Aaron Bear on Looking Back at Life of Out Philanthropist, Microsoft Insider Ric Weiland

You might not know the name Ric Weiland, but you've probably felt the impact he had on LGTBQ rights through his astonishing philanthropy. In aggregate, Weiland gave tens of millions of dollars to various equality organizations, including (but by no means limited to) GLAAD, PFLAG, GLSEN, Lambda Legal, and OutServe.

Weiland was one of the original gang behind Microsoft, getting in on the ground floor even before there was a ground floor – he went to prep school with Bill Gates and the others behind the firm. Openly gay back when the company started in 1975, Weiland wasn't about to hide the truth about himself, and the others didn't ask him to. Weiland's focus, efficiency, and brilliance were what mattered.

In his private life, Weiland was a lonely man, as Aaron Bear's new documentary about him, "Yes I Am: The Ric Weiland Story" shows. The film's world premiere takes place at the AmDocs Film Festival from March 26 - April 4.

With access to Weiland's innermost thoughts via his journals and plenty of people who knew him willing to step behind the camera for interviews – including Gates, friends, and lovers – Bear creates a portrait of a man whose mind was flawlessly rational, but whose heart was fiercely passionate. In this, he's helped by the casting of actor Gil Bar-Sela, who portrays Weiland in highly stylized scenes that suggest the intense isolation of a programmer deep in his work... and the same isolation as it plagues Weiland in his off hours.

Tragically, Weiland – who struggled with depression – took his own life in 2006, but not before using his brilliant mind to determine which pro-equality organizations to benefit. Weiland was careful and strategic in planning his contributions to have maximum impact over decades, providing the organizations that fight for our rights the funds they need for the long-term goal of full legal and social equality. (He was also hands-on when he had the chance to be, prompting Microsoft to be an LGBTQ-friendly company and using his shareholder status with GM to convince that company to set aside its discriminatory hiring practices.)

In another casting coup, Zachary Quinto narrates the film, his delivery contributing to the film's overall dignified and understated sensibility.

"Yes I Am" is, like Bear's 2016 doc "Finding Kim," about a transgender man, focused on a fellow Seattleite. There's more than a touch of hometown pride in this moving documentary, along with an unexpected current of tenderness for the subject.

EDGE had the great pleasure of chatting with Aaron Bear about his process of learning about Weiland, putting the film together, and his Seattle-based projects.

EDGE: You've had experience as an actor, including several appearances on a TV show from 2014 called "Capitol Hill." What took you from there into making documentaries?

Aaron Bear: I don't fancy myself an actor, really. I have a lot of friends that always ask me to be in things, and I willingly end up saying yes.

My road has been weaving and bobbing a little bit. I spent thirteen years in the corporate world – I worked for Microsoft, and I worked for Starbucks corporate, basically doing commercial work for them. That could be doing an interview with a CEO, doing commercials... I just got this feeling one day, like, "Is this it? Is this what I wanted to do?" I went to film school, and when we landed in Seattle, my husband and I, the corporate world was the first thing that paid me. I felt like I got a little trapped there. I was at Starbucks and I started to feel like I wanted to do something that was just for me, that I didn't have to answer to an art director or creative director.

EDGE: You've made films about LGBTQ people with a Seattle connection, like "Finding Kim" and now "Yes I Am – The Ric Weiland Story." Being from Seattle yourself, is this a matter of hometown pride?

Aaron Bear: [When it came to making] my first feature documentary, "Finding Kim," Kim was a friend of mine, and we were hanging out one day and he goes, "Hey, I want to tell you first – I think I'm going to transition." We talked a lot about him transitioning, and then I asked him, "Hey, would you be up for having this documented, because I feel like this could educate a lot of people," and he hesitantly said yes. Kim's a very, very private person. However, we shot for three years, and then there was a whole entire year of editing. Then we were at Seattle Film Fest and it went on [from there] – it has its own life now.

