2025's TOP 10 Intentional Investor Moments (w/ Ben Hunt)

A year-end, best of, top 10, highlight clip show is probably a terrible way to argue against modern reductionism and slop, but here I am.

If all you do is consume TikTokified shorts, you’re playing with puzzle pieces and never seeing the completed picture. This episode is my attempt to make the puzzle visible again.

And, let me be clear, I love good editing. I love the craft of refining sprawl down to storytelling. I believe, to my core, that storytelling is undefeated. Outside of procreation, it’s the most important act of creation humans can take credit for.

But these clips, despite being edited out of way larger arcs, are merely meant to act as invitations back into the full conversations, and not replacements for them.

I’m all about the connections. Yes, across the episodes when you step back to reflect, and especially to the stories they’re cropped out of. And, I’m never above doing what works to bridge that gap. So, that brings us to The Intentional Investor best of 2025 clip show.

I brought Ben Hunt to go down this list with me. In talking about it we realized - these moments surprised us, even though we already knew many of these people. Which means the clips are the trailer, not the movie. You need to see the full thing.

Real friendship is helping someone move the couch. Yes, it sucks. Yes, you’re doing it out of love (and for pizza and beer after). But real connection lives in that uncomfortable process, together. These aren’t “scrolling on the couch” clips; they’re help move the couch conversations.

With a full year of these to reflect back on, I know this is true: I love listening to people. I love the performative act of listening in the sense that the audience performs a role with the performer. The feedback as a guest tells the story, the way the audience can draw more out of them - and that’s always my goal. That’s why I’m smiling and upbeat and making sure the guest knows I will embarrass myself before I let them feel embarrassed.

Any moment can be special if you really lean into it - and that’s what I’m chasing in these conversations.

Even playing these back with Ben, I slip into audience-performer with him. I want his multiple Wolf/Wolfe/”not Tom” riffs, and I want to shine another light on guests who gave me so much of their time.

It brings me so much joy to do this. To listen at work, for work, and for fun, and to fight the urge toward simplification and reductionism or letting AI do it alone - because this is the way I feel most alive. I embraced that in 2025. I plan to lean harder into it in 2026.

The one-on-one nature of The Intentional Investor is a special thing, and it allows for special moments. These clips are a collection of those moments, but they are begging you to come check out the full episode.

No, you have to move a couch and miss the game or hurt your back. But yes, you’ll hear some incredible stories, probably get inspired, and maybe even gain some appreciation if not shared values for a person you see out there in the world doing something really cool, which is the way I approach pitching guests for this show in the first place.

I loved putting this list together, because I loved revisiting these conversations so much. I’m grateful to friends and partners like Ben Hunt, and of course, Jack Forehand (making edits and rolling clips!), for encouraging me to not stop.

And, most of all, I’m grateful to the guests for sharing these stories, in the format, for all of us to hear.

Help spread some of my joy this holiday season, will you? Pick one guest, queue one full episode, and treat it like helping a friend move their couch.