Ali Feller is one heck of an entrepreneur. She started her own podcast called the Ali on the Run Show five years ago after developing a passion for running. Since its creation, the show has taken off with more than 500 episodes and is one of the most listened-to podcasts in the running community. The popularity of the show is not only due to the great content – she has interviewed the best in the sport – but also because of who Ali is. Ali is a charismatic, hard working, and thoughtful person who focuses on making human connections with her guests. That’s one of the reasons the interviews resonate with so many listeners. Plus, she doesn’t just interview elite runners, but also everyday runners, who are normal people with fascinating stories to tell. Success is never a coincidence though, but rather than tell you Ali’s story, I’ll let her do it.
Ali! Thank you so much for coming to speak to The Stern Opportunity. It’s not often that we get to interview badass females like yourself.
It was an honor to be asked, and I’m so excited to talk with you today!
Let’s start with a little bit about where you’re from and where you went to undergrad.
I grew up in New Hampshire, which is where I live now. I was a dancer and my whole life revolved around dance: competitive dance, tap, jazz, ballet…I did a little bit of everything. I grew up reading a publication called Dance Spirit magazine. I loved writing. My goal was to become the editor-in-chief of Dance Spirit. I went to Quinnipiac University for college, where I majored in print journalism. I had a very specific goal in mind. I got an internship at Dance Spirit going into my senior year. I was commuting from Hamden, Connecticut to FiDi for about three hours each way. It was an unpaid internship, but I didn’t care because I loved it so much. It was the dream. I freelanced for them a little during my senior year. I think I got paid like $50 an article. I would have paid them. I was so excited.
As soon as I graduated, I emailed the magazine asking them to hire me. They responded that they would keep me in mind as things opened up. I was ruthless and persistent though. That September, I got an email from them saying, “we are creating a new position for a web editor. We think we should have a website,” which is aging me a little bit. I got hired as the web editor for the entire company. At the time, they also published American Cheerleader, which was huge. I managed the websites for all those magazines. Then, I transitioned into editorial and became the editor-in-chief of Dance Spirit.
Wow, so you were obviously very young – 21 or 22. Did you find it difficult being that age and managing people who were probably older than you?
By the time I was the editor-in-chief, I was 25, which is still very young. Sometimes I look back and think, “what were you doing giving me that job that young?” It is a small publication. I managed a team of six people, plus a rotation of interns. A few of them were older than me, but I was so excited. I loved it so much and I think that everyone could feel that.
I’ve always loved managing. I’m a natural leader, so I’m very comfortable in leadership positions. I care a lot about making people feel valued in the work that they do. There were certainly times where I had to give negative feedback. However, I think part of me was oblivious to a lot of the realities of corporate America. We were a group of mostly young women, who loved dance and loved living in New York City. We would spend all day writing and interviewing dancers and then every night we would all go to dinner and go to various Broadway shows or the ballet. It was the ultimate New York City experience that included free Broadway and ballet tickets…except that we were making very little money. I could barely afford to live. I was eating either pasta or dollar slices of pizza, which is actually how I found running. I was too poor to afford a gym, so I decided I guess I’ll learn how to run.
Okay, that’s incredible…except for the no money part. So, you started running for fitness reasons. How did that progress? Did running become the new focus of your career or was it a slow process?
Yeah, it was a slow process. Dance had been my life, but I knew once I graduated, I was ready to close the performance chapter of my life. Unless you’re looking at becoming a professional dancer, there is no career path. I wasn’t going to take dance classes for fun. But that also meant I went from being very active, dancing five hours a day, to nothing. I didn’t want to pay for a gym membership. At that time, I lived with four women in Harlem. My roommate had all these medals on her walls. I remember saying to her, “I love your necklaces. Are you like a wrestler?” She responded with “those are my half marathon medals,” and I was blown away.
(Laughs) That is the best thing I’ve heard all week! I completely forgot that it was not common a decade ago to see running medals everywhere. Whereas now, it feels like everyone and their mother has run a marathon.
I hated running at the time! I was the stereotypical anti-sports fifth grade girl who wouldn’t run the mile in gym class. But suddenly, it appealed to me because you could just put on sneakers, which I didn’t have. I ran in jazz sneakers. I wouldn’t recommend it.
