In this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo sit down with recruiter and entrepreneur Dylan Scroggins to discuss his unconventional path from software sales to launching his own recruiting firm, Kalmar Group. Dylan shares how his experience in sales, his exposure to the SMB and ETA communities, and a pivotal decision not to buy a business led him toward building one instead. The conversation explores what entrepreneurship truly looks like—its realities, risks, and rewards—as well as how Dylan helps small business owners find and develop leadership talent through intentional recruiting.

They discuss:

• The lessons Dylan learned at ETA Bootcamp that made him realize he didn't want to buy a business
• Why recruiting is a critical yet undervalued function in small business leadership
• The emotional and practical challenges of starting a business while raising a family
• How to evaluate whether you should buy, build, or lead a company based on your strengths and stage of life
• The value of intentional hiring and how owner-led businesses can think strategically about talent acquisition

Support our Sponsors:

The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager 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/

Links:

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

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

Topics:

(00:00:00) - Intro (00:02:21) - Dylan's career journey (00:04:02) - SMbootcamp (00:05:34) - Launching Kalmar Group (00:11:58) - Balancing entrepreneurship and family (00:16:41) - The reality of entrepreneurship (00:25:02) - The challenges and rewards of recruiting (00:30:37) - Support systems and family dynamics (00:33:35) - Navigating emergency work and boundaries (00:37:58) - Understanding the role of recruiters (00:40:57) - The importance of a recruiter in SMBs (00:46:21) - Confidential searches and client expectations (00:53:13) - Recruiting misconceptions and client education (00:57:57) - Pricing and payment structures for recruiters (01:02:57) - Final thoughts and contact information