A 2017 article in The Simple Dollar highlighted his work ethic and indie ethos, labeling Dailey a "middle-class musician.

[8] It premiered on Billboards Heat Seekers chart at #18 and won Album of the Year in the New England Music Awards April 19, 2015 as well.

Dailey is also a part of the John Mellencamp and Stephen King musical project Ghost Brothers of Darkland County.

In a 2009 review of one of his live shows in support of Torrent, Dan Aquilante of The New York Post called Dailey "the real deal", and compared his musical style to that of Tim Buckley and John Mayer.

[10] Since 2009 Dailey has been closely involved and performing regularly in Theo Epstein and Peter Gammons charity event Hot Stove Cool Music to benefit The Foundation To Be Named Later since 2010 in both Chicago and Boston.

[12] In 2013 Dailey was the artist ambassador to an East Boston-based nonprofit organization ZUMIX dedicated to building of community through music and the arts and continues to remain associated.

[13] In 2020, at the onset of the Covid lockdown and the cancelation of 2020 tours, Dailey began streaming concerts from his shower in support of Boston Venues and independent musicians facing economic distress.

Dailey instead relied upon his family and friends to generate publicity, a tactic which eventually gained him a mailing list of more than 25,000 worldwide.

[16] September 4, 2007 marked the release of a deluxe package of the song Rise exclusively to the Internet music and video download service iTunes.

Dailey's cover recording of Tears For Fears' "Everybody Wants To Rule The World" was made available as a bonus track to anyone purchasing the re-release of Back Flipping Forward on iTunes.

He was seen and heard performing "Rise" in a club, while Gary Sinise's character Mac Taylor played bass alongside him.

Torrent, Volume 1: Fashion of Distraction, which was inspired by The Byrds and features contributions from Roger McGuinn was released digitally on January 20, 2009.

The album is dedicated to his hometown of Boston and features guests like Elliot Easton of The Cars, Tanya Donelly of Throwing Muses and Belly, Kay Hanley of Letters To Cleo and Tim Brennan of Dropkick Murphys.

The DVD was released in the then-new ΧΟΔΕ audio standard, which is meant to have a much higher fidelity to the original recording.

Dailey willingly walked away from one of the largest labels in the world, took charge and involved his fans in a communal creative process through PledgeMusic to make National Throat.

[20] Journalist Jon Karr said of National Throat, "Dailey's latest album makes it clear that good songwriting isn't a matter of hiding behind shiny production or an over-stylized persona.

[23] The song and video were inspired by Dailey's experience at Zumix, a Boston-based nonprofit organization dedicated to empowering youth and building communities through music and the arts.