BOSTON — Two days to go. We have told the story of how the debut was made, walked through every song and followed the radio tour. Now it is your turn. Eleven songs, head-to-head, until only one is left.

How to play

Every matchup is between two songs from the standard edition of Taylor Swift. Pick the one you would rather hear right now. Winners move on, and if a round has an odd number of songs, one gets a bye. The order is shuffled every time, so play twice and see if your champion holds up.

Taylor’s Version watch

The other question fans are asking this week is whether a re-recorded debut is on the way. Here is what is on the record:

• 2019: Big Machine Records was sold, and the master recordings of her first six albums, including the debut, went with it.
• 2020 onward: Taylor began re-recording those albums as “Taylor’s Versions,” releasing four of them.
• May 30, 2025: She announced she had bought back the masters of all six albums. In the same letter she said the debut re-recording was finished, and that it could still re-emerge when the time is right.

As of our deadline, no release date for Taylor Swift (Taylor’s Version) had been announced. We will be watching on October 24, and so will everyone else.

Sources

• Wikipedia: Taylor Swift (album))
• WAMC / NPR: Taylor Swift buys back the rights to her first six albums (May 30, 2025)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — In 2006, there was no playbook for a teenage country artist on a brand-new independent label. So Taylor Swift and Big Machine wrote one. The debut album found its audience the old-fashioned way and the brand-new way at the same time.

Station by station

“Tim McGraw” went to country radio in June 2006, four months before the album came out. Then Taylor went on the road, visiting radio stations across the country on a radio tour that lasted about six months, through the end of the year. It was slow, unglamorous work: introducing herself, playing the song live and thanking programmers one station at a time. It worked. The single reached No. 6 on Hot Country Songs.

The Myspace generation

At the same time, Taylor was doing something few country artists did: talking to fans online. She used Myspace to post blogs and share song information, and it drew in teenagers and young adults who did not necessarily listen to country radio. That direct line to fans became a hallmark of her career.

Opening for the biggest names in country

The live shows came next. Taylor opened for Rascal Flatts in late 2006, then for George Strait in early 2007, toured with Brad Paisley through 2007, and in July 2007 opened for Tim McGraw and Faith Hill, the couple whose name was on her first single.

Crossing over

By 2007, “Teardrops on My Guitar” had crossed from country into pop radio, reaching No. 13 on the Hot 100 and the Top 10 on several pop and adult formats. More than a year after release, the album kept climbing, peaking at No. 5 on the Billboard 200 in January 2008.

The lesson

Show up, play the song, talk to your fans yourself. Twenty years later, it is still a pretty good marketing plan.

Sources

• Wikipedia: Taylor Swift (album), release and promotion)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — Forty minutes and 28 seconds. That is the entire running time of the standard edition of Taylor Swift, 11 songs that introduced one of the defining songwriters of her generation. Every song carries her name in the credits. Here is the whole album, one track at a time.

1. “Tim McGraw”

Written by Taylor Swift, Liz Rose · 3:54

Nostalgia for a relationship with an older boyfriend, built around the songs that remind you of someone. It became the first single.

2. “Picture to Burn”

Written by Taylor Swift, Liz Rose · 2:55

A sharp, funny kiss-off to an ex who did her wrong. It reached the country Top 10.

3. “Teardrops on My Guitar”

Written by Taylor Swift, Liz Rose · 3:35

Unrequited love for a boy who likes someone else. Her first big crossover hit, reaching No. 13 on the Hot 100.

4. “A Place in This World”

Written by Taylor Swift, Robert Ellis Orrall, Angelo Petraglia · 3:22

A teenager’s uncertainty about where she belongs and what comes next.

5. “Cold as You”

Written by Taylor Swift, Liz Rose · 4:01

A relationship with someone who never appreciated her.

6. “The Outside”

Written by Taylor Swift · 3:29

Loneliness after her love of country music set her apart at school. One of three songs she wrote alone.

7. “Tied Together with a Smile”

Written by Taylor Swift, Liz Rose · 4:11

Written about a friend struggling with an eating disorder, and about how people hide pain behind a smile.

