Brian Hamilton—entrepreneur, philanthropist, and founder of LiveSwitch—shares his journey from mowing lawns as a kid to launching a fintech empire. In this episode, he breaks down what’s actually stopping landscape businesses from scaling, why self-awareness beats spreadsheets, and how showing up on time is still your best marketing tool.
“If you can manage people well and serve your customers like a maniac, you can screw up everything else and still grow.” — Brian Hamilton
[00:00] Introduction
Rob welcomes listeners and introduces Brian Hamilton:
Brian Hamilton is a nationally recognized entrepreneur, philanthropist, and advocate for small businesses. He co-founded Sageworks, one of the first fintech companies in the U.S., which was successfully acquired in 2018. Today, he is the founder of LiveSwitch, a leading communications platform using instant video to help home service businesses grow faster and smarter.
[01:38] From Snow Shovels to Startups
Brian shares how he went from shovelling driveways to building a tech company with a global footprint.
[06:25] What the Heck is LiveSwitch?
LiveSwitch helps landscapers do virtual estimates, document job progress, and even capture before-and-after footage for marketing—all through video.
[08:00] The Real Growth Killer: Not What You Think
Spoiler alert: it’s not money or employees—it’s a lack of business knowledge.
[09:42] The Only Two Skills That Matter
You want to grow from 10 to 50 employees? You’d better get sharp at leading people and wowing customers.
[12:43] The Mirror Doesn’t Lie
Why being a better boss starts with being honest about your own blind spots.
[19:20] Guard Your Mouth, Grow Your Culture
If you bash your customers in front of your crew, your team will follow your lead (and not in a good way).
[22:42] Do the Work Even If No One’s Watching
A landscaping story from high school reminds Brian why integrity still matters most.
[30:41] Train the Person, Not Just the Role
Developing your team means investing in who they are—not just what they can do with a shovel.
[36:00] Must-Read Business Classics
Brian’s two go-to books for any entrepreneur:
• How to Win Friends and Influence People by Dale Carnegie
• Think and Grow Rich by Napoleon Hill
[37:38] The Brian Hamilton Foundation
Helping people escape poverty through entrepreneurship—not pity.