I Went from Nobody to Substack Bestseller

How a failed college blog, a forgotten novel draft, and a rooftop conversation led to 5,000+ subscribers and a second chance at a writing life

I might be a “Bestseller” on Substack today, but a year ago, I was a nobody.

I’ve been on Substack for just over a year now, and I’ve certainly learned a thing or two about online media and writing. I’d like to say that I reached success in just a year, but my Substack story really begins over 10 years ago with the birth of Pens and Poison in 2015. If you didn’t know, Pens and Poison has been (symbolically) around for quite a while now: It was the name of the blog I started during my freshman year of college on Squarespace. In 2015, blogging was the way to become a successful writer, so, after persistent nagging from my peers, I bit the bullet, made a website, threw together a logo in Microsoft Word (Canva had not yet caught on) and got to work on my first blog post.

The original Pens and Poison 2015 logo. If you recognize this piece of work, it’s because it’s the same logo I still use today. Today, I typically cut out the corny tagline, but I love the font and the ink pen—as well as the purple color scheme.

The only problem was I had no idea how to be a blogger.

I was a writer, sure, but what the hell was a “blogger”?

I had written countless essays for school at that stage of my writing career, but I did not understand how to “blog”—nor did I realize that as a blogger, I could literally just write essays. In my mind, “blog posts” were artificial and gimmicky, and if you've been following me for a while, you’ll know that those are two of my greatest pet peeves. So for my first two posts, I decided to write my heart out and publish two personal essays—one on teenage insecurity and one on ephemerality—and to see what happened. I announced my blog on Facebook and soon had several thousands of visitors on my first post. Feeling optimistic, I started up a Pens and Poison YouTube channel—the same channel that has grown to 22k subscribers today—and kept writing my idiosyncratic essays—which, frankly, sounded like unhinged diary entries from a bad Victorian novel—and publishing my newest posts on the Pens and Poison Facebook page until several of my classmates made fun of my old-fashioned writing style, and I grew self-conscious. From there, my viewer count dwindles, and after about a year, I stopped writing blog posts on Pens and Poison and secured an internship writing for a college magazine—where I was expected to push out artificial gimmicky posts such as “11 Songs to Improve Your French” (to my chagrin, this post is still on the Internet, and I cannot figure out for the life of me how to take it down, but I hope that if you are learning French, I can still be of help).

As you might expect, I soon grew bored with this genre of gimmicky writing and retired my public-facing writing efforts entirely. I felt most at home with creative writing, and my yearlong effort of publishing dumb essays on the Internet was getting me nowhere. My YouTube videos—which took hours to shoot and edit—had gotten no more than 200 views, and my blog views had been steadily on the decline ever since my first post. Pens and Poison, my most beloved brainchild, never really took off.

For the next couple of years, I put Pens and Poison on hiatus, shifting my focus instead to my grad school apps and my tenuous future career. By the time I had graduated from my Master’s program in the midst of the pandemic and had made the difficult decision not to continue with my PhD, I was too preoccupied with my existential crisis to properly care about my status as an Internet writer—I had devoted twenty-two years of my existence to my dream of becoming a professor of English literature, and the academy had shattered the idyllic vision I had always harbored of lecturing on the virtues of T.S. Eliot.

Now what?

Pulling myself out of graduate school, I was also faced with the challenge of making money. I had student loans and rent to pay, and I couldn't just sit around making YouTube videos that nobody watched and writing essays that nobody read. From 2020 to 2023, I wrote a grand total of two essays and made a grand total of one YouTube video. I kept telling myself that I was going to get back to Pens and Poison, but by late 2023, I was making almost $300/hour at my college consulting startup and had little incentive to get back to my writing career. What was the point of spending hours doing something that made me zero dollars—that brought me zero attention—when I could make money as an entrepreneur and live fairly peacefully?

But despite not producing much public-facing writing, I was still writing copious amounts of poetry and fiction every day during my free time. I was a writer at heart, and I could not live without putting words to the page on a daily basis—I had simply renounced the frivolous idea that anyone was ever going to read my unorthodox writing. In 2021, I released my first poetry book on Amazon—Broken Weekend—and in 2022, I completed my first novel, Man a Museum. My poetry got several negative reviews, and zero literary agents requested to read my novel, so by the age of 25, I was convinced that I was just not cut out to be a writer. Meanwhile, my business was thriving, and I was making more money than I could have ever imagined with an English degree. Was my purpose on this planet not to be a writer but an entrepreneur? Certainly, my success as an entrepreneur gave me an ego boost, and with an income that outpaced that of many of my friends in STEM, I no longer felt ashamed of having majored in English. I was comfortable: I could afford many more things than I had ever dreamed of with my degree, I was living a great life in Manhattan, and I was respected by my peers as an entrepreneur.

