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“Choose your early team wisely.” With Mitch Russo & Corbett Drummey

Culture first; most of the success we’ve gotten in different spurts of the company’s life all have to do with just having the right combination of people. Ultimately culture is just the mix of people and values you have in your company. Being intentional about your culture can help you be more discerning about the […]

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Culture first; most of the success we’ve gotten in different spurts of the company’s life all have to do with just having the right combination of people. Ultimately culture is just the mix of people and values you have in your company. Being intentional about your culture can help you be more discerning about the people in your org and the values you’re all expressing, so spend time early being deliberate about that.


As part of my series about the “5 Things You Need To Know To Create a Successful App or SaaS”, I had the pleasure of interviewing Corbett Drummey. Corbett is the Co-Founder and CEO of Popular Pays. He was named to the 2018 Forbes 30 Under 30 in marketing and advertising and is an alumnus of Y Combinator (W15). While working at Leo Burnett, Corbett discovered the growing influence that social media was beginning to play in our digital lives and felt a need to change the methods that marketers used to produce content and engage with consumers in an online world. Corbett left Leo Burnett to start Popular Pays in 2013 along with his two co-founders.

Corbett is a student of advertising, content, and social media and believes in the power of technology to expand our realm of possibilities and to bring efficiencies to the ways that we work.

He graduated from the College of William and Mary in 2012 with a Bachelor of Business Administration. After taking a class on entrepreneurship he changed his focus from music to business and started his first successful startup that connected local K-12 students with tutors and helped him win the Student Contribution to the BBA Program Award.

Drummey and the Popular Pays team are currently based in Chicago, working together towards the company’s mission: Create Something Worth Sharing.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Igrew up in Johnstown, PA, went to school at the College of William & Mary in Virginia, and then moved to Chicago after graduating. In college, I was working on perhaps the first startup out of William & Mary since Thomas Jefferson, but had a chance encounter with a recruiter from Leo Burnett while working in a coffee shop who convinced me to intern there my junior year to work on the Coca-Cola and MillerCoors accounts. After graduating, I moved to Chicago to work on the Allstate “Mayhem” commercials. I gravitated toward the social media side despite everyone’s focus being on TV commercials at the time. My co-founder and I tried to do a project within Burnett, which would eventually become Popular Pays, but after we got blocked internally we decided to quit our jobs to pursue our startup. Through some trial and error –mostly error — for about a year, we developed the product which is the Pop Pays people know of today: software for collaborating with content creators and influencers. We joined the Y- Combinator class of Winter ’15 with just a few teammates and have been growing ever since. We’re now about 40 people, mostly based in Chicago, but all remote at the moment due to the pandemic.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

When starting Pop Pays, there was both the background gestation of the idea as well as a ‘spark’ moment that provided the activation energy we needed to start. Working on the Allstate Mayhem account, I knew that there was no way we could produce content the way we do for TV or with regular video production, and still get an ROI on social media. Across all the accounts I worked on in the agency world, the cheapest video we made was probably $40K, and we simply couldn’t dedicate that kind of budget to social. However, we found that we could get content from a creator or influencer for 10–100x cheaper, and often it performed better since it was native to the medium itself and it was made by someone who knew the social media channel we wanted to be on. To start a company in general, you need domain experience in an industry to see a problem and the opportunity that could come from fixing it. Plus you need partners with complementary skill sets and I had that with my roommate at the time, Allan Holmes, my co-founder. We met when we interned at Burnett. One of the interesting things about the “spark” moment is how inauspicious the start was: we were in the middle of a party at our house and Allan said, “We should throw a party that you can’t get into unless you have 500 followers on Instagram”. At the time, Instagram had just come out and that was a lot of followers. We pitched that idea to a client, and then that later became a site where you could get things (free products, etc) in exchange for a post, and that finally turned into software for collaborating with influencers and content creators. Cut to today, and that software has processed tens of millions of dollars in budgets in the last few years and has produced tens of thousands of pieces of content. But that brings me to this: one other key piece of starting a company is you also need to be crazy enough to quit, which Allan was. One day after we had been working nights and weekends for a few months, Allan informed me that he quit his day job to focus on Pop Pays, and also — he told them I’d be quitting too. So he made that easy.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Early stage startups are mostly hard times. I can give plenty. Thinking back on them, they occurred most frequently and most severely when we were early on. Thankfully, each year that has gone by we’ve become more and more secure as a company, but there’s something so exciting about those early days: you feel almost equally as likely to be bought for $100m next year or fail a few months from now, and often those extremes are days right next to each other. It’s so early you’re not even sure if you’re getting traction or not, or even just doing the right things day-to-day. And compounded by that, little problems can take up your whole day which can be really demoralizing. I think on day number three, after moving in with Allan and our other co-founder Nathan Michael, and starting full-time work, I spilled coffee on my computer and spent the day frantically trying to find a loaner laptop because we only had a few months of runway to begin with. We struggled and scraped by in the early months, eating the cheapest food we could make in our low-rent house, and by the time we secured our first $20k investment check three months later, rent was due that same day and I overdrafted. Running out of money was a constant plague for the first 1.5 years up until we graduated Y Combinator. However one of our hardest morale hits was during our App Launch party when we announced a date to our whole network of contacts then discovered a bug that crashed the app for everyone upon opening it and we didn’t have enough time to get a new version approved by Apple before our party. After much panic, we wrote some code to circumvent the issue on the server side without a new iOS app, but that was a tough day. It’s not very glamorous, but oddly one of the most motivating and un-spoken of factors is fear of failure. We got incredibly creative when confronted with such tough challenges every day, every week. I’m very comfortable overall with trial and error with different initiatives or projects, but when it came to quitting our jobs and starting Pop Pays I was incredibly unwilling to fail. Startups are insanely hard, but pitted against failure, they’re do-able.

