“When you unlock your heart, you unlock everything,” TBB wants to tell me.
Her experience is that the more authentic she became, the more she stopped blocking her trans nature, the more she blossomed and became seen as authentic, the more she was able to be present, and the better she got at life. The ultimate tranny operation has always been the toughest: pulling the stick out of your own bum, letting go and trusting that you can flow free.
I went to the first day of Startup Weekend hiding in plain sight, in my androgynous jeans and polo, no polish to my appearance. “Why don’t you have a nametag?” someone asked. “Lack of buy in,” I replied.
I went for a simple reason. I wanted to see if I was still smart. A decade of being a full time caregiver to my parents, which ended a few months ago with their deaths, took a lot out of me. I may have been a smart person who did startups in my prime, but I felt way past that prime now.
I also knew that I like being around smart people with a short thinking radius. My brain fires fast, and having people who can keep up with the twists and turns of a sharp conversation lets me feel alive.
The best startup businesses have one thing in common: they are empowering, pulling the best from each member of the team to create the best outcomes possible. Every scrap of energy that people can deliver needs to be valued, encouraging more and deeper contributions to the shared goal. It is that very feeling of being used well that lets you wake up invigorated, ready to come back the next day and offer more. Startups demand diversity, because the more people bring to the team through their unique skills and viewpoint, the stronger the shared effort is. The solutions just get more considered and more creative.
From his death bed, my father’s instructions were clear. “You have spoken for your mother. You have spoken for me. But now you have to speak for yourself.” That was his message, though his actual words were more strained.
Could I trust my voice? I have never had a problem trusting my relationship to my creator, my mother in the sky, but my relationship to others, well, that has always been tougher. How could they see past their prejudices and expectations to see who I knew myself to be?
That’s why I was in mufti that first night. From the start, though, I could keep up conversations, with a salesman, a student, with the techie from Microsoft.
I got on a team about an app that would help enforce medication compliance, especially in seniors. From the brainstorming session the first night, we realized that validating compliance was too big a hurdle to handle without dedicated hardware, which was beyond our scope. We went to a phone based reminder system, but the problem was how to avoid the clinical coldness of robo-calls.
It was my suggestion that we make the calls entertaining. I gave examples by doing some of the Jonathan Winters style characters that have always been a part of me. And the idea was born.
That night, I tossed and turned in bed, my mind racing. So much to process.
But I had the product concept by the morning. Caroline Calls, an engaging radio style reminder service for seniors and the carers who love them. Caroline was at the center of the brand, a friend on the phone, whose automated calls would contain entertaining content and valuable reminders. Caroline was a gracious and thoughtful caregiver, who called to help your parents, funny and concerned.
I pitched the concept the next morning — “I always feel better when Caroline Calls!” — and the team bought it without question.
The young programmer and the advertising guy had other obligations, so we were down to myself, Tom, a blue-collar retiree who liked to watch Shark Tank and imagine himself having a hit product, Avani, the college student who had the first idea, Marc, who knew he didn’t want to sell insurance all his life, and Chris, a savvy guy who had done startups and understood the process well.
Since Chris and I had the experience, we lead the process, and since we both understood the culture of startups, we were collaborative from the beginning. From the first night we knew we could easily spark off each other, easily keep up with each others pivots, and that meant we knew the other had our back, which is a key to being able to take the leaps required to get as far as possible. We both knew technology well enough, both had the scars of failed startups. We would toss things back and forth, adding value in the handoffs, creating a kind of mind meld to hold a shared vision, which we shaped in our own ways.
As we went through the day, Marc and Avani kept up with the process of creating brand, product, and business plan, learning quickly.
Avani joked that she tought of Caroline as Mrs. Doubtfire, and I suggested we get Chris a wig for the pitch. “No,” she answered. “You should be Caroline. You have all the voices.” I just mumbled “It’s possible.”
Coaches came through all day, and we trade off going through the idea for them, answering questions and developing the ideas. Avani and Marc would take the market research, Chris the business plan, and I had the brand and product piece. Our favourite coach was the product manager, because he got the whole picture fast, reminding me why I had become a product manager in a past life. He validated what we told Marc, that it wasn’t following the rules that got the win, it was doing it the best way while ticking the boxes.