This is getting better and better! I can’t believe you, the person who is associated with all things running, started out running in dance shoes!
I know, crazy. That roommate eventually took me to JackRabbit to get fitted for proper shoes, but the idea that I could just walk out of our apartment, go for a run, and come back was appealing to me.
Starting out running is incredibly difficult. Even though I now fancy myself a long distance runner, I will never forget how hard it was to get started. What was that process like for you?
I went on my first run and it was like four seconds. My next one was six seconds. I measured my runs by lampposts. I knew nothing about all of the technology that goes into it. Then, one day, my roommate took me out and showed me where to run in Central Park.
I am having flashes of the Friends’ episode, where Rachel brings Phoebe to run in Central Park…
Seeing Central Park, at night, after work… I mean, it changed my world. It changed everything. After we finished the run, we sat on the steps at the Met – this was during the Gossip Girl era – and we thought we were the coolest girls in the city. We were just sitting there in our sweaty cotton T-shirts, looking out at 5th Avenue, being like what is the difference between Serena, Blair and us; we are one in the same.
Those were probably the endorphins speaking.
A little bit, yeah. Maybe a little out of touch with reality, but it taught me how to explore New York and gave me a whole new way to learn my way around by foot. I signed up for a four mile race in Central Park, which was my first race. From there, I decided I could do a half marathon. I think I got drunk that night and signed up for a half marathon.
As drunk decisions go, that ain’t a bad one.
Absolutely! It progressed to more races and running became a bigger part of my life – to the point where I started a running blog. I talked all about my runs. It was called “Ali on the Run.”
I recognize that name!
The name has been around for a long time. This is October 2010. I would go for my run in the morning and then on the subway – I worked all the way downtown – I would write a blog post on the notes app on my phone. I would get off the subway, email it to myself, upload it really quickly from my work computer, and then go about my day at Dance Spirit. All the while, I’m thinking about running. I’m starting to obsess about running and really getting into it. Then, I got some opportunities to write freelance pieces for Self and Shape. Running magazines started reaching out because they found my blog, which had grown a community. I realized I loved writing about running. I loved writing about my experience as a new runner. I documented my journey to my first marathon and I connected with so many people. Running blogs were very big at the time.
How long after you started running did you start your blog?
I started running in 2008 and I started the blog in 2010.
How did you promote yourself in that era where social media existed but was not utilized on such a public platform as it is today?
Twitter was very big at the time and the Twitter running community was awesome. There were so many young women like me who were running in Central Park in the morning and wanted to meet other runners. I would tweet, “Going for a run in the park this morning, let me know if anyone’s out there who wants to join,” which I would never do now. But, at the time, that was how you would meet people. I promoted myself on Twitter and would comment on other people’s blogs with a hyperlink to my blog. It was guerilla marketing by shamelessly linking my work while commenting on someone else’s.
That’s absolutely a business strategy for brand awareness.
Which now I’m good at, but then it wasn’t a business for me. I wasn’t making money off my blog. It was just a fun thing that I did. It was very much a creative outlet for me. I could see that my passions were shifting and I realized I might want this to be a bigger part of my life. I thought if I could turn dance into a career, maybe I can do the same with running.
At what point did you decide that you wanted to take the plunge, leave Dance Spirit and try to make this into a career?
It was hard. I was 26 at the time and I spent my whole life working toward this dream job. Then I got it, and I thought “what’s next?” I’ve always been a “what’s next” person, for better or worse. I also was dealing with a lot of health complications at the time. I have Crohn’s disease. My health had been really bad for about a year at that point. I’d had to go on medical leave. I was so sick I couldn’t leave my apartment. I was in a really bad emotional place from that. It kind of felt like my world was falling in. I finally got this dream job, but I’m in the hospital. I’m sick and I can’t do the things I want to do and I can’t manage my team.
For my health, I knew I had to make a big life change. Even though this is my dream job and I love the work and my team, I have to make a change if I’m going to get healthy. I left my job for something less demanding, which sounds silly because I was running a dance magazine, not saving lives, but it meant everything to me. I left that job and, within a month, I was healthy again. Go figure.
It’s bewildering how much stress can impact our health. Where did you work after your health improved?
