We all have a passion project we’ve kicked around in our minds for years, but many of us never get around to following through. Yet Don Cheadle actually pulled it off, bringing his lifelong love for jazz icon Miles Davis to the screen.

After crowdfunding $345,000, Cheadle makes his directorial debut with Miles Ahead, which closed the Pan African Film Festival and hits theaters April 1st. The veteran actor is one busy guy, starring in Showtime’s House of Lies, the fifth season of which premieres April 10th, and the various Iron Man and Captain America movies.

We asked him what it takes to be as cool as Miles and—as his character does in the movie—how to make a comeback if you’re feeling like things aren’t going your way…

“You only lose if you stop. As long as you are pushing and striving, and trying to figure out the next thing, that’s the best thing you can do.”

As the co-writer and first-time director, you have wanted this project to be birthed for years. How does it feel, now that it’s done?
Insane. Crazy. It’s been a lot of work. Very exhausting but ultimately, crossing the finish line, rewarding. I’m glad to be able to show the film, people seem to really be responding. It’s everything that one could hope for.

Miles was the epitome of cool. What does cool mean to you?
Wow, I don’t know! Miles was also someone who thought, Is it cooler to tap my foot inside my shoe or tap my whole shoe? Cool has a lot of different ways that it gets displayed. I think cool is not worrying about being cool at the end of the day. It’s just being you.

What does it take to follow one’s passion?
Stubbornness. Not quitting and understanding that if it’s easy, it’s probably not worth it. But it can be hard… especially when you are out here, trying to do something like this.

Any advice for a guy who wants to get into filmmaking?
You need irrational investors; you need people who understand they are not into it for some quick return, that really what they are trying to do is support things that they think matter. That’s challenging because when the bottom line is a check in dollars and cents, it’s hard to push things like this through. But luckily we had people who believed in it and here we are.

What’s your favorite Miles Davis album?
Oh I can’t pick one! I have 15! Depends on the mood!

If you were to recommend a jazz CD to a first-time listener, what would you say?
I would recommend several. If you want to listen to someone current, check out Kamasi Washington’s album. It’s insane. You can grab any John Coltrane album. Blue Train. There are so many; it’s hard to pick one.

Miles never gave up, no matter what his circumstances were. What advice would you give guys in need of a comeback?
If you were to ask Miles, he would say he didn’t go anywhere! You only lose if you stop. You are only a loser if you say, “I am done.” As long as you are pushing for and striving for, and trying to figure out the next thing, that’s the best thing you can do.

Showtime’s House of Lies is first US TV show to be filming in Cuba. Give us a hint on what we can expect this season.
Everybody dies! Well, that’s not really a hint; that’s more of a spoiler!