RO Letters #3

Originally published on 04/08/2025

Dear reader,

I hope your summer is going fantastically well. Mine is.

After manually assembling the RO locomotive in a warehouse for over two years, I feel like I’ve finally put it on rails and turned the engine on. It’s not at full-speed yet. The engine is sputtering in ways I didn’t predict, meaning I spend a lot of time manually investigating problems I didn’t anticipate. I have to fix these things while the locomotive is in motion, restricting how fast I can go. On the other hand, some problems I anticipated simply didn’t happen or if they did, were a piece of cake to manage.

Since I’m not going fast yet, I spend a lot of time comparing different maps and deeply reflecting on which one I want to follow. I’ve opted for the map that takes the longest, but goes the furthest. I envision the RO to be the last company I ever build, replete with various digital and physical products underpinning the global startup scene, which I view as this century’s most important economic sector. “Conglomerate mentality”, as I put it in RO letters #2.

Rail metaphors aside, here are some updates from July 2025.

On the fundraising side, we cashed in €15,000 in July, which brings the total raised to €39,000. We’re welcoming two new investors:

Another €20,000 cheque has been signed by both the angel investor and myself, with the wire supposed to arrive in August. This means we’ll cross the €50,000 mark at the end of this month. The €300,000 target remains unmoved. We’re ~20% there.

I’m confident that the multiple, ongoing conversations I’m having will push us to the €100,000 mark fairly soon. From there, I’m betting on a snowball effect of existing angels introducing me to new ones, and the beginning of conversations with family offices that can put in €50,000+ cheques to accelerate the fundraise.

I’ve been emailing Xavier Niel’s (a French billionaire who owns France’s largest newspaper, Le Monde) family office. They said I should get back to them when I’m a bit further advanced, and that they could potentially close the remaining €50,000-€100,000.

This is an email exchange, not a term sheet. I’m well aware. What excites me is that they’re responding, reading what I have to say, and want to stay updated. Surely, I can find a couple of other family offices candidates with the same interest. If you know any, do respond to this email.

Now, time for the customary, scattered reflections from last month.

Qualitative insights are the RO’s bread & butter

This month, I read “Queen of the Oil Club”, a biography recounting the life of Wanda Jablonski, an American journalist who founded “Petroleum Intelligence Weekly”, a publication known as the bible of the oil industry.

The parallels with the RO were stunning. I picked up on a few, which I’m keeping in mind while we scale the RO.

First, Wanda covered an industry which quickly globalized. As appetite for oil grew, Western oil companies both pumped and sold oil in a growing diversity of places. This globalization came with a flurry of localized complexity to decipher. Dealing with the Saudis differed from dealing with the Iranians. Rulers were different, context was different, political systems were different, culture was different, language was different.

Wanda’s reporting shook Westerners’ simplistic orientalist views (another great book I read this year was Edward Said’s “Orientalism”) about the region. It also gave oil-producing nations better information, insights into how their Western oil overlords thought. This crucial need for local granularity in a rapidly globalizing economic sector fits with the global startup scene the RO is covering.

Second, while Wanda included exclusive data in her reporting, that wasn’t her publication’s main value proposition. What Wanda gave her readers was an exclusive look into how other market participants, whom readers couldn’t interact with due to lack of time, geographical distance, or simply the fact they didn’t know them, thought.

These textual (as opposed to numerical) insights could include the rationale behind a decision, an explanation of how someone dealt with a problem, an expression of qualms, or an outline of future plans. These qualitative insights is what the RO focuses on. Other actors will take care of the chunky data products. If we glean exclusive numerical data, we’ll share it of course. But it will be an enhancer to the qualitative insights we provide, not a replacement.

Lastly, Wanda’s work shaped narratives. One of the RO’s mantra is “change minds and redirect flows of capital”. Many of Wanda’s articles gave an outlet for government officials in oil-producing nations to expose their frustration with the extractive terms imposed on them by Western oil majors. The story goes that Wanda even introduced two men (a Venezuelan and a Saudi) who were foundational in the creation of OPEC. Wanda’s reporting led Western majors to, gradually, recognize oil-producing nations as sovereign nations rather than all-you-can-eat oil buffets.

I know for a fact that the RO’s work is changing people’s minds. When RO subscribers from Harvard Business School read an RO story about a Syrian founder recounting the difference between the Assad and post-Assad Syrian startup scene, they have a richer, more complex view of Syria than before, when the only Syria-related articles was New York Times pieces pounding on how messed up, violent, screwed Syria was.

