Here are a few select stories from my days as an early member of Venmo, leading up to our acquisition by PayPal. Grab some popcorn, this’ll be fun.
It was the spring of 2013 and I was coming off a year touring with my band, Wildlife Control. We were the epitome of indie rock in 2012, featured on the all the blogs, topping Hypem, and our song Analog or Digital hit #12 on the alternative radio charts. I was in Midtown Manhattan, catching up with an old friend, Iqram Magdon-Ismail over Thai food, when he asked “so with all the music success, are you making any money?” I loved his directness, I also knew he’s great at math and that he knew, despite Wildlife Control crossing millions of streams and topping physical sales charts, our revenue probably wasn’t reflective of our global audience size. So I nodded and said “you know, a little bit I guess, it’s the music industry, so…”
I first met Iqram and his co-founder Andrew Kortina back in 2007 after a solo piano show in Chelsea where I debuted some new songs. The three of us hit it off immediately and developed a deep mutual respect for the each other, our shared love for innovation, rhythm, and the NYC hustle. So here we were about 5 years, many post-show after parties, and several failed startups later, when Iqram suggests we join forces. “What would you think about bringing all your expertise from launching Wildlife Control over to Venmo?” At first I didn’t get it, but as we chatted I realized two things: 1) Iqram knew I dreamt big, followed my heart, and for this reason his proposition was interesting to me and 2) the various parts of Venmo, between the product, the brand, and the vibe needed to come together in a way that people would love. I knew how to do that, so we shook hands and our story begins.
A few weeks before officially starting at Venmo, I was in line at my favorite neighborhood sandwich shop, ‘Snice. As usual, there was some great music playing in the background. The two women in front of me struck up a conversation about it. Pointing up, one says to the other, “This is a great song isn’t it? Yeah, its Arcade Fire, aren’t they so good?” Now, I knew the indie rock catalog very well back then and though I didn’t know this particular track, I did know it was certainly not Arcade Fire. But in 2012, Arcade Fire had somehow managed to own the category of all music that sounded evenly remotely like indie rock. It was cool to identify with them, it was cool to talk about them, and it was cool to recognize their songs.
In that moment, as I ordered my avocado-kale panini, I knew what we needed to do to bring Venmo to the masses – button up the product and make sure that it was not only solid and easy to use, but also cool to talk about, cool to know about, and ready to ride the network effect to mass popularity. I knew this playbook, straight out of the music industry.
I’d known Iqram and Kortina for a few years and so had a lot of context on Venmo heading into my official start day. I was one of the first users of Venmo, on SMS before they had even launched an app, providing early feedback. By the time I walked into our nice new open office on West 25th St., the team consisted of a small group of engineers, a designer, an office manager, and an operations lead. The mobile app strategy was finding its market fit in the early days of the App Store, and the team was finally achieving a monthly active user base in the thousands, with users they didn’t personally know.
But growth in active users was plateauing, certainly not hitting the hockey-stick curve every startup wants. Which is why they brought me in. While it was amazing to have engineers ship lightning fast and own their respective features, it also meant there wasn’t strong cohesion across the touch points that a user experienced on Venmo. For example– from the site, to marketing materials, to the app, I found over 30 shades of blue — all of which should have been the same single color.
I sat down and interviewed everyone to understand how they thought about Venmo, and how they might describe it to friends. Their descriptions were similar, but also slightly different. It was an engineering culture and the description was very functional. “An easy way to send someone money.”
Form follows function is a great way to build a solid product. This was one of the best examples of simplicity of design. The velocity of the team, how fast they shipped, was incredible and I didn’t want to slow things down.
However, payments is full of potential frictions points, and user growth is exceedingly challenging for a new financial services brand. For compliance alone, Venmo required sensitive information like bank account, birth date, and social security numbers from its users. I knew Venmo needed to immediately feel inevitable as a brand and instantly build trust. It would take a certain je-ne-sais-quoi. The same hidden quality that Arcade Fire conveyed to music fans. “It’s Arcade Fire, aren’t they great?” When someone splits a bill, we needed the default response to be “Venmo me” — no further explanation given or necessary.
Two months in, during the summer of 2013, I had plan. Apple had announced iOS 7 with its flat design aesthetic and Android was trending in the same direction. This was a radical departure from the skeuomorphic style that had dominated the early app store. The team fully embraced this as the moment to refactor our apps and button up our vibe.
I decided simplicity and speed were paramount. When someone is sending a payment they want to get the job done and feel confident in the experience. Zero friction. A few examples:
- Helvetica Neue would be available on both Apple and Android devices, not requiring any additional lag time of an external font. Easy choice there.
- We picked a single blue, which would feel immediately trustworthy yet distinct enough that it would be Venmo’s Blue. I chose a palette of cool grays that lent to the feeling of speed, lightness, and simplicity.
- We worked hard on our own custom line-based iconography that was as straightforward as could be.
In total, brand, design, and communication guidelines were a was a huge evolution for Venmo, now all buttoned up and ready for the masses.
In music, releasing a big record is like throwing a big wedding. The key is a lot of planning, various partnerships, and coordinating everything for maximum impact. It’s a moment in time and you get one chance to get it all to go just right. You need to pour your heart into it.
Since we were ready with an app that embraced the flat aesthetic of iOS, I knew that topic would be a great conversation point with Apple. They wanted apps to help encourage their developer community to move away from the popular skeuomorphic aesthetic and embrace this new design direction. We knew we nailed it and we needed Apple to see that. Conversations went well, and we worked hand in hand pulling all nighters to update our site per Apple’s requests. We timed our big release with the release date of iOS 7 and like magic– Venmo was one of a handful of iOS 7 ready apps that were featured in the App Store on launch week. It was a huge moment.