EDGE: What drew you to make a documentary about Ric Weiland, in particular?

Aaron Bear: During Seattle International Film Fest I was approached to do a film about Ric. You know when you're at a film festival, and you're having all of these five-minute conversations, and people say, "Oh, yeah, I'll contact you, I'll email you" – and they never do? Well, this person actually did. Initially, I really had to think about it: "Why should I tell this story? Why does anyone want to hear about this?" All I knew about Ric at that point was he was this rich Microsoft guy. And I thought, "Why would anyone want to know about him?" And then the further I dug into his life, the more I realized that Ric deserves to be known for his accomplishments, and his legacy lives on and on. He inspired me not only as a filmmaker, but as a human being. I just want to be a better human being because of Ric.

EDGE: Ric Weiland felt that he was socially inapt, which is not uncommon for people who work in creative fields at a very high level. From what people told you about him, did you get a sense of why that was the case? Maybe because he was so rational and analytical, whereas people are irrational?

Aaron Bear: You know, I wish I had a solid answer for you on this, and I've thought a lot about it. Ric was on some sort of genius spectrum of thinking and analyzing life, but also, to his own detriment, in certain instances – i.e., being social, and not being able to connect with people on that level – yes, he had a group of friends that loved him and were solid, but even Bill Gates says in the film that Ric was a hard guy to get to know. I do think that there is a correlation between having this genius-like brain and not having social skills.

I think that we don't get all the best things in life, and I think that Ric just didn't get that. But he got so much else, and he cared so much, too. In trying to answer the question of why he cared so much, he just did, and he knew how to operate in a way that would benefit the LGBTQ community, specifically, for decades to come – not just years, but decades.

EDGE: It's also not unusual for highly intelligent, creative people to suffer from depression, as Ric did. Had you researched the connections between those all those things while making the film?

Aaron Bear: Yeah, as I was diving into making the documentary I went through, for the first time in my life, my own mental health crisis of just figuring out, "What am I doing with my life? What's actually important to me?" Really looking at my friendships, and how I carry myself in this world, and suffering from my own bouts of depression while making a movie about someone who truly suffered. I kind of felt I was running this very strange parallel path to Ric's life, in a sense, and trying to accomplish so much. Making a documentary takes so much emotional energy, amongst many other things, but I think that mental health has just been so top of my [concerns] for the past four years that there's no way I couldn't focus on myself and getting the resources to help myself.

EDGE: The last four years? That aligns pretty neatly with our last president. I can certainly sympathize!

Aaron Bear: Yeah! As queer folk, we're even more... the suicide rates are even higher for us, and when I made "Finding Kim" – and this applies to "Yes I Am" and Ric's story – [I felt that] the success of the film isn't contingent upon selling it or anything like that. I really feel like if this film helps somebody, if this film helps a young kid, then the film has succeeded. I always try to make films that I would want to watch, and take something away from that would either help me or inspire me, and I think that at the core Ric's story and his accomplishments and his legacy are so inspiring, there's no way you can look at them and not think, "Wow, this guy did an incredible amount of work and never asked for the limelight, and never wanted fame, and all the things that people sometimes do things for." He didn't want that. So, it's been inspirational to me to ask, "Why am I doing the things I do? Why am I a filmmaker?" And it really is an embedded core passion that lives within me – that's the best way that I can describe it. I think Ric had the same thing. It's almost like someone else is operating the machine.

EDGE: You bring up an interesting point that the film touches on in citing a journal entry in which Ric wrote, "I hope my legacy is one that is everlasting, where I am not the hero." It's such an interesting and paradoxical thing to say.

Aaron Bear: Yeah, because most people would never say that! You want to be a little bit of a hero after all of these incredible accomplishments, but it was never a factor for him. So, again, looking at Ric's life and the things that he did, and not wanting anything from it – it's unlike most human beings.

