The Realities of Leading and Scaling Multiple Businesses - Palmer Higgins - Partner at Chenmark
Release Date: 08/14/2025
The Realities of Leading and Scaling Multiple Businesses - Palmer Higgins - Partner at Chenmark
The Intentional Owner
Palmer Higgins joins co-hosts Kaustubh Deo and Sam Rosati to discuss building Chenmark, lessons from operating small businesses, and maintaining a long-term approach to leadership. Palmer shares his early career in finance and a startup, the path to acquiring multiple companies with family members, and the importance of agency in shaping his career decisions. He reflects on the challenges of hiring operators, stepping into a CEO role without prior management experience, and the operational intensity of turnaround situations. The discussion also covers Chenmark’s philosophy on growth, capital...
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The Intentional Owner
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The Intentional Owner
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The Intentional Owner
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The Intentional Owner
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Podcast Announcement! - The Intentional Owner
The Intentional Owner
Quick Update for the listeners! We're excited to announce that we will soon be bringing guests onto the show, as well as moving to a release cadence of every other week. See you next Thursday!
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The Intentional Owner
In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack what it looks like to build a fulfilling life around small business ownership without sacrificing long-term goals. Framed around personal goal setting, competing priorities, and everyday tradeoffs, the episode offers a candid look at how both hosts are trying to design lives that support sustainability—not just scale. They share stories of recent chaos, from moving mishaps and work-life boundaries to surprise break-ins and activity trackers, all while reflecting on how much structure is enough to keep life...
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The Intentional Owner
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The Intentional Owner
In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack the concept of personal non-negotiables and what it takes to make business ownership sustainable over the long haul. What begins as a reflection on physical health quickly evolves into a broader conversation about habit formation, time prioritization, and the limits of willpower. Kaustubh shares his recent experience becoming a certified arborist while leading Blooma Tree Experts. The two reflect on the difference between project-based discipline and long-term personal routines. Together, they explore a...
info_outlinePalmer Higgins joins co-hosts Kaustubh Deo and Sam Rosati to discuss building Chenmark, lessons from operating small businesses, and maintaining a long-term approach to leadership. Palmer shares his early career in finance and a startup, the path to acquiring multiple companies with family members, and the importance of agency in shaping his career decisions. He reflects on the challenges of hiring operators, stepping into a CEO role without prior management experience, and the operational intensity of turnaround situations. The discussion also covers Chenmark’s philosophy on growth, capital allocation, and supporting CEOs for sustainable success.
They discuss:
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How Palmer transitioned from finance to entrepreneurship through small business acquisitions
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Lessons learned from failed operator hires and the value of developing leaders internally
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The challenges and rewards of running a company without prior industry experience
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Why Chenmark prioritizes long-term orientation over aggressive short-term growth targets
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Strategies for blending work and personal life to maintain balance and sustainability
This episode offers valuable insights for aspiring business owners and operators who want to build enduring companies while preserving quality of life.
Support our Sponsors:
Kalmar Group
The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Director to VP level hires in sales, marketing, operations, and finance across multiple niche industries.
Website: https://www.thekalmargroup.com
Twitter: https://x.com/thesmbrecruiter
LinkedIn: https://www.linkedin.com/in/dylanscroggins/
Aspen HR
Please contact our valued sponsor Aspen HR (www.aspenhr.com, [email protected]) for a quote on PEO services and a complimentary HR due diligence assessment
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
Chenmark - https://chenmark.com/
Palmer on LinkedIn - https://www.linkedin.com/in/palmerhiggins/
Topics:
(00:00:00) - Intro
(00:01:18) - Work-life balance and office chaos
(00:04:18) - Palmer's background and career path
(00:04:43) - The genesis of Chenmark
(00:08:53) - First acquisition and early challenges
(00:13:58) - The decision to leave finance
(00:17:00) - Exploring entrepreneurship
(00:33:46) - The first business acquisition
(00:42:15) - Taking charge: From search to CEO
(00:47:00) - The intensity of business ownership
(00:50:11) - Sustaining long-term success
(00:54:23) - Managing multiple businesses
(00:57:22) - Work-life integration strategies
(01:04:10) - The future vision for Chenmark
(01:16:54) - Fitness competition updates!