From what I can see Jordan, your journey as a founder began with idk tonight, so I wondered whether journalism was something you studied?
Yes, it was. Although that decision was originally because, more than I wanted to study journalism, I wanted to be in New York City. I was like, what college is in New York City? And my dad went to NYU, and he said “NYU is the only college in New York”. I was totally misled! I went to the Gallatin School of Individualised Study where you’re able to take classes in different schools and essentially design and name your major. Looking back it was quite entrepreneurial to select that program – I wanted to make my own thing.
I graduated in December of 2015 and had a job lined up at CBS This Morning, which was my first official job. Prior to that, I was interning at NBC and Refinery29 so I dipped my toe into several different types of journalism.
It’s pretty cool that you got internships at such big names when you were still studying. Was doing those a part of your course or did you just have that ambition yourself?
I never studied abroad (only short summer programs) because I didn’t want to leave the City when I was in school, and I felt compelled to have an exciting internship every semester. I would work at least three full days a week and then sort of cram all my classes into the two other days. NYU really allowed for that. It felt very manageable and I really enjoyed my time. Although there was definitely a pressure. It’s sort of like if you don’t have an internship, what are you doing?
“I would work at least three full days a week and then sort of cram all my classes into the two other days. NYU really allowed for that.”
My first semester at NYU, I started applying to every single thing I could find on the NYU job board, and ended up landing an internship at the very first blowout only salon called Blow Pro. I remember telling my parents, “I got an internship at Blow Pro!!” and they were like, what the f*ck is that? It was amazing! I was writing for their blog, and they were so nice. They definitely took a chance on me. Then my first big internship that I landed was Cosmopolitan, and after getting Cosmo it was easy to get the rest of those internships, which is really strange – just having that name got my foot in the door at Yahoo and NBC and Refinery29 and all the ones that came after that.
Yeah it’s one of those things that if you’ve got that name, then great because you get to move forward on that journey, but it is also such a specific filtering mechanic. I understand that everyone’s time poor, but it does mean that so many people get stuck, just trying to get that first foot on the ladder
So then you graduated and joined CBS?
Yes, I was a news associate there, which is the entry level job, and I started in January 2016. It felt like the longest six months of my life. I very quickly understood that I didn’t want anybody else’s job there, and that was sort of scary. I didn’t want to be Gayle King, and I didn’t want to be the Executive Producer. I didn’t feel like I could see which direction I was going in. I was seeing so many amazing people come in and talk about businesses they were starting and I just thought ‘I really want to try to start something’. I can fail and hopefully come back and have this wealth of knowledge, but I wanted to give something a shot. So I decided to leave.
So what was your first business idea and how did that play out?
My original idea was to create a way to get plans on demand. So you would say, “I want to go out on this day, it’s me and three girlfriends”… you would fill out this quiz and get a customised plan. That was the first concept and I basically blew all of my savings on that. I did the website and the projections—it was a subscription service. Very quickly I realised that people did not want to pay for this. I then made it free, and a lot more requests came in. The one thing I learned from the experience and what really sparked everything following, is that almost all of the requests coming in were from couples.
I decided to take a step back and just create content for couples and see if I could grow that audience, which is how I started idk tonight, the Editorial site, Instagram and newsletter that featured really cool curated plans for couples in New York.
Maybe a year into that was when I thought of the idea for Cobble, as a technology and space for couples to make authentic decisions together without any pressure. This concept of fun—like a dating app where you’re swiping—but you are only connected with your significant other. And when you and your partner both swipe right on the same restaurant, movie, or recipe, we make it really easy to sort of follow through on those plans.
When you decided to commit to Cobble, what was the first expertise that you brought on board that wasn’t yourself?
First thing I did was literally sketch out the rectangles of a phone screen on a piece of paper – I essentially did my first attempt at a wireframe. I was in a WeWork at the time, and in that office I met another group that did really beautiful app design. So that was one of the first costs. They did a great job and we went through several iterations. After that we hired an agency to actually develop the MVP. And from there we hired our first in-house developer Josh, who also brought on one of his former co-founders, who’s now our lead backend engineer.
