One mid-March night, my Fort Greene roommate Shannon Byrne (@shannonleebyrne) returned home late and gasped as she opened a letter from our stack of mail. It was past midnight, and we both looked defeated by our respective days. Next to my computer in the living room were two opened bills, totaling nearly $500 from two minor doctor visits (a small portion of the final tally, you’ll recall). Shannon’s news was worse than my own: She owed nearly $6,000 in taxes and fees before the April 15 filing deadline just a few weeks away. I assumed it was another unexpected cost associated with her music startup A Song A Day (@asongaday.co), which delivers daily song recommendations for dozens of genres—”from humans, not robots.” However, it was a tax return from a job she had held the previous year. “I was a 1099 independent contractor working full time for a French company,” she explains. “They hadn’t incorporated in the U.S. yet, and I didn’t save enough money or plan well. I’ve been doing my own taxes since I was 21, and lately spending too much on my New York life, and didn’t realize I was going to have to owe that much so quickly.” She shook her head as she read the details of the notice, unsure of how she’d come up with the money, but sure of something else: She would figure it out. If anything, when you’re struggling to get off the ground, you get good at avoiding that final six-foot descent into your own grave.
Shannon launched A Song A Day a few months before we met. She cites its birthday as October 21, 2014, the day it first popped into her head. “It started as an idea while I was on a run, which is funny because the demand of operating it has since prevented me from having any time to run,” she laughs over brunch in Prospect Heights. We’re speaking just after @asongaday.co’s first birthday, for which she held a party that doubled as a fundraiser: The startup’s Kickstarter was in its final week, and needed more than half of its $25,000 ask in order for Shannon to receive any (and all) of the money. On why she had the idea for ASAD: “My friends knew me as the music lover, and would ask me how I found new songs and artists. It was such a routine thing for me. After sharing lots of my secrets with them, I realized on that run that they were all too busy to hunt for the songs themselves and just wanted me to hand them over, but not in some algorithm-style way. They liked the personalization. So I got home and bought the domain, then started laying out the site. I sent the link to a few friends who for some reason were also awake, and they all tweeted about it. A few people with high-quality tech networks re-tweeted it, and the next day it was featured on the site Product Hunt, which showcases the most innovative new efforts in tech.” One day, A Song A Day didn’t exist. The next day—and the next year—it controlled Shannon’s life, bringing her the highest highs and lowest lows.
Just before our catch-up brunch, I got an email from the A Song A Day Kickstarter: Shannon would be hosting a telethon each of those final three nights to try and make up the $15,000 deficit. That was very like Shannon, to fill every pocket of her free time with @asongaday.co, right up until the last minute, and to send off an email seconds before I arrived at the restaurant. I was glad to take her offline for a couple hours, even though I knew she wanted to be emailing editors and friends. The campaign had a strong launch: It was featured on Kickstarter’s music vertical, and more than 300 people contributed. It overwhelmed Shannon, who had spent nearly eight months planning the precise details of the fundraiser, down to when it should launch, how to reward donors, what the video pitch should say, and exactly how much to ask for (fundraisers can set their goal, but that target must be met entirely). At our catch-up brunch, I ask how she is planning to make up the difference, in the event that the campaign wouldn’t receive its full amount. A lot of my friends had launched their own Kickstarters, and many of them had an angel donor waiting in the wing, to make up the difference with a personal loan (and only sometimes did mommy and daddy want it paid back). “I have no fallback,” Shannon replies. “Friends are volunteering to cash out their stocks at work, but I’ll never let them do that for me. I might just move the campaign over to Indiegogo.” (That’s a crowdfunding site that doesn’t set ceilings and pays out whatever you receive, which then also prevents you from setting and clearing ambitious goals.) “If I do that, I’ll lose most of the original donors, but I’ll still end up with a few thousand dollars, which will help. People have come out of the woodwork this week to tell me things they did to get their Kickstarter funded, and they’re not things I’m ok doing. It feels a bit dishonest. I’d rather fail in funding than do something unethical. And maybe that makes them better businesspeople than me, and more successful than I will ever be.”