8. “Stay Beautiful”

Written by Taylor Swift, Liz Rose · 3:58

Admiring someone from afar, without him ever knowing.

9. “Should’ve Said No”

Written by Taylor Swift · 4:04

Confronting a cheating ex. Written alone, it became her second country No. 1.

10. “Mary’s Song (Oh My My My)”

Written by Taylor Swift, Liz Rose, Brian Maher · 3:35

A love story that lasts from childhood to marriage.

11. “Our Song”

Written by Taylor Swift · 3:24

A couple who make a song out of their everyday moments. Written alone, it went to No. 1 on Hot Country Songs.

The writers’ room

Seven of the 11 songs were co-written with Liz Rose, who met Taylor through her publishing deal and became her most important early collaborator. Robert Ellis Orrall and Angelo Petraglia co-wrote “A Place in This World,” and Brian Maher joined Taylor and Rose on “Mary’s Song.” Three songs, “The Outside,” “Should’ve Said No” and “Our Song,” are Taylor’s alone.

A note on “Tied Together with a Smile”

One of the album’s quietest songs carries one of its heaviest subjects. If you or someone you love is struggling with an eating disorder, support is available from the National Alliance for Eating Disorders.

Sources

• Wikipedia: Taylor Swift (album), track listing and songs)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — Before there was a debut album, there was a teenager who refused to wait. The story of how Taylor Swift came to exist is a story about saying no to the wrong deal and yes to the right room.

Walking away at 13

When Taylor was 13, RCA Records offered her an artist development deal. On paper it was a dream. In practice, the label wanted to keep her in development until she turned 18. She did not want to wait five years to make an album, so she left.

A songwriter at 14

At 14, she signed a songwriting deal with Sony/ATV in Nashville, becoming the youngest songwriter the publisher had ever signed. The family relocated to the Nashville area so she could write with professionals after school. That is how she met Liz Rose, the songwriter who would go on to co-write seven of the debut’s 11 songs.

The Bluebird Café, November 2004

The Bluebird Café is a small room with a huge reputation. It is where Nashville’s songwriters play their songs in the round, and where industry people go to listen. In November 2004, Taylor played a showcase there. In the audience was Scott Borchetta, a music executive who was starting his own label, Big Machine Records.

Borchetta offered her a recording contract. About two weeks later, she said yes, choosing an independent label that did not yet exist over the safety of a major. Big Machine partnered with Universal Music Group for distribution, and the contract was finalized by July 2005.

Finding the sound

The label tried several producers before settling on Nathan Chapman, a little-known producer Taylor had been making demos with. It was the right call. Chapman produced every song on the album except “The Outside,” and recording took about four months, wrapping up near the end of Taylor’s freshman year of high school.

Why it still matters

Every decision in this story points in the same direction: songwriting first, control over her own work, and betting on herself. Twenty years later, those are still the throughlines of her career.

Sources

• Wikipedia: Taylor Swift (album), background and development)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — In ten days, one of the most important debut albums of the century turns 20. On October 24, 2006, a 16-year-old songwriter released Taylor Swift on a brand-new Nashville label, and nothing about popular music was quite the same afterward.

The Boston Made Newsroom is marking the occasion the only way we know how: thoroughly. Starting today, we are publishing a new story every other day, each with something to play, leading up to the anniversary itself on October 24.

What’s coming

• Oct 16 — The Bluebird night. How a teenager with a guitar went from a Pennsylvania Christmas tree farm to a Nashville publishing deal and a record contract.
• Oct 18 — Track by track. All 11 songs on the original album: who wrote them, how long they run, and what each one is about.
• Oct 20 — Radio, Myspace and opening slots. How the album found its audience one radio station, one blog post and one arena opening set at a time.
• Oct 22 — The Debut Bracket. Eleven songs, head-to-head, until you crown your favorite.
• Oct 24 — Twenty years. The full anniversary story, with the stats, the masters saga and a 10-question trivia game.

