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Passenger Profile Sherry Marcus Milano
Sherry in the late 1980s right before she played a gig.

You’ve had quite an interesting career over several decades, including your most recent incarnation as a business partner with your sons Marcus and Ethan Cohen in your company, Take us back to the first moment you realized you wanted music to be a big part of your life and eventually, your career.
I started being affected by music when I was very young. My dad would take me to Broadway shows, and I’d beg him for the soundtrack albums and learn every word. I loved the way music felt; singing along with songs like “Leader of the Pack” in the mirror, dancing around to James Brown, seeing The Beatles on Ed Sullivan, and all the emotions that music brought that made me feel fully alive. I think I always knew.

Did you learn an instrument as a kid?
I taught myself how to get music out of the piano in my aunt’s house, which was a piece of furniture that held photos. Nobody played it. But my whole childhood, whenever we’d visit, I’d sit there playing quietly the whole time. In 6th grade my dad got me my first guitar, and after that, I was never alone again.

Do you remember what the first song you wrote was, and how old were you at the time?
I actually wrote poetry for years before I ever thought about putting the words and the music together. When the dream started growing wings and I started seeing that I could “make” music, I was more fascinated with figuring out the chords to the songs I listened to, so I could sing them and feel them. I wanted to be a singer first. I started writing and performing my own songs in high school, and always tried sneaking in a couple of originals on all my gigs through my whole career.

Your website shows that you are a Creative Marketing & Communications Specialist, Music Composer, and Producer. But that’s not all! You also have this description on your LinkedIn page: “Creativity, enthusiasm, inspiration and experience drive all my projects and collaborations, whether they involve representing a musical artist, branding and promoting a product, company, or special event, or developing an out-of-the-box strategy for an ongoing campaign. I've been able to build a track record of successful results and satisfied, returning clients for over three decades. Now, I'm proud to add a partnership with my two sons, and launch our new company, ‘WeWillWriteUaSong,’ combining our collective musical, recording, and marketing skills into one production agency, where we write, arrange and customize songs, beats, ads, soundtracks and jingles for artists, businesses, film and TV.”

Normally, when I see that many skills offered, I tend to think the person is a Jack or Jill of all trades, and discount their expertise in any one of the fields. You however, have already been successful in all of those areas. Has it been a linear progression, or do you often find yourself juggling several of those types of jobs at once?
It all grew as I grew. I started as a girl in a band, and never imagined ever running any kind of business. I was part of an amazingly progressive and rebellious generation growing up in NYC, and I was on the musical side of that. My “coming-of-age” happened at a time when life was saying “yes” to every kind of music, so those of us coming into it felt unlimited. It was all about being different and unique. We wrote and performed and recorded in whatever ways we were inspired, and I carried that intuition/ inspiration-led way of doing things with me wherever life took me. I never had a list of organized goals and steps or business plans; I’m not wired that way. I always have way more than one thing going on at a time, so I learned how to be a plate-spinner, and I still juggle many business hats.

"Don’t settle for who you think you are or you’ll never become who you want to be."

Plate-spinner. I love that! How old were you when discovered you could earn income with your music?
Well, I played for free most of the time with my first bands; we were happy to have gigs. My first paid music gig was at 17, but it took a number of years before you could call it “income,” lol! There were tip bowls and free dinners at first, then little paid gigs here and there, side jobs, and plenty of hungry years; it took a long time before it was all I did. But I always knew it would be, eventually. And I never considered doing anything else, regardless of money. It was the whole reason I was here; I never doubted that, and I trusted my path.

What’s your desert island genre or era of music?
Late 70s to late 80s.

What do you listen to in the car?
I love pulling out old music for the car, anything from Al Jarreau to Michael Franks, Patti Austin, Stevie, Chaka, Tower of Power, Brian McKnight… CaiNo (that’s Sherry’s talented son, Marcus).

Do you listen to learn or listen to enjoy?
In the car I’m usually just listening to stuff I love. Listening to learn is a different mind-space, taking notes, paying attention to different things.

Please correct me if I’m remembering this incorrectly, but I think you referred to yourself as a “hippie” during one of our conversations. Assuming my memory is accurate, how does somebody who has the Woodstock ethos as a big part of her DNA, also have the business chops that you clearly possess?
I’m a “functioning hippie.” [Laughter] I’ve had to develop the aspects of me that were necessary to survive and succeed without sacrificing my hippie spirit or annihilating my wonder child. I really began to enjoy the business game. I also grew up with a male role model. I’m an only child. I was Daddy’s little girl whose mom died right before my 3rd birthday. My dad was a magnificent man who introduced me to art and words and music and the power of dreams. I grew up consciously choosing a very different path.

Passenger Profile Sherry Marcus Milano
Sherry in in Central Park, NYC, circa 1975

Wow, I’m sorry you lost your mom when you were so young, but happy to hear your dad was such an awesome parent and role model.

