Dear reader,
I named last month’s RO Letters “cabin crew, get ready for takeoff”.
A month later, the RO aircraft is sputtering, shaking, and the pilot is deciphering the cockpit’s gazillion buttons in real-time. But ladies and gentlemen, we have liftoff.
I’ll never repeat the following maxim enough. To succeed, the RO needs to excel at two things: writing articles and selling subscriptions. January 2026 was invigorating because we improved at both. I also suffered from an existential crisis regarding our sales process which, while painful in the short-term, leaves us better off.
Today’s RO Letter menu:
Appetizer: An explanation of RO’s three subscription tiers, and the associated growth strategy for each one.
Main course: my sales existential crisis.
Dessert: A reflection on the RO’s editorial line.
The RO’s revenue stack
100% of our revenue comes from paid subscriptions. It is split in three tiers.
Individual, self-serve subscriptions (€9/month or €99/year)
We launched this on January 16th, 2026. I’m happy with the uptake so far. We’re approaching €200 MRR which is small but significant considering that:
This is self-serve revenue. No long sales cycle associated with it. It, quite literally, brings in revenue while I sleep.
This is recurring revenue. As MRR becomes more significant, it’ll provide a reassuring financial cushion for us to take risks.
The diversity of paid subscribers is insane. These first paid subs work at Speedinvest (global VC), Alaya (LATAM VC), Growsari (Filipino startup), BaadMay (Pakistani startup), Carta (global startup)… A student from Stanford and a student from London Business School also bought subscriptions.
Our TAM for self-serve subscribers, geographically-speaking, is massive.
Converting that TAM to RO paid subscribers requires some strategy (if you want to grab yours, you can do so here).
In that vein, we started working with Paul, who joins us on the tech & product side as a freelancer (to start). Paul has three missions:
Develop “shareability” features within the RO product to leverage existing RO paid subscribers as an acquisition channel. This “shareability” focus comes from this internal memo Aakash wrote, which I’m strongly aligned with.
Disclaimer: the memo includes many ideas we’re not acting upon like the “emotion” one. None of those Murdoch-like strategy for us, thank you very much.
Construct the RO’s data stack. Paul has plugged analytics tools into the website, crafted some RO data dashboards… These help identify where our website traffic comes from and how it interacts with our articles. This informs us on topics such as SEO, UX, growth, etc
Implement conversion-friendly UX. Our website was designed by me (ie: not great). The data we recuperate in 2. guides us towards creating user journeys that optimize seamless conversions into paid subscriptions. After Paul’s first audit of the website, there are many low-hanging fruits for us to pick in that arena.
Small group subscriptions (~2-20 seats)
These are RO subscriptions that companies (mostly VCs in our case) buy for their teams.
The ticket size for these subscriptions is too low to warrant a structured, dedicated sales process. However: many of these potential group subscribers lie hidden in our free and paid subscriber list. All they need is a little personalized call and a demo from me to make the jump.
On a weekly basis, I will manually go through our subscriber list and reach out to 25 relevant prospects. This should yield a steady flow of these subscribers, filling our coffers in a semi-predictable way.
Large institutional subscriptions (20+ seats)
For now, these refer to large RO subscriptions sold to universities. We have sold our first one (50 annual subscriptions) to this Ivy League school last month. I spent the month of January searching for intros to other schools, and we’ve gotten a few solid leads.
These schools don’t convert cold (not yet). We need to run a free trial, collect student testimonials, and use those to pitch the admin. Our Q1 objective is opening 10 university trials.
I’m confident we’ll get there. Our value prop for schools is crystal-clear: more and more students are interested in tech ecosystems beyond the US scope. However, their university library often lacks quality resources that cover such ecosystems. The Realistic Optimist plugs that gap.
Since we’re positioned as a quasi-journalistic publication rather than a data provider, our rates are generally much, much more competitive than the other resources universities librarians are used to buying.
If you’re interested in the RO’s university offering (whether you’re a student, professor, or admin), feel free to book a slot with me here or email me ([email protected])
My sales existential crisis
For group subscriptions and institutional subscriptions, I was dead-set on setting up a true “sales machines”. Replete with advanced outbound tools, data providers, AI-powered lead monitoring across socials, blablabla.
In January, I ended up spending more time benchmarking these various sales tools, drowning in their complexity, having mini-seizures when attempting to harness the bulky CSV files of “leads” I had “scraped”. I sent Aakash on a kamikaze mission of sending massive, generic outbound sequences to various universities we wanted to open. Abysmally low response rates followed.
Then, over the weekend, I listened to a podcast by Tyler Denk, co-founder of Beehive. Tyler writes Big Desk Energy, his own founder newsletter, which was the initial inspiration for these RO Letters.
Tyler explained how he spent an inordinate amount of time, during Beehive’s early days, doing manual, personal outreach to prospects. No automations, tools, AI-powered SDRs. Just a dull email grind.
I was immediately assailed by the tidal wave of my own stupidity.
What was I doing trying to implement enterprise-level sales processes for a company that logged a little over €2,000 in revenue last month?
Resolutely, I concocted my new sales strategy:
Just sell the thing, innit.
We haven’t deserved the right to automate any part of our sales process. Not until we reach €500K ARR. Which is an entirely arbitrary metric, but one which I feel we can attain by manual grinding (especially considering schools, which will yield contracts between €2K-15K). The first €100K will be gritty as hell, but we should be able to surf the intro/referral waves after that.
To close this interlude: I now dedicate 4-6h a week to quality, hyper-customized outreach to group & institutional subscriber prospects. I’m already seeing the results. This shall compound. I’ve even cancelled our subscription to the sales automation tool we used. No shortcuts.
The RO’s editorial strategy
The RO now publishes two types of articles:
In-depth, written interviews with founders & VCs around the globe (written by Aakash and I)
Long-form, researched articles on more macro topics (written by freelance writers)
We currently have four long-form articles in the pipe. I’ve been thrilled by the level of these writers and humbled that they choose the RO as their writing’s home.
These articles should come out in the following months. They will cement RO’s position as a respected, credible, global publication in this space.
On top of the excitement of publishing such great writing, these articles will likely create paid subscriptions spikes. To give you a taste, these are the four articles we’re working on:
An exploration of Japanese VCs’ activity in the African startup scene
An analysis of the Iraqi fintech scene, with a special focus on the regulatory component
A granular account of the “battery-as-a-service” model touted by many startups in East Africa
A questioning of European late-stage VC’s pertinence, especially in light of perpetually better-funded US VCs
If you want to receive these, you know what you have to do: become a paid RO subscriber here ;)
Conclusion
You might be left wondering about the title of this RO Letters (shedding my Gen-Z-ness).
Here’s the explanation.
My generation tends to over-romanticize the “creator economy” and profess disdain for “legacy” institutions, especially media.
The RO aims to become a legacy publication. Not a ‘creator economy’ one. We’re not snappy, “bite-sized”, engaging, fun. We’re long-form, serious, complex, nuanced, thoughtful.
If person cannot sit down and read for 15 minutes straight, they are simply not our target customer. That’s okay. Enough people can and want to spend 15+ minutes reading.
The generation I grew up made me vulnerable to falling into the trap of “new media”, publishing shorter, snappier, more visual, potentially polarizing content. We won’t fall into that trap.
We are a publication written for long-form readers. Period.
On that grandiloquent note,
See you next month.
Tim
PS: I appreciate the irony of my professed “departure from Gen-Z” while building the RO in this hyper-public, transparent, “informal” way (a very Gen-Z founder thing to do). Yours truly isn’t dogmatic - I also take some of the great things my generation equipped me with :)