It’s really easy to get down into the details and lose the big picture, which loses everything. I realized that was the problem with so many support relationships, that rather than recontextualizing and seeing the forest, they looked at details, becoming obsessed with trees. For me, this weekend had to be about seeing the big view once again, the possibilities I hold, not the picky bits, because it is only big connection that can lift us out of the mud.
One of the coaches, a mature plus-size woman, seized on the market, but to her the key was to use the portal to support caregivers. She had to deal with this with her mother, and she needed someplace to turn for information and energy to take care of her failing parent. Having been through many caregiver support groups, I saw the need, and how Caroline’s voice could reach out to assist carers watching their loved and loving parents decline.
It was clear that the character of Caroline was at the center of our product and our brand, and if we wanted to be at all successful, she had to be present in our pitch. Chris offered to have his wife, who does voiceovers, record a script, but that was a lift and not as present as we could be.
The product & branding piece was my responsibility, and I promised I would handle it. Somehow.
I knew why I wanted to remain somewhat hidden when I came to this event. It was because I knew I would need to use my voice, and I was afraid I would feel inhibited and constrained if I felt the need to be at all convincing as a woman. My voice was tenuous enough that first night, and if I throttled myself even more, well, that wouldn’t be good. I had spoken for my parents for a decade. Could I really speak for me?
That night was a struggle. I knew that I had to bring Caroline to the pitch. I knew I could do that. I also knew I had to get past my damn self to do it, which was possible, but not at all easy. Would these people who knew me from a day and a half of work know me when I showed my prettiest face?
In the end, it was musical theatre that helped me. I was going through some Jinkx Monsoon videos and found her performance of “Show Off” from “The Drowsy Chaperone,” an energetic number I loved since I heard Sutton Foster’s Broadway version. And Deborah Lippmann said that when I had a chance, “I Hope You Dance,” which had caught me before the weekend. So even though it had been almost a month since I hauled myself out with my best face on, I knew I had to do it. I put on a black dress, a pair of my mother’s shoulder pads, my big shaman dichroic medallion, grey burnout velvet scarf, black tights and fake uggs and got in the car.
I pulled in and parked right next to my team member Marc, who had also just arrived. A guy’s guy, I decided not to engage him in the parking lot, but to get some breath first.
I entered the classroom we had claimed as ours and he didn’t recognize me. Until he did. We chatted a bit, him admiring my courage.
“You know,” he said. “I wasn’t sure if I liked you. But now I know. I do.” Somehow, looking like a woman snapped things into focus for him, and suddenly I made sense.
“This is an important part of me,” I told everyone. They got it quickly. This wasn’t an act I put on overnight.
“I realized that Caroline was about me,” I told Chris.
“Yeah,” he replied. “That was pretty obvious yesterday.”
I had been giving Caroline the power of voice. Now I could also give her presence. And to the team, it just made sense.
We went through the day, and while there were times I would just sit in the back and be silent — “Are you a member of this team?” the organizer asked — I did find my voice. One of the coaches, the mature plus sized woman came back through and afterwards Avani asked if I noticed. “Yes,” I said, “she was checking me out.” I was in her zone, and therefore possible competition.
The only creepy time came when the ad-man dropped back in. He had told his friend who did voiceovers about my idea on Friday night, and he came up with a minute call from Lieutenant Columbo that was where we were when he left, but we had come so far from. “I like your voices more,” Chris said. “They are much more playful.”
He asked about the guy with the grey pony tail. My team caught my eye, but I said nothing. When he got it, got a bit wild, coming back to have his picture taken with me, but feeling the need to pound hard on my back to prove he wasn’t gay. I’ve watched Mad Men, and know that I’m not the first woman to have to tolerate a creepy ad guy. One of the challenges of internalized phobia is that people often feel the need to destroy what attracts them, so we need to know that the more they pound us the more attracted they are.
The team had my back, even if they weren’t quite sure how. They knew that I had brought Caroline and that she was the heart of the product. They knew I brought the heart.
The film crew came by while I was out of the room. I stayed out until they left. They came back in and asked for a representative to speak to the camera. I looked for someone to volunteer, and when someone else did, they had to be more clear. “We want you,” he said, pointing at me. “I’m not really interested, thanks,” I told him.