Above all else, Shannon wants A Song A Day to be a large community of music lovers. She wants conversation about songs and artists, running dialogues where people can share their love or hate or indifference about something they’ve been recommended. She currently sends automated emails every weekday to her thousands of subscribers, each of whom is assigned to a genre that fits their taste. She has 44 curators, including herself, and 500 more people who have volunteered to be one. (I’m the curator of the Dance Pop playlist, I’ll have you know. I derive so much happiness from sharing five of my most recent favorites to this pool of strangers, and to have them respond to my emails with rousing support or bitter—albeit friendly—disgust.) But building that community, which includes managing the conversations and all of the automations, takes tons of time. Two of Shannon’s best friends, Danielle (@danifleisch) and Maria (@bhimtastic) have been by her side since Day 1, and have sacrificed their own nights and weekends for a project they feel strongly about, and quite selflessly to support the honest efforts of their pal. Every weekend, the three women would be churning away in our living room, scheduling and responding to emails, fixing bugs, assigning subscribers to playlists, and planning the eventual fundraiser. “They’ve taken on a lot of work,” Shannon says. “It’s nice to have people in the trenches with me, with whom I can talk about it. They’re both such good advocates for the brand. It really keeps me going. They also know when to make me stop and take breaks. They make me live my life. If they weren’t there, it’d be hard. I need those people to talk to. I would be less motivated to keep going, especially now. Having their emotional support is far more important than making money. But I think we all agree that the money would be nice.”
Shannon seems certain that she won’t get the $25,000 funding, but I remind her that she has still filled her entire week’s slate—on top of a part-time job—with efforts to get there. She can’t help but state her regret, though: “I wish I had only asked for $10K or $15K. But I was certain I could get to $25K, too.” A Song A Day doesn’t die if the funding doesn’t come through, but it is significantly hindered from growing: “This money would buy us time. It would allow me to explore a more sustainable model for the business, and to get it monetized. There are steps that need to happen in order for us to get there, like streamline the admin stuff. I need that to be able to approach sponsors. And going out and selling the product would take time. I also want to build a curator database. I want a curator spending 10 minutes at most, and for those emails to arrive in each subscriber’s inbox at the time that is best for him or her.” So, most of that money would be Shannon’s livable income—allowing her to pay her own bills, as well as the various costs that @asongaday.co throws her way, like registering the LLC, hiring consultants, and talking to lawyers—while she builds the community between curators and recipients. Another regret: “I wish I had a mentor. It’s not too late, but I really need a businessperson or someone in the music industry giving me advice, calming me down or pointing me in the right direction. Someone to help me filter all of the unsolicited feedback I get from everyone else, and to save me from impostor syndrome.” I ask her to explain that last part—impostor syndrome. “It’s when you feel like you don’t deserve the attention, or the leadership on something. Like, how did I get here? Why am I the one calling the shots? Why are thousands of people using this thing that I created? Am I doing a good job, or at least doing my best? Do they know I’m a fake?”
“Getting bed bugs when we did…that affected me in the worst way possible,” Shannon says. “It stretched me so thin. I work from home. I was fortunate to be going out of town a few times when it happened, but I just didn’t have time to deal with it, to make it better. I also didn’t have time to move out nor the money to afford it.” For all three of us in that Vanderbilt Avenue apartment, cost was the first concern when the bugs showed up. Dry-cleaning expenses, replacement furniture and bed sheets and pillows and clothing. Not to mention the mental cost: the dread of going home each night, the fear of falling asleep, the disbelief that any poison will effectively rid of the pests forever. The existential crisis that ensues: Why do we live in this dirty city? Why do we tolerate this shit for such high cost of living? “I even messaged my brother in Florida,” Shannon admits. “Wondering if I should move home for a bit to save money. It’s so expensive and hard to get off the pavement here. The cost of moving home—of sacrificing opportunity—however, or of leaving New York in general, is too great. I can have so many meetings here within the industry, and go to every concert I want. People take me more seriously by being here. I’m where music is, and with so many tech resources. I either need to take better advantage of it, or I need to do something else with my life. Someplace where bed bugs aren’t likely to follow.”