Now Playing

‘Judah Is Gone. Now It’s Jessica.’

Son, soldier, husband, father, widower, adman, inventor, CEO, woman: Jessica Schiller’s long path to emancipation.


(1 of 10)

(2 of 10)


Though people always gravitated toward Judah Schiller—a “sexy, fun California boy”—Jessica recognized from an early age that they weren’t seeing the real her.

(3 of 10)

Schiller as a 25-year-old soldier in the Israel Defense Forces.

(4 of 10)

With her three children seven months after the death of their mother, Galit.

(5 of 10)

With former girlfriend Heather Ryan, who helped Schiller come out as transgender.

(6 of 10)

Attending the Riviera Water Bike Challenge in June, one of her first public appearances as Jessica.

(7 of 10)

The Schiller Bike and its creator, photographed on July 26 off Tiburon.

(8 of 10)

(9 of 10)

(10 of 10)

From the opening salvo, it was clear that Judah Schiller was not publishing any ordinary LinkedIn post. For the first time in years, Schiller, the buff, long-haired CEO of the Mill Valley–based company Schiller Bikes, wasn’t using the platform to sell a business vision or hype a new product. Instead, his March 27 missive was intended as an official coming-out announcement, a celebration, a eulogy, and a farewell. “At the start of this year, I finally just said, ‘Screw it,’” Schiller wrote. “I’m transgender, hardwired that way, plain and simple. I’m flat-out done wasting time. Judah is gone. Now it’s Jessica.”

For those who didn’t know the 46-year-old well, the post might have evoked little more than curiosity. But for Schiller’s closest confidants, the news prompted total, gobsmacking shock. The Judah they had known was a swaggering ladies’ man, brusque and bombastic—the kind of guy who could captivate a crowd with his tales of life in the Israeli army, then drink everyone under the table. Few friends or ex-girlfriends had suspected that the stocky guy with the arm full of tats, the muscular calves, and the biblical mane had been carrying around a secret so weighty for so long.

For Schiller, however, the post was the first day of the rest of her life—a Declaration of Independence of sorts. She’d kept her real self hidden for more than four decades, and the truth simply had to come out. It was just the latest epochal chapter in a life filled with them.

Jessica Schiller
had known she was different for as long as she could remember. Growing up in a conservative Jewish household in Los Angeles, a young Judah found herself identifying more with women than with boys or men. (Following Schiller’s lead, female pronouns will be used for the remainder of this story.) During quiet moments at home, she often caught herself staring at her mother’s figure, wondering, Why don’t I have that body? By sixth grade, Schiller had started pondering whether it was possible for someone to be born into the wrong body. Because she had two younger brothers who looked up to her, because her parents expected her to become a lawyer or a surgeon like her father, and because she had no idea what the hell was going on, she ignored those feelings and pushed on with her life.

On paper, teenage Judah seemed just like any other good-looking straight boy—she had girlfriends, lost her virginity to one of them, and hooked up with a bunch more. The women at Brandeis University, where she went to college, were enamored with this “sexy, fun California boy,” Schiller says. Beneath the surface, however, the questions nagged at her: What might it feel like to wear those clothes? Or to have that hair? What would it be like to be looked at like that?

“It was confusing, because I knew I identified as a woman, but I also was attracted to women, so I knew I wasn’t gay,” Schiller says. “It was a dual identity—a male side of my brain and a female side. The female side would have these thoughts, and then they would disappear. Then the male side would be like, What the fuck are you thinking? ”

This feeling of dual identity has a formal name: gender dysphoria. Psychologists describe it as a conflict between a person’s assigned gender and the gender with which they identify. Judah Schiller fit the profile perfectly. Unconsciously, Schiller overcompensated with masculinity on overdrive. She worked out aggressively. She always made sure to be the loudest person in the room—even if she didn’t have that much to say. She actively cultivated an exaggerated sense of self-worth. She partied like the end of the world was nigh. Adam Werbach, a close friend since the 1990s, describes the twentysomething Schiller as a “type A alpha male…someone you definitely wanted on your side in a rumble.”