EDGE: You cast an actor, Gil Bar-Sela, to play Ric, and he brings the kind of intensity to his performance that makes sense for someone as focused, methodical, and thorough as Ric was. What other qualities were you looking for in terms of who would portray him?

Aaron Bear: I was looking for somebody who could really connect to and understand Ric's emotional state and how we go through life. Some days are better than others, and connecting to Ric as a professional person, but also as a private person, and being able to understand that... I was looking for that tone, and it's so nuanced, and it's so delicate. I wanted someone to treat it with the respect and the delicacy that Ric's life deserved. Gil – and Zachary Quinto [who narrates the film] – had it dialed in from the very beginning. I gave them access to Ric's journals [as a way of] helping them understand who he was in private. I couldn't be happier with how they both portrayed his actions, and Ric's voice.

EDGE: How did Zachary Quinto come to be involved?

Aaron Bear: I thought of ways to help elevate the story, and I thought, "Wouldn't it be amazing to get a real celebrity to do the voiceovers?" I made a very short list. It was important to me to have out queer actors. Zachary was my number one choice, and I reached out to his agent, and they said, "He wants to hear more." Sight unseen, because the film wasn't done at this point. They said, "Write him a letter," so I wrote him this very heartfelt, from the gut one-page letter about why I thought he should do this, and he said yes. It was just a matter of asking, really, but it still amazed me that it happened.

I flew to L.A., I recorded him, and at the very end I said, "I really respect and admire you taking this on," and he said, "You know I said yes because I connect so much to Ric's story, and because of the letter you wrote me."

EDGE: As your film makes clear, Ric has had an enormous impact on helping to advance legal equality and social acceptance for sexual minorities, not just with the sheer volume of his financial contributions, but also through the way he looked strategically at where he was going to make those contributions. Do we need more of his sort of rational, highly targeted style of pinpoint philanthropy to sustain our struggle for equality?

Aaron Bear: Absolutely. Ric was a planner to the extreme, but I think that's why his legacy continues to live on, because he was... using the word "thoughtful" seems to minor, but the thoughtfulness behind his planning and his execution of his philanthropy is astounding.

EDGE: Do you think he'd have been embarrassed or abashed at having a doc made about him?

Aaron Bear: This was the very first question that I asked myself four years ago. I think I can throw it on when I need to, but I am also kind of a shy person, and I think I was looking at myself [from the perspective of], "If I had all of this, if I did all of these things, and I was no longer here on this earthly plane, and a filmmaker found my story and connected to it, [how would I feel about that?]" My answer was, I think Ric would be proud. It's not necessarily showcasing him in a way that is based in ego. I tried to delve into the human parts of all of us, and the things that we all suffer from. Him being inspirational was also key. I think he would be proud.

EDGE: You're executive producing an upcoming TV series called "There is a Light That Never Goes Out." What can you say about that?

Aaron Bear: It's based on true events, and it's about growing up and being forced out of your house in Milwaukee in 1989. It's based on the life of another producer of the show, basically about him being forced out and then finding his way downtown and finding his way to this building called The Norman, which was kind of like a Chelsea Hotel of Milwaukee, and meeting all these queerdos and punks and all kinds of other people who lived there. Richard Druse is his name, and Richard would always tell me all of these really amazing stories. I said, "You really need to write all this stuff down," and then he was like, "Actually, I have," and then it quickly developed and we got a whole pilot script written. We're starting to cast for it and we want to shoot it all in Milwaukee. It's moving along quite nicely.

What I have been realizing is that I really do like telling stories of people who survive, in some sense, and I think I do fairly well at that. I think that was true for "Finding Kim," and even with Ric, and now with "There is a Light That Never Goes Out," of [talking about] people who come from adversity and are able to rise above it, or are able to help other people rise above it. I'm paying more attention to the stories I'm telling, and why I'm telling them, and I'm very much connected to this [new project] for many reasons.

"Yes I Am – The Ric Weiland Story" plays at the OUTshine Miami Film Festival April 24 - 28.