Madeline York | FMTY & Boulder
@msyork.bsky.social
Corporate Counsel & Executive Coach
Wit, beauty & questionable legal advice
✈️ Seattle Feb 16th-20th | Austin Mar 9th-12th
💌 Free pitch deck when you subscribe
🔗 msyork.substack.com
🔗 meetmadelineyork.com
🔗 https://www.instagram.com/milehigf/
Wit, beauty & questionable legal advice
✈️ Seattle Feb 16th-20th | Austin Mar 9th-12th
💌 Free pitch deck when you subscribe
🔗 msyork.substack.com
🔗 meetmadelineyork.com
🔗 https://www.instagram.com/milehigf/
Pinned
Getting ready for another trip to Seattle Feb 16th-20th. Get on my dance card while you still can.
Getting ready for another trip to Seattle Feb 16th-20th. Get on my dance card while you still can.
January 24, 2026 at 8:49 PM
Getting ready for another trip to Seattle Feb 16th-20th. Get on my dance card while you still can.
Passed the barre today
January 23, 2026 at 6:44 PM
Passed the barre today
Just saw an ad for a "beautiful mid-evil Tuscany getaway". When I behave wickedly, it's always top shelf.
January 21, 2026 at 1:31 PM
Just saw an ad for a "beautiful mid-evil Tuscany getaway". When I behave wickedly, it's always top shelf.
"“…your cleverness and double/triple entendres has me seduced from a thousand miles away…" -- Mr. L
January 18, 2026 at 5:45 PM
"“…your cleverness and double/triple entendres has me seduced from a thousand miles away…" -- Mr. L
"I've only ever been with submissive women. I'm not into any whips or chains or any of that, but I like that you seem very...assertive." Indeed.
January 16, 2026 at 4:04 PM
"I've only ever been with submissive women. I'm not into any whips or chains or any of that, but I like that you seem very...assertive." Indeed.
A glimpse into my inbox: “After reviewing your prospectus and digital media assets, I have found the opportunity to step into your office to be quite intriguing. I am confident that setting up a strategic partnership with you and...
January 14, 2026 at 4:15 PM
A glimpse into my inbox: “After reviewing your prospectus and digital media assets, I have found the opportunity to step into your office to be quite intriguing. I am confident that setting up a strategic partnership with you and...
Can't stay away from the Emerald City! I'll be visiting Seattle Feb 18th-21st. Get on my dance card while you can!
January 11, 2026 at 5:45 PM
Can't stay away from the Emerald City! I'll be visiting Seattle Feb 18th-21st. Get on my dance card while you can!
“You had me at ‘return on investment’.” I’ve always been a romantic.
January 11, 2026 at 12:35 AM
“You had me at ‘return on investment’.” I’ve always been a romantic.
"You are both a luxury and a necessity." -- Mr. SF
January 5, 2026 at 6:15 PM
"You are both a luxury and a necessity." -- Mr. SF
To my date 13 years my junior, this one's for you
MRE: Mrs. Robinson Experience
What will we bring out in each other?
open.substack.com
January 4, 2026 at 10:49 PM
To my date 13 years my junior, this one's for you
Luna della Lupa. Celebrating the Wolf Moon.
January 4, 2026 at 4:17 PM
Luna della Lupa. Celebrating the Wolf Moon.
Required reading
January 4, 2026 at 3:17 PM
Required reading
Rewarded Secretary with a friend. 4 peas? Really?
a woman is sitting at a desk with papers and a lamp behind her
ALT: a woman is sitting at a desk with papers and a lamp behind her
media.tenor.com
January 4, 2026 at 2:01 PM
Rewarded Secretary with a friend. 4 peas? Really?
New year, new account. Follow all my 2026 adventures www.instagram.com/milehigf/
January 4, 2026 at 3:56 AM
New year, new account. Follow all my 2026 adventures www.instagram.com/milehigf/
Excerpt from my origin story post, working title No Man Knows My History:
“At a research conference, I had the good fortune to sit by a fascinating older woman. She offered me chocolate (I liked her instantly). She revealed she was a retired anthropology professor working as a dominatrix...
“At a research conference, I had the good fortune to sit by a fascinating older woman. She offered me chocolate (I liked her instantly). She revealed she was a retired anthropology professor working as a dominatrix...
January 3, 2026 at 5:48 PM
Excerpt from my origin story post, working title No Man Knows My History:
“At a research conference, I had the good fortune to sit by a fascinating older woman. She offered me chocolate (I liked her instantly). She revealed she was a retired anthropology professor working as a dominatrix...
“At a research conference, I had the good fortune to sit by a fascinating older woman. She offered me chocolate (I liked her instantly). She revealed she was a retired anthropology professor working as a dominatrix...
Hot off the press
Ms. York's 2025 Quantified
A look backward and forward
msyork.substack.com
January 3, 2026 at 3:42 AM
Hot off the press
Getting in the mood. Get in on the Office Playlist - Las Vegas Edition open.spotify.com/playlist/57h...
Office Playlist - Las Vegas Edition
open.spotify.com
January 2, 2026 at 8:52 PM
Getting in the mood. Get in on the Office Playlist - Las Vegas Edition open.spotify.com/playlist/57h...
Preparing my 2026 travel itinerary. Where should I go?
January 1, 2026 at 6:21 PM
Preparing my 2026 travel itinerary. Where should I go?
Reposted by Madeline York | FMTY & Boulder
Ms. York is kicking off 2026 at CES in Las Vegas Jan 6th-9th. Get on my dance card while you can.
December 7, 2025 at 2:47 AM
Ms. York is kicking off 2026 at CES in Las Vegas Jan 6th-9th. Get on my dance card while you can.
What's Ms. York's favorite New Year's tradition? Winding down the year right with one last executive coaching session. Happy New Year!
December 31, 2025 at 5:16 PM
What's Ms. York's favorite New Year's tradition? Winding down the year right with one last executive coaching session. Happy New Year!
"I’ve realized that I want to see hockey-stick growth too—in our relationship."
GARY: This relationship has been such a value-add. You have been an absolute rock star.
CINDY: I feel the same, Gary. The ROI on this relationship has been unbelievable.
#McSweeneysTop25of2025
CINDY: I feel the same, Gary. The ROI on this relationship has been unbelievable.
#McSweeneysTop25of2025
A Marriage Proposal Spoken Entirely in Office Jargon
GARY: Hey Cindy, remember the other day when we were talking about optimizations? CINDY: Yeah, I wanted to circle back on that. GARY: Me too. You s...
buff.ly
December 31, 2025 at 5:12 PM
"I’ve realized that I want to see hockey-stick growth too—in our relationship."
Making new friends on the Gram. Come say hi! @ milehigf
December 27, 2025 at 2:04 AM
Making new friends on the Gram. Come say hi! @ milehigf
Reposted by Madeline York | FMTY & Boulder
What can you say during sex but also at a philosophy dinner?
August 13, 2025 at 2:11 PM
What can you say during sex but also at a philosophy dinner?
I just learned about adult content protection apps called Covenant Eyes and Net Nanny. Those would make for excellent gangster names.
December 26, 2025 at 1:29 AM
I just learned about adult content protection apps called Covenant Eyes and Net Nanny. Those would make for excellent gangster names.
I could really go for a Negroni right now. No, I'm not talking about the drink.
December 25, 2025 at 7:01 PM
I could really go for a Negroni right now. No, I'm not talking about the drink.