The album in 60 seconds

Taylor Swift was released by Big Machine Records on October 24, 2006. It has 11 songs on the standard edition, every one of them with Taylor’s name in the writing credits; she wrote three on her own. It produced five singles, including country No. 1s “Our Song” and “Should’ve Said No,” and its 157 weeks on the Billboard 200 made it the longest-charting album released in the 2000s. The RIAA certified it 8× Platinum in September 2025.

Sources

• Wikipedia: Taylor Swift (album))

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — When our founder emailed a parking director in Kansas City in the hope of getting a message to Taylor Swift (the full saga is on bostonmade.com under the title Where’s Taylor!?), the Boston Made Newsroom was given an urgent assignment: become fluent in Taylor Swift before she writes back. Just in case. You never know.

We took it seriously. Possibly too seriously. Somebody made a color-coded spreadsheet. Somebody else cried during the evermore section and claimed it was allergies. What follows is the result: a complete, fact-checked, deeply affectionate field guide to every era of the most successful songwriter of her generation, written for longtime Swifties, brand-new fans, and anybody who has ever been dragged to a concert by their kid and accidentally had the time of their life.

Before the eras: a Christmas tree farm in Pennsylvania

Taylor Alison Swift was born on December 13, 1989, in West Reading, Pennsylvania, and spent her early childhood on a Christmas tree farm. (Imagine being the kid whose family job is literally making the holidays happen. Of course she grew up to sell out stadiums.) She was reportedly named after the singer-songwriter James Taylor, which, in hindsight, feels a little like naming your kid “Future Grammy Winner.”

She fell hard for country music, played anywhere that would let her, and at 14 convinced her family to move to Hendersonville, Tennessee, just outside Nashville, so she could chase it full time. Let that sink in: at 14, most of us were negotiating a later bedtime. Taylor was negotiating a relocation plan.

Taylor Swift (the debut)

Her first single, “Tim McGraw,” came out in 2006 when she was 16, followed that fall by her self-titled debut album. Songs like “Teardrops on My Guitar” and “Our Song” turned a teenager with a guitar into a country-radio fixture. She wrote or co-wrote every track.

The Boston Made take: Naming your first single after a more famous artist is the music-industry equivalent of emailing a parking director to reach Taylor Swift. It is bold, it is a little ridiculous, and it absolutely works. (For her, anyway. Our results are pending.)

Easter egg you might have missed: The number 13 was already part of her story. She has said it shows up everywhere in her life, starting with her birthday.

Fearless

Fearless gave the world “Love Story” and “You Belong With Me,” two of the defining pop-country songs of all time. At the 2010 Grammys it won Album of the Year, making her, at 20, the youngest artist to win the award at the time.

The Boston Made take: Fearless is the album that made every middle-school talent show in America sound exactly the same for about three years. We mean that as the highest compliment.

Easter egg you might have missed: Her 2021 re-recording, Fearless (Taylor’s Version), kicked off one of the boldest business moves in music history. More on that below.

Speak Now

For her third album, Taylor wrote every single song by herself, with no co-writers, partly in response to critics who questioned how much of her music she really wrote. The result, including “Mine” and the fan-favorite “Enchanted,” is one of the most personal records of her career.

The Boston Made take: Writing an entire album alone to prove a point is the most “fine, I’ll do it myself” energy in music history. Every founder of every small business in Boston is nodding right now.

Easter egg you might have missed: Speak Now (Taylor’s Version) arrived in July 2023, mid-Eras Tour, because sleep is apparently optional when you are her.

Red

Red mixed country, rock and pop and gave us “We Are Never Ever Getting Back Together” (her first No. 1 on the Billboard Hot 100), “I Knew You Were Trouble” and “All Too Well,” the song many fans consider her masterpiece.

The Boston Made take: Red is the album you put on when it is October in Boston, the leaves are turning, and you need to feel something on the Green Line.

Easter egg you might have missed: In 2021, Red (Taylor’s Version) included a 10-minute version of “All Too Well,” which became the longest song ever to hit No. 1 on the Hot 100. Ten minutes! That is longer than most Boston Made meetings. Barely.

