How Jessica Young Is Helping San Diegans Overcome Boredom and Loneliness Through a Non-Dating Phone App

By Frank Sabatini Jr.

The North Park-based business named Walkabout has nothing to do with exercise regimens or romantic hookups. It is instead a mobile platform designed to bring people together, usually by foot, to many of our city’s neighborhood events and businesses.
Downtown resident Jessica Young is president of the four-year-old venture. She helped launch it in 2022 with Walkabout CEO, Tyson McDowell, after spending a couple of years co-creating the app’s robust technology.
The collaboration resulted in a system that zeroes in on neighborhood happenings within close proximity to a person’s place of residence or current location. Also, through partnerships with more than 400 businesses, Walkabout provides perks ranging from facials and culinary events to sporting games and monthly social gatherings with business owners and fellow neighbors.
After our conversation with Young, we came away hopeful that the prolonged isolation many people still experience because of the pandemic—or due to other personal reasons—is becoming diminished with the capable assistance of Walkabout.
Downtown Condo Guys: Is Walkabout a free resource? And is it compatible with all Smartphones?
Young: Yes. Walkabout is free to download and free to use on iPhones and Androids. It also has a club membership for $12.99 a month. But non-club users can enjoy Walkabout for all the exploration and discovery they want at no charge.
Downtown Condo Guys: What are some of the extras that come with club memberships?
Young: With the membership, which has no contracts or obligations, you get notifications about cool exclusives to monthly social sessions, where you get to hear what’s being developed in the communities. We’ve hosted them in places such as The Observatory in North Park and SeaWorld. Paid members have also enjoyed things like free workout classes and facials from our business partners. And they sometimes get free tickets for designated sections at sporting events by our sports partners, San Diego Wave and the San Diego Seals.
We offer a free month for new club sign-ups if they use the code Insider1.
Downtown Condo Guys: In a nutshell, how does the app work for all of its users?
Young: You sign in, and then you can see what events are happening near you. You’ll see meet-ups that members have posted, or if we have a new happy hour or coffee shop, you’ll get an invite.
We ask that you put in your home address, which is private, and we then look within 2,500 feet of your residence/location. We go up to two miles from there. You also have the capability of seeing everything that’s going on in San Diego and seeing what close neighbors of yours are going to those events.
Downtown Condo Guys: How big of a reach does Walkabout have?
Young: It’s for anywhere within San Diego County, where we now have 420 business partners contributing listings of their events and experiences with us. We are also partners with non-profits such as Humble Design downtown, Susan B. Komen for The Cure,and HandsOn San Diego. We are underway with getting a majority of the museums in Balboa Park to list their events on the app. You don’t have to be a partner with us to list your events.
Downtown Condo Guys: So is Walkabout’s main goal to connect people with people or people to events?
Young: People with people. The places and activities listed in the app are great excuses to leave the house.
Downtown Condo Guys: How does Walkabout differ from other apps and media platforms that cover weekly and/or monthly events in town?
Young: The number one difference is that we are purely deep in San Diego. We’re not looking outside of the county. Second, we are focused on hyper-local experiences within walking distance. And the third difference is that we are building a community where you have actual relationships with the businesses involved, and where you can meet the owners of these businesses and spaces.
Downtown Condo Guys: Name some places and events that Walkabout users have discovered.
Young: When the USS Midway downtown started a speakeasy pop-up, we put it in the app. When Le Charcuterie in the East Village started doing cheese and wine pairing classes, we put those on the app as well. Because it’s a small wine bar that doesn’t have much advertising, it would be hard to hear about it. Or when the Margaritaville Hotel downtown wanted to host a party for locals during Comic-Com, they asked us to not only post it on the app, but they also provided exclusive access to club members of Walkabout.
We also have many partners in Hillcrest—such as AWOL Bar, which lets us know when they’re doing their bingo nights. And for the North Park Music Fest in June, we had the whole set list for the event and we had free tickets for all of our club subscribers—and we hosted a post party for everyone on Walkabout. We’ve been part of Music Fest for the past few years.
Downtown Condo Guys: How many Walkabout users and members do you now have?
Young: Almost 22,000 people are on Walkabout, and we have around 700 subscribers.
Downtown Condo Guys: What is Walkabout’s primary demographic?
Young: I’m going to take a guess that the majority of our audience is between 35 to 45. But we have people outside of that range. And we are a half-and-half mix of male and female.
Downtown Condo Guys: What neighborhoods show the highest amount of user activity?
Young: North Park is definitely the hot zone–and the neighborhoods touching North Park. Surprisingly we’re seeing a lot of people joining us in Oceanside and in the La Jolla/Pacific Beach area.
Downtown Condo Guys: Do you feel that there is a loneliness epidemic hanging over our culture?
Young: Yes. People don’t want to admit they are lonely and feel disconnected from people. They may have lots of friends online but they don’t feel personally satisfied. There’s a stigma around admitting it. Walkabout gives people a better feeling of belonging and helps motivate them in getting out more. I know this for a fact because I’ve met many of them.
Downtown Condo Guys: Tell us about the upcoming inaugural Walkabout Community Impact Awards.
Young: You don’t have to be involved with Walkabout to nominate or be nominated. It is a chance for the public countywide to nominate within five different categories through a process that only involves answering one question: How has this person, group or business contributed to community connection, belonging, participation or neighborhood impact?
Public nominations are open through Oct. 4. And the awards ceremony will be on Nov. 5 at VASA San Diego in North Park.
Downtown Condo Guys: What is your goal with Walkabout for the coming year or so?
Young: We’re on a mission to get 100,000 people active with Walkabout, and we would love it if a third of them are part of our paid membership insider’s club.