RO Letters #2

Originally published 01/07/2025

I won’t be able to write a solemn, drunk-on-ambition memo like RO Letters #1 every month, so I’ve been brainstorming alternative structures.

This RO letter will feature multiple small sections, blending company updates with reflections.

Treating my personal finances as a VC-backed startup

The Realistic Optimist has cashed in its first angel checks, amounting to €23K. This is more money than I’ve ever had in a bank account to my name. Since I’ve been 19, my only rule has been to avoid that my balance drops below €1,000. That’s one hell of a buffer you might say. Yes, I am a prudent man. The truth is that I can cosplay extreme financial risk-taking, because if all else fails I can move back in with family and I’ll be fed (at least that’s been the case until now).

Since taking financial risks early likely correlates with chances of successes, and that downside for those financial risks is limited to personal frustration and embarrassment (in my 20s at least), why not max out those risks?

I’ve treated my personal finance as I would a VC-backed startup: spending a lot on (personal) growth, verging on bankruptcy, with an iron conviction that this will yield exponential returns (financial & personal) long-term.

While the money I’ve raised is obviously the RO’s money, those checks are a result of years of trying, failing, and losing money. My financial theory is slowly materializing. It’s about time, because I wasn’t far from eating into my €1,000 buffer.

Anyways, a further €36K are supposed to flow in soon. I’ve been having encouraging conversations with other potential angels, and I can feel the momentum building up. It’s full-push on fundraising until end of August now, with the 300K target unmoved. I need to find a couple of larger, 20-50K checks to accelerate the process. If you know anyone, reply to this email!

Angel investors backing out & emotional regulation

I’ve also experienced my first retractions: people who pledged a certain amount, who later reduced it or cancelled it. Others who I thought would definitely invest and actually can’t. There is no animosity here: angels are investing with their personal money, and they are free to do as they please. They each have valid reasons to retract. If I were in the same position and life priorities changed, I’d cancel my angel commitments. The sting I feel is more a logistical frustration than a philosophical one.

Enforcing a mental distance between verbal commitments and personal excitement has thus become a new habit. The founder journey is an emotional rollercoaster, and anything in the service of emotional regulation is welcome. That mental distance is one of those things.

This also plays into my company management. I’d previously considered verbal commitments as quasi-guarantees of future money inflows. I don’t anymore. I spend money pretending as if committed angel money won’t come in. I’m all the more elated when it actually comes through.

This ethos has already proven productive. For example, I set out to redesign the RO’s website, which needed a serious freshening up. I toyed with the idea of spending €5K and a couple of weeks on a freelancer.

Instead, I hunkered down for an entire Saturday, scoured for cheaper options, and managed to ship what I consider to be a decent effort for €156 (I bought an already made template and played with it). This took me a solid 6-7 hours instead of weeks of back-and-forth with a freelancer. Also, I made my new logo and visual identity in 15 minutes with ChatGPT.

The sweetness of first checks

I had this irrational fear of going through the company’s legal incorporation (for which my dad loaned me money), to then be met with a resounding €0 invested. Imagine my relief when the first wire transfers arrived!

I have deep respect and gratitude for my first angels, because they probably held the same fear when wiring that first check. What if their check is the only check I raise, and I go bankrupt in a month? They’re only putting in sums they can lose, but still. It takes conviction in my ability to take that risk. Some angels wait to see “who else” invested before sending the money. But first angels are a different breed. They didn’t ask who else had invested. They signed the contracts, wired the money, and trusted me. That puts them in a special category.

Shout-out to Juliette (ex-colleague, also basically a family member), Paul (my ex-boss), Robin (a reader), Bernardo (a founder I interviewed), and Gaspard (a friend, who pretended to invite me to dinner to ask me if he could invest). You’ve given me the initial fuel, both practical and mental, to kickstart this fundraise. I won’t forget that.

Taking advice

By virtue of pitching The Realistic Optimist an ungodly amount of times, I’ve received a deluge of advice. I used to take in that advice in an unrefined way, throwing it all into my brain and letting it marinate. Recently, I’ve crafted the inklings of an “advice filter”, which I consult before putting a specific piece of advice into my brain.

A blatant red flag is people who give advice in an authoritative manner. One cannot be intellectually-honest and 100% convinced of advice they give. The world is too complex for that. Either they are too lazy to enunciate the caveats, or they are delusional.

There is a clear difference between how founders and non-founders give advice. Founders almost always listen more than they speak, and prelude their advice with “take it or leave it, this is what I think”. They understand the frustration of interacting with someone giving firm advice that is either a) something you thought about 1,000 times b) something that’s utterly irrelevant to your current situation c) something that falls way outside of your values spectrum.

Another trope is to only listen to advice from people who’ve built something you aspire to build. I agree to an extent. Advice from people in your space is richer and more refined, because it is curated by years of relevant context and experience.

