September 20, 2026
This week I brought my friend Braden back onto the podcast. He’s a wedding industry lawyer, a repeat guest, and one of maybe three people I actually enjoy talking business with instead of performing it for an audience.
We covered a lot of ground, from employee classification and conflict, to juggling your priorities as a business owner to (of course), AI, but it all kept circling back to the same idea: the thing that actually sets a business apart isn’t information anymore. It’s how you treat people, on your team and off it.
Building Your Team the Right Way
Should you classify people as contractors or employees first?
Function should come before classification. Founders tend to do this backwards: decide how they want to classify someone, usually because it’s cheaper or easier, and then try to make the role fit that decision after the fact. Braden and I both build our teams from the other direction. Figure out what you actually need, bring in the right kind of support, and let the classification follow the reality of the role instead of dictating it.
How do you actually follow through on your priorities?
Sort your to-do list into what’s actually non-negotiable and what isn’t, and be honest with yourself about which is which. Braden calls his version “green flag” priorities, the handful of things that have to happen every single week, no exceptions. Everything else is allowed to be flexible, or even fall off entirely, without it meaning your business is falling apart.
How You Handle People, On and Off Your Team
What should you do when someone steals your work?
Start with an email, not a lawsuit. I once had someone repackage an entire service and sales page of mine, slap a different name on it, and charge significantly more than I did. My instinct was to escalate immediately. Braden’s advice was simpler: reach out first. Most people are embarrassed before they’re defensive, and a direct, calm email usually gets you further than an aggressive legal one ever will.
Why do people quit small teams that seem to like them?
Because liking someone and acknowledging their work out loud are two different things. In our exit interviews at Paradigm, one pattern shows up constantly on small teams: the creative or behind-the-scenes person, the one doing the graphics or the backend work nobody sees, quietly deciding their contribution doesn’t matter. Meanwhile, everyone else on the team is privately singing their praises. Small teams assume closeness means people already feel appreciated. It doesn’t work that way, and there’s rarely a formal system catching the gap.
The Bigger Shift Behind All of This
Why doesn’t information make a business stand out anymore?
Because it’s not scarce. AI can hand you a content calendar, a template, or a set of talking points in minutes, and it’s often good, sometimes better than what businesses like ours used to charge real money for. What actually differentiates a business now is what AI still can’t fake: creativity, leadership, and an actual relationship with the people you serve.
What’s the takeaway?
Every question above is really the same question wearing a different outfit. How you classify someone, how you respond when you’re wronged, how you acknowledge your team, how you spend your own time, it all comes down to whether the people around you can feel the difference between working with you and working with anyone else. Braden and I covered a lot more ground in the full episode, from tax tips to team retreats, but that’s the thread running underneath all of it.
