Originally published 07/10/2025
Hello,
The RO’s seed round is coming to a close.
We recently welcomed Karim Jouini, one of France’s most active angels, as the RO’s newest investor. That puts the total cashed in at €74,000. We have an additional €35,000 committed, which should hit the bank account this month. Hopefully, October will mark the official close of the RO’s seed round, slightly surpassing €100,000.
Once that’s done, I’ll embark on a media announcement tour. My friend Ahmed made a good remark that the simple fact of announcing the round professionalizes the RO’s stature, helping sales down the line. If you have tips to share on announcing a round, please respond to this email.
As usual, below are some reflections on key topics from this month.
Selling our largest subscription ever
We recently received payment from A&A Collective, an African VC network, for the RO’s largest subscription to date (€460). This prompted a few reflections.
I might’ve underpriced it. I sold 14 seats for under €500, whereas an individual seat is technically €250. I felt jittery during the negotiation phase, impatient to close a great logo and what still is our largest subscription to date. A&A is a special client, since they aren’t a VC per se but rather a network, where members pay dues. I assumed they didn’t have a large budget, which was also a convenient self-justification of underpricing the subscription.
There’s another way to look at it. A&A readers now have a year-long RO access, non-renewable. Many readers work at VC firms of their own. If, when their A&A sub expires, a fraction of them buys B2B group subscriptions for their own VCs, my gambit is a winning one. These A&A readers are also additional nodes in the RO’s word-of-mouth web, which compounds.
What I learned from the A&A subscription is that, for clients where the benefit of selling a sub surpasses the subscription revenue (because of associated credibility, network effect), pricing strategy should be flexible.
But I recognize the temptation of going ridiculously low, just to “get the account”. How low should I allow myself to go when negotiating with Harvard when their free trial ends in December, for example? Advice welcome.
More than anything, the A&A episode comforts me in the superiority and flexibility of the bespoke, B2B group subscription pricing model.
Updates on RO correspondents
One of the seed round’s big cost centers is hiring RO correspondents from around the world. These correspondents have three tasks: write articles covering their region, organize RO events in their region, and attend events in their region on behalf of the RO.
The RO is already working with its first correspondent in Asia (Aakash), who’s been doing a fantastic job. I’m intentionally delaying the search for other correspondents until the seed round is officially closed. Working with Aakash is helping me craft the RO correspondent blueprint.
Some early lessons:
Differentiating areas where the correspondent has creative freedom (such as organizing events) versus areas where I maintain full, centralized control (such as final review of articles).
The compounding effects of covering a single region. Aakash is now fully focused on Asia and while it’s still early, I believe continuous coverage will turn him into the region’s reference on the topic. He’ll also be able to get any intro he wants. Each RO correspondent should be their region’s premier tech journalist.
The grind of organizing events: maybe Aakash and I have been unlucky, but it’s been a pain to organize events so far, digital or physical. I made the mistake of considering these events as “ad-hoc” opportunities rather than a repeatable objective. As a result, I mentally viewed them as “ad-hoc” opportunities rather than something to create processes around. That needs to change.
I’ll embark on a push to recruit 4-5 other RO correspondents once the round is closed. I’m well-aware this will create short-term chaos, quality assurance challenges, scattered initiatives from individual RO correspondents… But if we are to build a global-first publication, we need to learn to manage a global team. Intentionally stirring the pot is a great way to get started.
With Aakash, I’ve also already noticed my mind expanding on topics/initiatives I didn’t necessarily think of before. Adding more correspondents to the mix will create bursts of creative energy. It will be my job to harness them.
Setting up an outbound machine
The Realistic Optimist is a direct sales company. We’re not optimized for self-serve subscription. I want to get on the phone with prospects, understand their pains, negotiate group subscription pricing, iterate our positioning... Sales calls are also implicit market research, which is useful to me as a founder.
The first couple of years will be founder-led sales focused. RO correspondents will take care of the writing and top of funnel initiatives, but I’ll be handling sales. I want to build the company’s revenue engine from scratch and get my hands dirty.
September thus marked the beginning of setting up that revenue engine. Some early initiatives I took:
Setting up automated, weekly LinkedIn outbound campaigns via Lemlist.
Results have been decent so far, and I’ve already booked a couple of demo calls through campaigns I’ve launched.
My campaigns are divided between cold campaigns (targeting people I’m not connected to) and warm campaigns (targeting people that I’m connected with, follow me, have interacted with the RO’s content)
There’s still a bunch for me to optimize on Lemlist but there’s a hard cap. LinkedIn has weekly invitation limits, which means there’s a hard stop on your prospection numbers. I want to max those out safely, and turn Lemlist into a continuous source of qualified demo calls.
Setting up a Granola account
This is an AI notetaker tool for sales calls, which I’m quite impressed by. It transcribes the conversations, but then allows you to prompt the transcript for specific parts of the call, ask it where the prospect was reluctant or excited… I view it as a training tool to get better at the skill of sales.
This month, I’m going to open up the cold emailing part of my prospection strategy, playing around with tools like Clay. Cold prospection is one of those areas where AI is truly a multiplier, and I intend to make great use of it.
Overall, I’m setting up an outbound sales machine. Inbound will come from various initiatives, word-of-mouth, events organized by correspondents… But inbound is simply less predictable than outbound, at least at the beginning. We need an outbound machine that yields predictable new revenue month-over-month.
Our first churn
We got bad news this month, as one of our paid subscribers (Norrsken22), cancelled their yearly sub. They said they weren’t reading it enough, which can mean a ton of different things.
I’m investigating the issue and trying to get on a call with their team. It was quite unexpected, so there’s something I messed up on or didn’t follow attentively enough. It’s a good case study for me to tighten a few screws.
Closing remarks
Something I’m struggling is the concept of speed. Across the board, I feel like things are moving at an excruciatingly slow pace. Karim invested very quickly by all standards (less than a month between our first meeting and the money arriving) but it still felt like an eternity.
As a founder, I believe this is virtuous. I’m in an precocious position life-wise because of this clinical inability to stand still and relax. That constant sense of urgency is a powerful driver and I want to foster it, not tame it. What I need to improve on is harnessing that jitteriness towards productive decisions, not botched ones that end up slowing us down.
See you next month,
Tim