Insights from the Founder of Hopeless Visionary – Ryan Armour

“Hopeless Visionary”, just like “jumbo shrimp”, there’s almost humor in the word pairing, but Hopeless Visionary (HV) is no laughing matter. 


Started in the midst of the global pandemic and on the heels of other failed attempts at starting a business, Ryan Armour created the stylish clothing brand with a clear-cut mission in mind: “Aspire to Inspire”.


We sat down with him at his home/warehouse/Hopeless Visionary HQ to talk about his brand, why he started it, and what it means to run a business in college.

Aaron Wazana: Tell us what HV is and what it’s all about


Ryan Armour: Hopeless Visionary embodies the idea around dream chasing, passion seeking, and how to deal with facing adversity. 


People have their dreams and passions, but they don’t know how to pursue them or take the next step.


We’re trying to give people that positive message and motivation to push through.


AW: How’d you get started doing it?


RA: It’s funny, I’ve always wanted to do something like this. 


Since junior year of high school I’ve attempted three other [businesses] that all did not work. I never really stopped thinking about it, though. 


With the pandemic, a word I would use to describe it was ‘hopeless’. It was lonely and depressing, but there was a lot of downtime, which presented an opportunity. 


I was sitting in my room one day thinking to myself: “I have this vision and I don’t know what to do with it… oh! ‘vision’, I kind of like that” so I added it to a running list of words I like. 


Coincidentally, I had ‘hopeless’ just above ‘vision’ on the list and I thought I could do something with it. 


So, I extended ‘vision’ to ‘visionary’ and that’s where I got the name.

Hopeless Visionary, HopelessVisionary

AW: So it was kind of just luck of the draw?


RA: Totally. 


I knew I was capable of figuring out the business part of it, but the creative part was a little tougher. Photoshop and illustrator weren’t so simple. When I asked myself who would be able to help me, my friend Sabrina Bernstein came to my mind.


AW: Do you go to Wisconsin with her?


RA: Yeah, she does graphic design and she’s done design and marketing for other companies. I gave her a call:


“Hey Sabrina, what do you think of when you hear the name ‘hopeless visionary’?”


“I don’t know… clothing”


“What would you rate it out of 10?”


“I think i’d give it an 8”


“Alright perfect, here’s my idea”


I explained the concept to her and the next morning we were on the phone. For the next 6ish months, we we’re grinding on facetime cause she was in NY and I was here (in LA). 


I deal with all the business and finances while she handles the graphics and creative parts.


AW: Was it always gonna be fashion or did you have ideas for other business?


RA: I always knew I wanted to do fashion. I’ve always had an interest in streetwear and lifestyle brands. 


Seeing how people express themselves through clothing, you can see the different types of things that exist. 


It’s always been fashion just because of the expression that comes with it.


AW: Is Sabrina a partner in the business?


RA: Yeah, she’s a partner. I feel like we would both be more inclined working together in a partnership.


AW: Is it tough managing a friendship and business relationship?


RA: I thought it would be, but we separate our relationships. 


We could be frustrated with each other about something at work and then we could see each other later that night (not working) and it’s like it never happened.


AW: What were the other businesses that you tried to start early on?


RA: They were clothing as well. The most recent was called “Walk Off”, it was kind of the same ideology but i just couldn’t get it off the ground. 


It was junior year of high school and I didn’t really know how to approach starting a business. 


There was still some immaturity of a 16 year old in high school.


AW: Did you give Sabrina free range with the designs or did you give her some general direction?


RA: We both had ideas that we talked about.


The funny story about our TV Designs is that I was trying to express that premature ideas could evolve. And it struck me that TVs are perfect, they’ve gone from old metal boxes, to these flatscreens today.


I told Sabrina what I was thinking and she sketched it up, and that’s how we got the design for the TV hoodie. 


I kind of just throw up ideas and she makes them happen. She’s super creative like that. 

Hopeless Visionary, HopelessVisionary

AW: Are you trying to keep your designs simple, overall?


RA: I think the simplicity with a meaning behind it is what makes it special. 


AW: It is just you and Sabrina?


RA: Right now it’s just us two, but my sister is getting a little more involved with the marketing and advertising. She’s been running the social media a little more, giving some advice about the website, and stuff like that. 


She’s a senior in high school, so she wants to deal with that stuff before really jumping in.


AW: What’re you studying at Wisco and how much does it play into running HV?


RA: Retail and Consumer Behavior


It’s awesome. It gives me ideas on how to approach marketing. 


