Aug 5, 2022

Goodbye, New York. Hello (again) Philadelphia.

Plus, Tangle's three year anniversary.

NOTE: This is a free preview of today's subscribers' only three-year anniversary edition. If you're not a logged in subscriber, toward the end, you'll see a button to subscribe to finish reading the piece if it interests you and you want to take the survey.

Today's read: 10 minutes.

Tomorrow, my family of two — and Tangle headquarters — will be leaving New York City and moving to Philadelphia.

I promised myself I wouldn't say goodbye. I told every friend and family member I could that I'd never utter those words, never accept that this chapter was over in a real, meaningful way.

Instead I've said things like "it's an hour and forty five minutes" or "I'll be back a lot" or "New York or nowhere, forever."

This city has given me so much. My wife, first and foremost. An incredible group of friends. A world championship. Splendid late nights I can’t even begin to count. Nearly 10 years of what has unequivocally been the best decade of my life. My first dream job (a lead role at a news company) and then my real dream job (this newsletter). A memory every day in a city so wild, so out of the ordinary, so bursting with uniqueness and strange people and talent that you'd have to be buried to go a day without seeing or hearing something new.

My start in New York City came through my first journalism job at Huffington Post. I took the job not because I was a bleeding heart liberal, but because I was broke, living in Israel, and looking for a path to come home. I applied to 40 other jobs and they were the only ones to accept my application. It wasn't even a real job, but some kind of "fellowship program." I worked 40 hours a week, making $10 an hour, commuting two hours each way to and from my mom's house in Philadelphia every day. I did that for six months, competing with 40 other fellows for a handful of full-time jobs, before I became one of the few who were selected.

They offered me $38,000 a year, and I countered for $40,000. They accepted. I moved into a six-bedroom, one bathroom, hostel-like apartment in Harlem, where I paid $600 a month in rent and felt successful and independent.

About three months into that full-time gig I got an email from a guy who claimed to be a business partner of Ashton Kutcher, the actor and venture capital investor. He told me Ashton was starting a new media venture and they wanted me to be one of their first full-time hires — to help lead a newsroom and build a media outlet that focused on the people fixing things, not breaking things. They wanted someone young and hungry who had a track record of stories going viral, and that was me. I thought it was a phishing scam but set up a call for a few days later, just in case. Before I knew it, I was on the phone with the dude from "That 70's Show" accepting a 50% salary bump and taking a leap of faith on a group of guys I'd known for about an hour.

The company was called A Plus, and I walked into a position created to help run the politics vertical — then poached two of my closest friends from HuffPost on the way out the door.

The next eight years were a whirlwind. There were CNN appearances and long-form investigative pieces and interviews with members of Congress and letters from Hillary Clinton and citations of my work in Fox News and direct messages from WikiLeaks and trips to Singapore and India and Thailand and all the stuff young reporters dream of. I got to be in the field. I got to interview famous people and help make regular people's stories famous. I saw articles of mine get millions of views. Sometimes I made some enemies, and other times I got recognized by my peers for my work.

At our peak, we had a 30-person newsroom full of legit talent, and I was really proud that it was something I had helped build. I developed my own sources, my work got published in TIME Magazine, and I saw my name in articles from The New York Times and Forbes highlighting people disrupting the media space; the kinds of milestones most journalism students only dream of.

I worked my ass off and climbed from $10 an hour and two-hour Philly commutes to having enough money to eat out sometimes, and gained a small, loyal following of my own. That led to the creation of Tangle, and the modest success that’s come with it.

And yet, I knew even before I took the job at HuffPost that this industry was screwed and dying. I knew people didn't trust reporters, I knew news feeds were crushing dissent and trapping us in ideological bubbles, and I watched even my first dream job at A Plus turn into a series of mass layoffs, buyouts, and the dreaded “pivot to video.” By the time I launched Tangle, writing in the wee hours before I went in to work and the dark hours after dinner when I got home, I was fairly certain that if it didn't work out my future would be a series of unstable jobs, broken promises and being forced to churn out content for clicks.