“First thing I did was literally sketch out the rectangles of a phone screen on a piece of paper – I essentially did my first attempt at a wireframe.”
And you’ve just done a huge funding campaign right? Would love to hear how you actually got the funds to get Cobble off the ground.
Yes, so initially we raised a friends and family round of about $250k, to be able to get those designs and first development done. And also to continue paying our writers. And now we’ve raised a serious seed round ($3 million).
How did you work out what you needed money wise? Did you use another model that you had or did you just kind of start from scratch in terms of working at what you felt like the key components?
Well, the big thing about a friends and family round is that they are investing in you. Honestly, it was mainly my family saying, “Okay, I see this idea”. When it came to the seed round, that’s when there was an official deck and a lot of options for where we could take the business model. And, of course, the traction – the fact that we had the app built and our beta testers loved it. Even in the pandemic, people were swiping – all that stuff was really what got us to the $3 million.
Yeah, well I can see the economic potential for this is huge because you’ve got so many businesses essentially invested in the active use of the app if they’re on there. Have you netted out exactly how you want the economic model to work?
I think advertising is the most obvious route to go. However, because our purpose is so rooted in being trustworthy and really serving up great content, first and foremost, the challenge is whether advertising means people question: “is this really something that they’re recommending or is this because they’re getting paid?” So where I see our business model is kind of two facets. The first is revenue share. We don’t need to get paid by a restaurant in order to get a kickback in that restaurant when someone makes a reservation, buys tickets etc. There are larger platform partnership opportunities.
Then beyond that and sort of the far bigger idea is that for the first time we’re reaching both halves of the decision maker, whereas everyone else, you know Facebook and Google all target the individual. The example that I always give is, I like chocolate ice cream and Big Brother knows that I like chocolate ice cream, they can figure that out. And they know that Nick loves vanilla ice cream. But they don’t know that when we buy ice cream together, we get coffee and that’s the compromise data that only Cobble knows about.
“for the first time we’re reaching both halves of the decision maker, whereas everyone else, you know Facebook and Google all target the individual.”
Yeah, fascinating! Okay some quick questions…
Do you have any favourite quotes or sayings that you kind of go back to, to keep you motivated?
Yes, there’s this one quote by Rumi that I really, really love, which is: “What you seek is seeking you”.
What’s something you’ve learned this year that you’re glad you’ve learned?
One thing I have done and started during this year is journaling – writing down when I’m in the depths of despair, and to then see, you know those journal entries change and be like, Okay, I’m feeling really positive. When I’m in the really high moments I try to read back the dark ones because I want to understand, now that I’m up here and I was down here. I think it’s important not only to just look at those positive ones when you’re in the dark, but vice versa, as well.
“When I’m in the really high moments I try to read back the dark ones because I want to understand, now that I’m up here and I was down here. I think it’s important not only to just look at those positive ones when you’re in the dark, but vice versa, as well.”
Yes, I was talking to someone last week about mental health for entrepreneurs and the challenges with it, because your job is never done. How do you find that, and particularly having such ambitions and such a future vision for Cobble?
I definitely take breaks. I definitely take time for myself. However, I would say what we’re doing at Cobble is especially difficult because for example if Nick and I ever have the conversation… “what do you want to cook tonight?” I immediately go “why isn’t the app working for this right now”. Our life is so mixed up with the success of the app.
But to answer your question about, you know, being able to separate work and life, I think I know when I’ve had a really good day and I know when I haven’t. When I have an amazing day I just keep going. I’m firing on all cylinders. And then the way I unwind is watching something really good, taking a bath, lighting candles, reading—reading is my saviour.
I have always loved reading. But it’s funny, I think as a CEO and as a founder, you always have to be like “I’m reading this business book…” and I’m like, “No, I’m reading Agatha Christie and that’s all I want to read.”