Downloads went through the roof. We were quickly moving up the charts. Then Google followed suit, featuring Venmo in the Google Play (Android app) store. We were cooking.
It was time to turn up the juice. We looked at our social ad spend and realized the ROI (return on investment) wasn’t what we knew we could get. First we moved our ad spend into the “invite friend” feature of Venmo, testing out giving users $5 instead of $1 when they invited a friend. It worked so well we reverted almost immediately. But we now had a powerful growth dial and knew our hypothesis on ROI was correct.
Emboldened, Iqram and Kortina gave me full reigns to think of the most effective way to spend our remaining marketing budget to blow growth through the roof. It was time to think about subways and taxis, the blood stream of NYC.
Unimpressed by ad agency pitches, we decided to go our own direction. I set up a DSLR in the office and took some high res portraits of our devops engineer Lucas Chi, Movember stubble and all. Sandra Rubinchik stepped in as copywriter and away we went. Lucas does yoga, Lucas wears jeans, Lucas likes to dance, Lucas uses Venmo. So much rhythm. So much vibe. This was gold and we knew it.
Let me explain…
Earlier I mentioned the importance of trust in a payment app. Andrew Staub, our growth engineer, found that an invited or referred user was 10x more likely to become a monthly active. We didn’t need to generate downloads, we needed word-of-mouth.
With a solid user base to build upon in NYC, I knew if I could get these pictures of Lucas plastered across subways, we’d get folks talking. Just like the two women grooving to what they incorrectly identified as Arcade Fire, we were on the precipice of capturing all the hipness that comes with knowing about something cool, or people’s tendency to pretend to know about something they think will make them cool.
I called up CBS Outdoor (now Outfront Media) and asked for their last minute subway ad inventory. They gave me a great price, knowing full well that it would be next to impossible for me to meet the printer deadlines to get these large ads delivered. I also bought an ad takeover of Bedford Ave, the subway station at the center of Williamsburg — the epicenter of hipsters slinging FOMO. CBS Outdoor definitely didn’t think we’d make the deadlines but knew we would owe the fees regardless.
Hearts racing we signed the papers, got the print specs, and I brought in Robin Spencer, a seasoned production file expert. We cranked through the assets, got everything delivered and our ads were up just in time for the holidays. We even got some kudos from the folks at CBS Outdoor. It was a Christmas miracle.
What happened next was beyond what we’d imagined.
NYC went absolutely bonkers over the ads.
Back then, most subways ads were ignorable boring corporate product marketing. Or Dr Zizmor. Our ads were in your face and patently not ignorable. People were talking, then Buzzfeed and Gawker, then major outlets like Fox News, Fast Company, and the New York Times — as 2014 rolled in, everyone in NYC, and many more across the country were up in arms about Lucas and Venmo.
Venmo had entered the national consciousness and “Venmo me” became vernacular. Job done.
Going from thousands of users to millions requires a type of growth mindset in teams that is constantly open and fluid, yet executes extremely fast and well. Setbacks are fine, as long as they are fast too.
Instincts are powerful.
Go with them, ride them. Almost nothing we did could have been read in a book. There was no example or model for drumming up that much interest in Venmo. Today, subways are full of ads for startups with big bold fonts. Back then, start ups didn’t advertise in subways because no one knew how effective an out-of-home advertising strategy could be for an app. It was all instinct.
Great decisions have massive long tails.
The design of Venmo that we launched in 2013 lasted over 7 years, well into 2020. During that time the user base grew from thousands to tens of millions. Transaction volume increased exponentially. Word-of-mouth never stopped. Anyone who lived in NYC in 2013–2014 knows that Lucas rides bikes.
Trusting each other’s ideas is a secret weapon.
I have met so many teams and professionals who need to have ideas validated by expert speakers and online articles. All good, but don’t ignore the brilliant ideas of the person sitting next to you, who’s living through the same challenges with you day in and day out. They probably have the best ideas– ask, listen, and believe in them.
Efficient multi-threading is essential.
Not the programming variety, we’ll save that for a different day. Executing multiple aspects of a focused business strategy leads to the hockey stick. I often hear this advice given to CEOs: “know the one thing you need to get right and if you just do that everything will be ok.” It’s important, but that one thing merely get you survival. If you want amazing growth you need to solve multiple big problems at once, that all happen to be part of a singular vision. It means tough, intentional, and fast decision making—being in a constant state of flow. Easier said than done!
Leadership is all about bringing the very best out of people.
Iqram and Kortina saw something in me and knew I was capable of solving an incredibly abstract growth challenge. They gave me the charter and license to figure it out. I’m grateful to them for that incredibly unique opportunity. They were great at spotting unique talent. I relate. As a Grammy-nominated music producer this is exactly what top producers do with artists—bring out the underlying essence and channel it into a track. This is how I approach working with teams not just in the studio, but in any business. I’ve always found it to be tremendously rewarding for everyone involved.
Last but not least– everything is related.
When I was first starting out, I was encouraged to think of making records and starting businesses as two completely different things. Against my own intuition, I separated my interests based on how I thought the world sees them — music over here, tech over there, etc. After going from Wildlife Control to Venmo, it validated what I’ve always known, that these various pieces are all part the same stuff. These unique combinations make us who we are. Humans aren’t built as a series of compartments the way businesses and products are organized, and even those are built in compartments due to logistical and operational necessity. Bring your whole self to everything you are involved with and your impact will be 10x, guaranteed. You do you.
There are so many more stories and learnings from my time at Venmo and that era of innovation. I hope you find some inspiration in these. ’Til next time.