What a Successful 20 years in SMB Looks Like - The Intentional Owner #26

In this episode of The Intentional Owner, cohosts Kaustubh Deo and Sam Rosati take a reflective look at the realities of small business ownership, personal growth, and the long road toward sustainability. Their conversation begins with an honest assessment of the emotional cycles that define entrepreneurship and evolves into a thoughtful exercise in imagining advice from their future selves. Along the way, they explore comparisons with peers, the tension between ambition and personal values, and the challenge of balancing financial security with meaningful control of time. They also discuss delegation, team building, and what it takes to create optionality as an owner. They discuss: • How Kaustubh and Sam would advise their younger entrepreneurial selves • Why comparisons with peers can both motivate and distract • The ongoing struggle to balance work, stress, and long term sustainability • Lessons learned from early management challenges and evolving values • The importance of building team capacity to reduce day to day volatility • Opportunities for nonlinear growth, including new service lines and commercial work • How long term financial security shapes decisions and personal fulfillment 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/ 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 Topics: (00:00:00) - Intro (00:02:24) - Introspection and entrepreneurial mindsets (00:06:18) - Comparing journeys and business strategies (00:11:10) - Balancing work and personal life (00:19:02) - Evaluating financial security and time independence (00:29:41) - Looking ahead: Future goals and reflections (00:31:35) - Balancing the emotional rollercoaster of small business ownership (00:32:57) - Delegating tasks to manage business setbacks (00:35:29) - Reflecting on business growth and future expansion (00:38:03) - Exploring non-linear growth opportunities (00:39:43) - Challenges of adding new service lines (00:47:08) - Considering commercial and residential market differences (00:53:54) - The importance of optionality in business strategy (00:56:22) - Tax and financial management insights (00:57:55) - Concluding thoughts and future plans