1989

Named after her birth year, 1989 was her official leap into pure pop, with “Shake It Off,” “Blank Space,” “Style” and “Bad Blood.” It won Album of the Year in 2016, her second, and turned her into the biggest pop star in the world.

The Boston Made take: “Shake It Off” has now appeared in a business email about parking. We believe this is a first. We believe she would want to know. That is the whole point of this article, honestly.

Easter egg you might have missed: Her 1989 World Tour included a long list of surprise guests. The Eras Tour later turned surprise songs into a nightly ritual, with two acoustic picks fans never saw coming.

reputation

After a stretch away from the spotlight, Taylor returned with darker, harder-hitting reputation, led by “Look What You Made Me Do” and featuring “Delicate.” The reputation Stadium Tour became the highest-grossing tour in U.S. history at the time.

The Boston Made take: reputation is proof you can disappear for a while, come back, and absolutely run the place. Boston Made’s inbox is currently in a reputation era. Silent. Mysterious. Possibly plotting.

Easter egg you might have missed: Snakes were everywhere on that tour, including enormous inflatable ones on stage. Turning criticism into stage design is an all-time power move.

Lover

Lover was bright, romantic and colorful, with “ME!,” “You Need to Calm Down” and “Cruel Summer.” It was also the first album she owned the master recordings to outright.

The Boston Made take: Lover is basically the inclusion page we just built at Boston Made, in album form. Pink, blue, every color, everybody welcome.

Easter egg you might have missed: She met Benjamin Button, her Ragdoll cat, on the set of the “ME!” video. Boston Made Pets has an entire investigation into her cats, which we cannot recommend enough.

folklore and evermore

During the 2020 lockdowns, Taylor surprised everyone with folklore in July and then did it again with its “sister album,” evermore, in December. Quiet, story-driven and made largely remotely, folklore won Album of the Year in 2021, her third.

The Boston Made take: Two surprise albums in five months, during a pandemic, while the rest of us learned to bake one (1) loaf of sourdough. We have nothing more to add.

Easter egg you might have missed: Fans named a whole fashion moment after “cardigan,” and the cardigans came back in a big way. Boston winters thank her personally.

Midnights

Midnights, a concept album about sleepless nights, gave us “Anti-Hero” and “Karma.” It broke streaming records the day it came out, and at the 2024 Grammys it won Album of the Year, making Taylor the first artist ever to win the award four times.

The Boston Made take: An album about lying awake at 3 a.m. thinking about everything is the most relatable thing a billionaire has ever made. Small business owners everywhere felt seen.

Easter egg you might have missed: A lyric on Midnights about making friendship bracelets launched the Eras Tour’s biggest fan tradition: trading handmade bracelets. Travis Kelce later tried to give her one with his phone number on it. You know how that turned out.

The Tortured Poets Department

Announced at the Grammys and released in April 2024, The Tortured Poets Department arrived with a surprise double-album edition just hours later. Its lead single, “Fortnight,” featured Post Malone.

The Boston Made take: Releasing a second batch of songs two hours after the first is exactly what our founder does with ideas at 2 a.m. The difference is that hers win awards.

Easter egg you might have missed: A new TTPD section was added to the Eras Tour in 2024, so later shows ran well over three hours. Endurance athletes everywhere took notes.

The Life of a Showgirl

Her 12th studio album was announced in August 2025 on the New Heights podcast hosted by Travis and Jason Kelce, and released in October 2025. It earned about 3.5 million equivalent album units in less than a week, the biggest opening week ever for an album, passing Adele’s long-standing record. Its lead single was “The Fate of Ophelia.” In September 2026, The Life of a Showgirl: The Encore added four new songs: “Patient Zero,” “Cleveland!,” “Pink Clouding” and “Babylon.”

The Boston Made take: Announcing your album on your partner’s podcast is the celebrity version of putting your business card on a friend’s bulletin board. We understand that kind of networking. We are, after all, writing to a parking director.

