Entrepreneurship and the Spiritual Path: Interview with FITTED Underground Founder, Eric Steffen
This week’s interview is with Eric Steffen, the founder of FITTED Underground, a brand known for its custom made denim jeans. In 2014, Eric left his investment banking job to go all in on the side passion that was demanding his full attention. He had no prior experience in the apparel industry and would spend the next 10 years honing his craft and growing the business solo before hiring his first employee in 2024. Earlier this year, a video featuring his story went viral and generated an onslaught of brand awareness and sales. Notably, one of his denim jackets was recently worn by Amar’e Stoudemire at a New York Knicks playoff game!
I felt compelled to reach out to Eric, not because of the recent success, but because of the courage he had to explore different paths prior to starting FITTED. Out of college, he worked as a teacher and finance professional before leaving to join the Peace Corps, eventually returning to attend grad school and transition to a job in investment banking. After several years in banking, he could no longer ignore his growing passion for custom clothing and denim and made the decision to go full time on his business.
For most of us, making one career transition can be fraught with terror and fears, yet Eric had the courage to do so multiple times. I wanted to know: what helped him embrace change so readily? He told me it was a willingness to continually listen to his inner guide and surrender to the direction that voice was urging him toward. What ensued was a conversation about spirituality that ultimately surprised me and resonated deeply. We talked about the ways in which Eric’s belief in something greater than himself has helped him overcome fear and self doubt, deal with uncertainty, embrace the all consuming nature of running a business and being a father, and iterate through 10 years of learning and building to create the foundation for his business today.
Eric told me that if he were to ever write a book it would be called Entrepreneurship and the Spiritual Path. When it came time to think about the title for this interview, I could not think of a more fitting phrase.
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
How would you describe what you do for work?
That's a good question. I guess I make jeans these days. I made jeans by myself for a decade from 2014 until 2024, and then last year I hired my first person. Earlier this year, I hired a second person. So now we make jeans. We also make shirts and jackets, but the core of our product offering right now is denim jeans.
We'll definitely talk more about jeans, but I want to go back and talk about your background. You have a very interesting career trajectory having made some big transitions multiple times. For most people, making one major transition is a huge leap, and it’s easy to give into the sunk cost fallacy and be held back by fears of starting over or fears of what others might think. What made you feel comfortable starting over and making those transitions at multiple points?
I always tell my workers I'm a little crazy. I don't know, I guess part of it is just an openness to being willing to follow a certain inner guidance. When I graduated from college, I didn't know what I was going to do, so I kind of fell into teaching math and physics. I was good at it, enjoyed teaching it, and then I had a decision to make about whether I'd be staying in that career or transitioning out of it. There's always been something in me that I feel like is pushing me in a certain direction, and as much as possible, I try to surrender myself to that inner guide. For better or for worse, I've become pretty good at doing that.
I want to double-click on that because I think a lot of people hear that inner voice and then try to mash it down or ignore it. What’s helped you become comfortable at listening and surrendering to that voice?
If I ever wrote a book, it'd be called Entrepreneurship and the Spiritual Path. I don't want to get too heavy, but as I do more of these interviews and tell my story, it's hard to get away from the spiritual component of what I've done and gone through. When I was 19, I went through a depression and, at some point, I recognized that the solution needed to be on the same level as the problem. Certain things like therapy, meditation, and yoga just didn't touch me where the suffering was. So I started going on this spiritual journey and that led me to developing a certain faith. It's atypical, I’m not talking about a typical form of Christianity, but I do have a very clear and definitive spirituality. As much as possible, I just try to come back to that, surrender, get myself out of the way, and listen to that voice. I started that process when I was 19, and I'm 47 now, so I've had some practice with it.
When your life is really challenging and you're down in the dumps, it's a great opportunity to make a change. Some changes are external, some are internal. This happened to be a very deep internal shift that I went through, and I've always been true to that process ever since. I think it cuts against a lot of the self-help narrative about overcoming your fear, but for me it's always been much more about a process of inner surrender. You have to do that before the external action, and then it looks like you're being brave and courageous, but you're actually just following guidance.
How would you describe that faith or philosophy?
Broadly it's a belief in something greater than myself, and the core of it is basically love. Just trusting that there's an inner kindness that wants me to be happy and successful. I think the real challenge isn't so much external success, it's internal peace no matter what happens. Even if the business blows up and there are lots of challenges in my life, there is a way to be peaceful internally, even if the external is going haywire. That's a framework within which I can make decisions.
