The ROI of Radical Generosity

In early 2019, I made a list — 808 founders and CEOs from the Inc. 5000 list. These were people building the fastest-growing companies in the country, and I wanted to talk to them about something you don’t usually hear in a high-growth business context: gratitude. Not funding rounds. Not exit strategies. Gratitude.

I wrote one email to all of them. “Would you like to come on our podcast to talk gratitude?” I didn’t have a podcast yet. No episodes. No audience. Just gratitude. And somehow, 84 of them said yes.

One of them was Ben. At the time, Ben was the founder and CEO of the fourth fastest-growing private company in the country. We didn’t talk scale that day. We talked soul. We just connected. Then we wrapped the interview, thanked each other and went on with our lives.

A few months later, I was booked to give a keynote just outside of Denver. I called Ben and said, “What if I stayed an extra day? What if I rented tables and chairs, went to Whole Foods and came over to cook dinner for you and 15 of your friends?” No pitch. No business angle. Just dinner.

Ben said yes.

That night changed everything. That one dinner turned into a spectacular friendship and a flywheel of professional opportunity. Ben brought me in to speak at his company. He introduced me to people. He vouched for me. He flew across the country to interview me at my book launch. He became one of my biggest champions.

And all of it began with an act of generosity that wasn’t scalable, but was unmistakably human.

This is the part most people miss. We assume business growth comes from leverage, scale and strategy. But the best business decisions I’ve ever made didn’t feel like business decisions. They felt like friendship. They felt like cooking. They felt like chatting with a stranger on a call about gratitude. I’ve done a lot of things to build my speaking career. Funnels. Decks. Outreach. But nothing — nothing — has matched the ROI of giving a darn.

My friend and mentor, the late John Ruhlin, knew this better than anyone. John built his career — and his legacy — around the idea of Return on Relationship. He taught that the real value isn’t in the pitch or the product, it’s in how you make people feel. He believed that generosity wasn’t a tactic; it was a way of being. His bestselling book, Giftology, says stop sending swag. Instead, start showing up for people in meaningful, unexpected, thoughtful ways. He used to say, “Relationships are your greatest ROI,” and he lived it.

Even a year after John’s passing, I still hear his voice. I hear it when I’m packing up ingredients to cook for a client or step on stage. I hear it when I write a handwritten thank-you note. I hear it every time I stop trying to impress and choose, instead, to be present.

Generosity doesn’t always look like a gift. Sometimes, it looks like belief.

In 2023, I bombed a keynote in front of a room of high-level execs. My talk was off. My energy was off. I felt like I had let everyone down, especially Ben, who had stuck his neck out to bring me in. The next day, I called my friend Adam Smiley Poswolsky and said, “That sucked. I’m lost. What should I do now?” Smiley didn’t coddle me. He didn’t sugarcoat it. He gave me a gift. He told me to join Impact Eleven, a keynote speaker community.

He opened a door. He made the referral. He believed in me so much that he was willing to elevate my game, even if it meant adding competition to the very space he was thriving in. That’s generosity. Generosity isn’t always what you give. It’s what you’re willing to risk on behalf of someone else’s success. That one moment, that one nudge from a friend, turned into the single best professional decision of my career.

Over time, I’ve come to see that one of the most underappreciated forms of generosity is asking questions. Not sales or strategy questions. But questions that come from genuine curiosity. When I emailed those 808 CEOs to talk about gratitude, I wasn’t offering them exposure or status. I was offering them the space to be seen. And they said yes. Because people are hungry for real connection. Asking someone about their values, their hopes, their pain — that’s a form of love. It says, “I see you. I care enough to wonder.” And when you ask like that, people open up. They remember you. They trust you. Sometimes, they hire you. But more often, they just remember how you made them feel.

To guide how I show up in the world, I use a simple framework. I call it PASTA. Pause. Ask. Savor. Take Action. Appreciate. It started as a personal rhythm, but it’s become the backbone of my work, my relationships and how I lead. Pause long enough to notice what matters. Ask the bold, beautiful questions. Savor the moment instead of rushing through it. Take action from the heart, not just the head. And appreciate — people, presence, the process, the plate.

When I made the decision to cook dinner for Ben and his friends, that was PASTA in action. I paused. I asked. We savored the night. I took action without an agenda. And years later, I’m still appreciating everything that one dinner gave back.

Radical generosity isn’t a branding move. It’s not always efficient or visible. But it works. It’s what turns strangers into friends, clients into advocates and mentors into lifelines.

So here’s what I’ll leave you with: What’s your version of the dinner?

Who’s someone you admire? Someone you’d love to build with, learn from or serve? What could you offer — not to close a deal, but to open a door?

You don’t need a podcast. You don’t need a platform. You don’t need a perfect pitch.

You just need to go first. And maybe — just maybe — cook the meal.