MON­DAY MORN­ING.

Esquire (Singapore) - - Feature -

Anew day, a new week, a new op­por­tu­nity to mas­ter your destiny, to bite the ass off a bear, to be a cof­fee achiever, to hus­tle harder, to get shit done. Bren­dan Alper’s out the door by 8:41am. He swipes his of­fice key card just be­fore 9 and steps onto the poured-con­crete floor of the lobby, where the tableau that greets him is com­posed of bead­board pan­el­ing, hang­ing globe-shaped light fix­tures, ex­posed pipes, a mid­cen­tury patch­work sec­tional sofa, ban­quettes for lap­top rovers, a gran­ite cof­fee bar (with La Colombe brew in the urns, Ronny­brook dairy prod­ucts ar­ranged neatly in a refrigerator and bot­tles of Sriracha sauce), a sec­ond bar with taps (Sierra Ne­vada, An­gry Or­chard), a large glass wa­ter­cooler lined with grape­fruit slices, an ac­cent wall with a mu­ral of a starry sky and mys­te­ri­ous hands ply­ing a cat’s cra­dle and an­other wall fes­tooned with a neon word sculp­ture. HELLO BROOK­LYN, it reads.

You might rec­og­nize in these touches the zip­pered-hoodie aes­thet­ics of WeWork, the com­pany that op­er­ates the build­ing. You might even be a WeWork tenant your­self. Per­haps you’ve taken a meet­ing or two in a WeWork build­ing, or else you will soon enough, as twenty-first-cen­tury Amer­ica con­tin­ues its head­long shift to­ward the gig econ­omy.

Fi­nally, Bren­dan gets to his pod-en­closed desk on the fifth floor, ready for some TCB: Tak­ing Care of Busi­ness. Bren­dan is 30 and the founder of a tech com­pany. He is bright, cheer­fully hand­some, well-re­lated, well-con­nected, an alum­nus of Brown Uni­ver­sity and Gold­man Sachs, where he did op­er­a­tional risk man­age­ment, which he con­cedes was “not ex­actly a crush­ing-it kind of job.” One day a cou­ple years ago, Bren­dan looked at his bosses and saw his fu­ture self: “chart­ing num­bers un­der flu­o­res­cent light, two kids at home, count­ing va­ca­tion days, and at what cost?” He quit and tried writ­ing com­edy sketches but found it too soli­tary, plus he didn’t want to move to LA.

Last year, Bren­dan scraped to­gether his life sav­ings and started a dat­ing app called Hater. It adds value, as the Shark Tank- ers say, by match­ing peo­ple ac­cord­ing to their shared dis­likes. He fin­ished the beta and timed Hater’s Fe­bru­ary 2017 launch in the App Store to co­in­cide with some canny PR stunts—cov­er­age on The View, Good Morn­ing Amer­ica, CBS’s Sun­day Morn­ing, and Fox & Friends; fea­tures on seven blogs em­bar­goed for the same day; a vi­ral pub­lic-art in­stal­la­tion de­pict­ing Trump and Putin nude and locked in an em­brace. Within three weeks, he had three hun­dred thou­sand reg­is­tered users world­wide. Then, per an agree­ment he reached with po­ten­tial in­vestors, Hater re­ceived a mar­ket val­u­a­tion of $4 mil­lion, even though the com­pany had yet to bring in a cent.

Which pretty much brings us to this fine June morn­ing. Bren­dan’s wear­ing a striped T-shirt, jeans cuffed well above the an­kle, and flip-flops—an ideal uni­form if you’re hang­ing out at your condo swim­ming pool all day. That’s part of the fun of be­ing your own CEO, he says. “But there’s that ex­is­ten­tial prob­lem I wasn’t

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