I did a short stint at JackRabbit sports, which was kind of fun, because that is the store where I bought my first pair of running shoes and where I met my husband. JackRabbit did this campaign, where they trained runners to run a marathon and that’s how I ran my first marathon. I have a long history with JackRabbit but I went there as a transition job to pay the bills for a bit. I was working on their marketing team, despite having no marketing experience. It involved social media management and working on events. It was a fun job at a running store. I think it was the palate cleanser that I needed. I did that for about eight months. By that point, the blog was doing really well. I had formed a really great community of readers and followers.
I was running a lot. I had done a handful of marathons at the time, and I was getting a lot of freelance opportunities; both ones that I was pursuing and ones that were coming to me. I was on vacation in December of 2014. My husband and I got engaged on that vacation. Everything was blissful and dreamy and I decided that I was going to quit my job and go full-time freelance. I came home and put my notice in, which didn’t go great.
It’s hard to have those conversations, but you knew it was right for you and you didn’t forget what your goals were. How many articles were you typically writing in a week or a month?
So many. It felt like a content farm, where I was just churning stuff out. Some weeks, I would write about 30 to 40 pieces.
I’m going to start calling The Oppy a content farm. You must have been making a lot of contacts during this that would be very useful in the next steps of your career growth.
I was very fortunate to work with a lot of great editors and then sometimes I was actually freelancing in an editing role and I was working with writers.
Would you say that writing that much was not sustainable? 30 articles a week is no joke.
Correct. I became burnt out. I started freelancing in 2015 and I was also planning a wedding at the time, which took up plenty of my time. By 2016, my husband and I moved to New Jersey. After we got married, we got a dog and we wanted to give her a better life. We decided to cross the river to New Jersey, where she could go to the bathroom on grass.
The things we do for our dogs.
In so many ways, it was such a good change for us. But it meant that I didn’t have Central Park, which meant that I didn’t have my running buddies. I was like, okay, I guess, I run alone now, and that was a hard shift for me. So, I started listening to podcasts for motivation, which made me realize that I wanted to launch a running podcast as a side project.
Like the blog, it was never meant to be a source of income. It was never meant to be a career path. It was for fun.
What was your original intent for the podcast? Was it going to be a spoken version of your running blog or did you have different ideas?
A lot of people think the podcast grew out of the blog because they have the same name but that’s because I’m not creative. I couldn’t come up with a better name.
No need to reinvent the wheel. A great name is a great name.
It got to the point where I had recorded these conversations. I had everything ready to go but I could not think of a name for this thing. I hated having my name in it because the whole idea of this was I was sharing other people’s stories. My blog was about me, The podcast wasn’t about me and was never going to be.
Sometimes what makes a brand is the person behind it, and in this instance, you’re the entrepreneur with this massive following from a blog. The common name is a great way to create a bridge for your followers from the blog to the podcast.
I didn’t see it at the time. I wasn’t strategic. I wasn’t thinking of it as a business venture. I wasn’t thinking with a marketing mindset. I was just trying to get the thing launched. I started by interviewing people I know in running, who I thought had interesting stories. One of my friends runs ultra marathons and also has a blog with a massive following, so I knew to launch with her because I could tap into that community. The second episode, I interviewed my husband on what it was like being married to someone with Crohn’s Disease. He had two beers and I had some wine, and we recorded an episode. It was weird that it was the second episode on a running podcast because it is not about running. But people who had followed me for a long time loved it. They were like, “Oh, we get to hear from her husband and get an inside look at her relationship.” I still get messages about that episode all the time.
I know you didn’t have a formal strategy here but that was definitely strategic. You unwittingly knew what you were doing by launching with a friend who has a massive following and then giving insight to your relationship with your husband. Most of us love human interest stories and when people are frank, which is what I always appreciate about you and your podcast. They’re real conversations, not superficial. You talk about people’s biggest trials and have been so forthcoming about difficult areas in your own life.
Not everyone felt that way. I dated this guy back when I first started running and blogging. He was embarrassed by my blog. He and his family would joke about it, so I wouldn’t talk about it, even though I loved it so much. We would go out with his friends, whom I loved. I remember coming back one night, and he said, “it’s kind of embarrassing going out with you. You like to interrogate people. You don’t know how to have small talk. You’re always asking about their hopes and dreams and childhoods. It’s weird.”
