A pet pony, a driven dad and unbridled ambition: Megan Agnew drives from Pennsylvania to Nashville to meet the teachers, classmates, neighbours and musicians who helped shape the singer before superstardom.
Every few months, Scott Swift would hit the phones. The agenda: his teenage daughter, Taylor. Most likely sitting in his study at the family home in Hendersonville, near Nashville, Tennessee, overlooking the Cumberland River, he caught up with her former teachers, his business buddies, family friends, session musicians who had recorded demos with her and the producers who had mixed them, giving them a detailed download of information about his daughter’s ascent.
Scott talked well. A third-generation banker and former radio salesman, he updated them on which songs she had cut (I am told he spent US$10,000 on building her a recording studio at their home); which singles were coming out next (by the age of 15, Taylor had a record deal with a company in which Scott had bought a 3 per cent stake); where she was touring (he had bought Cher’s former tour bus for her); and the awards for which she needed votes. Nashville, after all, was an industry town where careers were built on fresh young faces and smoky old networks.
And — it worked. Today Swift, 34, is a billionaire, more of a phenomenon than a pop star, who sells so many concert tickets she shifts national economies. She arrived in the UK on tour on Friday. Her albums (11 original studio albums, 4 rerecorded albums and 4 live albums) are devoured immediately by her insatiable fans, the Swifties. She has sold the equivalent of five million albums this year alone, making her the top-selling artist of 2024, and has become the first artist in US history to sell 100 million album-equivalent units — the industry measure in the streaming era.
For the past few weeks I have been driving the Taylor Swift trail through the US to try to understand how she came to be: through Pennsylvania, where she was raised; New Jersey, where the family spent long summers; and Nashville, where they moved when Taylor was 14, to help her make it big. What I found was a story of megawatt talent, intense family nurturing and canny investment; of magic and money; of how a star was born — and then made bigger and bigger and bigger.
“What do I do with this child?” Scott reportedly asked a family friend, stunned by the sparkling talent and determination of his young daughter, who arrived in this world dead-set on stardom, who chatted endlessly and felt things so deeply she couldn’t bear the death of birds she found in the garden; and who wrote poetry so relentlessly it was as if she couldn’t stop.
The hills of Pennsylvania, just northwest of Philadelphia, are rolling rather than mighty, populated with rust-coloured barns, stables, worn American flags and copses of ancient oaks. Swift’s first home — Pine Ridge Farm, a former Christmas tree farm near Reading, where she spent the first decade of her life — is a Norman Rockwell painting of a place.
Her father, Scott, now 72, grew up nearby. He was a financial adviser at the investment firm Merrill Lynch. Swift’s mother, Andrea, now 66, was a marketing executive born into a wealthy family who grew up between Singapore and Houston, Texas. Andrea’s father was the president of a construction company, her mother an opera singer. Andrea met Scott at a drinks party and they married in 1988. Taylor was the Swifts’ first child — born on December 13, 1989 — followed two years later by Austin, 32, who was quieter but cheekier.
I pull up outside the Swifts’ old farm — a modest clapboard house overlooking the paddocks where Taylor kept a pony. Scott kept the farm as a hobby, mowing the meadows before work. Upstairs, in a corner room, was where she asked for three books to be read and five songs to be played to her every night. “We’re not supposed to talk to anybody but People magazine,” say the couple who live there today — referencing a popular celebrity tabloid in the US. And they have been instructed by Swift’s team? “Yes,” they say, closing the door.
Taylor went to a Montessori kindergarten and then Wyndcroft, a private school in nearby Pottstown, where the Swifts were known for their wealth. According to family friends they drove a Chevrolet Suburban — an SUV fit for the secret service — sent Christmas cards showing their impressive holidays and brought their daughter’s pony to school for show and tell. They were also known for their generosity. Each year the people who had donated the most money to Wyndcroft had their names published and the Swifts were often at the top. The family would also give teachers the keys to their holiday home as a thank-you present.
Scott seemed to know everybody, his friends often becoming clients and vice versa. One was James MacArthur, famous for playing Dan “Danno” Williams in Hawaii Five-O, with whom he apparently holidayed. I’m told Andrea played tennis at the Hillcrest Racquet Club in Reading, a members’ club where she often socialised.
Maureen Pemrick, 77, Swift’s teacher at Wyndcroft in first grade, says the first thing she noticed about Taylor was her wild curls — “She was strikingly pretty” — and her animated chatter. “She was a little sunbeam who just bounced around,” Pemrick says. One afternoon when it was time to go home, Swift suggested that the class had a group hug. “She gathered the children and started squeezing them together,” Pemrick says. “And from then on she was like that.”
