Founder, two ventures · Founder · advisory
How a founder with several inboxes stopped only answering the ones he opened
Impact
Several inboxesOne per venture, each in its voiceTo RespondThe one list he actions
Nothing to installNo new app to open
“Before, I would ignore all emails and only respond to the ones I read into action. Now I have To Respond, which I'm actually remembering to action. I think I'm more alert and aware — I feel less worried.”
Upile Chasowa · 2x Founder
- Work
- Two ventures plus advisory work, after an exit
- Mailboxes
- Several, one per product or engagement
- The habit
- Open the ones that look relevant, ignore the rest
- Interviewed
- January 2026
He lives in email, and each inbox needs a different him
Since leaving the company that acquired his startup, Upile runs several ventures at once and each has its own mailbox.
“Emails are basically like life for me. I live in emails. I've got multiple different emails for different products or advisory stuff, and I'm firefighting different things. And it's a different voice — one startup I'm dealing with, I have to respond to them in a certain way.”
His coping strategy was triage by instinct: open what looks like it matters, leave the rest. By his own count that left 68,407 emails he had never opened.
His first reaction was that it wouldn't help
He said so on the call, before using it, and it is the sharpest objection anyone has put to us.
“You're trying to shift my focus away from living in emails, but I will still be living in emails, because I can imagine just how busy I get. I'm going to have loads of drafts to review.”
It is the right worry. A pile of drafts to approve is still a pile. He had watched a feature fail for exactly this reason before: two years building a booking flow at his last company that users never adopted, “because they have to install it and then they have to remember to click on it.”
He argued that reviewing drafts is still work
The objection sharpened as the call went on, and it went further than most people take it.
“Isn’t that the whole point? Just send it for me. What’s it down for if you send it for me? Have you found that you physically need to review this email before you send?”
It is the right question and the answer is that yes, for now, you do. A reply sent in your name that is subtly wrong costs more than the minute it saved, and there is no way to know which ones those are without looking. What can change is how many you have to look at, and how much of each one you have to fix.
The compromise he ended up living with is the one the product is built on: it drafts, he decides. What he stopped doing was starting from nothing.
Nothing to install, because he has watched that fail
His other objection was about adoption, and he had scar tissue for it. At his last company they spent two years building a booking feature nobody used.
“It was the most painful experience I ever went through, because users were not adopted into it. They have to install it and then they have to remember to click on it.”
His benchmark for a tool that survives is one you switch on once and stop thinking about, and he named it: the version of Grammarly you install and never consider again, that follows you wherever you are typing.
Which is the case for living inside Gmail rather than beside it. There is no window to open and nothing to remember. The mail arrives sorted and the reply is already there.
Keep what he owes on one list he actually clears
The answer to his objection was not fewer emails. It was that the ones he owes now have a name and stay visible until they are done.
“Now I have To Respond, which I'm actually remembering to action. I feel less worried.”