I learn about what people like and what works for them, so that definitely helps. Overall, it’s definitely had a positive impact on the company.

AW: Do you feel like you’ve learned more from your major that applies to your business or more from your business about your major?


RA: That’s a good question, I think they complement each other. When you see something first hand, you comprehend it so much better. But, things from class definitely come in handy with the company.


For example, learning the consumer strategies in class was way easier and more effective. But learning about timing, that was just from experimenting with the business first hand.


It’s funny, I applied to school undecided and had no idea what I wanted to do. But once I started the brand, the major just seemed really cool.

AW: So you chose your major after you started the business?


RA: Yeah.


AW: It sounds like you have a vision that’s consistent with this idea of “aspire to inspire” and a positive impact.


RA: Yes, when I started this I knew that I didn’t want it to be just about clothing. There are thousands of brands out there and the question for every brand is “what makes you different?”


We are different because we want to spread something positive. And were not the only brand that does that but we are of a smaller percentage that does have that goal in mind.


We have things like the vision board on our site. The board is a page full of interviews about people who have followed their dreams or passions in some sort of way. And those are the kinds of things we’re about. So it’s not just about clothing. 


AW: Overall, are you trying to build the brand into something bigger?


RA: Yeah, in the future we want to team up with organizations that are similar to us and do things like community service.


Moving forward, we are gonna add a podcast starting in January where me and Sabrina are just kind of talking about a different theme each week. So one week it could be inspiration, one week could be motivation, one week could be aspiration. 


We’ll have guests and do stuff like that to help people wear our clothing knowing that we stand for something.


AW: What were some of your inspirations behind the brand?


RA: Our biggest inspiration was Mad Happy. Those guys started in Beverly Hills with their message being about mental health and being aware of it. I think that’s something the world has to get more comfortable with. They figured out how to make it fun in some sort of way.


AW: A lot of this mental health stuff is what we’re focusing on, and as a college student, how do you take care of yourself with the stress of everything that you have to juggle?


RA: This may sound cliche, but you really have to balance your time.


As someone who’s personally struggled with anxiety and depression, I know that sometimes I need to just relax and put my work aside to be on my own. The work will always be there, but I remember that life goes on and we kind of have to figure it out as we go. 


I go for a drive, take a walk, and just take time by myself.


AW: Do you manage it differently at home and at school?


RA: It’s different, what’s nice about being at home is that I have my family to back me up when I’m having some struggles. At school it changes because I don’t like to show my sadness or stress in front of other people because I like being seen as the positive/happy guy. 


[At home], I feel like I can express a little bit more but at school I hold it in a little more. 

hopeless visionary tshirt

AW: I think a lot of people share that same sense of comfort at home…


Yeah, definitely.


AW: Do you spend more time socializing at school?


RA: Yeah, totally. Here, I make less of an effort to stay in touch with people.


AW: How do you juggle HV and school?


RA: I figured out a way to just deal with them at the same time. While I was at school, I made a schedule with my partner and we broke it down by school, work, and other.


It gets hard because your partner has a different schedule when you’re both students. But luckily, school was online and that let me stay in one place to manage everything I had to do. 


AW: Are you worried about it going off online and having to juggle all that?


RA: Yes, but I love what i’m doing so I’ll figure out how to deal with it because even though it’ll stack up and be a little more stressful, I love spreading positivity and making the designs.


AW: Do you feed off the positivity of your own brand?


RA: Yeah, it’s a cycle. You give positivity and you get it back. I can’t remember the exact saying but you get what I’m trying to say… I put out a message, and people see what i’m doing so it kind of comes back.

Kind of like if you’re around happy people, you get happy. But being around sad or negative people, you get negative or sad.


AW: Where do you see hopeless visionary going?


RA: If I looked 5 years in the future, I’d like Hopeless Visionary to be a brand that people recognize. But, I also want people to see us and think: “wow, that brand really wanted to get their positive message across and inspire people”.


I want people to know that you should do what makes you happy because that’s what gives you a good life. Yes, I’d love the brand to succeed and be recognized, but with that recognition I want a message to get across. 

Hopeless Visionary, HopelessVisionary

AW: Do you ever have second thoughts?


RA: No, i think i’ve learned so much and will take so much away from it regardless of what happens. So there’s not really second thoughts. 

To Check Out Hopeless Visionary, you can visit their site here.

Make sure to drop them a follow on IG: @hopelessvisionaryla


This interview has been edited from the original recording for length and clarity.

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