Easter egg you might have missed: Sharp-eyed fans spent weeks decoding the album’s orange-and-glitter visual clues before release. Classic.

The Eras Tour: the biggest show on Earth

From March 17, 2023, in Glendale, Arizona, to December 8, 2024, in Vancouver, the Eras Tour played 149 shows on five continents. Each three-plus-hour concert was organized as a journey through her albums, with costume changes, a collapsing stage dive, and two surprise acoustic songs every night. It became the first tour in history to gross more than $2 billion, and the concert film became the highest-grossing concert film ever.

It also caused actual, measurable seismic activity. At her July 2023 shows in Seattle, fans dancing and cheering produced shaking that seismologists compared to a small earthquake, which the internet promptly named the “Swift Quake.” Boston Made would like to note that our office has also experienced seismic activity, but that was the copier.

Taylor’s Version: the business masterclass

Here is the part every entrepreneur should study. In 2019, the master recordings of her first six albums were sold without her getting the chance to buy them herself. Instead of accepting it, Taylor re-recorded her old albums from scratch and released them as “Taylor’s Version,” starting with Fearless in April 2021, followed by Red, Speak Now and 1989. Fans streamed the new versions instead of the old ones. Then, in May 2025, she announced she had bought back the masters to her catalog.

Read that again as a business plan: when you lose control of your product, rebuild it so well that your customers follow you, and then buy the original back anyway. It is ownership. It is leverage. It is genius. Boston Made has it printed on a sticky note on the fridge, right next to the parking director’s email address.

The Kansas City chapter

In July 2023, Chiefs tight end Travis Kelce said on his podcast that he had tried to give Taylor a friendship bracelet with his phone number on it at an Eras Tour show. Two months later, in September 2023, she was at Arrowhead Stadium cheering him on. They announced their engagement in August 2025 with an Instagram post joking that “your English teacher and your gym teacher are getting married,” and they married on July 3, 2026, in New York, with Adam Sandler officiating, according to reporting at the time.

Which brings us back to our founder’s email. If one friendship bracelet can launch the most famous romance in sports, surely one well-punned letter to a parking director can at least earn a thumbs-up emoji. Surely. Right? (Please write back.)

Play: The Era Sorter

You have read the field guide. Now prove it. We give you a song; you tell us the era. Your streak counter is watching.

The Ultimate Newsroom Swiftie Quiz

Why a Boston company cares this much

Boston Made exists to build things with heart, keep good stories alive, and connect people across every corner of our ecosystem. Taylor Swift built an empire by writing honestly, owning her work, rewarding her fans and turning every setback into a new era. That is the playbook. We are just over here taking notes, refreshing our inbox, and saving her a parking spot.

Follow every chapter of the saga in the Boston Made Reader: the original letter (Where’s Taylor!?) on bostonmade.com, and the feline investigation on Boston Made Pets.

The fine print, in the smallest font we own: Boston Made is not affiliated with, endorsed by, or (yet) on a first-name basis with Taylor Swift, Travis Kelce or the Kansas City Chiefs. Nobody in this story has replied to us, and we have not made anything up about anybody. Photos are freely licensed from Wikimedia Commons and credited under each image. No parking attendants were harmed in the making of this article.

As midterm campaigns sharpen, the cost of living is returning to the center of the conversation. Voters are measuring promises against rent, groceries, insurance and the cost of getting to work.

That focus creates a demanding environment for both parties. The candidates who can connect national policy to the weekly household budget will have the clearest path to trust.

New England is moving into another consequential Senate cycle, with New Hampshire and Maine drawing national attention. The region remains politically competitive, and small shifts in turnout, cost-of-living pressure and candidate quality can change the map quickly.

The broader story is local: voters are weighing national arguments against the practical record of the communities around them. Housing, health care, energy costs and the future of work are likely to matter as much as party labels.

For New England, the contests will be an early test of whether independents still hold the deciding power they have carried through recent cycles.

