We’re excited to introduce you to the always interesting and insightful Cameron Darwin Bossert. We hope you’ll enjoy our conversation with Cameron below.
Hi Cameron, so happy to have you on the platform with us today and excited to chat about your lessons and insights. Our ability to make good decisions can massively impact our lives, careers and relationships and so it would be very helpful to hear about how you built your decision-making skills.
I remember something early on while getting Thirdwing off the ground. I couldn’t make a decision about how many weeks my first show was going to run. I kept going back and forth, weighing the pros and cons. I got more stressed because people were waiting to hear from me about it. And I was walking to the train it hit me why it was taking so long to make the decision.
Part of the reason was obvious: it had to do with something happening months in the future, so I couldn’t know 100% for sure how it was going to go. But the second reason was less obvious: I was waiting for someone else’s approval. I was waiting for someone to tell me “yeah, that’s the right way to go.” But not just in the sense of somebody giving me advice – you can ask people for advice but you can’t hold them accountable. I literally felt like there was supposed to be another person to sign off on it. But there wasn’t. And as soon as I realized that, I made that decision and never looked back.
Running a company requires building momentum constantly. That actually makes decisions easier. There’s a time limit on every single one of them. You have to discard some of the variables and the endless what-ifs that crowd the process.
Also because my company involves a lot of creativity it gets difficult. Creative decisions, for example about scenes and acting and lighting are even more subjective. There are an infinite amount of things you can do that could be good. So you need to be able to start ruling things out based on something besides quality. When I started building Thirdwing, I actually made a kind of a rule book, or “culture deck,” which helps me decide things, like what kind of project to take on. There are lists of very simple things like “No musicals until at least our fourth year.” Or, “no science fiction.” A lot of small creative decisions behind the scenes will help people start to recognize what to expect from you, and that’s how you can build a brand.
Looming decisions create anxiety because we think that there are good ones and bad ones. But that’s only partly true. You can act like every decision you make is going to be a good one, and then work to make that true. The quality of a decision is 70% when you make it and 30% what you do afterwards to make it the right one.
A secret I recently realized while talking with my business advisor: if you keep going back and forth on a decision endlessly, it’s a good sign that you can’t go wrong either way.
Sometimes making a decision IS the action you’re taking, period. And that’s good on its own.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
I’ve always loved film and theater equally, so couldn’t choose which one to pursue first, speaking of decisions. But as I tried to write plays, I wanted to see more of other people’s work on stage and I just couldn’t afford it. So I scoured YouTube for whatever I could find to get inspired. And that’s how the idea for Thirdwing was born: what if I could make theater that was designed for streaming, but then use the streaming business model to make it affordable for someone like me to actually then go see things in person?
We’re still very small as a company, but between live shows and streaming shows we’ve created 30 hours of entertainment in 3 just years. All of our mainstage productions have been critically acclaimed. I’m working with a wonderful team of people to make a very specific kind of entertainment, where you can see live theater and streaming series that connect to each other.
Thirdwing has two aims: first, make live theater way less expensive than any other in New York. Second, to make a more rewarding, expansive streaming experience. We’re doing this by putting them both into one subscription. Then we design all of our content to fit into that model creatively. After streaming something at home you can come out to a live show and see a different angle to the story, with some of the same characters, coming to life in the room with you. And you can connect with other fans before and after the shows.
I’m really excited to be bringing back one of our most successful shows, BURBANK, about Walt Disney and his fight to make Bambi while losing half of his staff to an animator’s strike in 1941. We got our first The New York Times review for that and they called it “smart and entertaining,” and so we’re really thrilled to get the opportunity to present it to more people.
It’s an example of the Thirdwing streaming business model I was talking about too. A whole separate show about the Disney Studio, THE FAIREST, is streaming on our dedicated platform. You can stream one show, and see the other in person on stage, and see the progression in one character’s life.
We really believe in the business model so we’ve stopped selling tickets to our shows. You can become a member for just $4.99 per month and see our critically-acclaimed Off-Broadway play and stream its companion piece. That’s cheaper than Netflix even used to be.
There’s a lot of other great stuff on our streaming service and more live events coming up through the year. Objectively it’s a great deal, but because people so are used to buying tickets we actually had to take that option away. Tickets are more expensive, but people still would chose that option because it’s what they know. That was one scary decision I had to make, and while I definitely ran it by some knowledgable people, I had to just go ahead with it because nobody has done it before. And now I’m working hard to make it the right decision.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
Casting. Meeting great people, seeing great people in other shows, and finding ways to work together. You build a lot of trust and good faith that way, because everyone’s tired of the audition process. Great actors are constantly getting rejected because of this speed-dating system we usually have. And I try to see what people might be capable of that they’re not necessarily showing, so you can get a really interesting performance. Pushing and actor away from their type is almost like having a cellist play in the high range – it’s beautiful because there’s some extra tension.
Lists. Many people can tell you this stops procrastination. I keep mine really simple. And if I’m still procrastinating on something, I break it down even further. For example, if I have to get in touch with someone I’ll change the item on the list from “reach out” to “draft email,” and I’m more likely to get it started (and honestly, to get it finished). You can make the items smaller until the task at hand is insanely easy:
I’m trying to produce 7 shows and events, and hours of streaming content, in 1 year.
I need to write 5 of those.
I need to start with the one that requires the most research, say, about a chiropractor.
I need to research chiropractors.
I need to google “chiropractors.”
Yes, putting “google chiropractors” on a list before doing it can make a huge difference.
I guess decision-making would be third on the list, but we’ve already gone over that!
We’ve all got limited resources, time, energy, focus etc – so if you had to choose between going all in on your strengths or working on areas where you aren’t as strong, what would you choose?
For me it’s the second one. At least in the early stages when I don’t have a ton of people to fill in the gaps. Even if I don’t improve a great deal in some area, it will always help me communicate down the road. If I know a little bit more about something, I can talk to those who are more skilled than I am. I can at least ask more educated questions, which saves time.
And you don’t always even know what your strengths or weaknesses are. For example, for my last Off-Broadway show, I was determined to keep the overhead down on the production. So not only did I write and direct the show (my strengths), but I ran the lights and the box office (my learning areas). I had to learn how to hang lights and program a theater light board. I might not have to do that again, but I’ll be able to communicate with professional designers and tech people just that much better.
And when it came to running the box office, people would check in at the desk every night not knowing I’d written the show. I got insight into the customer experience, and see people’s pre-show habits and behavior. Someone told me they would have preferred a 7pm show to an 8pm show. I stood up and and asked everybody in the lobby, “Would everybody have been happier with a 7pm show?” I think it was basically unanimous. They wouldn’t have told me that if I was just the playwright walking around the lobby afterwards. But to the guy handing them their program? Yes. So my next show, that I’m writing and directing, but not running the lights or the box office for, will start at 7pm. And speaking of decisions again, 7pm may help more people decide to come see it.
Contact Info:
- Website: www.thirdwing.info
- Instagram: www.instagram.com/thirdwingltd
- Facebook: www.facebook.com/thirdwingltd
- Youtube: www.YouTube.com/thirdwingltd
Image Credits
Onstage and event pics by Valerie Terranova