Others remember her as dreamy but solid in confidence. “I want to be a stockbroker,” Swift wrote in her yearbook at six years old, “because my dad is one.” By second grade that had changed to “Singer”.
“Taylor was a determined little thing,” says Barbara Kolvek, 78, who was a music teacher at Wyndcroft. When Swift was given the part of Freddie Fasttalk in the play The Runaway Snowman, she went to Kolvek’s office every lunchtime to practise her solo. “She didn’t care that she had to play a boy. She wanted to do it. And so she did.”
Down the road from Wyndcroft lives Barbara Lenzi, 75, an art teacher who has taught there for 45 years and who had Swift in her class for four years. “We’re huggers!” warns Lenzi, who has peroxide-dyed hair with pink tips, glittering flip-flops and iridescent nails. So is Nancy Boerner, 79, the cafeteria manager at Wyndcroft for 26 years, who has joined Lenzi to meet me.
“Taylor was the type of child you were just magnetised towards,” Lenzi says.
Swift was adored at school, they say. “I used to see her walk through that kitchen every day,” Boerner says, “with her smile and she would say” — she puts on a sing-song voice — " ‘Hi, Mrs Nancy!’ And then she was off, ‘Bla bla bla bla.’ She’d always have something sweet to say. Always.”
“She was confident — the whole family was — but never too much,” Lenzi says. “Just the way she walked, never looking shy.” “The curls boppin’!” Boerner adds.
“I’m going to show you something,” Lenzi says, switching on an ancient TV in her snug. “Open sesame,” she says to the machine, popping a CD into a slot. There, in front of us, is a 13-year-old Taylor Swift, on stage at Wyndcroft on a visit to her old school. “I’ve been a lot of lonely places,” she sings, a song she wrote, “being here on the outside, looking in nobody ever lets me in.” After the performance she takes questions from the infant crowd. A water bottle appears, which she takes without looking. “Isn’t she just ador-baby!” Lenzi says.
Around three times a week until her early teens, Andrea took her daughter to Berks Youth Theatre Academy after school. Swift was the natural star: she played Sandy in Grease, Maria in The Sound of Music. “She was definitely the most gifted,” says Marjorie, 56, whose children were in the same group. “She stuck out. Once she was on stage, you couldn’t take your eyes off her.”
Swift gave out wallet-sized photos of herself as Sandy to the kids in the years below her at school, attended a performing arts summer camp run by Britney Spears and sang the national anthem at local baseball games on school nights.
Gena Levengood, 32, was two years behind Swift at the school. Levengood once asked Swift if she was going to audition for American Juniors, an American Idol spin-off for children. “She said she considered it but decided not to, because there was a line in the contract about not being able to release an album within a certain number of years.”
At about nine years old Swift moved schools to Wyomissing Area Junior/Senior High School in West Reading — teachers say to be closer to theatre rehearsals. The Swifts moved house into the same town. I drive up the hill to the historic Dutch-style home, with its pillars, balconies and perfectly preened lawn. From the age of 11 Swift learnt to play the guitar in a room on the side of the house. She was taught two or three times a week for three hours after school by Ronnie Cremer, 57, a tech support guy by day who was introduced to the Swift family by his brother, who ran the youth theatre.
“I said I’d teach her what I know,” Cremer says. “She was sweet and kind and eager. She was never a guitar virtuoso, but the idea was to teach her how to project into a microphone and play as if on autopilot — to allow her to perform.” They listened to the Beatles, analysing the different band members’ writing styles, and she learnt to put chords to her own lyrics in her notebook.
The parents “made a fuss” over their daughter, who they called “T” or “Tay” or “Tay-Tay”. “Scott was the cash guy,” Cremer says. “He could sell ice to the Eskimos. Andrea was the one who kept Taylor on point. She had her eye on the prize.”
Later, Cremer was threatened with legal action by Swift’s team — which he says was dropped — for creating a website called ITaughtTaylorSwift.com. Today he says he has been “written out” of her biography.
Everyone I spoke to talked about the consistently close bond Swift had with her mother. “There were times when, in middle school and junior high, I didn’t have a lot of friends,” she told the Great American Country network in 2008. “But my mom was always my friend. Always.”
Half an hour’s drive north, at exit 19 of interstate 78, is a petrol station and sheepskin shop owned by a man called Pat Garrett, who is, in his words, “as old as water”. Over the road is a stage in a field, the Pat Garrett Amphitheater, where he holds country music concerts, and next door he used to have a bar, the Pat Garrett Roadhouse, where he put on karaoke competitions. “Everything is Pat Garrett around here,” he says with a smile.