There are people in my life who are getting older, and they look back and realize that what was important wasn't necessarily what they did, but how they did it and the lessons learned during that process. I'm trying to take that to heart. My mom was a career counselor and one of the things that she was really helpful with, and I saw with all her clients, was giving people the courage to listen to that inner voice. I grew up with somebody who was constantly counseling others to do that, and I think that made it a lot easier for me to choose the less-traveled path.
I would love to hear more about how you use that inner voice on really tough days or moments where there is a lot of fear and doubt. What's that process like for you?
It's relatively simple. I did this by myself for 10 years, and it's an incredibly slow build. Since that video went viral at the end of December, which has been massive for my marketing awareness, my revenues have grown substantially and things are moving in the right direction. That said, it was really hard spending 10 years putting a platform of business in place.
We do something different—we make custom jeans. The customization aspect of my business is actually quite challenging. I have to make clothes that fit both a 6'11" client like Amar'e Stoudemire and a 4'10" client. The customization component and making it affordable has taken a long time to learn, especially when I was the artisan doing it all.
There were a lot of challenging moments over 10 years and times where people close to me were saying, "What are you doing with your life? You used to be in a job making a lot of money. Now you're doing this great, wonderful, creative thing, but you're not making that much money. You have a family to take care of." What I would do in those moments is take a step back from the business, take a step back from my family, take a couple of deep breaths, and ask for guidance. I'd get in touch with my fear, get in touch with the anxiety, and share that—almost give that over to my higher power. Then I would let go of it, let go of looking for the way forward, and I would join with God or love, and trust that the response would come.
The voice never said, "Hey, do this with the jeans and hire this person. Here's your marketing plan." It's never that specific. It's always much more directional. If I could turn that directional feeling into words, it would be "just keep going." There was something in me that was pushing me forward.
10 years is a long time. How has your relationship with uncertainty changed the longer you’ve been doing this?
In some ways, you just fall into it. Doing your own business is very much a trust exercise; you're just falling backwards and trusting that something good is going to come from it. I once heard somebody share an analogy that starting a business is like catching a flight. You do everything you possibly can to get to the airport on time. Sometimes things come up, life happens, and you get to the airport late, but then the flight is late and you make it anyway. Their point was that either you're gonna make the flight or you're not, and whether you do or don't, you're still going to be you. It's okay. Nobody's gonna take away your birthday.
Managing uncertainty comes down to making peace with the fact that there are things in life you can control and things you can't. You can be peaceful no matter what. In a sense, that's actually the lesson, it's not just building a successful business, which I obviously want to do, but the deeper lesson is that I can be peaceful no matter what. That means accepting uncertainty as part of that lesson. Easy to say, challenging to do.
I don’t think those fears and doubts ever fully go away but you can become better at learning to recognize them and not get so sucked in. There’s a quote I’m thinking of which has been attributed to Viktor Frankl, "Between stimulus and response, there is space." The practice is learning to take that space in between.
I love that Viktor Frankl quote. Going into entrepreneurship is really challenging because it's such a pressure cooker. Number one, trying to get the thing off the ground, and number two, once it starts to get off the ground, more responsibility comes in because usually more people start working for you. All of a sudden, their livelihoods are dependent upon your decisions. Then there's the personal aspect around what's going on at home and how people are feeling about what you're doing. In my case, I have two little kids who are the absolute light of my world to take care of. I’ve learned to stay in the eye of the storm and find my peace within that. One thing that's really helpful is if you connect with the work on some level. When I come in and I'm actually doing the thing, I lose myself in it and get in that flow state. That's a special place to be because it becomes nourishing as you're doing it.
I wanted to ask about doing this solo for the first 10 years. One challenging aspect of being a one-man band is that it can feel like the only way to grow the business is just to work more, and I've seen that lead to pretty serious burnout. Have you experienced that? Are there any shifts that have helped you manage burnout and work more sustainably?
Not really (laughs). I'm supposed to say yes, but I mean, I have always done this very beautiful dance with burnout where we just kind of flirt with each other. I've run marathons, done long, hard things, and learned that a business is very much like that. You just have to know your limits and pull back from time to time. You want to get to the end of the race, not have a great mile 17.
What's been really good for me is my wife saying, "At some point, you're not working weekends. We're going on vacation, and that's just the way it is." It's frustrating at times because I want to do more, grow faster, and have more money coming in, but there is a balance. Having my wife and family has definitely helped me achieve that.
I think it's really important to work hard at first, though. There's a lot of sentiment about four-hour work weeks and passive income, and that's all wonderful if you can manage it. But when you take on something novel and different that’s outside your skillset, there's just a learning curve you have to go through. I think it actually builds great character to go through it. I'm a fan of hard work and not shying away from that.