That guy can go to you-know-where.
That really bothered me for a while. I worried that I didn’t know how to go out and be social, but now I see it as a strength of mine. I don’t want to talk about the weather. I want to get to know you as a human. I always say, “I don’t do small talk. I do big talk.” It’s helped me throughout my entire career.
That genuineness and level of empathy leads to connections that you don’t attain otherwise, but I think it can be scary for people who aren’t able to do that easily.
My interest in others is a skill that is always evolving. It’s a mix of what I learned in journalism school, what I learned in my various jobs, and just me being human and having conversations.
I do a lot of prep and research for the episodes of my podcast. But what I am really curious about is why I’m interested in this person: Why am I talking to them? What do I want to know? There is no agenda. These conversations can go in any direction. I’m not trying to be sneaky. I’m not trying to break hard news, I want people on the show to know that they are in a safe and comfortable place.
Well, we, at The Oppy, are always breaking news. Kidding. The only thing we regularly break is WordPress, the antiquated publishing platform we use. Your goal is to make genuine connections with your guests.
Yes, but I am not trying to be best friends with the guests.
Except in my instance, because we are actually best friends now. Right?
Of course! But in general, I want everyone who is on the show to know that they can and should be comfortable talking to me. I always tell them before we record that this isn’t live. If anything comes up that you’re uncomfortable talking about, let me know and we won’t go there.
Going back to the timeline; you had your first four episodes. You’re starting to develop a larger following. What was next?
I was putting out one episode a week. I think I was about 40 episodes in when I had my first professional runner on the show. I realized after one pro said yes that I could get more professional runners. I didn’t care that much about professional running at the time, but the more I talked to the pros, the more I started to follow the sport.
It never became just elite runners. I always wanted to have a mix of inspiration, aspiration, and relatability. I get that question all the time, “how do you decide who to have on the show?” It’s people that I’m interested in. That is the criteria. It’s like when I saw you on Humans of New York and thought, wow, she’s a runner. I’m going to find her and hear her story.
I think you have an ability to know what the average listener wants to hear. It was only really after you interviewed me that I realized how many people are obsessed with you. You are running royalty, the original runfluencer.
It really goes to show the importance of the running community right now. Running is different. Unlike other sports, we get to run the same courses as the professionals. The pros are oddly accessible. If you run in New York City, you see tons of professional runners out on the bridle path and that’s really cool. But we also need to see ourselves in this sport, so I think people like hearing people on the podcast that they can relate to.
You’ve remained so grounded despite how big you are in the running community. That’s one of the reasons you’re very relatable.
Thank you. The community is everything to me. I do a lot of live shows and events. Every single time I think no one’s going to show up. I’m going to be talking to an empty room and that’s never happened. I’m beyond grateful for that.
Which brings to mind another topic that I could talk endlessly on; imposter syndrome.
Oh yeah. Everyone’s suffering.
Especially women. Let’s talk about the moment you transition this from a hobby, a side gig into a career path.
There wasn’t a moment per se. I was podcasting for about a year before I took on my first sponsor. Before that, I was losing money on making podcasts.There was the cost of my time because I worked for myself as a freelance writer and there was the cost of the hosting platform, cost of the equipment, costs of a zoom membership, etc.
Strava was the first brand that ever reached out and said they wanted to sponsor some episodes.
Wow! Strava doesn’t just sponsor anyone.
Then my next sponsor was Shokz. They have been sponsoring the podcast now for four years straight, every single week. I was able to build from there. I had more brands reaching out.
So there wasn’t a moment. It was a gradual shift, where more of my time was being spent on the podcast, which meant less of my time could be spent writing. The financial offset was huge. I could make more money on podcasting than I could writing. I would have to write two articles, which took a lot of time or I could make that same amount of money on one podcast episode which again takes time, but not as much.
Last year was the first year that I did not write a single freelance article. I get plenty of offers but it’s not what I want to do right now.
That’s incredible. Did you feel like at any point you had to search for sponsors, or because the pod was doing so well, they just came to you?
This sounds terrible, but I’ve never been the one to reach out to a sponsor. They’ve always come to me. I know how lucky I am to be in that position.