So many creative people—artists of all types—typically seem loathe to engage in selling themselves or their product, which in your case is often times the music you create. You’re not a shrinking violet by any stretch. Do you have any advice for our songwriters, artists, and composers who would like to be more accomplished at marketing or selling their own wares?
Yes. Learn! Be willing to be uncomfortable, don’t settle for who you think you are or you’ll never become who you want to be. And you’ve got to leave where you are, where it’s safe and comfortable, to get there. Selling yourself is the outward display of your confidence and belief in yourself and your abilities. It feels awkward to toot your own horn, I’ll give you that. But when you get serious about succeeding, you become willing to take responsibility for that success instead of just hoping it happens. Watch videos, read books, articles, blogs—immerse yourself. TAXI offers a wealth of information, and it’s FREE! I’ve spent many hours watching the archived TAXI TV videos, learning more there than I ever imagined or expected. Utilize what your TAXI membership offers.

"When you get serious about succeeding, you become willing to take responsibility for that success instead of just hoping it happens."

Let’s go back Sherry the performer. How did you start that business?
There wasn’t a business through most of my performing career, there was just the artist living the dream, looking to get the record deal, the hit song, the tour, the Grammy… I wish I had a fraction of the knowledge and confidence I have now back in those years, or at least the right person in my corner to teach and guide me. Now I manage an amazing singer/songwriter/performer, and get to be all the things I wish I’d had back then.

How did you go about the booking aspect of that business, which of course, goes back to selling one’s self.
I spent the first 5-10 years at the mercy of agents and wannabe managers, not understanding that I had any control whatsoever. But I was growing and evolving as a person, and discovering more mindful ways to fully participate in my own life. So I stopped waiting to be rescued and taken through the door by the hand, and decided to fill in my own blanks. All business is about sales. I got proactive. I read books. I took a Dale Carnegie course. I visualized. I practiced. I prayed. I learned the psychology of sales. And I stopped letting fear call the shots.

Wow, you really get it! Actually, you reached out and got it! Tell us about the jingle company. I’m fascinated by anybody who can contact a business owner and get him or her to pony up the money for a jingle. What did a typical client look like? Mom and pop, mid-size company, or General Motors-sized companies for the most part?
The jingle company was “the Dream” reborn with mommy wings. It was my answer to getting off the road and working late nights once Marcus was born. I was still able to write songs and be in the studio, but it took getting really good at sales to be able to get to the part I loved, which was the music. It started with small businesses and culminated with big casino and auto dealer accounts over about 11 years. I expanded into copywriting, voice-overs, slogans, full service marketing campaigns, media placement, PR… It’s a great story, but a long one!

Did you need to cold call and pitch them, or did they hear about you and reach out?
Ninety-five percent of the time they were targeted, researched cold calls. I went in prepared, often with something already written. I’d get to the decision-maker and walk in with my briefcase and boom box, play my demo of jingles that were getting a lot of airplay, and work toward the close.

What was your initial pitch like?
I always did my homework, so I could open with genuine compliments about their product, service, store, etc., then say how all that wonderfulness deserved better, more professional and memorable advertising, a real theme song of their own, or their competition was going to corral all their prospective customers. Then I’d use examples, like the way Coke separated itself from Pepsi in all their marketing with songs, and ask thought-provoking questions, like “where would McDonalds be without ‘You Deserve a Break Today?’ I’ll tell you where: just another hamburger joint! And how is Burger King giving them a run for their money? I’ll tell you how; with ‘Have It Your Way,’ so people don’t have to pick out the onions with their fingers and have them smell funky all day! That, Sir, is the power of the Jingle!!!” Within 15 minutes, they were usually signing on the dotted line and writing me a check to get started.

"I stopped waiting to be rescued and taken through the door by the hand, and decided to fill in my own blanks."

Every one of us who has succeeded as an entrepreneur knows what it feels like to sit in that pitcher’s seat! What was your batting average?
Oh boy, a numbers question! I’m not a counter of closing percentages; for me that becomes stress-inducing. I just always do my best, so that I know if it didn’t connect, it wasn’t my “fault.” Let’s just say I did well enough for a solid 12-year run with hundreds of accounts. After one successful presentation, the client remarked to his partner, “she just sold me the shoes I was trying to walk away from her in…”

Was there a technique that really helped nail “the close”?
Friendliness, persistence, knowledge, and supreme confidence. Often the close happened after the pitch, when I would stand up and excitedly say, “this is what I wrote for you!” and start singing at them, stopping between lines to say “and here come the horns!” and sometimes go full-on Liza Minelli on them as I demonstrated my rough idea. Some of them were petrified, but they couldn’t question my enthusiasm, and wanted me on their teams.

I can certainly see why! It sounds like you could be successful at anything you’ve got a mind to. I can’t wait to hear the rest next month!

Don’t Miss Part Two Next Month!