Schiller’s gender dysphoria ebbed and flowed, following her from Los Angeles to Israel, where she also had citizenship, in her 20s. During a stint at a kibbutz, Schiller and some friends dressed in drag for a party, and the ensuing shenanigans made her feel comfortable in a way she never had before. A few years later, Schiller was drafted into the Israel Defense Forces, where she bristled at the oppressively macho culture. One night, Schiller was assigned to stand watch in the desert with an M16, a grenade launcher, and six magazines of ammunition. There in the darkness, beneath a sky bright with stars, she asked herself: What the fuck am I doing here? Who the hell am I pretending to be? How much longer am I going to have to live in this body?

“The constant questioning became exhausting,” Schiller recalls. “By the time I was 25, I pretty much knew I was trans, but I wasn’t even close to comfortable coming out. So I just put it aside. I vowed to make the best of my life as Judah.” Deep down, though, she knew she was living a lie.

Schiller passed
the next decade in a liminal state. At 26, she married an Israeli woman, Galit, and soon the couple moved back to the Bay Area, where Schiller attended UC Hastings College of the Law, became a corporate lawyer, then switched to career coaching and advertising. Over eight years, Judah and Galit had three children: Tomer, Naomi, and Satya. Almost by accident, Schiller had assembled the pieces of a good, rich, family-filled life.

Then everything went horribly wrong.

It was June 15, 2007, three days after Satya was born. The day started as a celebration. Galit had come home from the hospital the day before, and she and Judah were planning to entertain family and friends on the back patio of their San Anselmo home. Hours later, during dinner, Galit complained of chest pains. As Judah helped her into the car, she fell unconscious. An ambulance rushed her to the emergency room. Galit died on the operating table later that night.

“One minute we are all together, happy, celebrating life, and the next minute I am there at the hospital and it’s midnight and this woman who was my love and my wife and the mother of my kids is dead,” Schiller says. “The most agonizing part of it all came the next morning—facing the weight of this responsibility alone and having to tell my bigger kids that their mother wasn’t ever coming back.”

The immediate aftermath was nearly impossible for Schiller to endure. Every minute proved a struggle. Instead of seeking therapy or counseling, she focused her attention on the kids. Between raising a newborn and caring for the two other children, however, Schiller never gave herself time to grieve. When she did pause to think about what life had taken from her, the reality was too agonizing. As she had with her dysphoria, she simply shut it all down.

Gradually, Schiller’s family and close friends helped her recapture some semblance of normalcy. Her youngest brother, Aaron, pitched in with the kids; Aaron’s wife, Megan, became their de facto nanny for about a year. Schiller hired a night nurse so she could catch up on much-needed rest. In an effort to regain happiness after such intense pain and suffering, she started dating again. Eventually, she entered a second marriage, which lasted less than two years.

“I was never very good at playing the widower,” Schiller admits. “That didn’t mean losing my kids’ mom didn’t affect me—it did, and it’s the kind of thing I’ll probably never completely get over in my entire life. I just wanted to move forward, you know? I had to. Constantly forward. It’s the only thing I’ve ever known.”

At the time
of Galit’s death, Schiller was working with Werbach at Saatchi & Saatchi S, a division of the global advertising agency that focuses on sustainability, and was making regular trips to Bentonville, Arkansas, to work with Walmart on a big project. All those hours on airplanes gave Schiller the opportunity to process Galit’s death, to make sense of her new life as a single parent, and to ruminate on the notion of purpose. All along, though, there was the grueling self-interrogation: When, if ever, am I going to embrace my true gender?

Schiller couldn’t bear to think about how having a transgender parent would affect her kids. She was also conflicted about the nature of her work. While the agency job was exciting, it revolved around promoting the achievements of others, and Schiller wanted to leave a mark all her own. Even after she started her own marketing agency in 2011, she felt she hadn’t gone far enough. She yearned to invent something, to produce something out of raw materials.

That something ended up being a bike you can ride on water. Schiller got the idea for this curious machine in early 2013, smack in the middle of a boat tour of the soon-to-open eastern span of the Bay Bridge. She’d signed up for the tour with an acquaintance named Karl Isaac, who at the time was head of brand strategy and innovation at Adobe. There, bobbing in the bay, staring up at the towering concrete supports of the new span, the duo, both cycling enthusiasts, lamented the fact that its bike lane hadn’t been extended onto the older, western span—that it didn’t run from Yerba Buena Island to San Francisco, and wouldn’t for quite some time. “Neither one of us could believe there wasn’t a convenient way to bike from Oakland to San Francisco,” Isaac says. “We started tossing around ideas.”