That’s a testament of who you are as a person. Did you feel like you ever had to actively build your market share of listeners or did that happen on its own?
Again, it’s not something that I have consciously put effort into. It’s been a gradual build. I am also lucky that I got in early. Right now it’s going to be hard to start and launch a huge podcast if you don’t already have a built-in audience.
I started in 2017, when there weren’t many running podcasts, and I had people who came with me because they had read the blog or followed me. I had a leg up.
What would you say are the most difficult elements of running the podcast and being an entrepreneur?
There’s so much to do and it’s so hard to relinquish control. I am struggling to keep up right now. I have a lot going on, and it’s all great stuff. But I can’t do it all. My inbox is a scary place. I’m trying really hard to do it all and be a good mom and be a good partner. The hardest thing is trying to make sure not too many people are waiting on things from me.
My inbox gives me anxiety if I don’t stay on top of it, and I have nowhere near as much going on as you. All of this is hard because you are someone who’s incredibly organized, probably Type-A. Can I say that?
A little bit.
You want things done and done well. At the rate your show is growing, it sounds like you need some interns and an entire team going forward.
Are you available?
I was going to say, should we get you a business school student? Hey Sternies, if you want to work on Ali’s pod, reach out. (Laughs)
It’s hard to decide what to offload to others and that’s something I’ve struggled with. The editing process takes the same amount of time as recording an episode. These are huge chunks of time. Every episode takes me about two hours to edit and when you’re putting out four episodes a week, that’s a lot of time. But I also want to know the final product is as perfect as it can be.
I’ve so many more questions. I wish we were at a bar, drinking the evening away, and I could ask them all. But I’m going to have to prioritize. I wanted to ask how you got into race announcing. For the readers, Ali announces runners at the finish lines of major races like the New York City and Boston Marathons. That is a big deal.
This is a fun story. A couple of years ago I said on a show, “You know what I think a cool job would be? To stand at the finish line and cheer for runners as they accomplished something amazing. Wait, that’s kind of what race announcers do.” I had never paid any attention to race announcers before. Now, as a race announcer, I can definitely say, most people do not pay attention to us.
As we’re telling you it’s time to get into your corrals at the start…no one’s listening.
Everyone’s nervous or stressed, looking for the nearest porta potty.
Yeah, they’re definitely like stop talking and let us start. Anyway, I kind of put it out into the universe. Then one of the Vice Presidents of New York Road Runners, who organizes most of the races in NYC connected me with the right people. I was like, “Do I go back to school for this or take a course?” They just laughed at me. And before I knew it, I had an email from NYRR telling me the first race I would be announcing. I realized no one teaches you how to do this. I showed up and they were like, “There’s your stage, there’s your microphone, and here’s your script. Feel free to read the script or not.” I was drunk with power.
I started announcing at the New York City Marathon in 2019. This past year was the first time two women were on the microphone announcing the professional winners. We’re pretty sure we made history, which is cool. Then, we announce the final finishers which is from 6pm until the final finisher crosses the line. We’re out there, throwing a party in the dark with glow sticks and a DJ, having as much fun as possible, because we want every runner to feel celebrated. Yes, the pros are the ones taking home the really big paychecks that day, but everyone is going from Staten Island to Central Park. We want to celebrate every runner who made that journey because it’s a really far one and it’s amazing, no matter how long it takes.
One last question for people who are thinking about starting their own business post-MBA. After taking the risk, are there any words of wisdom you would like to impart?
Stay true to your core values. I know that sometimes doing something great or even okay takes a long time. There are a lot of people who are going to take shortcuts and take the easy way to get ahead. In the long run, there’s a lot more pride to be found in doing the long, slow grind, just like marathon training. Everyone’s going to want to give you advice, but you get to decide what to do with it. Part of the beauty of being an entrepreneur is getting to be the one to call the shots, and there’s no shortage of resources. So, stay true to who you are. That’s going to be the way that you’re going to get ahead.
An incredible end to an insightful interview with the one and only Ali Feller.
Ali, thank you for taking the time to talk to me. After hearing countless episodes of you sharing other runners’ stories, it was so fun to hear part of your story today. You are an inspiration.