I think my approach also plays into this one. There are two approaches to building a business: you can be a gardener or an architect. For me, I'm more of a gardener where I'm throwing things in the ground and all of a sudden they start sprouting up. I want to help develop and grow whatever’s coming out of the ground. In the life cycle of a plant, there are times where it just needs to push off the old bark, grow a new skin, and have a new identity begin to emerge. You have to be in tune with yourself and the business to determine when that process is actually happening, as opposed to when you're forcing it to happen. I always thought I was a decent manager and wanted to hire people and grow the business, but for 10 years I didn't feel like the business could sustain that. I've done it organically without outside investment. I felt like I needed to answer a lot of the questions before bringing in people and saying, "How are we actually going to grow this thing?" I do think you have to move through a certain amount of uncertainty to find some certainty and grow from there.
A common fear I see in businesses where demand can be somewhat unpredictable or where there is a decent amount of seasonality is having to manage the fear of “Will I ever have sales again?” Does that resonate with you? If so, what has helped you through those moments?
Yeah, for sure. Where's my next client going to come from, right? It's such a hard thing. At some point you do want to build and structure your business so that you're taking ownership of your marketing and client acquisition strategy, but when you're small and starting out, it's very unformed.
When my mom needed a new client, she'd say a prayer, "Okay, I'm ready for more clients,” and then she'd just let it go. I didn't necessarily do that, but I did just trust that the right people would come at the right time.
On one level, it’s about having some trust, getting yourself out of the way, and allowing those people to come in. I also think there’s an aspect of working to get better and better everyday because the better your business is, the easier it is to sell it. I think of building a business a little bit like drying gunpowder. It's not necessarily your responsibility to make it go pop, but you're given these raw materials, and it's your job to start parsing out the wheat from the chaff. What you're left with is a meaningful, valuable business. The more and more you do that, the higher quality product or service that you're providing, and the easier it should be for somebody to come along and say, "Oh, wow! This is something special. I want to tell my friend about it."
Another way to say the same thing is that when I started the business bespoke jeans were a novelty. The challenge is to make something that is novel without being a novelty; something that is different and differentiated without being beyond the pale. Initially, it's fine to be a novelty, and there will be a core of something in there that people want, but your challenge as an entrepreneur is to integrate that with what the market actually wants, and find it in terms of both the product itself, the pricing of it, and the marketing of it. That's when the business really starts to sing. But at first, you have to pour your creativity into it and see the direction that you're going in terms of clients actually showing up. Again, that's getting back to just making your peace with uncertainty.
Maybe there's more specific things that somebody could recommend. I've tried Facebook ads but none of that ever resonated with me. The only thing that really resonated with me was having great reviews. When people would go looking for me, they'd come across my Google reviews and they'd say, "Okay, maybe this guy's worth a shot." That's it.
That goes back to forcing it versus doing things that feel in tune with your philosophy and alignment. That resonates with me.
Going back to your question about burnout, it’s so important to be true to yourself. Shakespeare said, "To thine own self be true, and it must follow, as the night the day, that thou canst not then be false to any other man." You have to be true to that process. Somebody else said, "Do a business such that at the end of it, even if it fails, you're proud of it." Do what feels right to you, and it probably is going to resonate with other people.
The difference between an artist versus an entrepreneur is that the artist gets to do what they want, and whether the market understands it or not, isn’t for them to decide. It's their art, and they’re putting their creativity into it. There's a component of that in entrepreneurship, but you also have to listen to the market and say, "What's the meeting place between my own inspiration and what people want?"
Feel free to fact-check me on this, but if I'm remembering correctly you put the business on pause during COVID. What was that time like for you? Are there any reflections or learnings with the benefit of hindsight that have really stood out to you from that time?
Yes, when you asked about the fear around, "Will I ever have another sale again?" that's the first thing I thought of.
What I would say is that I think it's okay to put your family first. It was a crazy state of the world, and it’s what needed to be done. We needed childcare for our children. Still it was a very scary thing to pause the business I’d worked on for the prior 6 or 7 years at that point. At the end of the day, you do have to keep perspective. It is just a business, right? The business is never gonna wake up in the morning and say, "I love you." Sometimes you have to do what feels right and do what you have to do.
I didn't know if clients were going to come back after 8 months of basically turning the faucet off. During a global health crisis and an economic crisis, would people come back and want to spend money on custom jeans? I didn't think so, but my clients connected with me and the business and a lot of them did. Then it just started ramping up again. In fact, if I go back and look at my revenue projections over time, it's almost like covid happens, but then that ramp is just on the same path whether it was there or not.
We have to talk about your kids because fatherhood is a big part of your journey. How did becoming a parent change how you felt about entrepreneurship, or how you were approaching the business?
