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🔴 "Terrible" content works
Building a thriving newsletter-first business ft. The Bottleneck's Rameel Sheikh
Francis Zierer
November 01, 2024 • Estimated Reading Time: 14 minutes
Your guide to the newsletter world — new stories every Friday. Brought to you by beehiiv.
Today’s guest is Rameel Sheikh, a first-time newsletter operator whose experience as a serial founder and COO has backed a run from zero just over a year ago to 28k subscribers and $30k/month in revenue today.
His is a story of “riches in the niches,” community-building, and constant experimentation. You’ll enjoy
In this issue:
📈 A two-pronged approach to growth; paid ads and community engagement
💵 Generating enough newsletter ad revenue to build more businesses
🤒 Breaking out of a months-long stagnation period as a solo creator
❓️ One of the best-designed new subscriber surveys you’ve seen
— Francis Zierer, Editor
We’re hosting a live show!
Creator Spotlight’s Francis Zierer and Dirt Media’s Daisy Alioto will host journalists from three worker-owned publications at the forefront of independent media — Hell Gate, 404 Media, and Defector.
Join us at 7:00PM on Saturday, November 16th, in downtown New York City.
All proceeds go to the National Writers Union Service Organization’s legal fund protecting freelance journalists.
A logistics background sets the stage for a strong content business
“I come from a family of entrepreneurs. My dad has always owned gas stations and businesses. All my uncles and aunts, a hundred family members, no one has a job. Everyone has their own business.
When I first got my Uber job, I was getting so much pressure from everyone, like, ‘You're wasting your time. Please quit your job.’”
Right out of college, Rameel Sheikh started working at Uber Freight, the rideshare giant’s enterprise logistics product. Three years later, he quit to start his own business, which he was able to sell after just one year. He repeated this play before moving to New York to become a fast-growing software startup's chief operating officer (COO).
Two years later, with no job lined up, he quit again. His wife was pregnant, and it seemed foolish not to move back to Houston, where they could raise their child with “about 100 family members in a 15-minute driving radius.”
That was one year ago. Since then, Rameel has built a thriving business, which he says is currently bringing in around $30k per month, all around a newsletter called The Bottleneck.
“Riches in the niches”
Rameel was never a content person, not a LinkedInfluencer or Twitter talking-head. But he wrote a 359-word tweet when he left his job — about 59 more words than he had Twitter followers at the time — laying out his story. The coming baby, why he left, his plans, his intention to build in public.
The tweet stated one goal: “get to $10,000 monthly revenue by January.” He’d have 4 months to do … something: “I'll be exploring all kinds of ideas, big and small. Whether thats launching a new SaaS tool, agency, newsletter, I don't know yet.”
The tweet went, for him, viral. About a dozen multi-thousand-follower entrepreneur types popped up in the replies to congratulate and encourage him. His DMs filled up with job offers and consulting gigs, but he missed being a founder and wanted to see what he could spin up.
A closer look at The Bottleneck’s content
The Bottleneck is a prolific outlet. The first post in the archive came 421 days ago, and Rameel has published at least twice per week since. There are three types of content:
Ops tactics: Short (<500 words), opinionated recommendations on how to deal with a specific operations-related issue.
Case studies: Longform (~2,000 words), researched articles on operations practices at specific companies.
Interviews: As an experiment, Rameel joined another founder in cohosting an interview podcast called Operators Only. He turned each episode into a summary newsletter.
Growing the newsletter
For somebody with no experience making public-facing content and no real social media following, it took remarkably little time for Rameel to go from 0 to 21,000 subscribers.
Paid growth
As COO at Firstbase, Rameel learned how to run paid ads through Meta, at one point managing a “couple hundred thousand-dollar budget.” He applied what he’d learned to The Bottleneck.
“I decided to take on a few consulting jobs to funnel that money into paid ads, making sure there would be a payback period of one month.”
Organic growth
Rameel found was that nobody was really writing to or for COOs and BizOps folks, but there were some communities built around the topic; he participated in earnest.
“I wrote into these communities, just saying, ‘Hey, I've written this thing,’ or ‘I'm interested in talking to other operators to see what topics they would wanna learn about.’
I was finding a lot of enthusiasm for the topics, or at least the newsletter itself.
I would usually even get a couple of dozen comments in the beginning, like, ‘Dude, your content is terrible, this is so bad, but I'm subscribing because I identify with this group of people that you're writing for.’
This is a classic case of ‘don’t kill the part of yourself that’s cringe, kill the part of yourself that cringes,’ Of just ‘posting through it.’ His work was flawed, but it was an opinionated product in a hungry market.
Six months wandering the plateau
If you look at The Bottleneck’s growth graph, you’ll notice that it was stuck for half the newsletter’s lifetime, even sliding on the downslope for some months.
“On a personal level, I got in a funk.
