Hack Idea: ~Calendly for the self-aware

Posted on November 27, 2018. Filed under: Uncategorized |

I was scheduling a call this morning with my friend Greg via iMessage and something occurred to me. Normally I am scheduling in email, and I have a pretty routine flow for moving between my calendar and email and suggesting times, etc…but I guess b/c i was on my phone, and in iMessage which feels more natively mobile than Email, when it came time to suggest times, I toggled to my calendar and instead of picking a few times and messaging back, i just screenshotted my calendar, sent the screenshot in imessage, and asked if he was free when I was. It was very easy but I was worried it might be offensive. There is something about this action which evokes Calendly…and I’ve always hated Calendly and other scheduling tools that put the work of calendaring a meeting on the other person in an interaction. When someone tells me to pick a time on their Calendly my immediate (and maybe unfair) response is “what an asshole, do your own calendar work.” I was worried that the screenshot might have a similar feel, but there’s something about not making the recipient click through a link, select a time, input their email credentials, etc…that felt more lightweight and friendly and helpful. It felt like the lightest possible way to sync on calendars without using an overbuilt or presumptuous tool to do the job. I asked Greg if he liked being on the other side of it, or not, and he was a fan. I asked if he’d ever seen anyone else do that, and he said no. Neither have I. One reason why, might be trust and transparency. I know Greg really well and trust him without question. So him knowing who else I was meeting that day wasn’t a big deal. But I think this flow could benefit from a very light software build to mitigate this trust requirement. In it’s simplest form, I think the hack would be to build a native app that runs in the background and:

1) auths with your camera roll
2) detects screenshots
3) determines if screenshot is a calendar view (maybe clarafai API can do this easily as a service. it’s a trivial ML problem, no idea how plug and play they are)
4) blurs all text in calendar view
5) deletes non blurred version
5) saves blurred view back to camera roll

The user experience would be identical to the UX I had with Greg, except when selecting the screenshot from photos to share in iMessage or email or whatever, my selection would automatically be the blurred version.

I’m not sure if anyone else would value a simple tool like this that fits within your mobile workflow and let’s you continue to schedule in your preferred channels with a light enhancement of a screenshot for availability, but if you want to do a little hack with (or without me), I’m up to put a little elbow grease in or at least test/use it if you build it without me. jordan.cooper@gmail.com.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at Jordan.Cooper@gmail.com (p.s. i don’t use spell check…deal with it)


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