Justin has felt the urge to create—whether it was creating websites and apps, or, more recently, building start-ups—since he was in middle school; a tendency that he partly attributes to his entrepreneurial father.
His sense of adventure has seen him move from Oklahoma to San Francisco to New York—and even on a 3-month RV trip travelling around the US to promote his latest (and recently acquired) start-up, Avenify.
Justin’s burgeoning interest in architecture has also seen him undertake some new adventures—including starting a newsletter, beginning to design his dream house and falling in love with Palm Springs.
In our chat, we discuss the overlap between product, design and architecture, finding relaxation in sailing, and letting hobbies be hobbies.
To start off, I would love to learn more about your interest in architecture. How did it come about?
Yeah, definitely. My interest in architecture is a fairly new one. It was only over the past year and a half that I got interested in it—but I've always been a student of design.
I've always been really interested in bits-and-atoms digital experiences in the real world.
I think there's something really energising about seeing things come to life, and architecture was the perfect blend of both of those, where I got to learn more about design and lean into that creative edge.
It sounds like architecture is a recent interest for you. How did design or creativity come into your life before then?
It really kicked off for me when I was in middle school. I grew up in a fairly entrepreneurial family—my dad was running his own software business and, through that I picked up coding. I would work with him on side projects and weekend projects starting from when I was in middle school. At that time, learning things like databases or APIs was out of reach for me, so I leaned into the other part, which was designing what the website would look like or learning how to use various CSS frameworks.
Now, I've doubled down on that as what I like doing and where I like to fall into projects—mostly on the digital side of things and the product design side of things.
With this interest in architecture, I started trying to sketch buildings and figured, if I can look at a website and figure out where the lines go on the website, maybe I can do that on a physical piece of paper. So I just found buildings that were inspiring or interesting to me and started sketching those.
When you start sketching, you start noticing things that you hadn't noticed before. That led me to learning more about why those columns were there or how people did interesting things with the shape of a building.
Ah, that's interesting. You’re interested in desert architecture at the moment—how did that start?
My interest in desert architecture really kicked off when I took a trip out to Ojai, California, and stayed in a really pretty house there.
It was a really interesting style of architecture that I stayed in there, and I ended up visiting Palm Springs with a couple of friends later on. Also, the desert is an environment that I never had any exposure to, so I'm drawn to the surrealism of the desert—it's so different from anything else I've experienced.
Let’s dive in and talk about your background in product. You mentioned that your family's an entrepreneurial family. How did you get started?
Yeah. We built these apps and websites on the weekends, and similarly to architecture, I was really energised by seeing them come to life. Instead of going outside and throwing the ball or playing catch or something, we'd be inside working on our laptops. I'm sure my mom hated that.
We would build these things and I’d get to see them be usable. At the beginning, it was obviously something that looked like it was built by a middle schooler and his dad—so it didn't have very far reach outside of my mom who used it once before she went to the grocery store or something, I'm sure.
I did that long enough that I always felt this urge to keep doing it—to keep building something new. As my former employers can attest, I'm very impatient and always wanting to leave my job and go start something on my own again. I'm always hacking on something.
Wow. Then that translated into you founding your first start-up, Kite?
I went to the University of Oklahoma for a little bit studying Management Information Systems, which is this blend of business and computer science, knowing that I either wanted to go and work in tech or in start-ups.
We attended this hackathon in Atlanta, and we had 36 hours to build something. There was an award there for the best solution to online harassment. We decided that the easiest way to combat that would be to build this service that developers or website owners could integrate into their platforms that would automatically be able to detect this kind of abuse or harassment and classify what kind of abuse or harassment it was and who it was targeted against.
We built that into this developer API, piloted it with a couple of apps and companies, but we didn't get very far. It's a really hard problem to solve. But it was the first project that I had built that I felt like had a lot of potential, and so while we were working on it, I ended up leaving Oklahoma. I transferred out to a business school in San Francisco, where I got even more exposure to investors and start-ups. A little less than a year later I would raise money to go full time on my most recently sold start-up.
Amazing. What did your friends or your family say when you left to move to San Francisco?
It was certainly a big change. It kicked off the first in many events that I would do something out of the norm that didn't quite follow the traditional path of going to Oklahoma, staying in the area, getting my degree after four years.
After I got an offer to join Product Hunt I FaceTimed my dad first. I told him that I was thinking about leaving college, taking a year off and joining Product Hunt full time. It was obviously shocking to him. We figured out the game plan on how to tell my mom about it and told her. I think both my family and my friends would all say that at this point it's expected. If I FaceTime them out of the blue, it's probably that I've either quit my job or I'm moving somewhere else to go and do another startup or something.
Nice. Did you know since you were a child that you wanted to be an entrepreneur?
I knew that I wanted to work in tech and create things as early as middle school. Part of that was a side effect of being around my dad and his business for so long. I was always exposed to tech conferences or meetings that he was going to.
I don’t think I actively considered the idea of what being a start-up founder would be like as kind of a job until later in high school—and even then I was still leaning towards the classic, going to work for Apple or Google or as the roadmap. Even now, I think it's interesting to have the drive or the desire to be a start-up founder. I don't think that you can just quit your job and decide that you're going to be a founder someday.
