Kaustubh Deo and Sam Rosati return for a wide-ranging episode that blends personal updates with deeper reflections on business building and investment philosophy. They begin by recapping Sam’s family trip to Hawaii and updating their ongoing fitness tracker challenge, before diving into a detailed reflection on their recent interview with Chase Murdock. The conversation explores Chase’s unique approach to building a HoldCo in Salt Lake City, emphasizing leadership, locality, and a low-leverage, high-growth strategy. From there, the hosts discuss the appeal and drawbacks of various HoldCo models, the nuances of risk management, and their evolving approaches to cash management, M&A, and side hustles. They close by reflecting on the power of writing and teaching as a tool for community building and legacy.

They discuss:

• Chase Murdock’s approach to building a local, low-leverage HoldCo and why it works

• The pros and cons of operating with a partner and staying in a narrow geographic market

• How both hosts are thinking about personal cash allocation, passive investing, and risk barbell strategies

• The case for buying small add-ons in industries you already know

• Building a long-term content and syndicate platform through consistent writing and investing

An insightful episode for entrepreneurs balancing operations, investing, and long-term life design.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00 ) - Intro
(00:01:10 ) - Hawaii vacation recap
(00:04:51 ) - Fitness and activity tracker update
(00:05:52 ) - Reflecting on the Chase Murdock interview
(00:19:39 ) - Personal reflections on business models
(00:22:23 ) - Diverse investment strategies
(00:32:53 ) - Risk management in investments
(00:33:13 ) - Cash management strategies
(00:35:02 ) - Approach to M\&A and industry focus
(00:38:35 ) - Sourcing and outreach in M\&A
(00:46:39 ) - Building a side hustle
(00:50:53 ) - The importance of creative writing and communication
(01:03:04 ) - Upcoming guest and conclusion