Four Years of Investment Talk

Investment Talk turns four, and my thoughts on why you should write more

This time last year, I reached a milestone of 20,000 readers at Investment Talk and shared my eleven learnings for fellow writers. Despite my best efforts, the newsletter has grown. Over the past 6 months, I deliberately pruned ~5,000 subscribers to focus on the quality of readership and today Investment Talk is read by more than 23,700 investors across 169 countries. I offer my continued thanks to those who frequently read and support the newsletter.

After revisiting my thoughts from last year (shared below), I stand by those remarks. I have continued to subconsciously lean on them. Number nine of my list in 2023 was ‘change things up’. Then, I was alluding to my decision to start building the supporter base of the newsletter again, after nullifying it the year prior. While the supporter base is considerably more modest than its peak, it’s better than where it was in early 2023, and I enjoy writing considerably more.

1. Writing is learning

2. Don’t underestimate network effects

3. Be Genuine, and give more than you want back

4. Finding your own voice is hard, but worth It

5. Realise that nobody cares about you

6. Don’t sweat the bad days

7. Tell people when their work is awesome

8. Readers are awesome

9. Change it up

10. Saying less can sometimes say more

11. Enjoy yourself

Two things I have done to change things up in the last 12 months. One, I started to focus more on the supporters of the newsletter to make this a sustainable outlet. They now receive 60 to 80 articles per year, monthly issues of the TLDR, and 6 months of Koyfin Plus. Secondly, to add focus to the Investment Talk newsletter, I created a sister newsletter called Notes to Self. This newsletter is a space for me to exclusively write about companies I own from a shareholder’s perspective. No deep dives, no more than 1,000 words. Investment Talk will remain a place for me to share articles that get deeper into the weeds. But sometimes I want to rattle off some notes in an informal manner, and Investment Talk never felt like the right place to do that. This has helped me mentally separate the two activities and Notes to Self now has more than 250 subscribers.

This year’s single learning

In place of a list of learnings, this year I will share just one; the benefit of writing inside of a journal. I’ll illustrate why I think this is important by sharing some of my notes from the last few years; specifically the notes I wrote to myself in 2022 when liquidity evaporated from the VC market. At the time, I was working for a small start-up, which gave me a front-row seat for what was about to unfold. I am grateful for this experience for various reasons, but most of all because I had a great mentor. As a younger man, I had read about the importance of mentorship in countless books. I wasn’t aware of how one could find a mentor. Do you reach out to them first? Does everyone experience mentorship? Do they float down from the heavens and bless with your worldly knowledge?

The company and its primary mission were ultimately unsuccessful; depending on your definition of unsuccessful. Nonetheless, it was a whirlwind experience that taught me more in a short space of time than I had ever experienced before. This mentor taught me a great deal about working in smaller, fast-paced, companies and helped me understand the dynamic between a start-up, its backers, and the broader funding environment. The advice was always candid. Little did I know it at the time, but this helped me a lot when I began to migrate towards the role of a product manager. One of the simplest pieces of advice they gave me was to pick up a notebook and pen and write in it now and then. Despite my habit of writing daily to an audience, this was a practice that I hadn’t adopted before.

Entries needn’t be submitted on a regular cadence. The topic matter could be about anything; work, life, relationships, goals; whatever your internal urge willed you to write. And so I did. At times my entries would be weeks apart. Sometimes they would fall months from one another. The important catalyst was that I only wrote when I felt compelled to. Naturally, this meant that whenever I did make an entry it was because of some heightened sense of emotion. Whether that be excitement, anxiety, concern, frustration, etc. It meant that each entry had a purpose; a message that it wanted to convey to my future self. Having done this for several years now, I occasionally read back through the entries. The topic matter is varied but tends to gravitate towards career, life goals, relationships, appreciation, mistakes, and occasionally some notes on investment processes. I think this practice is excellent and allows you to learn more about yourself in an honest and open matter.

