About Iman Wilkerson

Most people who live in San Diego moved here from another city, so it’s appropriate that our first interview spotlights a Chicago transplant. Iman bucks any notion that only San Diego natives care about or have an important role in the San Diego community. Iman is an avid runner, entrepreneur, and local community builder. She has launched several businesses in the last several years, including Step x by Step Run Co, which provides guided runs and run tours to visitors, and a running app called The Run Down. Iman has become a familiar face and central figure to the local running community, and she’s just getting started. In our conversation we cover topics from the journey of entrepreneurship to the local business climate. Whether you’re a runner, an entrepreneur, or just interested in the latest happenings in San Diego,  you’ll walk away with some great inspiration and useful tools.

Iman Wilkerson, Founder of Step x Step Run Co. and The Run Down.

Iman, we would love to learn about your current entrepreneurial pursuits, why you started them and how they’ve evolved to where they are now. 

I started Step x Step Run Co about two years ago with the purpose of helping people who are traveling and who are runners to explore San Diego in a new way. We provide guided runs and run tours, including a Sunset Cliffs at sunset run, a North Park brewery tour, and a North Park donut run (a very popular run!). We also provide run buddies to help people who are traveling stay accountable to their active lifestyle goals.

I first had the idea for Step x Step Run Co when I lived in Chicago. I had just moved there and was training for the Boston Marathon during the winter. It was one of the coldest winters ever, so it was very hard for me to stay accountable to my own training. I also had friends who would visit and ask me to pace them on their runs while giving them a tour of the city. So then I wondered, if people didn’t have a run buddy in the town they were visiting, how would they explore it like a local? 

I never did anything with the idea in Chicago, but when I moved to San Diego friends would still ask me to take them on runs, wanting to get a tour of the city. That’s when I decided to pursue the idea further.

My immediate thought was to partner with hotels so that their guests would be able to hire someone to give them a tour. Hotels at the time didn’t really see the value in that. Their logic was that if the harborfront is right there, where most people stay and run, then why is a guide needed? Of course there are so many reasons to have a run buddy, like safety and accountability, but if you’re not a runner those nuances can be easily overlooked.

"Running came into my life when I was battling my own dark side. There were a lot of parallels to running and me trying to achieve accomplishments in my own life."

— Iman Wilkerson

I’ve noticed that Airbnb offers experiences for folks visiting the area.

Yes–I actually utilized Airbnb Experiences to find a majority of my current running clients. It’s a great way to build a clientele coming into San Diego, knowing that these kinds of experiences aren’t going to be commercial tourism. It’s going to be, “Hey, do you want to run? Do you like sunsets? Let’s go on a Sunset Cliffs run at sunset.” That’s been really exciting. It’s been eye opening, knowing who my customers are. I thought it would be the gung-ho runner, but really it’s anyone who wants to be active and wants to learn something new. Oftentimes it’s a woman. There are solo women travelers who still want to stay active while traveling. I’ve learned a lot in these past two years.

After starting Step x Step Run Co, I created an app called Pace Partner. The idea was that while you’re traveling, you can hire a vetted local run buddy, similar to the way Uber works. You can hire a run buddy to go on runs, and it was a platform for runners to get paid to pace other runners. You could also use the platform to dial into local running communities, find places to run, discover what places and trails are out there, or find local run clubs. It was a hub for all things that serve a runner’s lifestyle. 

So basically Pace Partners was the app version of Step X Step Run Co?

Exactly. That was an exciting thing, because I never thought that I would create an app. My background is in fashion. I am so far removed from that sort of thing. But we live in a time where, if you have an idea and you are absolutely willing to see it out, you don’t have to have a technical background. All you have to do is ask around. Last year I worked with a developer, and while it didn’t work out as well as I had planned, that’s OK. That’s how you learn, and you pivot.

Earlier this year I decided to pivot away from Pace Partners towards something that would  better serve the community with an app called “The Run Down.” It occurred to me that The Run Down would be a weekly digest where runners can find local run clubs,  races, and running events. Essentially The Run Down is what I wanted people to get out of Pace Partners when they traveled to another city, but The Run Down is useful in your own city as well. 

The whole point is to connect the running community, make it smaller and tighter, more inclusive. So that’s where I am right now. Last week I launched the alpha version of The Run Down app. You can explore all the places and neighborhoods that have been crowd-sourced by local runners.There’s a calendar of events where you can learn about everything going on during the week. You can also read about local runners who serve the community in different ways. Whether it’s an elite runner who has gone to the Olympic trials or a run leader, we want to highlight local runners in the area. There are just so many people that have great recommendations and things to say about the community.

Since it’s the alpha version of the app is it limited to certain users?

That’s a great question. We are limiting it to about 250 people. You can go to the therundown.run and submit your e-mail and we’ll send the download link.

Wow, that’s exciting! Congrats on getting your second app launched and moving forward with that. I’m curious, how did your personal passion for running develop in the first place?

Well when I was in high school I ran track. I ran the 400 meter and the 4×4. I dabbled in the 4×2. I had no intention to run anything further than 800 meters. Honestly to run a mile was like asking me to run a marathon at that time. I ran to stay fit. I didn’t want to gain the freshman 15, so I stayed active in that way. 