The first thing is that it just changed me as a person. It was a big change from doing what I wanted to do when I wanted to do it. First of all, you have so many responsibilities with entrepreneurship, and now you have so many responsibilities with being a parent. If I could name this period of my life, it's just "responsibility” and surrendering to that.
Being okay with the idea that this is what's up next and saying, "Okay, I can take this on." It's definitely a humbling process because you're no longer the center of the universe. The kids are. So in some ways it makes you a better person, right? It gets you away from yourself and gets you outside of yourself. You realize that those little people are really looking to you not just to put food on the table, but also for love and connection and time. So one of the things that I really try to do is take a step back and be present with my kids. Spending quality time with them where you let them dictate the conversation and determine what they want to do. If my daughter wants to have a tea party, then let's sit down and have a tea party.
For any new parents out there, my parental revelation is that kids need two things: love and structure. The love thing is obvious, but the structure isn't necessarily. Getting kids to a place where, within a loving context, you teach your kids to become comfortable with you saying no, even if it entails a massive meltdown, which it will. You can't always be the cool parent, and that's okay. Love and structure.
I think the work self can become so all-consuming that even when you're not at work, it's present in your thoughts. Are there any revelations or things that have helped you be present when you are with your family?
I think the first thing is actually what you just said—the work self can become overwhelming. It's not to resist that. You go with that and become aware that the work self is overwhelming. It’s enough to recognize that this is a season that you're going to have to move through.
You can become aware of it, and then you can also recognize, "I have other responsibilities.” That way when you do need to be obsessive and respond to clients and really go down the rabbit hole, you can do it, and you’re able to recognize the moments when you need to compartmentalize and step away.
The other thing that helps is, as revenues become stronger and more money comes in, you recognize there's a little bit more tolerance and the business can bear some stronger winds. That does take the pressure off a little bit. But it can be a really long, challenging cycle. So my advice is not to resist it, lean into it, and be aware that you're leaning into it. You want to shed that as quickly as possible. I almost think it's a disservice to other entrepreneurs to say "don't do that" or "resist it" because it’s an incredibly strong force. Having your own business is like having another child. You're raising this other thing, and you're pouring yourself into it. So pour away, but be aware of what you're doing.
Many people I interview for the No Directions blog have created lives that are uniquely theirs in terms of how they live, work, and build their lives. How are you intentionally building your life?
In a certain way, I'm not intentionally building. I'm almost intentionally deconstructing my life. I'd much rather get myself out of the way and let that inspiration guide me and animate me and my actions.
It's funny because I think at first you go through this process, and you think you become the window for something to pass through. Eventually you realize, "Oh, I'm not the window. I'm the thing that's coming through." So for me, it's really about getting myself out of the way, letting a deeper guidance guide me, and surrendering to that.
There's a Zen saying, "Chop wood, carry water," and I feel like that's the perfect analogy for having a business and integrating with spirituality. There's always going to be stuff that comes up that's going to throw you off course, and it's going to be frustrating. For example, I'm looking beyond the computer, and there are five rolls of fabric that cost me about $5,000, and I got hit with Trump's tariffs which added a $500 bill that I wasn't expecting. I, of course, got mad but then I realized, “This is the opportunity, right?”
It sounds like things are changing. You’ve now added a second person and new product lines. What's next for you?
Your initial question was "What do you do?" and I said, "I make jeans," which was then refined to "We make custom jeans." Hopefully, when we talk in a year, I'll say, "Well, we make custom jeans, shirts, and jackets." Right now it’s all about building capacity.
My direct to consumer business is quite strong, and there's a lot of interest in the bespoke jeans that I make. My hope is that over time I'll be able to diversify the product offering, and then also have both our base collection and seasonal collection so we can get into wholesale as well.
It's just managing that growth. I spent 10 years cultivating the business by myself and not knowing what was going to happen. I think I made the gunpowder relatively dry, and then that YouTube video showed up, and that threw a match on everything. Now it's my job to continue shepherding that growth along.
We just talked about all the things that can go wrong. I think my business is what I just told you, right? It's diversification, it's growth, marketing, sales, etc. But it's really none of those things. It's actually dealing with all those little stresses and the lessons that come from that. The business and its growth sets the context for it. Every time something goes wrong, those are my opportunities to forgive, let go, and surrender because you don't want to get to the end and be a Rupert Murdoch type who has tons of wealth but his kids don’t like him. Everyone wants their business to work out, but you also want to be able to step away and say, "I'm a better person, I have strong connections, and my heart is filled with gratitude and love." If the business fails, but your heart is filled with gratitude and love, then who cares about the business?
That feels like a good place to end it—on gratitude and love.