I caricature. But I will stand on the fact that RO articles give readers a more realistic, useful, granular, optimistic understanding of countries they usually understand through the stereotypical, essentializing ‘war, poverty, violence’ prism many Western legacy media seems keen on recycling over, and over, and over again.

Entrepreneurship as the mix of the most interesting and most boring tasks ever

I spend time trying to understand what makes a good founder. The answer is subjective, because “good” is tightly tied to one’s inner value system. Some might see a good founder as someone who maximizes the economic upside of their company, disregarding the negative, societal externalities the company creates. Others might see a good founder as someone who places the “mission success” of the company above the well-being of its team.

At my very humble level of managing a grand total of 0 full-time employees (but an increasing number of people working with the RO in various capacities), I set a holistic target for what makes a “good founder”. I want the company to be societally useful, financially successful (mostly to reinvest in the usefulness of it), and a place where people feel cared for, intellectually stimulated, and personally improving.

That was a slight tangent. One of my realization’s this month has been how critical it is for a founder to be both capable of unique, high-brow personal vision setting while also assiduous at the most mundane, boring tasks. You need both.

One of those boring tasks is following up with people. Circling back. Bumping up. Gently nudging. Following up is simultaneously mission-critical and extremely mind-numbing. It’s counter-intuitive how such a simple, boring task can make the difference between someone buying or not, someone investing or not. All of the work you put it can be rendered useless if you don’t send that 4th freaking follow-up email.

I’ve now internalized that this following up has to get done no matter how boring it is, and that it is just as important as the very fun, stimulating activity of writing these RO letters. These follow-ups can’t be automated (at least I don’t them to be) because there’s always a mini-personalization element I want to add to them.

I’ve found a little strategy for myself. I keep a to-do-list with all of the follow-ups I am due for that day. I set 30 minutes aside, get my speaker out, and blast house music while I diligently write one stale “hey, gently bumping this up, hope you’re well” email after another. I turn my room (aka RO international HQ) into a mini nightclub while I get the follow-ups over with.

Within the 30 minutes, I usually get 1-3 responses that actually move the needle on a specific topic. That instant gratification combined with the festivity (aren’t you jealous?) yielded by the (excellent) blaring house music playlist curated by my sister turn a dreadful daily ritual into a semi-enjoyable one.

Successfully doing a thing once is a potent gateway drug for whatever that thing is

In the past two months I’ve proven to myself that I can:

Maybe this is a weird personal quirk but once I manage to do something once, I’m fully convinced I can do it again, a thousands times over. But, and this is the important caveat, until I haven’t done it once, I anguish over my capability to do it at all.

I now direct all of my energy at getting a single win in something I’m still unsure of being able to do. Because once I do that, I have somewhat of an irrational confidence in my ability to keep doing it till the end of time.

This is why, until December, I’m 100% focused on converting Harvard Business School from their current free Realistic Optimist pilot to a paid subscription. Theoretically, I could go around other universities and open up a bunch of other free trials. But I don’t have that intense conviction that RO can sell subscriptions to universities yet.

What I do know if that once I sell a subscription to Harvard, I’ll have a burning confidence in being able to sell an RO sub to any university in the world (the fact that it’s Harvard helps). While I focus on Harvard, we’ll keep selling 1-5 seats subscriptions to VCs, whom I know we can sell to (9 VCs have already purchased team RO subscriptions).

This single-minded, obsessive fixation on the “first-win” is beneficial. Plowing all of my energy and focus into getting that very first win avoids shooting wide and diluting my chances of getting that first win in the first place. And that first win is all I need to fill up my tank to the brim with the motivation and self-confidence that I can get the 1000 next wins.

This is true of these RO letters. When I sat down to write the first one, I was unsure whether they would be a waste of my time or not. I got some nice encouraging messages on the first one, but nothing that truly moved the needle (at least visibly). I was still unsure of its utility when I wrote the second one. But on the second one, a potential angel I’d been chasing for weeks read it, responded enthusiastically, and booked a call. I finally got to pitch him.

That “first win” is enough fuel for me to write the next 998 RO letters.

Thanks for reading. That’s all for this time. I’m still fully focused on fundraising in August, with the hopes of opening up a ton of new conversations. My plan is then to start actively prospecting and selling subscriptions again in September, while I continue and convert some of these summer conversations into investments on the side.

If you receive this email, there’s a high chance I believe you’d be interested in investing in The Realistic Optimist. If that’s the case, let’s chat. Minimum ticket is €5,000. If you’d like to learn more, feel free to book a 30 minute call with me here.

And if you can’t invest but know someone who might want to, please feel free to forward them my deck (here is the link) or/and intro me at [email protected]

Enjoy your summer and I’ll talk to you in September,

Tim