#549: Learning the Business End of Business with Brian Kiley episode artwork

EPISODE · Mar 16, 2026 · 28 MIN

#549: Learning the Business End of Business with Brian Kiley

from Above The Business

In this episode, Bradley sits down with Brian Kiley, an insurance agency owner and longtime business leader with more than three decades of experience across multiple industries. From running bike shops to founding a nonprofit ministry and now leading an insurance agency, Brian shares the winding path that shaped his perspective as a business owner.They discuss the realities of the early years in business and the lessons Brian wishes someone had shared with him sooner. The conversation explores topics like slowing down as a leader, stepping out of the day-to-day whirlwind to think strategically, and the importance of defining core values before a company begins to grow.This conversation also explores the practical systems that help businesses grow. Brian shares how building scorecards and tracking the right metrics can change how leaders manage performance and make decisions.If you are building a business and looking for practical insights from someone who has spent decades learning through experience, this conversation is for you.Visit blueprintos.com/assets to register for the upcoming Above The Business Quarterly.Learn more about Brian Kiley:https://www.linkedin.com/in/brian-w-kiley/Check out the book referenced in the conversation, The 4 Disciplines of Execution:https://www.amazon.com/4-Disciplines-Execution-Achieving-Wildly-Important/dp/145162705XCheck out the sales book Brian mentioned, SPIN Selling:https://www.amazon.com/SPIN-Selling-Neil-Rackham/dp/0070511136Referenced by Bradley: The Road Less Stupid by Keith Cunninghamhttps://a.co/d/0g14dJCuThanks to our sponsorsCoach P ConsultingCoach P found great success as an insurance agent and agency owner, leading a large and stable team of top-performing professionals. Today, he shares the systems, delegation strategies, and specialization methods he developed along the way. Gain access to weekly training calls and mentoring at:https://www.coachpconsulting.comBe sure to mention you heard about it on the Above The Business Podcast.Autopilot RecruitingAutopilot Recruiting helps small business owners solve staffing challenges by taking the stress out of hiring. Their dedicated recruiters work on your behalf every business day. Optimizing your applicant tracking system, posting job listings, and sourcing candidates through social media and local communities. Save time, reduce hiring costs, and receive pre-screened candidates without paying traditional hiring fees or commissions.https://www.autopilotrecruiting.comMention Above The Business Podcast when you reach out.Direct ClicksDirect Clicks is built by business owners, for business owners. They specialize in custom marketing solutions that drive real results. From paid search campaigns to SEO and social media management, they provide comprehensive digital marketing support to help your business grow.Exclusive offer for listeners:https://directclicksinc.com/abovethebusinessGet a free marketing campaign audit where their team reviews your website, social media, SEO, content, and paid advertising, then provides actionable recommendations. If you partner with them, all setup fees will be waived.About Above The BusinessAbove The Business is hosted by Bradley Hamner, founder of BlueprintOS, and focuses on helping small business owners transition from Rainmaker to Architect by building systems, teams, and operations that scale without their constant involvement.

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#549: Learning the Business End of Business with Brian Kiley

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This episode was published on March 16, 2026.

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In this episode, Bradley sits down with Brian Kiley, an insurance agency owner and longtime business leader with more than three decades of experience across multiple industries. From running bike shops to founding a nonprofit ministry and now...

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