Singer Songwriter

Milestone Mentorship


Transform from a bedroom songwriter to confidently writing, performing and releasing your music...

With expert guidance from someone who's been exactly where you are.

šŸŽø

This 1:1 coaching program is for intermediate to advanced singer-songwriters ready to write songs that land with impact—and finally break out of the bedroom and beyond their inner circle.

It’s for musicians who are done with hiding their talent and are ready to perform live, release powerful tracks, and grow a real fanbase—without quitting their day jobs or vanishing on tour.

In this mentorship, you’ll finally:

🤘

Finish your songs

(or get started with new ones)

🤘

Feel confident

performing live

🤘

Release your music with a

step-by-step plan tailored to you.

You can go from "someday" to "hell yes, I did that" and achieve your next big music milestone.

šŸ˜• You’ve written some, or even dozens of song ideas, but none of them are or feel finished.

šŸ˜• You want to perform, but the idea of stepping on stage makes you anxious.

šŸ˜• You keep telling yourself "someday" when it comes to recording.

šŸ˜• You're tired of YouTube tutorials that leave you more confused or missing personalized feedback.

šŸ˜• You don't want to torpedo your day job, but you dream of having thousands love your music and have no clue where to start.

About Me

Hey, I'm James.

I’ve toured the world for over 20 years, played with Beck and Old Crow Medicine Show, won major folk fest awards, and racked up 1.5M Spotify streams—but I started out in the New England hardcore scene, terrified to sing in front of people.

I know what it feels like to be unsure, and I know how to help you overcome the same fears and technical challenges I faced...

Without taking 20 years to figure it out.

šŸŽø How You'll Get Results


🤘 Personalized song feedback to help you actually finish songs you’re proud of.


🤘 Goal setting and accountability to make consistent progress.


🤘 Real-time coaching so you feel confident before your next performance.


🤘 Step-by-step guidance for recording and releasing music without getting lost in the tech.

What Happens After You Work with Me


You’ll perform your next gig

feeling confident and prepared.

You’ll release your music and

start building a real audience.

You’ll call yourself a musician

and mean it.

What we'll do together

Depending on your specific needs and goals, we'll focus on:

🤘

Co-writing guitar and vocal parts

so your songs feel polished.

🤘

Feedback on lyrics and melody

to help your message land.

🤘

Performance coaching so you

nail your gigs and recording sessions.

🤘

Guidance through the full successful Song Cycle: write, record, distribute, and promote your music with confidence.

What You'll Get

  • 1:1 coaching Zoom calls (multiple or one-off single sessions)

  • Weekly goal tracking and midweek check-ins

  • Custom action plan based on your musical goals

  • Optional co-writing, performance prep, and recording advice

The Investment

šŸ‘‰ Payment Plans Available

"Jumpstart"

Single 1 Hr Session

Perfect for an artist who needs a one-off jumpstart to:

  • Tackle a song that’s been stuck for weeks—and finally finish it

  • Prep for an upcoming gig or open mic with expert feedback

  • Reignite their writing momentum with a focused creative kickstart

  • Walk away with a personalized action plan for their music goals

$175

šŸ‘‰ Split Payment Plans Available

"Breakthrough"

12-Pack

🤘BEST VALUE🤘

$125/1 Hr session (28% discount)

Perfect for the artist who wants to stay creatively accountable and get guidance on:

  • Writing their next EP or full-length release with expert support

  • Overhauling their artist identity to match their true sound

  • Navigating every phase of the Song Cycle—write, record, release, promote

  • Building a long-term plan to consistently grow their audience

$2100

$1500

(Sessions must be used

within 6 months)

šŸ‘‰ Split Payment Plans Available

"Rise"

4-Pack

$149.50/1 Hr session (15% discount)

Perfect for an artist looking to:

  • Build a clear growth strategy to attract local or online fans

  • Finish and refine multiple original songs with expert feedback

  • Plan and prep their first single release—from structure to rollout

  • Clarify their unique sound and artistic identity with focused guidance

$700

$598

(Sessions must be used

within 3 months)

šŸ‘‰ Split Payment Plans Available

Next Steps

šŸ‘‡

1ļøāƒ£ Click below to book your first session or package.

2ļøāƒ£ You’ll receive a quick intake form to tell me about your goals.

3ļøāƒ£ We’ll meet on Zoom, set up your roadmap, and get to work.

4ļøāƒ£ You’ll start making serious progress in your songwriting, performing, or releasing—fast.

FAQ

  • Who is this best for?

    Anyone who wants to become a part-time professional artist with thousands of people loving their music—without quitting their day job—but feels stuck on key steps like songwriting, performing, building an audience, or releasing music.

  • What will we work on?

    Every artist has different needs. If you’re not sure what to focus on, we’ll figure it out together. Most sessions focus on things like improving your songs through feedback or co-writing, leveling up your guitar skills with step-by-step guidance, building a plan to build a local audience, or getting you ready for a gig or a recording session.

  • What if I don’t have anything ready?

    That’s what I’m here for. We start with whatever you have, even if it’s just an idea.

  • Are the 1:1 Sessions at a set time every week?


    They can be, if you prefer it that way! Students typically get best results with a regular weekly schedule, but you have the flexibility to book your sessions whenever it works best for you, as long as it’s within the time frame provided:

    āž”ļø 4-pack: use within 3 months

    āž”ļø 12-pack: use within 6 months

  • Do I keep 100% of the song writing credits if we co-write?

    Yes, always!

You can achieve your singer-songwriter dreams with step-by-step mentorship designed to get you tangible results in record time...
Without spending years stuck in procrastination or trial and error.

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Contact Support: james@guitarlessonswithjames.com