I Was Offered to Own SF’s The Bold Italic. Then It Didn’t Happen.

What began as an opportunity to own one of San Francisco’s most beloved publications eventually collapsed — and would serve as a jumping point to start my own.

When I launched Underscore_SF on September 1st of this year, it was a day filled with jovial release and renewal. In just the span of a month, I had effectively built the publication from the digital ground up. 

(I bought the domain; I made a cute lil’ six-page check-list of vital tasks to complete; I compiled, edited, and produced over thirty essays — twenty of which were from writers other than myself; I dyed my hair platinum blonde [mildly out of crisis] and got new headshots; I debuted all the social handles with a familiar twang and tongue-in-cheek irreverence; my interview with Axios went live, announcing the new publication… after I formally left The Bold Italic and published my farewell letter on the site the day prior.)

But the exact catalyst for why I so suddenly, so swiftly, and so adamantly decided to start my own publication remained a mystery to many. From the outside looking in, it appeared — at least before September 1st — that I was still serving as editor-in-chief of The Bold Italic, a role and opportunity I held in esteem and had immense amounts of gratitude for. 

Alas, my contract with Medium, the still-struggling online publishing platform, to oversee the entire publication was abruptly cut. Moreover: My relationship with The Bold Italic unexpectedly came crashing down… after months of talks about me taking over the brand.

Yes, reader: I was considered first to be the new brand owner of The Bold Italic, not the right-wing political advocacy group GrowSF, as it was announced yesterday, December 8th in the San Francisco Chronicle. 

Because I never signed a fucking Non-Disclosure Agreement and have literally zero fucks left to give and am so fucking livid… I think now is a perfect time to pull the curtain back on my contentious working relationship with Medium.

For what was nearly two years, I served as not only the editor-in-chief of The Bold Italic, but also as its newsletter writer — its copywriter, its social media manager, its PR agent, its producing partner, and any and all other roles associated with helming a beloved Bay Area-based publication. To say I wore many hats would be a misnomer; I had a hat rack super glued to my lower lumbar.

However, I was more than happy to run the entirety of a publication I held in such high respect for what began as a decent amount of compensation. But as time went on — months marked by a change in four contract negotiations, three managers, and two CEOs at Medium — my pay trickled. Frankly, it dried up.

What people (those outside my closest circle of friends) don’t know is that The Bold Italic was actually going to shutter on November 1st of 2021. Medium cited a need to further cutback on its financial assets for hosting and running on-site partnered publications, which included The Bold Italic; it, to this day, remains the only publication Medium has ever acquired; once-popular publications like ZORA and Elemental were ideated and launched by Medium and not purchased from an outside entity. 

In what was my last Hail Mary to try to save the brand from crumbling, I negotiated with Medium that I would continue running The Bold Italic for $500 a month — almost a tenth of my initial pay. 

“Y’all just need to give me the keys to The Bold Italic,” I said over a Zoom meeting in regard to my ongoing relationship with the brand and Medium. “I’ve been running this publication by myself for [at that time] nearly a year, and, frankly, if we work on a trade-off of ownership for it, we can work in a clause that I agree to keep The Bold Italic hosted on Medium in exchange for the IP, domain, and trademark. We both win, and we can stop these back-and-forths with contract negotiations.”

My manager at the time nodded and agreed to bring my concerns to He Who Shall Not Be Named — a higher-up at the company who would later become the most spineless human being I’ve ever had the unfortunate pleasure of connecting with in my editorial career. Eventually, it was agreed that Medium would now renew my contract, and we would keep the door of ownership open for later discussion in 2022.

Before leaving to cover Outside Lands over the Halloween weekend in 2021, I signed that revised (and heavily negotiated) contract to ensure the brand’s survival… and cement my flickering hope of, someday, owning The Bold Italic. I also knew I had just committed a form of financial suicide — how am I going to pay for my life in San Francisco with what’s basically a full-time job that pays $500 a month? But if there’s one thing I pride myself on above all else is that I’m resilient as fuck — I’ll make it work, and I always have.

