Margin of Safety Investing

Margin of Safety Investing

Share this post

Margin of Safety Investing
Margin of Safety Investing
The Capital Doesn’t Fall Far From the Pinetree
Copy link
Facebook
Email
Notes
More

The Capital Doesn’t Fall Far From the Pinetree

More than a Constellation Software copycat

Simon Handrahan's avatar
Simon Handrahan
Apr 17, 2024
∙ Paid
11

Share this post

Margin of Safety Investing
Margin of Safety Investing
The Capital Doesn’t Fall Far From the Pinetree
Copy link
Facebook
Email
Notes
More
1
2
Share

**Disclosure**: The author of this post personally owns shares in Pinetree Capital.

---

A Hidden Gem in the Investment World

In the vast universe of investment opportunities, there are those that shine brightly on everyone's radar and those that remain hidden, only to be discovered by the most astute investors. Pinetree Capital appears to be the latter. This holding company, which specializes in investments in public vertical market software (VMS) businesses, has demonstrated a remarkable ability to grow its book value over time (albeit in a lumpy way).

The firm invests primarily in minority equity stakes in public VMS businesses. The VMS part is the aspect where its Constellation Software DNA comes in. Where they differ is they do not buy whole businesses. Because of some net operating loss carryforwards, Pinetree is able to rinse and repeat without any tax drag for the time being. This strategy longer term is not as appealing as Constellation but it is something that very well might evolve with time. Because they are small they are able to concentrate in a dozen or so positions with relatively small businesses that are not at sky high valuations. You can also look to enter Pinetree itself at times when it is trading at fractions of book value. It recently traded below 4$ with a book value now approaching $6.

Damien, Son of VMS Gandalf

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 Simon Handrahan
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share

Copy link
Facebook
Email
Notes
More