San Francisco Uncovered: Prerna Gupta’s Picks

The Founder & CEO of Telepathic—an app that makes reading addictive for younger audiences—reveals her favorite spots in San Francisco.

Fast Company’s Most Creative People in Business share their favorite hometown restaurants, bars, shops, and activities in our new series in partnership with Aloft Hotels, Destinations Uncovered.



This atmospheric little wine bar near the Mission features a hand-curated selection of natural wines from around the world. They take their bio-dynamics seriously here. No flavored yeasts or unnatural additives, just pure wine goodness. It’s also a great, cozy place for an intimate conversation.
1116 Folsom Street, San Francisco, CA 94103



When you think of San Francisco, you probably don’t think of pizza. Especially not gritty walk-in joints selling giant slices the size of your head. But my favorite “NY slice” in the entire world is found on the trendy streets of San Francisco’s Mission District. These are the highest-quality ingredients you will ever find on a NY-style slice, and the servers are even known to smile from time to time. Standing room only! This is the real deal.
509 Valencia Street, San Francisco, CA 94110

Royal Cuckoo

Trendy bars with overpriced sugary cocktails? Not my thing. But I love this under-the-radar spot in Inner Mission. With great live jazz, comfy couches, and a selection of local IPAs, it’s an awesome place to unwind with your founder buddies after a hectic day. They make stout Manhattans too, and have a charming back patio.
3202 Mission Street, San Francisco, CA 94110

Montara Mountain Trail

San Francisco has no shortage of artisan bakeries and hipster bars, but what sets this city apart is its proximity to breathtaking nature. My favorite outdoor activity near the city is the Montara Mountain Trail, a 7-mile hike that gains 2,000 feet in elevation from its starting point at sea level, and boasts spectacular ocean views throughout. There’s no better way to clear the mind, connect with nature, and get a butt-kicking workout in the meantime.


A good bar of chocolate is like a fine wine. Once you experience just how complex and sophisticated chocolate can be, it’s hard to settle for anything but the best. Dandelion is dark-chocolate excellence. The first time I sampled a square from the San Francisco bar (amazingly named for San Francisco de Macorís, the town in the Dominican Republic where these cocoa beans are sourced), I was hooked. The hot cocoa is amazing too!
740 Valencia Street, San Francisco, CA 94110


The Mill

Bread gets a bad wrap, but that’s because there are so few bakeries in America that have the skills to work with healthy whole grains, like dark rye and kamut. The Mill is one of those few, and it is among the best bakeries in the world. This is how bread is supposed to taste. And when it’s this hearty, it’s good for you!
736 Divisadero Street, San Francisco, CA 94117

Ruins of Sutro Baths

This picturesque beach vista is an amazing place to spend an afternoon. It’s also a great location for a photo shoot!
680 Point Lobos Avenue, San Francisco, CA 94121

Bi-Rite Market

You haven’t experienced the joy of Northern California living until you’ve spent your weight in gold on a basket of fresh summer fruit at Bi-Rite Market. The berries and nectarines here are simply heaven. They taste like candy! It’s a splurge, but so worthwhile.
3639 18th Street, San Francisco, CA 94110

Trouble Coffee

I’m not afraid to admit that I have a slight obsession with coconut water. But I like it straight from the source. This sweet café near Ocean Beach serves fresh coconut water, right out of a coconut. I love stopping by here after a day at Ocean Beach.
4033 Judah Street, San Francisco, CA 94122

Off the Beaten Path

Bars and bistros aside, the way to truly understand San Francisco is to embrace the spirit of exploration that defines our culture. I love discovering hidden neighborhoods in and around the city, and going off the beaten path to find a steep hiking trail or a peaceful stretch of beach to call my own. Because it’s in venturing into unmarked territory that you find yourself.


Prerna Gupta is the founder and CEO of Telepathic, and an angel investor.

Do Prerna’s recommendations have you planning a trip to San Francisco? Check out Aloft San Francisco Airport, the newest and hippest addition to the San Francisco area. Enjoy a signature cocktail at the W XYZ® San Francisco bar, and visit local attractions like the Golden Gate Bridge or Fisherman’s Wharf.