goodwater Capital said: “Howbout has the potential to become the go-to calendar for an entire generation.” Howbout that?