It’s more of a hammer in search of a nail. In my experience, the most success I've had as a founder has been when I'm doing other things I enjoy and letting my curiosity run wild until I find something that's worth working on—and then I go and commit to that full-time.
Tell me more about your most recent start-up, Avenify. How did that come about?
Avenify enabled nursing students to pay for school through income share agreements, which meant that they got funding up front in exchange for a percentage of their future income—and then once they graduated and earned more than $30,000 a year, they would start making payments as a percentage of their income—and those payments would pause if they lost their job or became unemployed.
We saw it as a really safe, affordable and flexible solution—especially compared to traditional private loans today. We didn't require a credit score or a co-signer, we'd underwrite it based on their academic performance and future earning potential.
And then on top of that, we tried really hard to build a brand around being invested in these students—not like the other more corporate or predatory lenders that we see on the market today.
It started in 2018 when my co-founder and I saw the rise of income share agreements at coding bootcamps like Lambda school—and it was frustrating to us that, as recent students, that this option wasn't available for us or our peers. We had friends that had worked four jobs to pay their way through school. I knew that if I didn’t have to take out student loans, I probably would have been much less likely to do things like leave school or move across the country or go and work for startups.
What was the start of that process like?
We raised a little bit of money for it. We moved into an RV, and we set off on this 10,000 mile road trip around the U.S. where we literally went and knocked on doors of financial aid departments with our pitch deck, asking them what they thought of the idea and if they were interested in using it.
We very quickly learned that it was difficult to sell financial software to financial aid departments when you're a young looking twenty year old living out of an RV. We also learned that it would take much longer than the four months of runway that we had in our bank account to actually get the solution up and running and make money. So we took a step back and thought about what it is we're actually trying to solve and what our core competencies were.
We figured out that the real problem we wanted to solve was that students needed access to funding, and we thought one of our core competencies was that we had this insight from this young person's perspective.
And so, in mid 2019, we launched our direct to consumer product, where students could apply directly for funding. And then on the backend, we allowed investors to buy shares, in students' future income—so we had this marketplace model that enabled investors to bet on that earning potential and fund students more.
Amazing. I want to rewind back to the RV part of things. Whose idea was it? And what was the thinking behind living out of an RV?
When we had started the idea of raising money to go full-time on this my co-founder, Timo, was still in school, and I was at another job. We were looking at what apartment rent would be and how much money we would have to raise to support ourselves. We were thinking, wow, that sounds really expensive—especially if we signed a 12 year lease, that's really long term.
We also didn't want to take any risks in terms of sales that our cold emails wouldn't work or that they wouldn't pick up the phone, and decided that if there was any risk of them not responding to our email, then we should show up in person. He and I had also talked about this idea of living in a van more broadly with what these people are doing with their converted sprinter vans, or just travelling around to these different national parks.
We were faced with this opportunity where we had no job other than the one that we'd given ourselves, we have a little bit of money to do something with, and we're also in a position where we're going to be talking with potential clients all around the U.S., and decided it would be a fun opportunity to do that.
We started in San Francisco and knew that we'd spend three months on the road. We wanted to do a loop around the U.S., and from there then we started driving and stopped where we wanted and would talk to schools in between.
Wow. What were some of the most memorable parts of the trip?
We stayed up on this big mountain that was at 9,000 feet elevation. It was this super pretty campsite, and of course it was the middle of the week and we were staying there for a week and a half, so it wasn't that busy. We had the place to ourselves. I think the highlight for me was just getting to see that scenery—and especially the change in scenery. I don't think a lot of people get to experience that many places in that short amount of time.
We also got the benefit of having hours on the road to just talk about the business or work on the business. I often joked to our investors that if you can survive the first three months of your business in an RV with your co-founder, the rest of the road is going to be pretty easy.
At the start of our conversation, you called yourself a student of design. How does that impact your start-ups and entrepreneurship?
Yeah. I think something that I've realised is how much the experience matters to the customer.
It's not just about how it looks, but also how it feels—whether it's encouraging messages throughout a long application process or whether it's creating moments of joy and delight in a process that typically feels like paperwork.
The more that I've worked with start-ups I realised how important that was to me and how much priority I placed on that. When I think about the design of start-ups, it's really about how you make your product feel to the customers. Just having a better experience for your members and really showing that you care about them and you're building an empathetic product that serves them.
That's really interesting. How do you think your recent interest in architecture and design has influenced the way you look at product or tech?
When I look at houses now, I find myself putting myself in the shoes of the architect, thinking about the flow of the building or what purpose that building is trying to accomplish.
I don't think that there's a huge difference in whether you're designing a building or whether you're designing a website. You’re still dealing with the idea of space. You're dealing with the idea of constraints, and the idea of attention or focus. The only thing that really changes the medium of that message or the scale of that message.
You also have a newsletter. Do you consider yourself a writer as well?
I definitely enjoy writing. I haven't done it as much recently as I want to, which is part of the reason that I put a newsletter out this week. I’m trying to get back into the routine of things.
