Two crazy guys walk into an Afghan restaurant. No punchline. That’s literally how Made Simpler started.
Sitting with Jamie Bennion and Brandon Sherwood on Glad You Asked, I found myself sharing stories I usually keep locked away. Maybe it was their genuine curiosity. Maybe it was the way they turned a CEO interview into a debate about breakfast cereals.
The Starving Entrepreneur’s Education
The conversation opened with questions about my journey, and I went straight back to the beginning. Twenty years old, buying a window cleaning business from a friend who promised I’d “make money hand over fist.”
Reality hit hard. I was starving from day one.
Learning to Get Scrappy
“Because I had no other choice, I had to just start figuring out the business. And I had to figure out how to go sell new accounts, and I had to get really scrappy, really fast.”
Listen to this moment
That desperation taught me everything. No MBA program teaches you what hunger does. You learn grassroots techniques because you have to. You figure it out because failure means not eating.
Working at Sysco later, I saw the pattern everywhere. Small restaurant owners dying on the vine, not because they couldn’t cook or serve, but because the system was built for giants.
The Dark Chapter That Created “Be the Better”
“People become who you tell them that they are. If you tell somebody they can win, and you set a path that helps them to win, then they can win.”
Watch this powerful moment
I rarely tell this story, but they pulled it out of me. I was an embedded CMO for a CEO who would 5x his revenue, then walk in and destroy his team for sport. Demand I fire top performers for no reason. My wife said it was changing me.
That’s when I created Be the Better, my philosophy for protecting teams from toxic leadership. A moral framework that became armor for my people. The Success Acceleration Plan I built at MarketStar proved it worked: 35% better outcomes than traditional PIPs.
Building Wealth for the Team, Not Just the Top
“This isn’t about building wealth for Ben. This is about building wealth for our team members.”
When asked about success metrics, I was honest. First, we take care of our people. Then we help them impact their communities. Then we find other impact-driven people and multiply their reach. Revenue is just fuel for the mission.
The IKEA Confession That Changed Everything
Here’s where it got interesting. Brandon starts using IKEA as a metaphor for building Gladly, and I had to stop him.
“Can I make a confession? I have never actually walked into an IKEA.”
The whole room erupted. Twenty minutes earlier, we’re having this deep conversation about business philosophy. Now Brandon’s planning our IKEA lunch date at the Draper location.
That moment captured what made the conversation real. No pretense. No script. Just humans connecting over shared values and ridiculous tangents.
Thank You for the Real Conversation
Big thanks to Jamie and Brandon for creating a space where CEOs can be human. Where we can debate whether Made Simpler is more like Lucky Charms or Raisin Bran (it’s Raisin Bran – substance over flash). Where even admitting you’ve never been to IKEA somehow makes it better.
The Glad You Asked team gets it: the best conversations happen when you stop performing and start connecting.