Now I'm three years into this thing, and it's hard for me to imagine what life was like before it. As demanding as the work is sometimes, I don't know that I could ever work for someone else again. I can see clearly now all the broken incentives that exist in other media jobs, all the inherent bias in the media, the toxic effects of trying to hit revenue goals and drive traffic and woo investors and enrage the people who consume your content.

Through it all — that bizarre and winding career arc — New York City has been my home. This vibrant, absurd, delicious, dirty, beautiful, stressful, intoxicating city has been the grounding factor for me. I love it here, and know it to be the best city on earth, even with its rickety public transportation or low-patience citizens or filthy streets or offensive cost of living or scary crime stories.

The pandemic chewed us all up, and changed the city forever — leaving a scar on nearly every New Yorker that I suspect won’t go away anytime soon. But when it spit us out, there was something new here; dare I say, even something better. We were softer around the edges, more aware of what was around us. When the pandemic restrictions began to lift, I'll never forget noticing the strangeness of New Yorkers starting to acknowledge each other in the streets, of saying hi, of being intentionally polite.

It happened slowly, and somehow it has stuck. Just like the restaurants in the streets or the subway turnstiles that accept Apple pay or the new dedicated outdoor spaces or the (now fleeting) “rent reset,” the city has — in a lot of ways — changed for the better. And that's to say nothing of the general improvement we all experienced by shedding the New York fakers who left and never came back, claiming the city was dead, only to watch from hundreds or thousands of miles away as its revival began.

Now, though, I'm leaving, too. I'll be packing up and beginning my move to Philadelphia tomorrow, ushering in a few weeks of back and forth as we settle in. It is not at all the ceremonious exit I had hoped for. Instead of a week of drinks with friends and tearful hugs and a goodbye party, Covid-19 struck in its awful, particular way. I’ve spent the last week crammed into our office, surrounded by boxes, isolated from my wife Phoebe. She, in turn, has been trapped in the house, packing things up alone, and unable to have any sendoffs with her friends either.

So, tomorrow, we’ll move without any goodbyes, and in all likelihood we will stay in Philly for a long time — at least three years. Yesterday, Phoebe sent me something that she wrote about leaving, something that only someone who has lived here their entire adult life could write, something that resonated with me deeply. Somehow, without any formal training or ever really practicing, she has always been a great writer. So I asked if I could share it:

"There’s no good way to say how I feel about leaving New York. It’s like trying to explain why I love the worst parts about myself. Or why failure can be funny. Or how something impregnable can change everyday. The closest I come is saying that it’s both. Happy and sad. Right and wrong. Temporary and permanent.

As our last days have crept closer my biggest fear is that the person the city made me, allowed me to become, is somehow bound here. Inextricably cemented to the sidewalk. And that when I move I’ll lose it. The part of me that breathed for the first time here. What if all the things that I love about me only come about because the subway is late or my brother lives down the block or the ceiling in my bathroom could collapse again? What if the resilience I cultivated that feels so paramount to my identity is actually kept alive by proximity to restaurants I worked in, where people paid me in Monopoly money — or not at all?

Leaving the city feels like growing up. And I have always been a person who stays. Who returns to the same beach towns and restaurants and coffee shops because they are familiar. But also because they are like height markers against the wall. Who was I the last time I was here? Was that person sad or happy or broken? And I visit her.

Being 15 commuting everyday for an acting camp. Being 16 and dragging a drunk friend home to Jersey from Penn Station. Being 18 and living in my own apartment. Being 21 dancing with the people I love. Being 22 and falling in love. Being 25 and going to college. Being 27 and getting married. Meeting my niece. Grieving my friend. Getting into law school. Being 29 and packing up the first home I shared with my husband, where we got engaged, where we were kept safe from a pandemic, where I could be happily alone.

When I express this fear, my loved ones say, ‘New York will always be here.’ And I know what they mean and that they mean well. But really, in this way, it won’t. I will be a visitor returning to memories, not navigating through the city with a cheat code, a work around for time passing. When I move the illusion of timelessness will be broken and I’ll know that chapter is over. It will be the past. And there will be beautiful, challenging, exciting things to come in a new home and a new city. But my New York will be done. And that’s okay but also sad. It’s both."