When my next poetry collection, Vintage Lovers, got even fewer sales than Broken Weekend, my ambitions seemed further away than ever, and, gradually, I renounced my dream of becoming a writer. Witnessing my disappointment, my friends gently suggested that I focus my energies on running my company and that I was unlikely to make it in a world that hated my guts anyway (to be sure, the literary world does indeed hate my guts). I took their wisdom to heart and focused instead on making money, paying off my loans, and building my financial future.

But something was missing from my soul.

In the summer of 2023, I found myself at a networking event in Manhattan and got pulled into a conversation with an older gentleman. I wasn’t sure if he was trying to hit on me or if he was just an eccentric character, but he seemed deeply invested in asking me uncomfortable personal questions: How old was my boyfriend? When was I planning on getting married? What were my deepest life ambitions? I dodged the first two questions but was stumped by the third. Was my deepest life ambition really to run a college consulting firm? I loved working with students and managing our growth plans, sure, but were teaching and entrepreneurship really my callings?

No—I was a writer!

I was downright impassioned by the time that I blurted out this answer, but I was also ashamed—I had absolutely nothing to show for it.

The gentleman glared at me with his deep brown eyes. “Every week, shoot a set of twenty-second videos. Post them to YouTube and Instagram. You’ll build up an audience, and then you can start securing a readership.”

“But I run a company full-time,” I protested. “I have no time.”

He laughed. “It’ll take virtually no time out of your life. You can even be like a cartoon character and appear in the same outfit for multiple videos.”

Amused by this idea of embodying a cartoon character, I thought over his proposal for several minutes before dismissing it as silly.

Before we said our goodbyes, my new acquaintance made me promise to pencil in time this week to shoot videos. Begrudgingly, I acquiesced, but I did not intend to take him seriously. I was a writer, not a social media influencer. What did he think I was trying to do with my life?

The following morning around 9 a.m., I found myself writing emails on the rooftop of Soho House and was inadvertently pulled into a conversation with another young writer who had noticed a literature quote on my T-shirt (it was probably something by T.S. Eliot). We got to talking about writing, and I told him that I had a completed novel and was hard at work on my third poetry book.

He seemed astonished.

“I call myself a writer, but I work on my newsletter more than on my novel,” he admitted. “Kudos to you for having the discipline to complete a novel! Do you have a newsletter?”

A newsletter?

“All writers need newsletters these days,” he went on, chuckling. “You have a bit of what I’m missing as a writer—discipline to complete a longer work—but maybe you need to borrow some of my talents as well. Start a newsletter. You’ll build an audience that way, and maybe you can drive some poetry book sales.”

I was painfully reminded of my old college blogging days. A newsletter? What could I possibly put in a newsletter that people would actually want to read? The whole idea sounded even more gimmicky than the blog idea I had toyed around with during my freshman year of college. What news could I possibly deliver to random people on the Internet?

Proud and somewhat stubborn at the time, I took the advice of neither of these men; I neither shot videos nor started a “newsletter”—whatever that was. After all, I was a serious business owner, and I didn't have time for Internet marketing frivolities.

By early 2024, I was still a full-time entrepreneur with zero credentials as a writer. Almost 10 years had passed since my initial failed attempt of being a writer back in 2015, and I was still set on paying off the rest of my Columbia loans as fast as possible, so I had no intention of dialing back my commitment to my company. I enjoyed introducing myself as the Founder of Invictus Prep and felt that going back to being a struggling writer would be a massive step backwards. But with the conclusion of college application season in mid-January, I had some downtime between managing the company and acquiring new clients and, somewhat burnt out by the demands of running my own business, I decided to humor myself by sifting through my old writing and rediscovered an abandoned short story I had written about a year ago about a college nerd who sneaks into an elite Upper East Side soirée by pretending to be an FBI agent. I had left the story unfinished around the time I’d released my second poetry collection and was feeling increasingly frustrated about my writing career, but out of all of my abandoned writings, this particular piece was too good to leave hanging.

Sitting myself down on my couch at 12 a.m. with a cup of tea and a basket of chocolates, I set out to complete my story.

The way I had originally envisioned the narrative, the fake FBI agent, having introduced himself to the protagonist at the party, would be called to the protagonist’s office the following morning to deal with a dead body—only to have to confess towards the end of the story that he was not a real FBI agent and had only been trying to sneak into a fancy party. It would be commentary on misleading appearances and the pulls of wealth, but 14 pages in, finishing up the dead body scene, I was not convinced that the story was anywhere near its end—we knew virtually nothing about this young man’s motivations, and it seemed like the protagonist had some unresolved drama at her company. So I kept writing.