Writing gives me the ability to kind of formulate the thoughts that I'm having or synthesise those thoughts that I'm having and get them down on paper. If I had an idea for a house, I might sketch it out so I could see it more clearly—writing gives me the opportunity to clarify some of the thoughts I'm having.
It gives me the excuse to go and learn either from interesting people or about interesting topics that I might not have learned about on my own—so you create this web of insights and learnings that you connect later. So even though I didn’t really intend on learning about a new architecture or somebody through the newsletter, it often happens that I'll learn something new that piques my interest again.
You've mentioned looking at magazines for inspiration—are you a visual person or a word person?
Despite me spending a lot of time in the visual world, I think I spend a lot more time on the word side of things. I’m on Twitter 24 hours a day. I'll throw a bunch of books in my Kindle app and I'm always on my phone reading something.
Especially in architecture and design, it's really interesting to read what people write and their insights.
It’s really important to get that additional perspective, even if you don't agree with their perspective or their thoughts. It helps to become a more well-rounded critic of design. It's really important to have that informed growth.
What does your dream home or property look like? Do you have an idea of that?
I have a couple of things in the works. The thing that I often come back to most is this idea of a friends and family compound. What does it look like to have your ten closest friends or family members live on this property with you? Are you all in the same building with other buildings with amenities, or do you all have your own house—or is it spread out like a little neighbourhood or village?
Here in Brooklyn, I'm living in a co-living house. Our entire building has 21 people that live in it. I really liked that idea of community, and want to explore how to do that most effectively.
How far are you into that process? And what is your process like?
Right now I'm trying to create this mental model or this testing framework to think about. I'll put myself in the place of whatever I'm looking at and go, “If I had nine friends living in these little tiny houses around the woods, how would that work?”
Obviously nobody wants to spend their day in a tiny house all together—and if you have nine people and everyone has a tiny house it’s going to be hard for everyone to get together. Maybe you'd actually need a central house.
Trying to create this framework of—much like design or start-ups—what it is that I'm trying to accomplish.
In your Twitter bio, you mention that you’re a sailor?
I grew up sailing on lakes in Texas with my dad and my grandfather. I didn't appreciate it as much when I was a kid as I do now—there was so much involved that kids don't like doing. You’ve got to set up the sail or take it down or clean or do whatever.
Now, where I'm focused so much on work—and I also have these side projects or hobbies that can feel a little bit like work sometimes—there's a really big tendency to get overwhelmed or burnt out with those things. So last year I decided that I needed something that was away from my desk, out of my house.
I decided to go and get my actual sailing certification and ended up joining one of the sailing clubs, here in New York. It was really great. There's something really meditative about being on the water and being in control of the boat. It’s a great excuse to get outside.
You use a lot of words like meditative and gaining energy from things. What do you do to recharge or give yourself energy?
I'm certainly trying to get better at recharging and calibration. I might be in tune with how I'm feeling and what gives me energy or takes it away, but I have not been the best at acting on those insights.
That's one thing I tried to get better at last year.
Especially during the toughest year that we had at the company and with everything going on. Right now, I'm trying to get better at kind of doubling down on those things that work for me, whether it's realising that I'm burnt out and sitting down and reading a book or going sailing.
I've often found that the things that help me re-centre and refocus are more passive activities, like sailing or sketching—activities that allow me to sit and be still, without having to actually sit and do nothing. I'm awful at sitting and doing nothing.
Anything that allows me to reduce or remove that stimulation from Twitter or texting or meetings or managing my calendar has been really healthy.
How do you ensure that your hobbies stay as things that give you joy and not things that stress you out?
I'm a bad person to ask about that. My hobbies stress me out and get away from me. My dad was one of the first people to point this out, where I came up with this idea for something and he said, yeah, that would be cool—and then a few minutes later I sent him a logo I had made. He said, maybe you should focus on making it an actual thing before you go and make a logo for it.
With my architecture hobby, I start off just reading about them or looking at photos and then it's like, “What are your plans for this weekend? I'm going to design a house.” It’s like, “well, why don't you take it slow?”
I'm working on getting better at it. Part of that is appreciating why I do it, whether it's to relax and recharge and get away from business or whether it's to do something that I enjoy without the profit motive involved.
To finish, going back to your interest in architecture—where do you see that developing?
I was thinking about this the other week—especially thinking about where I wanted the newsletter.
There's one idea that it could spin into a broader newsletter. If you think about what Morning Brew did to newsletters, I could do for the Architectural Digest of the world and build something that is more appealing to young people and people like me who are not architects.
I was daydreaming about what it would look like if I started an architectural design firm with somebody, or worked with a designer to go and build some of these projects at some point—and I reminded myself that all of those options would be great and it would be a lot of fun, but wouldn't really be possible if I didn't have that audience for my newsletter.
I reminded myself that, especially for the hobby, it doesn't really matter what my long-term goal is—this is a thing that I enjoy doing today.
Editor's note: Since we last spoke, Justin has announced a new iteration of Clean Lines: Linear Magazine. We look forward to seeing this take shape! Keep up to date with Justin's work on X.