Isaac had just gotten back from a trip to London, where he’d seen cycle pubs—bars on wheels that up to a dozen people can pedal simultaneously. Schiller laughed and thought for a moment, then pulled an idea from thin air: What if someone created a bike that let you ride across water? “In the moment, I was kind of like, ‘Oh wow, that would be such a fantastic idea,’” says Isaac, who is now a vice president at eBay. “But I figured it was one of those situations where you sit around and riff off each other. Jessica was much more serious. For her it was a mission.”

Schiller stayed up most of each night that week, jotting down ideas and sketches, hitting the Internet to find industry forecasts. The possibilities were intoxicating. Great workout! Fun adventure! Sustainable! Potential game changer for transportation! It was as if the idea had recalibrated her creative processes to vibrate at a different frequency. For Schiller, it wasn’t a question of whether the water bike would happen; it was a matter of when.

Schiller incorporated as BayCycle in November 2013 and within a few months had changed the name to Schiller Bikes. She poured her own money into office space, hired a team of engineers, designers, and product developers, and scheduled the first whiteboard session for January 3, 2014. The inaugural sessions were all about design. Over the course of three months, Schiller’s team picked apart a variety of naturally occurring hydrodynamic forms—from surface-skimming water bugs to dolphins and sharks. At some point, someone mentioned the boom-and-mast construction of a catamaran. For Schiller, this turned on a light. She reached for a laptop and furiously searched for a picture of Philippe Starck’s Motor Yacht A, a giant catamaran she had spotted in the bay one day. Soon after, the team had a sketch.

In August 2014, the first Schiller Bike hit the water. Media buzz grew steadily, and soon wealthy customers, plus a number of beach resorts, were forking over $5,500 apiece. Forbes called it “the world’s most radically redesigned bicycle.” Lord Norman Foster, the legendary British architect, professed his admiration. Princess Charlene of Monaco and her husband, Prince Albert II, worked with Schiller to organize the Riviera Water Bike Challenge, the world’s first professional water bike race, which was held in June 2017 and raised more than $300,000 for charity (the second race was held this summer).

As they have been for Schiller, the past nine months have been the most exciting for Schiller Bikes. One of the water bikes appears in a forthcoming Verizon commercial, and the company has now sold thousands of models in more than 80 countries. Since December 2017, Schiller Bikes has amassed $3 million in funding from a phalanx of big-name investors, including Tevya Finger, founder of Bumble & Bumble; Dan Coughlin, an early Facebook employee; and Joel Lunenfeld, a former vice president at Twitter. “It’s not often that you see a new invention in the world,” says Lunenfeld, who’s now Schiller Bikes’ chief marketing officer. But the water bike is exactly that, he says: “something that literally didn’t exist” until Jessica Schiller came along and created it.

Late last year,
right around the time that Schiller Bikes was starting to take off, Schiller made the choice to leave Judah behind for good. The break was partly spurred by the previous several years spent building a company from the ground up, one life-altering decision lending her the confidence to make another. But there was an external catalyst as well: Heather Ryan.

Ryan, a beautiful, straight-talking brunette, was one of the first Instagram models for the Schiller Bike back in 2014. She and Schiller started dating, and things got serious fast. The relationship was different from Schiller’s previous romances. Ryan expected authenticity. She knew that something about Schiller did not compute, and she demanded to know what was up. “When we first met [back when Jessica still identified as Judah], she was charming and sweet and somewhat feminine,” Ryan says. “I liked that about her. Wasn’t quite sure if she was possibly gay or what. I just loved her presence. That was one of my first inclinations.” She laughs: “I quickly found out she was not gay.”

Under Ryan’s relentless pressure, Schiller began unpacking her gender dysphoria. During late-night conversations at the house they now shared with their five kids, Schiller told Ryan about all her years of questioning, effectively admitting to someone else for the first time in her life that she was trans. From there, the two went to couple’s therapy, where Schiller opened up even more. The only person (other than their therapist) who knew Schiller’s secret, Ryan kept pushing her lover to dig deeper and share more.