“They figured out that I am different,” I told the team as he left, and they understood my choice not to be the curiosity, just to be another team member.
We finished the presentation on schedule, even as everyone around us was running late and puffing hard. Some of the coaches thought we should have more panic, as it showed commitment, but we replaced that with working smart and honouring family, so Chris could go back to spend time with his family as they stayed at his parents house, and Marc did the same. We knew success is as much about knowing what to let go of, knowing what you say “no” to, as it is about sweating. Diluting your energy is not a way to succeed, but focus is.
We were the seventh to present out of ten, and our steady pace meant that we had lots of time to sit in the back of the hall and wait. To me, that meant I had lots of time to question my voice. Could I carry this off?
We got our shot and Chris started the pitch, managing our slides from his laptop. Avani talked about the market and Marc talked about the competition, and then he introduced Caroline, our product, our brand.
I stepped forward and started the script. Kate Bornstein has said that as a transwoman, people don’t immediately hear her, because they have to get over the shock. Would that be a problem for me?
I couldn’t worry about that. I only had a minute and thirty seconds in our five minute presentation to sell the product. Just step up, let the energy loose and do it. Boom.
Chris had focused on the slides, not the script, so he needed a cue to remember the clock, but we finished big and stepped to the microphone.
There were a panel of three judges who would question us, two women and a man.
The first thing the venture capital gal from New York said was “It’s so refreshing to see a pitch about a market for maturing people.” Then she followed with a note directly to me. “I love your voice! It’s great!”
I kept breathing.
We answered the questions the way we did everything, as a team with everyone pitching in. Many teams didn’t do that, leaving one or two spokespeople, but we knew that startups have to be about empowering people to bring it, and we did. Our presentation was sharp and energetic.
We waited for the results. One guy congratulated me, but I didn’t engage him as much as I should. And the salesman I sat with on Friday night came to congratulate me, wanting to talk about the product, not about my difference. Amazing.
The top two teams won with ideas their originators had brought to the event, both twists to enter existing markets.
We had nothing like that, coming to the weekend bare and going in a completely oddball direction.
And we came in third out of ten. We made the podium, as Marc said.
Marc took the lead when we came onto the stage. He went to shake hands with the judges, so I followed him.
As I greeted them, now both women said to me, very clearly, “I love your voice.”
I felt blown away by the universe, but kept standing. I even posed for pictures, not something a woman of size, let alone a transwoman of size does easily.
My voice resonated with these smart, successful, mature women. And my voice sold the product, this idea of a wise, kind, funny woman who helps with education, support and reminders.
I had no idea what I was getting into when I went to Startup Weekend. Other people may have been committed to products, but my only commitment was to the process, to follow it where it led.
And, for me anyway, it lead to me.
I have known for some time that my challenge is to become product, to get out there as an expert, a destination, a guru. I just wasn’t sure that product was going to connect with anyone.
It connected with my team, though. It connected with the judges. I became present, unlocked my heart and raised my voice and I got it affirmed, big time.
I know that whatever anyone does, they bring themselves to it. The themes in their life thread through everything they do, from art to relationships to life. I just couldn’t imagine how my themes would play out in this business oriented event.
The ethos, the culture, creates the opportunities. And this weekend, I lead creation of a micro culture, which left everyone in the room feeling smarter and more empowered. That is possible.
I called TBB to tell her the story. “You talked for ten minutes straight,” she told me. “You haven’t done that for years! You sound so happy!”
I called my overnight post “Super Collider” because what I feel is energy, which is better than happiness, at least for a compulsively thoughtful person like me, who can often feel isolated and get bogged down in analysis paralysis. And my title for this one was “Higgs Boson,” to review what was released in me by that energy. As I look at the New York Times website in this moment, their headline is “Chasing The Higgs.” More synchronicity?
So many things in my life, from the connection of the church around the death of my parents to a local misusing my address to sign up for Facebook seem like moments of synchronicity, pulses of energy to move me forward.
When you unlock your heart, you unlock everything.
And what I might have unlocked is the ability to trust that my own voice is engaging and compelling in the world, even as others tell me all the little reasons it will just create noise.
Unlocking my voice, knowing people can like and value it without getting bogged down, well, who knows where that will take me?
I just, I guess, have to commit to the process.