In a city of transplants, Stephen Green is a rarity: a Portland native, born and bred in this town where he’s lived for nigh on all of his 41 years. During that time, he’s worn many hats, notably as a banker, venture capitalist, TEDx talker, organizer of a pitch competition geared at African American entrepreneurs callled PitchBlack, and now the head of WeWork Labs, a network of start-up accelerators opened by the international coworking company.

So yes, he drinks a lot of coffee, much of it at Old Town’s Deadstock. The realm of Nike janitor turned sneaker designer turned café owner Ian Williams, Deadstock markets its wares as “snob free” and gathers all manner of clientele—with occasional Phil Knight appearances. “From the young blood rocking the latest Yeezys, to a creative working on their portfolio, or the footwear executive plotting next year’s releases, they all have a spot here,” says Green.

For a culture hit, Green recommends NE Killingsworth’s GreenHAUS Gallery. “It’s like walking into a business owned by one of your family members,” he says of this boutique meets art space, where assorted treasures—jewelry to vintage cameras to Trump toilet paper—share space with work from a different artist every month. “Cole and Dayna [Reed] will become instant family while you browse the store.”

To keep himself looking sharp—and abreast of local sports news—Green favors NE MLK’s Influential Grooming Lounge for, he says, “a fresh cut and the latest word on the street about how the Trail Blazers are doing.”

When it comes to food, it’s Mama San Soul Shack all the way. The St. Johns gem serves up serious soul food with colorful “dranks” to go with. “You will be looking for your auntie back in the kitchen with how good the fried chicken is there,” says Green.