By March, the story was over 50 pages.

I had no idea where it was going, but it was the start of my next novel, The Lilac Room.

In April of last year, I took a vacation to Mexico with one of my friends and was inspired to start up an Instagram account to post quotes from my novel and my poems. I had around 200 followers by the time that I boarded the plane to Cancún, and by the time I came back a week later, my account had grown to 500 followers. I shot my first Instagram reel about my favorite Shakespeare plays in a hotel room and later followed it up with a reel about the name “Jessica” (hint—the Bard probably invented it)! My friends made fun of me for trying to become an influencer, but I was successfully driving thousands of people to the poetry on my website through my Instagram presence and made several poetry sales of my newest release Illicit Kingdom after posting poetry quotes to social media. I had finished about half of the first draft of my novel the end of the spring. On the side, I pulled up some of my old blog posts and refashioned them into essays, sending them out to various publications in the hopes of seeing my words out in the world.

In June of that same year, Kveller picked up my first official essay, and I had become a published author—on the Internet, that is, but who cared? Kveller had over 500,000 monthly readers, and people were actually reading my thoughts! After countless rejections of my various essays, I could not have been more joyous. Elated at my $100 check from Kveller—compensation for my writing—I confused my friends, who did not understand why I was celebrating such a small sum when I was clearly not in need of cash. But I wasn’t celebrating money at all—I was celebrating the success of someone having seen value in my ideas. Inspired, I sent out my next essay and placed it in The American Spectator. These were small publications, to be sure, but after nearly 10 years of rejections, two back-to-back publications made my day.

It was around that time that I started posting some of my old blog posts to Substack, a platform that one of my friends had mentioned to me that I had no idea how to use. Nevertheless, having gone through the process of starting up a company from scratch, I had become decently good at branding and soon figured out how to import my signature purple to my new publication. My first Substack post—one of my old blog posts on the history of literary criticism—reached 35 recipients from the initial mailing list I had compiled from my Instagram followers and soon after racked up over a thousand views. I was feeling momentarily optimistic until my next post tanked with just 191 views and the one after that received just 243 views. I received more rejections from literary journals and publications, and my Instagram growth had stagnated. I was discouraged, but this time, I had learned my lesson about dropping everything. I had a dream, and I was going to attain it.

Over the next few months, I finished up The Lilac Room and dove back into writing essays around September. I pushed out a few more failed pieces, but my audience had grown from 35 to 100 over the course of several months, and with 100 people reading my work, I knew I had to keep writing.

What happened next changed my life forever.

When I first started the Pens and Poison Substack, I was careful not to let my grievances about the state of English literary study slip on the Internet. I had drawn immense ire from my Columbia classmates by speaking out about the over-politicization of literature and was forced to scrap my original graduate school personal statement about my experiences in the Columbia English department in favor of a more lukewarm statement about my interest in poetry.

Yet one lazy afternoon, I decided to repurpose my graduate school personal statement as a personal essay on my humble corner of the Internet. No one reads my Substack anyway, I thought. No one would get angry.

Two weeks later, “Leave Literature Alone” blew up the Internet. Sent out to just 178 subscribers, my piece skyrocketed to 40k views, amassed 1.8k likes, and gained me over a thousand subscribers virtually overnight. Days later, I had placed my first solicited piece of writing in Persuasion and continued to push out essays about the state of literature and my thoughts on the world as a whole—the same writings that many of you come here to read every week. I quickly attracted the attention of several other prominent Substackers and gained Bestseller status after less than a year of Substacking.

The rest, as they say, is history.

After one year of taking my writing career seriously, I’ve learned a lot not only about discipline and resilience but also about optimism. My writing career didn’t go anywhere until I believed that it would—and until I put in the work to get there. You might think that I’m some random writer who got lucky one day with subscribers, or that hard work has nothing to do with who makes it on this platform, but Pens and Poison has been over ten years in the making, and my ideas have been simmering for even longer. Today, Pens and Poison receives over 60,000 monthly views and delivers my hot takes to over 5,000 inboxes, but once upon a time, I faced only crickets and rejections. I still face crickets and rejections for my novels, and I still have a long way to go to get to where I want to be in my career, but looking back, I’d say that Year One of taking my writing career seriously has been a success, and if my writing experience has taught me anything, it’s that it’ll only be a matter of time until my novels get picked up as well.

To those of you out there just getting started, don’t ever give in. If I could redo anything in my life, it would be to ignore the negative feedback and the naysayers from 2015 and to keep going. After all, who knows where I’d be now if I had kept it up when I was just 18?

We’ll never know, but today, however, Pens and Poison still isn’t too shabby.

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