You have to understand — I go from being a COO, someone who's always in the background, not really looking for the spotlight in any way, to writing for an audience of 21,000 people. I’m still not expecting this to become an actual business.”
The solution really couldn’t have been simpler: talking to people. Rameel reached out to other newsletter operators who’d been doing it longer than him and asked for advice. They essentially just affirmed he was on the right path and encouraged him to keep going.
Newsletter Community Consultancy Venture studio
Rameel says the purpose of The Bottleneck and all current and probably future businesses built around it is “to help early-stage BizOps professionals get better at their work.”
Helping BizOps professionals may be the compass, but the point is to experiment, build, and launch various business ventures monetized towards that end. As he writes in his first-anniversary post, he’s already launched several businesses atop it, most of which he’s already decommissioned.
Consulting gigs generated the initial startup capital, but the newsletter itself is the platform upon which everything else is meant to build; it holds a captive audience of 28,000 (and counting) upwardly mobile, high-value professionals.
Rameel prices ads against that audience on a CPM basis and currently has four offerings:
The Bottleneck’s ad products at the time of writing.
Featured placement in a Thursday (Ops Playbook) edition for $1,200
Featured placement in a Sunday (longform) edition for $1,200
Featured placement in three issues for $2,800 (10% discount)
A dedicated Sunday deep dive about a specific company for $3,000
If he’s selling out every week — which is not always the case and sometimes he advertises his own services — that’s $9,600 for a four-week month; the newsletter itself directly generates a third of his current $30k/month revenue.
Cornerstone — an exclusive membership club
The first business arm to be built on the back of The Bottleneck is Cornerstone. Like Chief or Hampton, it is a vetted, higher entry fee members club for a specific type of professional — in this case, executive-level operations professionals at companies with some millions in funding or revenue and at least 10 employees.
This was initially a Discord community accessible by paying $10 per month. It launched in February; by June, it had become Cornerstone.
“Cornerstone was the first product that came up because a lot of these operators are not only lonely at the top, that they're actually not able to commiserate with other members of their team.”
Cornerstone’s core offerings
Future ventures
After sending the first issue, Rameel says, it took him about nine months to replace his previous base salary. The newsletter and surrounding businesses provide more than enough to support his young family; he continues to reinvest the rest in the business and experiment further
Has he reached anywhere near the top of his market? No, he estimates there is a ceiling in the “couple of hundreds of thousands,” looking at groups like a project management subreddit with around 160,000 members and a LinkedIn search of operations professionals that surfaces five to six million individuals.
“I’ll keep gathering as many folks into The Bottleneck as possible. People are really enjoying what they're reading.
I learn about their pain points, their struggles, what they might want or need, what they might want to spend money on, and then provide those products or services or partner with other people who could.”
COOs are not a front-of-house bunch, generally, and Rameel’s instinct tells him not to break that, but it’s a question that never leaves him — whether to lean more into a creator persona or keep operating behind the scenes. Regardless, he’s answering the question that matters: converting attention to revenue.
Connect with Rameel on LinkedIn or at [email protected].
Read and subscribe to The Bottleneck.
For the full story, listen to our podcast or watch it on YouTube.
🎙️ Rameel had much to say about his operation, and it was impossible to fit every topic we touched on in this newsletter. Listen to the pod for:
💔 All the spinoff businesses he’s tried — what’s worked and what hasn’t
👀 Thoughts on building a business on-camera vs. behind the scenes
💵 A full breakdown of all the ways the business makes money
Listen on your preferred podcast platform or watch on YouTube.
Making gathering audience data fun for the audience
The Bottleneck has an excellent onboarding survey. Rameel shared these numbers from just the last four weeks:
75% open rate for the email — around 6,500 people received it.
23% click-through rate to the quiz — around 1,300 people filled it out.
It comes in an email titled “⚙️ Free Goodie Inside” — the “Goodie” in question is a BuzzFeed-style personality quiz — “What’s your Operator Style?”
The front page of The Bottleneck’s onboarding quiz. To see it for yourself, subscribe.
Sixteen light A/B-choice questions about project management, workflows, etc., that are more fun — the personality quiz portion
Four high-signal A/B/C/D/E-choice questions that look more like a traditional onboarding survey, getting at particular pain points that signal what type of content and services participants might want from The Bottleneck
Four personal questions: first name, last name, email, and job title
“It's actually a Myers-Briggs personality quiz for ops folks.
I even say within the email, ‘Hey, I know this is super cringe, but I know this is also really fun, go do it.’ And you can see people really love that; they click into it.’
In other words, sugar for the pill; make data self-disclosure fun. It’s entirely replicable:
Identify, based on your audience’s interests, what would flatter them
Create a few bespoke, tongue-in-cheek personality archetypes based on that
Build a quiz based on those archetypes; add additional personal disclosure questions
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