Entrepreneur & Investor.
Entrepreneur & Investor.
recap of 2023

Issue #85: Recap of 2023

NOTE: this was a past issue of my weekly newsletter, Timeless Gems. Join my free mailing list so you don’t miss out on future issues.

Today’s gem is a recap of my 10 favourite gems from 2023. But before we dive into it, I wanted to reflect a bit on this weekly newsletter.

There are now around ~3,500 subscribers on my mailing list, I appreciate all of you who tune in each week. I use this weekly newsletter to share pieces of information I come across or dig up from my archive. Articles, book snippets, graphs, podcasts, interview excerpts, and letters that contain lessons/wisdom for entrepreneurs and investors.

This newsletter, named Timeless Gems, comprises of:

Timeless: content that’s relevant for many years to come and has been relevant for many years prior. This is in contrast to all the noise that typical investor-focused newsletters contain like recent events, temporary developments and the latest trends (hype).

Gems: content that’s bite-sized. I know we are all busy and our inboxes are flooded with all sorts of stuff. I wanted to make these emails something subscribers can digest in just a few minutes at most.

I also use this newsletter to share my thoughts, reflections and take “notes in public”. On top of being an enjoyable hobby, this newsletter has benefited me in 3 ways:

  1. Audience. I’ve talked at length about the incredible benefits of having an audience. It’s been a valuable source of opportunities, deals, ideals, capital, talent, network, access, and much more. Having an audience is a competitive advantage for any entrepreneur/investor.
  2. Writing. It’s like a muscle, if you don’t regularly train it, it will not improve. Writing is a vital form of communication, in work and life and can deliver clarity in thinking that no other tool can provide.
  3. Reflecting. This newsletter allows me to reflect on the information I consume. We all save great content or take valuable notes and promptly put them away only to be quickly forgotten forever. Pulling something out of my archive each week is a great exercise in re-internalizing important lessons.

So now let’s jump into my 10 favourite gems from 2023. In no particular order…

Outsider CEO Commonalities: A chart from the book The Outsiders that compares common traits across 8 legendary capital allocators. One trait that stood out to me was “tax focus” so I added some discussion around this.

Thomson Newspapers: This is my favourite article I read last year, a must-read for anyone interested in serial acquirers. It’s a 2-part writeup on Roy Thomson and his newspaper rollup. Roy and his business served as inspiration for Mark Leonard and Constellation Software.

Business Returns vs Investment Returns: Discussion around ROIC vs IRR, and how the quality of the business can differ from the quality of the investment.

Rarity of Sustained Growth: A chart from the book Get Smarter which shows the low survival rate of growth. A great reminder to avoid over-projecting recent growth too far into the future.

RIP Charlie Munger: A tribute to the late great, a handful of my favourite quotes and clips from Charlie.

Serial Acquirers: Took some notes on similarities I’ve noticed across high-quality serial acquirers like Constellation Software, Mainstreet Equity, and TerraVest Industries.

Sam Zell On Assessing Deals: An anecdote from another late great (P.S. can’t believe we lost 2 of the greatest in 2023). This is an important framework for all investors/dealmakers. Highly recommend internalizing this.

Howard Marks on Long Run vs Short Run: An anecdote on investment performance over the long run vs short run. Incredible framework. Read this if you are susceptible to FOMO and get envious when you see another investor’s outrageously high 1-year return.

The Harsh Truth About Startups: Some discussion on starting a business which requires venture capital. Originally posted on my Twitter, it went semi-viral so I decided to turn it into a long-form email.

Thorndike’s Rule of 10: If you’re an investor in B2B businesses this is for you. It’s a great framework for assessing quality businesses for sale at an attractive price.

And that’s it! Thanks again for being a subscriber, I look forward to sharing more timeless gems with you in 2024.