PICKS & SHOVELS · No. 10 · Specialty materials

Follow the supply chain far enough down and you reach a wafer of indium phosphide. Almost nobody makes it.

What it does

AXT Inc (NASDAQ: AXTI) makes compound-semiconductor substrates, mainly indium phosphide (InP) and gallium arsenide wafers. Most of the production happens at its China-based subsidiary, Tongmei.

The shovel it sells

The raw InP wafers that laser makers like Lumentum and Coherent need to build the lasers inside AI transceivers. This is the bottom layer of the optical stack.

What the numbers say

• Q2 2026: revenue was $47.6 million, up 164% year over year. InP revenue was $30.7 million, up from $3.6 million a year earlier.
• Q3 2026 outlook: about $66 million in “realizable revenue,” with upside that depends on more Chinese export permits.
• Capacity plan: quarterly InP capacity rising from about $20 million to $60 million by year-end and more than $130 million by the end of 2027.
• Customers: supply agreements with prepayments or deposits from Lumentum ($43.5 million), Coherent ($25.4 million) and Casella ($22.3 million).

Sources: Semiconductor Today, Aug 4, 2026; SEC 8-K.

What could go wrong

• It depends on Chinese export permits for InP.
• Manufacturing based in China brings geopolitical and tariff exposure.
• Small scale and concentrated customers.

Season one, wrapped

Ten companies, one chain: turbines and fuel cells make the power, switchgear routes it, chillers remove the heat, packaging and burn-in turn silicon into reliable chips, lasers and cables connect them, and a wafer company in the basement makes the lasers possible. Season two looks at Coherent, Fabrinet, Ciena, Astera Labs, Eaton, nVent and Amphenol. Start again at No. 00.

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PICKS & SHOVELS is a Boston Made Newsroom storyline from the BOSSTOX intelligence desk: one under-covered AI-infrastructure company at a time, explained in plain English with sources. Previous: No. 09.

Follow the whole storyline on the Boston Made Reader → Storylines · Track the companies in BOSSTOX Learn.

Not investment advice. Boston Made, Inc. and its writers are not licensed financial advisors. Figures come from the company filings and reports linked above, for the periods stated; check the primary filings before making any decision.

PICKS & SHOVELS · No. 09 · Switchgear

Between the power plant and the server sits a lot of steel cabinets full of breakers. Without them, nothing switches on safely.

What it does

Powell Industries (NASDAQ: POWL) engineers custom electrical equipment, including switchgear, motor-control centers and prefabricated “e-houses,” that distributes high-voltage power safely in plants, utilities and now data centers.

The shovel it sells

Medium-voltage gear, including the packages that tie on-site generation into a campus. That’s the same bring-your-own-power trend from No. 02.

What the numbers say

• Fiscal Q3 2026 (ended Jun 30, 2026): revenue was $312 million, up 9%. New orders were $934 million, up 158%.
• Book-to-bill: 3.0x. Backlog was $2.4 billion, up 69% year over year.
• The orders include a data-center order worth “exceeding $400 million” for behind-the-meter on-site generation assets.
• Management cited “increasing demand to support data centers and related AI capacity demand.” A yard expansion is due to finish by the end of fiscal 2026.

Source: Powell 8-K, Aug 3, 2026.

What could go wrong

• A long history of oil, gas and petrochemical cycles.
• Large fixed-price projects carry margin risk.
• Capacity is tight with a backlog this big.
• The big data-center orders are concentrated in a few customers.

Why it’s under-covered

Energy analysts have followed Powell for decades. AI analysts mostly haven’t found it yet.

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PICKS & SHOVELS is a Boston Made Newsroom storyline from the BOSSTOX intelligence desk: one under-covered AI-infrastructure company at a time, explained in plain English with sources. Previous: No. 08. Next: No. 10, AXT.

Follow the whole storyline on the Boston Made Reader → Storylines · Track the companies in BOSSTOX Learn.

Not investment advice. Boston Made, Inc. and its writers are not licensed financial advisors. Figures come from the company filings and reports linked above, for the periods stated; check the primary filings before making any decision.