The couple planned a series of secret getaways to San Francisco and Sonoma—mini-vacations during which Schiller wore feminine clothing and makeup. For Schiller, these weekends were critical test runs. For Ryan, they were bittersweet: She was delighted that Schiller was finally coming out, but she also dreaded what was coming next.

“When you’re faced with someone transitioning, it changes the relationship,” Ryan says. “She wanted to be treated like a woman, and she deserved it. But I wanted to be treated that way too. We’d get into fights over who should open the door for whom and sit there being like, ‘I’m the girl!’ ‘No, I’m the girl!’” Ryan knew that transitioning was the right move for Schiller, but she also suspected that her doing so likely meant the end of their relationship. “You remember the saying ‘If you love someone, set them free,’ right?” Ryan says. “It definitely was a little of that.”

By the beginning of 2018, Schiller was ready to begin her physical transition. She saw her primary care doctor in January and started taking prescribed doses of estrogen and a testosterone blocker. On the surface, the hormone replacement therapy seemed straightforward—all she had to do was pop a few tiny pills a day. Inside her body, though, the impact was far more intense; gradually and inexorably, the meds altered her biochemistry, and with it her appearance.

The second step of Schiller’s transition—fully coming out—was even less simple. She figured it was best to start by telling her kids, and she vowed to break the news during a road trip back from Los Angeles. Somewhere on I-5 outside Coalinga, she coaxed Naomi, 16, and Satya, 10, off their iPhones, had them remove their earbuds, and dropped the bomb. (Nineteen-year-old Tomer was at college back in L.A.)

“I want to tell the two of you something important that I’ve known my whole life, since I was a kid,” Schiller started. She had rehearsed the lines so often in her head, she remembers every word. “Basically, since I was younger than you, Satya, I’ve always felt like I’ve been in the wrong body. That I’m transgender.”

The kids remained silent for what seemed like an eternity. The brown and green of the Central Valley whizzed by. Naomi, who was sitting next to Schiller in the front passenger seat, responded first. “Good for you,” the teenager said. Then, without missing a beat: “What do you want us to call you?” Schiller guffawed. She had spent weeks imagining the kids’ reactions. She hadn’t prepared for this. “You can still call me Abba, if you want,” she said, citing the Hebrew word for father. “But from this point forward, I’m going to go by Jessica.”

The conversation continued for a while, with Schiller reassuring the kids that they were still a family and that nothing was changing except her. Satya remained mostly quiet until a few weeks later, when he pulled Schiller aside in the kitchen. “I had a father for 10 years but never had a mom,” the boy said. “Now I guess I finally get to have a mom.”

Later, after Schiller had come out to her eldest, Tomer, and the rest of her immediate family, she focused on revealing the news to everyone else. Except for a few phone calls and emails to close pals, she did this in one fell swoop, via LinkedIn. Responses ranged from congratulatory and supportive to downright gushing. Those whose reactions she feared most ended up shocking her anew, like Abdulla Hassan, an early Schiller Bikes adviser and the CEO and cofounder of Dhow Capital, an investment firm in Kuwait. Schiller didn’t know much about Hassan’s cultural background, but she was concerned that her transition might offend him. His email allayed that fear.

“Let me start by saying that I trusted you with my own money and the funds of my company, that trust and belief will continue,” he wrote. “Your personal life has obviously taken a new journey and our trust and belief in you will not change. Your honesty about the decision is appreciated and I am sure your zeal of doing business will always be the same.”

Once the wave
of catharsis subsided, Schiller was overwhelmed. Sure, she was living her truth, but she didn’t have any trans friends with whom she could connect to talk about her transition, her new life, and what it meant to now be operating in the business world as a female CEO. She felt she needed a mentor, someone who could give her a sense of the new challenges and opportunities that might arise. This led her to Vivienne Ming.

One weeknight, Schiller was in the kitchen of her Mill Valley home, making dinner for her kids, when she googled “transgender female executives.” The first to come up was Martine Rothblatt, the creator of SiriusXM radio and the founder of United Therapeutics. The second was Ming, a theoretical neuroscientist, an expert in artificial intelligence, and the founder of Berkeley-based think tank Socos Labs. Schiller watched Ming’s 2017 TEDx talk about the process of making a better person, during which she discussed her own transition. Schiller was blown away. She sent Ming a LinkedIn message that night.