So, how are things going today? How did your grit and resilience lead to your eventual success?

I feel incredibly grateful because things have continued to get better and better each year and have grown every year. Nothing is perfect and we still have challenges though — the impact of coronavirus has been severe across many industries, but we’ve worked hard to adjust as a team and it’s paying off. We acted conservatively to cut all non-essential costs early on, and we also pushed to be nimble with our sales strategy. Fortunately we’re in an industry where we can be remote, and our creators have the advantage of being their own models, photographers, editors — so even during a time when regular production shoots are canceled, they’re open for business. Because of that, we’ve been able to do some very cool work in the last few weeks, ranging from having our creators make at-home content that has appeared in TV spots to turning around much needed COVID-19 related content in 24–48 hours for our brands.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

In addition to the nightmare above about announcing our app launch party before we had a working version in the app store (that’s quite an easy lesson to learn), we also thought launching in this restaurant that used to be a bank vault would be cool because our app let you pay for things with social currency (an Instagram post). Although unlocking a bank vault to see an iPhone with our app running is an amazing visual, having no service for the app launch party was less than desirable. But perhaps the better lesson than “make sure you have cell service at your app launch party” is to launch early; not making a launch so precious and just focusing on talking with your users after getting it in their hands is a much more important lesson. Oh, and file your 83(b) elections. Just Google it. Almost all mistakes in the startup world are recoverable (which is itself a key lesson), but 83b’s are one of the rare simple mistakes that could perhaps crush you if you’re unlucky.

What do you think makes your company stand out? Can you share a story?

Something rewarding was that earlier this month we landed at #1 out of 176 competitors on G2 Crowd (aka Yelp for Software) in our competitive set, ranked by satisfaction. We’ve been flirting with #1 or #2 with each of the ranking categories after just starting on the list not too long ago. It’s been cool to see more and more examples where we know we stand out; for example, we’re currently the only marketing partner across Instagram, Facebook, Pinterest, and Twitter combined. But these markers of industry leadership change over time and rise up and down like the tides; besides seeing the markers of today, what really gives us confidence is the shared vision and culture we have. Our company was built on the question of “Is it worth sharing?” as in, “Is this so good that someone would want to share it?” We wrote down that north star before ever making a line of code or signing up a brand, because we wanted not just the content from our creators to stand out, but also our teammates, the experience of using our product, or even small things like what we share on social. Having that shared sense of mission is how we know we’ll be a standout company in the long-run; it’s baked into our DNA.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Momentum is critical because when you lose it, it takes a lot of effort to get going again. And sadly on a personal level, the same is true, in the sense that when things are going great it’s still a lot of work but not as draining as when things aren’t going well and you have to push even harder to get the ball rolling again. Momentum is key. There’s not so much you can do around burnout other than focus on moving the needle on the few tasks that where if you can improve those, it improves everything. So practically speaking, in tough times I’ve tried to focus hard on just those few really key things and it has helped me feel some freedom in letting all the other things slide. Out of 100 tasks, only a handful really matter, and not worrying about any of the others can help ease some mental bandwidth for you in times where you’re burnt out.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There are too many! Startups are built from the generous advice of founders who’ve started businesses beforehand. A good percentage of the advice I’ve given is just paraphrased from other mentors. Certainly Y Combinator has been an early and tremendously strong influence on us, especially Paul Graham’s essays, Sam Altman, and our group partners Justin Khan, Garry Tan, Kat Mañalacas well as Kevin Hale. Most recently, Amanda Lannert and our Board (Beringea and GoAhead) and Board Observers (Corey Ferengul and Ed Lau) have been the most key and frequent sources of feedback, but there’s many others I’m not listing who are very deserving. It’s important over time to develop relationships with a few key mentors who deeply know you and the context of your business, versus getting a little advice from a lot of people.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Approximately how many users or subscribers does your app or software currently have? Can you share with our readers three of the main steps you’ve taken to build such a large community?