The next six months continued on at a familiar pace. I wrote and published well over two hundred articles — a grab-bag of long-form essays, thought pieces, poems, news blurbs, and listicles; my body had acclimated well to the weight of that metaphorical hat stand mounted on my spine — keeping that nugget of possible ownership firmly placed in a fold of my prefrontal cortex. I found gratitude (on most days) in editing The Bold Italic; this was my barometer for contentment in relation to the brand — my North Star in calculating the states of burnout that inevitably came.

In May of this year, it finally happened: He Who Shall Not Be Named wriggled out from the garden soil, jumped on a Zoom call, and, by some means of biological trickery, managed to control his annelid-like body in front of a webcam and offered me ownership of The Bold Italic.

“Yes, yes, yes, I will absolutely take ownership of the brand,” I emphatically said. I worried the corners of my mouth might be permanently fixed in their perched positions. “Let’s figure out the logistics.”

The earthworm creature assured me that we can work on “getting the keys” to me, so I can continue running The Bold Italic absent of Medium’s oversight. I, too, agreed to keep any and all content on the platform. (For one, the idea of migrating over a decades-worth of content seemed maddening… and outright expensive. My deep-seated hope was that Medium, itself, would collapse as a company under my ownership, leaving it far easier to migrate those pieces off the host site — sans a six-figure price tag.)

The Zoom call ended. The terrestrial invertebrate wriggled back into the ground. The pragmatic tasks of transferring ownership began.

The weeks after that initial call can only be described as anxiety-inducing and outright inhumane. 

The entire company went on a seasonal break in July, and the company’s very senior segmented beast took an additional week of vacation, promising me before leaving they were “still figuring it all out on [their] end,” and would return from the break with “updates for [me].” Medium’s co-founder and then-CEO, Ev Williams — who played a pivotal role in the purchase of The Bold Italic — stepped down. A new CEO, Tony Stubblebine, was appointed in July. In the back of my mind, I knew this was inherently problematic to securing brand ownership of The Bold Italic.

After prodding the soil with a garden hoe to elicit a response from the said slimy, limbless critter, I managed to secure a follow-up meeting on August 1st to discuss what we had started earlier in the summer. And on that call, He Who Shall Not Be Named’s posture slumped and gaze veered left of the webcam as it informed me that Medium had decided to “move in a different direction” — “you know [Medium] is constantly evolving and iterating” — and that my contract would be formally cut as of September 1st.

I felt myself unraveling in real-time. The warmth left my fingertips. My eyes glossed over, attempting to hold back tears. 

“You don’t have to figure out what your relationship with The Bold Italic will be after your contract is over right now,” it said. Even in the midst of pruning my $500 monthly contract, it suggested that it wanted me to still contribute content to the publication… without secured pay. Any compensation would come through the company’s maligned and meek Partner Program.

“I can tell you right now that I’m done,” I replied, my sorrow quite quickly shifting to rage.

What was slated to be a thirty-minute meeting I decided to end in four minutes; I had no intention of spending any time playing convivial with this fossorial organism and company that utterly obliterated my mental health.

After closing my laptop, I remember running a ten-mile loop around San Francisco, stopping at Lands End… and just screaming fuck, fuck, fuck, until my voice became crass from liberation. 

On one hand, I was mourning; the most pivotal, joyous editorial job of my career, thus far, was ending. On the other palm, freedom was afforded by means of a clenched permission slip; the other shoe had dropped, and I had no excuse now to not begin the work of building my own publication. 

Something that I owned. That I operated, managed, and edited. Something no one could take away from me.

And that, dear reader, is why you’re reading this long-winded anecdote about my past role as EIC of TBI — one I’ve been eager to tell for ages — on Underscore_SF.

Matt Charnock