In addition to True Fans, you recently published a book called The Road Trip Pilgrim’s Guide. What did “pilgrimage” mean to you on your cross-country bike trips, and what does it mean to what you do today?

The idea of meaningful travel or going on a journey that kind of impacts you is huge for me. They have a spiritual component to them. You definitely return a different person than the one that left. And all the trips we’ve gone on that have been really impactful have had this really whimsical nature to them. I mean we took our first trip to a bar — that was our first long journey, and I think sometimes that’s lost when you talk about religion. It’s seen as something that has to be done, has to be somber, has to be heavy. I don’t think it’s that way at all. I think sometimes the life-changing experiences are kind of light and unexpected, and really powerful in that sense.

Sounds straight out of Jack Kerouac. Could you talk about a particularly impactful moment you had on the road?

Those moments come really unexpectedly. You go to Machu Picchu and you expect it to be this spiritual experience and it’s really cool, but it’s not like you have these spiritual experiences right when you’re supposed to be having them. A memory that comes to mind is [from] a few years ago: A friend and I were hitchhiking down the coast of Maine. It was three o’clock in the morning, and we had no idea whether or not we were going to get to the airport or not. It was just October, and it was beautiful, and I don’t know, I just felt lost to the road. They’re not thunderclap moments, they’re just kind of peaceful moments.

Why take a bike?

A bike is just a great way to just go fast enough to go from point A to point B. There’s something very free about riding a bike, and it’s just this great ritual, and everyone can remember their first bike. I really love the vehicle and what it does more than the bike itself. I’m not like a gearhead, no. I just really like the idea of a journey in a bike.

Why go to the Basketball Hall of Fame?

We chose the destination because we had this theme of having this ball signed by people that were “heroic” [by helping us out], and so we wanted a symbol of that gratitude, that generosity. There was this metaphor of going to the Hall of Fame, this Hall of “heroes” with this basketball signed by [our] heroes across the nation. But it was also that we just liked basketball. [Laughs]. It’s all whimsical, though. None of it is really serious.

Do you have a favorite cyclist?

Oh man, you know, I don’t follow cycling. I love watching the Tour de France, but I don’t really follow cycling in terms of the people, I really don’t. Yeah, I don’t race at all. I ride this big clunky mountain bike. I don’t own a single piece of spandex; I go really slow. I just kind of like to look around and enjoy the ride. I don’t really feel the need to test my mettle against others. I can totally see the value of that, but it’s just not me.

Do you still play basketball?

Well, I did until last fall. I ruptured my Achilles tendon. So I think that’s the end of my basketball-playing career.

The NBA dreams are down the drain, then?

[Laughs.] I’m afraid so. I was on the East Coast giving a talk to the school, and it was a prep school that won the state championship last year. They have guys that have gone on to play in the NBA, and I was just getting killed and it was embarrassing. And I just pushed it too hard, and I wasn’t warmed enough and it was BOOM! It’s a long rehab. I’m still a little shaky. So, yeah, the basketball career is over. I got a lot of good time in, though, so that’s OK.

But you’re still a true fan. Are there “better” fans than you?

[Laughs.] There are fans that are probably more fanatical. There are fans that are more devoted in terms of never missing a game. … But the idea of a “true fan” is that you have your team, you root for your team through thick and thin. You’re not just jumping on the Michael Jordan or Miami Heat bandwagon or whatever. … I guess it’s not so much being better or worse so much as it is being “true,” however that true fandom comes out, whether it’s just painting yourself or enjoying the games and just not jumping onto the next hot ticket.

That’s as profound as you get in the sports world.

[Laughs.] Thanks.

How did you make the transition from making these pilgrimages, writing books and filming documentaries to founding 88bikes, your nonprofit?

Yeah, it was seamless, probably because we didn’t plan it. We were biking to Cambodia and we found this orphanage and so we thought, “Hey, let’s give them our bikes.”… We launched a fundraiser so that all the kids could have bikes in the orphanage, and it was just such a scene of happiness that we thought, “Hey, this has been looked over in the nonprofit sector.” And we started giving bikes to kids and sending volunteers back that would help the kids with their bikes. … I think it was just a natural outgrowth of exploring the world and kind of wanting other folks to have that opportunity.

What is joy-based philanthropy, and why does it focus on bikes?

That’s looking at happiness as like a human need. Something that’s on par with food, water, shelter. … I think a lot of times happiness is overlooked [in the nonprofit world] because you’re focusing just on sustenance, like keeping people alive. Helping folks to be happy is every bit as important. … and joy-based philanthropy to me is working with people that are already doing the basics and plugging in that extra happiness element—with us through a bike—so that these kids are fed and going to school, and so they have this opportunity to be happy and have joy in their lives.

The bike in the countries we work with is just incredibly useful, and also incredibly fun. … You give a kid a bike who’s been through poverty and war and disease … and it just transforms their lives. … We have enumerable stories. … I don’t really consider us a bike NGO; we’re a happiness NGO. That’s what we’re concerned about.

How can Obies get involved?

We so much appreciate people giving us a note, or liking us on Facebook. If you’d like to donate, you can, but we’re like the softest sell possible. … Really, we’re just happy to have a vibrant community, and we’d love to have anybody who wants to join it.