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 Topics: 00:00 - Intro02:21 - Dylan's career journey 04:02 - SMbootcamp05:34 - Launching Kalmar Group 11:58 - Balancing entrepreneurship and family 16:41 - The reality of entrepreneurship 25:02 - The challenges and rewards of recruiting 30:37 - Support systems and family dynamics 33:35 - Navigating emergency work and boundaries 37:58 - Understanding the role of recruiters 40:57 - The importance of a recruiter in SMBs 46:21 - Confidential searches and client expectations 53:13 - Recruiting misconceptions and client education 57:57 - Pricing and payment structures for recruiters 01:02:57 - Final thoughts and contact information