We walk through the shop, past a platinum album by Swift, through his workshop and its scraps of fur — “Skins and songs, that’s what I do” — and into his office. “I made that vest for the girl up there,” he says, pointing at a photo of a glamour model in a gilet, adding: “There’s nothing underneath.”
“Anyway,” he continues, “one week they showed up — 11-year-old Taylor and a whole gang of her people for the karaoke competition. Whoever won got to open the show at the Amphitheater. She kept getting better, so she won — and so she opened.”
She played with Garrett’s band at fairs and country music festivals in front of thousands of people, saying: “Hi everybody, I’m Taylor!” “She had a little bit of showbusiness in her,” he says. Her notebook, he claims, was filled with pages of her own autograph. “But she did good.”
One day he says Scott came in, not knowing what to do next with his daughter. “I told him, ‘Up here in Hershey they make bars. In Detroit they make cars. And in Nashville,’ " Garrett lowers his voice, " ‘they make stars. Move to Nashville.’ And he just kind of nodded. The rest is history, I guess.”
The Swifts spent weeks of the summer at their holiday home in Stone Harbor, New Jersey, a small coastal town on a spit, the Atlantic on one side, a calm basin of water on the other. It’s a perfect little spot, with old-timey homes on the water — for sale in the estate agent’s window for US$6 million ($9.7 million) — crêperies and ice cream parlours. It is Springsteen country. During the long, hot summer days Swift would walk through town, her guitar slung across her back, much to the judgment of the local girls. “I think Taylor made herself known here,” says one of them, who still lives there.
Andrea handed New Jersey neighbours Swift’s early demos and would ring the local café, Coffee Talk, to ask if her daughter could sing at their open-mike nights.
Their former home has been knocked down and rebuilt, renamed Swift Waters. Lois Hamilton, 75, an old family friend of the Swifts who lives next door, invites me in. We walk through her living room and past the stone fireplace where an eight-year-old Swift opened her first guitar when she came over one Christmas. “Oh my God!” she said in a home video, surrounded by wrapping paper, “I. Am. Happy.”
“She was very bright,” says Hamilton on the deck at the back of the house. The Swifts’ old garden is next door, backing onto the still water. They had a hot tub on the patio, a jetty with a boat from which they waterskiied and two jet skis. They were also members of the sailing club.
Swift was “cute and confident” but she didn’t have a lot of friends, Hamilton says. “She was more solitary, very happy in her own room.” Instead she would sit on the decking and sing out across the water. “Constantly singing, constantly writing, then singing what she was writing.”
Jim Hand is the third generation to own Fred’s Tavern & Liquor Store, five minutes down the road, and has known Scott Swift for much of his life. “When Taylor was young, the family came over for dinner and the kids were all swimming,” Hand says. “They [Swift’s parents] asked me if I had the Disney channel and I said no. There was some country singer on that was Taylor’s idol — and so they got up and they left.”
Scott, he says, still manages his investment portfolio. “I couldn’t trust anyone any more than I trust him,” Hand says. “If he came to me and said, ‘Hey, I need $100,000,’ I’d borrow $100,000 and give it to him. And he would pay it back.”
In the school holidays, when Swift was 11, her parents took her to Nashville’s Music Row, where she went knocking on the doors of record labels handing out demo CDs. “I would say, ‘Hi, I’m Taylor. I’m 11. I want a record deal — call me,’ " she told Entertainment Weekly in 2008.
Aged 13 she was signed to RCA — a Sony Music Entertainment subsidiary — on a development deal, the youngest songwriter in the label’s history. And by 14 the Swifts had moved to Hendersonville, Tennessee, a town 25km northeast of Nashville, once the home town of Johnny Cash.
Cremer, the guitar teacher, says the family flew him from Pennsylvania to build a studio for Taylor in their new home when they first moved in, giving him about US$10,000 ($16,000) for equipment. In the driveway, in subsequent years, was Cher’s tour bus, which they had renovated, installing a sign in bronze script that read: “Never, Never, Never Give Up”.
Swift made an entrance when she first arrived at Hendersonville High School, says a former classmate, telling people she was going to be a star. “We kind of rolled our eyes because, being in Nashville, we hear that a lot,” she says. “It was just such a strong statement for someone of that age.”
Almost immediately she started dating an older boy. He was popular and had a “preppy look with a country flair” — he would fray the corners of his cap and stick a fishing hook through it. Within months, however, their relationship had ended.