Our platform has 65k+ content creators on it and we’ve worked with nearly a thousand brands over the years. Ultimately the key to true growth is retention and to get that you need to talk with your users and build something that solves their problems. If your community isn’t growing, talk to your users. Oftentimes in tech, people also misunderstand that early prototypes of products are just concierge-type service that is done manually at first, then once validated it becomes something scalable and coded into a product. As YC famously said, “Do things that don’t scale.”

What is your monetization model? How do you monetize your community of users? Have you considered other monetization options? Why did you not use those?

Right now our brands pay for access to our software on a SaaS basis or they run set campaigns on our platform. We’ve tried several models over the years: at first Pop Pays was a place where you could get free products in exchange for a post on Instagram but when we started charging brands we learned why that’s so key to start charging for your product early. People say, “If you want advice, ask for money”. We learned a lot when it came time to actually make something we were asking payment for. After that we tried a marketplace approach in the beginning, taking a set % of creator payments, but in the last year we’ve gravitated toward SaaS because of the tremendous benefits you get from retention, measurement, and predictability. Plus crucially we realized that connecting brands and content creators was only one piece of the value we provided, whereas most of our development and focus was in the collaboration that occurred after connection, or in tracking results. We realized we’re more of an operating system for content creation versus a marketplace. It’s important to line up your pricing model with how your customers get value from you.

Based on your experience and success, what are the five most important things one should know in order to create a very successful app or a SaaS? Please share a story or an example for each.

  • Choose your early team wisely; we were very lucky at Pop Pays to work with the right teammates at the right stages of the company, but I’ve seen so many other companies implode from having the wrong mix of co-founders or early teammates. Statistically, this is one of the most likely areas to fail, so choose carefully.
  • Charge early; if you are truly making something valuable, you can get people to pay for it. The best is if you can get someone to pay you upfront to finish building the solution you’re working on, because it’s that critical. I’ve seen this many times. What you want to avoid is giving away your product for free– you might be just avoiding the tough sales convos. If you’re set on a freemium model, make darn sure it’s well tested and you know users will pay for those pro features. Also, for SaaS, a good rule of thumb is to charge more than you think you should. A16z has written a lot about how most founders charge too little.
  • Keep cash burn low; the biggest expenses are people, and you have to resist hiring as long as you can and push to get cash flow breakeven as early as you can. In times like now it’s easier to see why that is important. If you run out of cash, it’s over, but startups are weird in the sense that if you can just stay in the game, you could be right around the corner from making it big.
  • Don’t give up; in general, you need to be working on something that you can work on for a decade, so pick something meaningful. Startup success is a long slow journey, and you need to be able to find value in the journey itself, so make sure it’s rewarding, whether that’s because of the people you’re with or the problems you’re solving.
  • Culture first; most of the success we’ve gotten in different spurts of the company’s life all have to do with just having the right combination of people. Ultimately culture is just the mix of people and values you have in your company. Being intentional about your culture can help you be more discerning about the people in your org and the values you’re all expressing, so spend time early being deliberate about that.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I wouldn’t say I’m of great influence, but we try to do what we can to help with the small resources we have. Right now that’s donating our software and service to help against the spread of COVID-19, helping many non-profits like How We Feel. Ultimately in the long run, the biggest challenges we’ll face I believe will occur a few decades from now due to the explosion of technology and what that means for humans. I want to help people navigate that safely. If you’ve watched Black Mirror you probably have some ideas about how tricky that might get, and with certain problems we’ll have to get it right on the first try. Sam Altman is doing some great early work in developing the first Artificial General Intelligence (think: something way smarter than us) and doing it safely at OpenAI. One thing is for sure– the next few decades will be a wild ride and I feel fortunate to be around for it.

How can our readers follow you on social media?

  • @corbettdrummey on Instagram, Twitter and most networks
  • @popularpays across all networks
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