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Jay Vasantharajah

Entrepreneur & Investor.

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Top 3 Books of 2025

Each year, I pick the top 3 books I read, write a small reflection on each, and share them with my mailing list. I will leave links to prior years’ top 3 at the bottom of this post. My top 3 book picks of 2025 (in no particular order) are as follows… #1 The New [ ] The post Top 3 Books of 2025 appeared first on Jay Vasantharajah .

Expensive Talent is Cheap

This concept took me far too long to internalize, but I wanted to share some thoughts on hiring in this post. The insight below is a combination of my own experiences and a book I read a while back called Topgrading. I highly recommend it, and I wish someone had recommended it to me 10 years [ ] The post Expensive Talent is Cheap appeared first on Jay Vasantharajah .

Long-Term Optimistic, Short-Term Pessimistic

That s my default answer whenever someone asks whether I m bullish or bearish as an investor. Here is what I mean by this Long-term optimistic Compound returns are made over the long run, so you need to be long-term optimistic if you want to make a lot of money it’s as simple as that. You [ ] The post Long-Term Optimistic, Short-Term Pessimistic appeared first on Jay Vasantharajah .

Why Debt Can Be a Source of Alpha

Why Debt Can Be A Source of Alpha Whenever private equity returns are compared alongside public equities returns, many investors chalk up any PE outperformance as levered beta or infer that, because of the use of debt, the returns don t count. That narrative treats debt as if it’s a simple multiplier, a button you press [ ] The post Why Debt Can Be a Source of Alpha appeared first on Jay…

Content Still Remains a Meritocracy

I met an impressive individual recently. He was your archetypal, super-successful finance guy. Went to Harvard, worked at Goldman, etc. Stacked resume. The topic of credentials came up, and how much they’ve helped his career, which obviously wasn t surprising. Credentials are rocket fuel Going to a top-tier school or working at a prestigious firm is [ ] The post Content Still Remains a Meritocracy…

Balance Sheets

In the most recent Berkshire Hathaway shareholder meeting, there was a gem that Warren Buffett dropped: I spend more time looking at balance sheets than I do income statements. Wall Street doesn’t pay much attention to balance sheets, but I like to look at balance sheets over an 8- or 10-year period before I even [ ] The post Balance Sheets appeared first on Jay Vasantharajah .

Hold Forever is a Flawed Framework

I often think about this (paraphrased) quote from Sam Zell: Every day you choose to hold an asset, you’re also choosing to buy it. Would you buy the assets you own at current prices? If the answer is no, then you should sell. The more experience I gain as an investor, the more this resonates [ ] The post Hold Forever is a Flawed Framework appeared first on Jay Vasantharajah .

Top 3 Book Picks of 2024

Each year I pick the top 3 books I read and share them with my mailing list. I will leave links to prior years top 3 at the bottom of this post. My top 3 book picks of 2024 (in no particular order) are as follows Pick #1 Private Equity Toolkit by Tamara Sakovska Tamara distills [ ] The post Top 3 Book Picks of 2024 appeared first on Jay Vasantharajah .

How To Build A Monopoly

I read Peter Thiel s Zero to One years ago but was too young and inexperienced to appreciate some of the key concepts articulated in the book. So I recently re-read parts of the book and wanted to share some important insights, particularly about monopolies. The book s intended audience is startups, but I think the concepts [ ] The post How To Build A Monopoly appeared first on Jay Vasantharajah .

Modern Toll Bridge Businesses

A little while ago, I shared a gem on the ​Detriot International Bridge Company​ with some discussion on ​Twitter.​ People asked for modern examples of this type of business, and some even concluded that these kinds of opportunities no longer exist. These businesses (and therefore investment opportunities) do in fact exist in the modern era. [ ] The post Modern Toll Bridge Businesses appeared…