During my freshman year of college I met a guy who ran three miles, and he asked me to go on a run with him around a lake in the morning, and that was completely outside my realm. I did it, but I hated it. I saw these people out there that loved it, but I hated it. I decided I wanted to try it on my own without holding anybody back. I went back to the lake and ran it by myself. I stopped a few times, and I walked and I ran. I remember the first time I ran the three miles around the lake without stopping–I was so happy! At that point I never tried to sign up for a 5k or anything. I just kept running to stay in shape.

I think a lot of us get into running later in life; maybe there’s a lack of confidence or depression, and you find running as a way to build confidence in yourself and overcome challenges. Running came into my life when I was battling my own dark side. There were a lot of parallels to running and me trying to achieve accomplishments in my own life. 

Say you commit to doing something like running a 5k, a really hilly 5k, you can’t stop in the middle of it–the only thing to do is keep going. You can slowdown, you can walk, but you have to keep going to the finish line. There are so many metaphors to life. You learn to dig deep. That’s what I love about running and runners. You don’t say you can’t do something–you most certainly can! It’s always within us. We’re always stronger than we think we are. I think that’s why a lot of people who have battled some kind of depression or addiction or something outside of themselves start to run. Running brings them back to who they are. 

Community is another big aspect of it. The running community I fell in love with is what I’m trying to recreate through the app. It’s a way for people to be really close and to know what’s going on. When I was in New York and really in tune with the community I didn’t have an app or website–I just knew, through word of mouth and conversations. New York is the largest city but at the same time I always felt like I was in tune. Here it’s not as densely populated, so I might not know about things going on in Encinitas just because I live in North Park. With the app I want to create a community where you know what’s happening at the palm of your hand, where you feel involved and included. 

As far as community goes, how do you feel about the business community in San Diego? Is it a good place for entrepreneurs and start-ups?

You know, I’ve lived in some different places. I lived in Chicago for a couple years, New York, and I’m originally from North Carolina. I say all of that to say, there’s a different vibe for every city, a different hustle. Chicago and New York, are very much about the hustle, just getting things done. Here there’s so much opportunity, but there’s also an interesting balance of relaxed-chill. 

San Diego is an excellent place for anything that’s new. It isn’t trying to be Los Angeles–it’s not trying to be anything, which is great. At the same time I miss a little bit of hustle to get things done. I have to change those expectations. I have to learn to re-frame my level of speed and willingness to get things done.

My company has been well received, but because it’s so new it’s about showing people what another opportunity is like or what another way could be. If I’m trying to partner with businesses like hotels, I have to convince those people a little harder why we should exist or why we should partner together. This is part of the entrepreneurial spirit though, you can’t expect everyone to be so gung-ho about your vision. There’s a level of convincing and pitching, proving to people why you should take up space here. 

When people aren’t as gung-ho about your ideas as you might hope, are there any books or podcasts you turn to for inspiration?

You know, I listen to podcasts a lot. I’m always on the move, so I don’t always have time to read like I want to, but podcasts are so digestible. My favorite podcasts right now are How I Built This by Guy Raz and Girl Boss Radio. How I Built This is really great because they highlight entrepreneurs and how they built their business. They look at how entrepreneurs funded their business and where they got their ideas. It really normalizes and humanizes the process of starting a business.

It’s also really important to me to be grounded and consider why I’m doing what I’m doing, you know, not just chasing the money. There are a lot of mindful podcasts I listen to that help me remember to breath, that remind me who I am or why it is that I’m doing something unique. Recently I’ve been listening to Ten Percent Happier with Sam Harris. A lot of doubt can circle you when you are trying to create something–it’s very isolating, so having those kinds of apps or podcasts in my life has really served me well.

That’s so good. I’ve spent a lot of time with various entrepreneurs, and I don’t hear many of them talk about staying grounded.

Yeah, last year was a huge lesson for me. I was running around doing all the things. I’m still doing all the things but in a different way. If something didn’t go my way it was so easy for me to break down and go into an emotional spiral, and when you go into an emotional spiral it takes a lot to get out of that. So, now I’m trying to practice a state of allowing, of learning how to pivot or flow with things. 

You can have a strong desire to push forward with something you want to do, but you have to  know there are going to be rejections. People are going to say no. Things are not going to happen on time or how you expect them to, but if you know how to move with the flow, with the changes, you’ll be ready. This is what California has taught me. I’ve become this California “It’s cool man.” I’m trying to balance this East Coast strive and hustle while being anchored by this California chill.

Iman, thanks so much for sharing your experiences and lessons with us. You’ve given us so many great takeaways. How can we keep up with The Run Down and the other great things your part of in San Diego?

You can follow me on Instagram @on.iman.opia and @therundown_sandiego. If you’re interested in utilizing The Run Down app and playing around with it (I would love to have feedback from local runners), visit therundown.run

I also lead run clubs on Monday at Milestone Pacific Beach at 6pm, Wednesday at Milestone North Park at 6pm, and Thursday at Eppig Brewing Waterfront Biergarten (in partnership with Lululemon) at 6pm,

Photography by Patrick Fore 
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