When Jason Calacanis launched Mahalo nine years ago, it was a search-engine company.
Then it became a YouTube company, and then it became a news app company. Now he is changing it again.
Calacanis is launching eight newsletters under the Inside brand today (he picked up the name during one of the pivots) — each aimed at specific topics like drones, VR or San Francisco. He says he would like to have hundreds of them, each produced by curators working remotely.
Welcome to the club, Jason! Newsletters are having yet another resurgence right now, and everyone from individual proprietors (like tech analyst Ben Thompson) to well capitalized publishers (like Quartz) to startups (like The Skimm) are figuring how to turn them into real money.
Or at least some money: Nick Quah, who runs the excellent podcasting newsletter HotPod, says his letter lets him pay his New York City rent.
Calacanis has known about newsletters for a long time — he had them back when he ran Silicon Alley Reporter, his first successful business. He had another win when he founded Weblogs, a blog network that included Engadget (small world!), which he eventually sold to AOL.
But his biggest win may have been an early investment in Uber, which he is happy to tell you about.
Calacanis has yet to turn Mahalo/Inside into a success story, though he says the videos he created at Mahalo are still churning out “hundreds of thousands” per year in YouTube revenue.
He says he’s trying yet again with the company because he’d like to be able to pay back investors like Elon Musk, Mark Cuban and Sequoia, who have put a total of $20 million into Mahalo/Inside. He says Sequoia has chipped in a new, small investment, which will give him another year of runway.
Calacanis says he wants to make money from the free newsletters by selling ads, but says he will also ask his readers for voluntary donations; he says 1,000 newsletter readers have kicked in $100 a year during a trial period.
This article originally appeared on Recode.net.