Brandon Comstock's Entrepreneurial Success Story

In this Inner Circle episode, Hector welcomes Brandon, a Calgary-based entrepreneur who built a landscape maintenance company with his partner Michelle, grew it to about 60 employees, and sold it around a year and a half ago, now living off the proceeds while building a niche software product, Site DNA. Brandon shares how their partnership worked by leveraging complementary strengths, why peer groups and mentorship mattered, and when the company shifted from survival to a real business as employee responsibility grew. He explains the power of specializing in condo maintenance and snow removal to simplify operations, training, and equipment, and discusses transitioning from field work to leadership by trusting strong hires and building repeatable processes. Brandon highlights structured planning (annuals/quarterlies), developing crews into financially literate managers, exit preparation, and the importance of vision, execution, recruiting, and pricing. Want in on the live Q&A? Join our OBS Inner Circle — where entrepreneurs connect, learn, and get their biggest business questions answered live. Join Today — don’t just listen, get involved! www.optimizebusinesssystems.com 00:00 Welcome And Guest Intro 00:56 Brandon Origin Story 02:19 Building As A Couple 05:43 Peer Groups And Support 07:58 From Survival To Business 10:09 Niche Focus Strategy 14:03 Leaving The Field Behind 17:22 Systems That Scale 19:57 Meeting Rhythm And PnLs 22:59 Deal Day Emotions 24:01 Build to Sell Systems 24:45 Exit Planning Team 26:38 Site DNA Overview 29:10 Niche Product Strategy 29:30 Freedom Through Execution 32:08 Vision That Attracts Talent 35:03 Lessons From the Journey 36:06 Scaling Gets Easier 37:49 How to Reach Brandon 39:07 Early Vision Reality Check 42:17 Closing Thanks and Q&A