The two women met for coffee in Berkeley about a month later. Schiller recalls the encounter as being like “sitting in the best college lecture of your life” and says that Ming did most of the talking. Ming’s recollections are slightly different. “I do a lot of these meetups with people undergoing transitions, and most of them involve me sitting there reassuring someone that everything is going to be OK,” she says. “Within minutes it became clear that this was not going to be one of those talks. Instead, Schiller wanted to know everything people don’t tell you about going through a transition—where to find new clothes, what kind of weight loss to expect, how people in the business world might treat you. She knew things would be OK. She just didn’t know what things to expect.”

And for Schiller, life since her transition has been more than OK. Even though she and Ryan split up, Schiller says she is happier than she ever thought possible—her contentedness amplified by the fact that she resisted it for so long. Most of her day-to-day interactions with strangers have been positive, not darkened by prejudice. Friends and acquaintances have asked lots of questions—mostly about what it means to be trans and which pronouns they should use.

Physically, the differences between Schiller and her former self are stark. She has noticed a new accumulation of fat at her hips, a loss of muscle mass, and reduced hair growth. While she has no plans for gender confirmation surgery, she did have rhinoplasty to “feminize” her nose, and her estrogen pills and testosterone blockers have enlarged her breasts.

Then, of course, there are differences of style: Bras, heels, dresses, and blouses have replaced the T-shirts and jeans that used to be her uniform. She also dons makeup—applying skills picked up from YouTube videos, Naomi, and Ryan. She has embraced manicures, preferring “holographic mirror chrome” nail polish because it reminds her of the shimmer of the water. These new routines couldn’t be further from the ones Schiller had when she was Judah. “Last year at this time, I could roll out of bed and be ready for the day in five minutes,” she says. “Now I get up, I spend an hour getting ready, and I’m still lucky if I get my kids to school on time.”

Schiller’s personality is different too. Before her transition, she struggled to stay focused on a single task for any period of time. Now, she says, her mind is like a laser beam—she’ll be so intent on completing something that hours will go by before she realizes she hasn’t eaten or stood up. Stereotypical though it sounds, she also feels softer, more vulnerable, more empathetic, and more in touch with her emotions.

By and large, Schiller’s friends and family members see these things too. “One of the most incredibly fabulous things about Jessica was that she was always searching for something—for lots of things,” longtime friend Werbach says. “It was always very exciting to be around Jessica, because her searching was frantic. After her transition, it feels as if the edge of that franticness has come off. It feels like she’s arrived.”

Schiller’s brother Aaron sees a similar transformation; he says Jessica is “lighter” than her former self and more fun to hang out with. Aaron, a spiritual adviser and relationship coach, adds that while one must acknowledge who Schiller was before her transition, it’s important to see her as someone new and separate from her past. “Life is about continued growth and change,” he says. “Jessica’s journey gives everyone in our family an opportunity to see someone we know and love in new ways.”

This concept is one that Schiller is grappling with as well. She’s happy to offer perspective on what she’s experiencing, but she knows that what she believes to be true today could in fact be radically different from what she perceives six months from now. She still has a long way to go.

“It really is like when you’re on a boat, and you leave the dock and you go out at dusk and the coastline starts to get smaller and the lights start to get dimmer,” she says. “You’re out at sea, and you feel the water underneath you. You don’t know what the destination will look like. You don’t know what the coastline you’re heading toward will be like. That’s what being trans feels like for me right now.”

“The coast that I left has started fading,” she continues, “and I feel like I’m out at sea and I haven’t reached the destination yet. I’m enjoying the experience. It’s deep and wild. It’s expansive and vast. The lights of the coastline I left are dimmer and dimmer every day and week. That old identity isn’t me anymore. I can barely see it. And I guess that’s scary at times. But the place I’m headed is going to be great. I know I’m headed in the right direction.”

Originally published in the September issue of
San Francisco 

Have feedback? Email us at
Follow us on Twitter @sanfranmag
Follow Matt Villano on Twitter @mattvillano