Like her, while I'm sad to leave New York City, and bummed about the circumstances of the last week, I'm also excited. Not just for a new city to explore and fall in love with, but for a return of my own. Having grown up just north of the city, Philly is a second home for me, populated with college roommates and high school friends and family. I'm also excited for Phoebe, who will be starting a new chapter that she went to the ends of the earth to reach.

Just as important, I also think it'll be great for my work. It'll place me back in a more politically diverse region, in a state that has been critical to every presidential election in recent memory. And surely, I'll be enjoying the reduction in cost of living — the accessibility of a city where pretty much nothing is farther than a 20 minute drive away and you can still find a meal for $15. I hope it keeps my feet grounded in reality, outside the bubble that is New York and, more specifically, Brooklyn.

This move and change of venue also coincides with a major milestone for Tangle: Our three year anniversary. Tangle's first test email to friends and family was sent on July 31, 2019 — and the first actual newsletter went out exactly three years ago today, on August 5th, 2019, to about 100 people.

Magically, the last few months have been some of the most interesting yet. Perhaps most excitingly, after just over a year of working solely on Tangle as a full-time job, I got my first serious inquiries from folks wanting to buy Tangle. A few of the conversations are ongoing, and a couple have been with people whom I've idolized in the media industry. I don't have any imminent plans to sell, though, as there’s a lot more I want to do. But there are some other pathways, through investment or partnership, that are interesting for me to explore. No matter what happens, their interest alone is a really rewarding affirmation that we are above the target — providing a new media service that has a lot of value and interest, even to the most respected eyes in the game.

Part of that is because we have a strong, sustainable business model. We had around 25,000 people on our email list a year ago — today it’s 40,000. We have over 6,500 paying subscribers driving $30,000 of revenue a month, enough to begin supporting the small (and growing) part-time team working on our products and invest in growth. Over the next year, we are going to start spending a larger chunk of that revenue on advertising the newsletter and marketing campaigns to get the word out about what we’re doing.

I am also excited to share that I recently accepted an offer to join the non-profit Summit Impact as a Democracy Lab fellow. There's a lot of really fancy and high-minded language to describe the program, but the upshot is that I'm going to get some professional help from industry experts about how to grow this thing — all because they think Tangle is good for democracy here in America. In return, I'll speak at some events for Summit and join their network of interesting thinkers and entrepreneurs. It's a very cool opportunity and one that, above all else, I hope leads to improving and growing Tangle.

There are other interesting tidbits, too: We finished putting together a pitch deck to sell ad space in the podcast, which will go out soon, and hopefully push the podcast from the red into the green. We extended two of our interns (Audrey and Watkins) after their stellar work on the newsletter and social over the last few months. We may have an incoming intern who will be based on the ground in Washington D.C. (giving our outsider-y newsletter a little insider-y insight). And we've got Tangle phone cases, Tangle coffee, Tangle events and a referral program (to earn swag and gift cards by sharing Tangle) in the pipeline.

In news that provokes a little more trepidation, we're also seeing new competition enter the space. Places like Media Bias Fact Check and AllSides have been around for awhile, and others like The Flip Side have a format similar to ours. But a well-funded media start-up called Semafor made up of former BuzzFeed, Bloomberg, New York Times and Wall Street Journal reporters, and with $25 million of investor money, is set to launch this fall.

This is how a recent Financial Times article described the founder's idea: "He plans to promote reader trust by splitting Semafor stories into separate sections, breaking apart the news from the reporter’s analysis. There will also be a section offering an opposing view, and a view from another region in the world..."

Sound familiar?

Competition, of course, is a good thing. It makes us all better and means we're doing something there is a lot of demand for. But it also brings me to the reason for asking you all to take this survey today: I am thinking about ways to make Tangle more competitive, from a growth and financial sustainability perspective.

One way to do that is by introducing advertisements to the free version of our Tangle newsletter.

There are a lot of reasons I'm thinking about doing this, but I have a lot of reservations, too. So, in typical Tangle fashion, I thought it'd be fun to break those reasons down — and instead of just giving you "my take," I'm asking for your take, too.

Why we shouldn't.