Soon after that it was the school talent competition and Swift got up on stage to perform Teardrops on My Guitar, a song she had written about him. “She’d better hold him tight, give him all her love,” she sang in front of the whole school, her ex-boyfriend and his new girlfriend. “Look in those beautiful eyes and know she’s lucky, ‘cause he’s the reason for the teardrops on my guitar.” It was ballsy. “Everyone was pretty taken aback,” the classmate says. “Like — she had just come out of nowhere.”
Many, however, thought she was “a bit of a brat”, from the moneyed side of town and modelling clothes for Abercrombie & Fitch. At 16, Swift bought a Lexus SC430 convertible, the car driven by Regina George, the meanest girl in Mean Girls.
Today it is thought that Swift’s parents still spend time in Hendersonville as well as at a home just outside Tampa, Florida, where they invite family friends for long weekends. Swift, I am told, calls them from her treadmill, singing her set list and running, rehearsing for her current 152-show tour.
In Nashville, Swift’s record label paired her with songwriters and producers. One was Angelo Petraglia, 70, a New Yorker whose work with Kings of Leon won a Grammy. “I was, like, oh my God, they’re bringing over a 14-year-old girl,” Petraglia recalls. “I didn’t know how to write with a 14-year-old girl.”
He called his friend and writing partner, Robert Ellis Orrall, 69, who had a similar-aged daughter and agreed to make a trio. “But it was incredible to write with her,” Petraglia says. “She had no fear. None at all. She seemed to know who she was already — she was Taylor Swift, even back then.” It was a confidence, he says, that never quite tipped into precociousness. “You can get plenty of people coming in here feeling a little too much of themselves, but she wasn’t like that at all,” he says. “She just knew what she wanted.”
The three of them wrote in after-school sessions, which she would always lead. “Between Angelo and I, we had over 100 years of experience,” Ellis Orrall says, “but I remember Angelo threw out a line and she just said, ‘Hmm, I dunno, Angelo, it sounds a little trite.’ And it was, like, ‘Boom! Shot down by the kid!’ Out of ten songs, one of hers would be perfection. Nothing could make it any better.” And every year the ratio has only got higher, he says.
Despite the quantity of songs they cut — about 25 — the label told her they needed 60 days to evaluate her when the contract ended, according to Ellis Orrall. After a family “huddle” between Andrea, Scott and Taylor, they walked away. “It was extraordinary. The biggest mistake in the history of the record label.”
With no label, Ellis Orrall suggested to the Swifts that they put together a press kit to hand out at a showcase at the Bluebird Cafe in Nashville, a haven for songwriters. He had a gig coming up and so he invited her to play. “That night we got her a record deal,” he says. Scott Borchetta — formerly of Universal Music Group and now setting up his own company, Big Machine Records — was in the audience, and “had found the one person he could build a label around”. Swift was 15. According to documents seen by Music Business Worldwide, Scott Swift bought shares in Big Machine at the time worth US$500,416.66, thought to be a stake of 3-5 per cent. Swift’s self-titled debut album was released in October 2006 and became the longest-charting album on the Billboard 200 of the decade, seven times platinum.
Until — again — she walked away. “For years I asked [Big Machine], pleaded for a chance to own my work,” she wrote in a blog post. In 2018 she left the label for the Universal Music Group, which gave her ownership over her music.
In June of the following year, Borchetta announced he was selling the company to the entrepreneur Scooter Braun for about US$300 million, a deal that included Swift’s back catalogue; her father, as a shareholder, is said to have made US$15.1 million from the deal. Swift accused Braun of “incessant, manipulative bullying”; Braun told Variety in 2021 that her reaction was “very confusing and not based on anything factual”. In 2020 the rights were sold again, to a private equity company. Swift, angry and determined, set about rerecording her first six albums — an act of brilliant business acumen, propelling her old songs back into the charts.
Today she has money (US$1.1 billion, according to Bloomberg); awards (14 Grammys, 39 Billboard Music Awards and an Emmy); Spotify streams (around 110 million listeners every month); and an A-list boyfriend, the Kansas City Chiefs Super Bowl winner Travis Kelce. Right now she is in Edinburgh on her Eras tour. Scott is probably on the tour bus too, the father linked to ten companies affiliated with his daughter, including merchandising and rights management; Andrea as well, described by the singer as her “guiding force”, who has a role in “every decision I make”; and maybe Austin too. “I always joke that we’re a small family business,” she told Time magazine in December last year.
And so just know that, when Swift is on stage in front of 100,000 people and the lights are flashing and there are sequins and dance routines and 44 songs and 10 acts and the ticket sales are pumping up the economy, this was always, always the plan.
Written by: Megan Agnew
© The Times of London