Corbett Drummey, Popular Pays

Founder: Corbett Drummey
Company Description: Marketplace for products or cash in exchange for posting about brands on Instagram
Company Site:, Facebook, Twitter, Instagram
Date of Interview: December 2014

Corbett Drummey, Popular Pays

Corbett Drummey, Popular Pays
Art by Brad Lacke

Corbett Drummey is the founder and CEO of Popular Pays, an online marketplace that connects local businesses and major brands with the influential Instagrammers of the world. Like Mark Zuckerberg (but he swears he was already doing this), he pretty much wears the same thing every day (with or without the holes) and saves his mental energy for his priorities. I caught him on the eve of his move to San Francisco to embark on his next big journey with the team – hacking it on the West Coast. He sings, plays guitar, and loves Hemingway.

On being in startups:
Corbett is one of those guys who always wanted to be an entrepreneur. In college he created and ran a tutoring company that connected college tutors with children.

 “I’m a wannabe college dropout. I worked on this startup in college and was always bummed out that I didn’t drop out to pursue it full time. I knew I could’ve – and we had a team that was ready to do it, but we chickened out.”

 After doing an internship at Leo Burnett, he took a full-time offer there after graduation. “The whole time I worked at Leo (which was less than a year) I was always itching to do a side project. This is definitely where I want to be. I didn’t feel fulfilled until I started doing this.”

“I love startups. I’ve met the smartest and most interesting people, and they do the coolest shit and have the best ethos and culture. You’re based on results. With startups you can’t fake it- you get it right or you fail. It’s not like school where you do homework to please a teacher. Startups are very real. You’re on your own – and that’s the scary part. No one is coming to check in on you.”

On the idea:
Corbett and his previous co-founder, Allan Holmes, came up with the original idea haphazardly at a party. 

“We had a whole list of ideas. The trick is doing it and persistence. I pushed him to actually take steps to do it. The next day I took him to Piece and made us pitch it to them. That slowly evolved into the idea of merchants offering something in exchange for a photo. It evolved organically, and keeps evolving. Small merchants are really cool, but they can’t float the whole business. So we have to start working with the Nikes and the American Apparels.” (In October, Popular Pays launched Paid Gigs, a new feature where brands can post paid gigs for Instagrammers to apply to.)

On money –  savings, funding, run rates:
In September 2014, Popular Pays closed a $500K funding round. Then, in October 2014, they launched Paid Gigs, which got up to a quarter million dollar run rate in the first 30 days. “It was a good feeling – up until then we weren’t making any money.”

“I quit Leo Burnett with only $3K in savings and we made it last 3 months – which is really amazing. I was down to $120 before we got our first investor check. I finally got the investor check in the mail and when I cashed it they froze my accounts because they thought it was fraudulent!”

“The first year was super, super stressful – but it got easier. The last 4-5 months have been like heaven. Things have been working so well that it makes me anxious, because I’m used to things breaking. Now we can turn down some offers and we can pick where we want to take it from. But up until that… gosh, what a struggle!”

At the time of the interview, Popular Pays had raised $775K in funding.

On lessons learned:
“I’m surprised we’re still around and I wish I would’ve known this stuff when I started. You want people who are just an animal in terms of their work habits. They are really passionate and very, very dedicated. Business is a minefield, and the further they can navigate the minefield without you, the better.”

“One of the things I learned how to do was focus. I tried to do everything when I started and that’s the wrong thing to do. You have to choose a few things that are really important and then let the rest slide. That would’ve saved me so much time. There are 1000 things you could be doing right now and 3 of them matter. If you just focus on those 3, then you have more time to work …. or go live your life. 

“So focus on the important things, choose your team wisely, and don’t stress as much – because it all works out.”

On how he personally feels about social media:
“So controversial. When I come in and I’m worried about taking a picture or checking in, then I’m never actually in the moment and experiencing it. But, I also love how my previous co-founder, Allan, used to always take photos and document things. I have no documentation in my life right now and I had so much when I lived with him. When I’m 40, I’m going to be so happy looking back on those times. I just couldn’t be the one to do it because I have to engage in the moment to be happy. So it’s a weird thing for me because I like being present instead of sharing – it’s a distraction.”

So how does one get in on this type of marketplace? “Like anything, if you really want to do it – then it’s just practice. I got up from 200 to 1200 followers because I posted a photo every day – because I knew I needed to. The cool thing is that if you are posting regularly and engaging in the app, then you’ll get good at it. All you have to do is care. I really hope that we are enabling a creative class.”

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