That being said, advice from people you love (even if they haven’t build a B2B media publication) is as important. These people understand your intrinsic, philosophical drivers. They also know a side of you which professional acquaintances have no access to.

A professional acquaintance might give you great, practical advice on how to achieve something. Your loved ones might question why you want to do it in the first place. My first port-of-call for advice is always my girlfriend.

My initial advice filter goes something like this: if the person doesn’t know you extremely well, or hasn’t built anything you aspire to build, take their advice with a chunky pinch of salt.

Building out the team

June was an exciting month because new people have or are slated to join the RO’s journey.

On the writing side, Aakash Athawasya published his first Realistic Optimist article on QuickLend, an Indian startup reinventing B2C lending. Aakash is a fantastic writer, and brings a wealth of knowledge, connections, and context on an ecosystem the RO has scarcely covered (India). Interestingly, Aakash’s future articles will cover ecosystems outside of India.

That’s my vision for the RO’s writing team: exceptionally talented individuals from around the world, cross-pollinating between different ecosystems, producing clear, insightful, unique writing for RO readers. If anyone jumps to mind, respond to this email!

I’ve also been having a couple of chats with Côme Chabaille d’Auvigny, who lives in Paris. He used to do growth at BeReal, a viral social media app that reached tens of millions of monthly active users. Côme is a compelling profile, because he brings a consumer growth, virality expertise which I haven’t explored yet (and that seems underutilized in a B2B context).

Our goal (if we start working together), will be to dramatically increases the RO’s brand awareness, drive free subscriptions, which I’ll then convert into annual, B2B subscribers. We’ll also have to conjugate those viral, hyper-growth techniques while maintaining the RO’s brand integrity.

We’ve had a couple of brainstorming sessions in Paris. Last week, I was able to pay for our coffees with the company card, a first. I diligently took a picture of the receipt for my accountant (another first).

I finally felt like a founder and yes, this is a stupid way of thinking about it because paying for a cappuccino with a company card doesn’t make you a founder, selling a product to customers makes you a founder blablabla… I know. Just let me have it.

Full-throttle on B2B

The Realistic Optimist has essentially been a B2B publication for the past 8 months. I’ve mostly sold subscriptions to companies, who buy annual subscriptions for their teams in bulk.

I don’t quite know why, but I oriented the first deck as “relaunching” B2C subscriptions. After hearing more “people don’t pay for media these days” than I could audibly handle, I’ve come to the conclusion that the RO was, indeed, a B2B publication. The final nail in the coffin for B2C subs was a conversation I had with Quentin Botbol, president of Indigo Publications.

Indigo owns four different, thematic B2B paid newsletters and if their shining new office is anything to judge by, it’s been serving them well. Their numbers are public, which confirms my intuition.

The predictability of B2B sales, the fact that I’m fighting for a slice of allocated company budget rather than with a person’s Netflix subscription, and the fact that you can charge for a year upfront brings the point home. B2B subs for the win.

As I reworked my deck, I realized this also made the market sizing slide more salient. The number of economic actors (companies, schools, governments) that will need to understand the global startup scene will increase exponentially over the next decades. These companies will need premium, qualitative information about this sector. Which is why they’ll buy RO subscriptions.

Conglomerate mentality

I’ve mostly been opposed to VC funding for the RO, because that type of capital doesn’t have the timeframe I envision for this company.

I want to build the RO into a conglomerate. That word is barbaric, stale, and evokes Nestlé baby powder scandal vibes. But its textbook definition perfectly encapsulates my vision:

I view the RO as the global startup scene’s informational backbone. It all starts with the current publication, which aims to become the no-brainer subscription economic actors in this space buy for their team/students.

More than an economic opportunity, this publication’s role is also to produce intelligent, incisive, scrutinizing writing that help readers turn the global startup scene into something societally-desirable.

As the publication grows, the RO will amass a global readership and cement a trusted brand. Both will serve as the fulcrum for new products such as:

This concludes RO letters #2.

The goal for July is to continue cashing in committed checks and continue working Circle 1 (networks, friends and family…). My estimate is that I can get to €100K from Circle 1.

I’ll continue to work on various grant applications, from which I believe I can glean around €50K.

Lastly, I’m starting a mass outreach campaign to potential angels with media experience, to fill in the remaining €150K. That will be a savvy mix between a brute number game and precise targeting. Those checks are unlikely to come in in July, but will hopefully yield some cash towards the end of the summer.

Other than that, I’m keeping up with the RO’s scheduled programming and I get on opportunistic, inbound sales calls to stay fresh. But 90% of the focus is on fundraising till the end of the summer.

Don’t hesitate to answer this email if you have thoughts.

See you in August,

Tim