One particular sequence of entries, stretching over several months, occurred in 2022 while I worked at this company. They had recently raised a Series A when I joined; at a valuation that was, in hindsight, not one which would fly today. Following the Fed’s decision to raise rates in 2022, the VC market witnessed a regime change in liquidity that had not been seen for more than a decade. Gone were the days of easy money and raising rounds with no revenue. Suddenly, VCs were interested in earnings; not just how you are going to earn them, but WHEN. As mystifying as this might have been I recall even at the time, being in the centre of a whirlwind, I felt grateful to be able to experience such a rare occurrence at such a young age. The entries related to this specific time in my life began in May of 2022. The first, titled “Surviving” was a foreshadowing account of the need to hunker down as liquidity dried up. It proved to be prudent advice to myself for the months ahead:

“Liquidity has dried up in private markets, and VCs have become increasingly vocal about the need to ‘survive’ by reducing both cash burn and extending runway. I find myself fearing redundancy. As such, I have begun to put capital aside for such an occasion. A reserve outside of my invested capital - to survive for 6 months should suffice.

One of the lessons I learned from Ben Graham was never become a forced seller. That’s a great way to interupt the power of compounding”.

The entry proceeded to outline a plan for some leaner expenditure. A few entries later, in June of 2022, I wrote a page titled “What Matters”. In the aftermath of a hiring freeze, I figured I was next out of the door.

“My role remains in limbo until next week’s board meeting. A hiring freeze was announced last week. Underutilised software is being hunted down and cancelled, marketing budgets have been nulled. Labour is the next line item to be recalibrated to the new market enviornment. It all feels so painfully obvious in hindsight. After having a month or two to ponder the prospect of becoming a casulty in the grand lean-ification of the great inflation era, I have come to terms with it.

Mentality is perhaps a human’s most powerful tool. It navigates like a compass, but the ultimate path is dictated by the individuial. Life has no set coordniates, no norths and souths. Mentality can transform anxiety into excitement. Fear into motivation. Crisis into opportunity. Mentality is a gift that is granted to all, used by many, and mastered by few. Life is as serious as I want it to be. The way in which things are precieved, is dictated by me”.

Another month passed and no layoffs occurred following the board meeting. In early July I wrote that despite my job being safe for now “I remain in survival mode”. I remember feeling particularly anxious throughout most of that summer. Just ten days after that entry, I shared another.

“After assuming no layoffs ten days ago, it turns out 7 members of our 35-person team were shown the door”.

I proceed to outline the intimate details of our cash burn runway that was communicated to us at the time but will leave that sealed in ink. We now had breathing room, and I had survived. I concluded:

“My haste in ensuring I personally managed my own cash burn was not wasted, and I will continue to adopt this mentality going forward despite no longer fearing immediate job risk”.

It’s safe to say I maintained a healthy sense of paranoia for some time after that. It was a stern reminder that your world, your comfort, and your situation can be flipped in the space of a day. Nevertheless, I am grateful to have experienced it; being able to relate what I was reading in the market data to my own experiences. Experiences like this are rare, and all feed into the mosaic of lifelong learning. The entries related to this role soon subsided. Crisis averted, it was back to regular programming. Despite staying for another 12 months, I never journaled about it after that. By then, I felt my learning had begun to plateau, and as timing would have it, I found a new role with greater responsibility, security, and a mission that I was emphatically passionate about. I ultimately left the company the following summer, and they were soon acquired by a household name.

In contrast to writing frequently in a public forum, putting pen to paper is the truest form of self-expression you will find. On paper, you can be sincerely unfiltered; and say things you’d never dare to vocalise to others. As much as I try to be candid in this newsletter, I won’t lie to myself in admitting that there is an added sense of security in confessing something to a leather-bound piece of paper. It’s the truest form of self-reflection in what you feel at a moment in time; because there is no holding back through even the deepest subconscious fears over what others might think. Like a balance sheet, these entries are accurate at a specific moment in time and provide valuable insight into your thinking process. It’s fascinating, to me at least, to have a glimpse at my thought process during a time of crisis. The same can be said for reflections on investments I passed on, sold, or acquired.

Writing publicly has its benefits, but carving out time to write for an audience of one has its own too. For these reasons, this year I have decided I’d like to convert at least a single reader into this practice. I implore you to grab a journal, adopt this habit, and see what interesting glimpses into your past self you end up within a few years.

Thanks for reading,

Conor