The Secret Life Of Pepper Massey

Pepper Massey life story could be called “All Roads Lead To The Black Hills.” From Rhode Island where she was born, to Canada where she followed her mother, to Florida where she became a single mother, to California where she arrived pennyless after a failed marriage and without the means the buy a car for transportation and consequently becoming a biker by necessity, to South Dakota that she visited for the 1st time in 1985, her life has followed a path full of personal and professional struggles but also of many huge successes making her today one of the most sought-after Motorcycle Industry Consultant.

In Los Angeles, at the age of 25, a Honda 450 was the only thing she could afford to go to work, and it’s the way, recommended by a co-worker impressed by her riding skills, that she found her first motorcycle related job, working for Richard Lester, specializing in biker rights, a business conducive to attract new clients. There, Pepper Massey started to write her first press releases and articles regarding motorcycle rights and got her first experience with public speaking engagements. In the recently published excellent book “Biker Chicz Of North America“, Pepper explains “It was not long before I came to understand that my path had brought me to a very good place. This felt like a great opportunity, possibly a career with a future, a place I might make a difference.”

And what a difference she made as soon as she understood the importance of promoting motorcycle safety riding courses, as she discovered the discrimination against motorcyclists, as she realized the intrusion of the government legislation into motorcycle rights. At MRO, at NCOM and its affiliate, the Confederation of Clubs, she created a grassroots movement and succeeded in eroding discrimination against all bikers, including patch holders. She also became  a regular contributing writer to motorcycle publications such as Easyriders, Super Cycle, Thunder Press, etc.

After 11 years on this job, she resigned when she perceived the conflict of interest between her employer, the Lester’s law firm suing motorcycle manufacturers for failing to incorporate leg protectors in their models while she was assisting in the fight against anti-motorcycle legislation. Because of her high integrity, of her enthusiasm for the biker lifestyle and the solid reputation she acquired in the motorcycle industry as an excellent writer and convincing orator defending biker rights and getting positive results for them, Pepper had no problem finding employment anywhere a key player was needed to advance the cause of all motorcyclists. After choosing a 2-year retail experience opportunity at LA Laidlaw Harley-Davidson, and already a frequent visitor to South Dakota where she fell in love the high spiritual energy of the Native Americans sacred places, she jumped at the opportunity to become the Executive Director Of The National Motorcycle Museum Hall Of Fame in Sturgis.

In 2002, she became the publisher of the Meade CountyTimes Tribune where, in addition to her duties to managing and collaborating the efforts of the editorial staff, she was responsible for special Sturgis Motorcycle Rally edition content, design and promotion. Strong of all her experiences in the motorcycle industry she got another dream job as Rally Department Director of the city of Sturgis, making sure that Police, Parks and Street departments had everything in control to welcome bikers during the event. She has also created her own consulting firm and is the Fundraiser Director at Dahl Arts Center. Her path around the USA led her to the Black Hills, and now that she has found the place in the country where she feels more in tune with, no doubt that Pepper is going to travel many more roads in South Dakota, all leading in one way or the other to more involvement with the motorcycle industry, always passionately promoting our sport and defending all of us with both charm and tenacity.

Cyril. Who were your childhood heroes? Pepper. John Wayne

Cyril. When you were a teenager you wanted to become a? Pepper. Journalist. Wrote all the time.

Cyril. Tell me about your first time on a motorcycle? Pepper. Early 70’s. I was hanging with some school friends and a couple of guys rode up on bikes and began talking to one of my friends. They looked incredibly cool with dark glasses and leather jackets, all laid back on those choppers. I imagine I was staring, or maybe flirting, and one of them asked me if I wanted to go for a ride. I think I was 14 – guess what I said… I don’t remember the guy’s name, or what he looked like, but I’ll never forget the bike or the ride. Triumph chopper, the sound, the smell. Everything looked and felt different when I was on that bike. It was raked and stretched with a King/Queen seat and my knees were up around my chin. I had a sore back the next day from that bloody seat but it was one of those moments in my life that forever changed me.

Cyril. If you were not active in the motorcycle industry, what would you do? Pepper. I’d be in art world. Not much of a leap, really. So much of the motorcycle industry is about art and the creative people who design, promote and market motorcycles, parts, clothing, brands and events. If you took art out of the motorcycle industry you wouldn’t have an industry. Motorcycles are pieces of art. Bikes out of the crates are just the beginning, some would say, a blank canvas. The same could be said for the creation and design of all the aftermarket bits we put on, the cloths we wear, the ads and banners we design, and the logos that identify us as who we are. Granted, working at a community arts centre is very different from running the Sturgis rally or the Sturgis Motorcycle Museum, but the similarities are present every day from the passion and energy of the artists to the excitement of the people that embrace and admire their work. Making art accessible to people, kids and adults, who haven’t felt they have a place in that world, that’s pretty rewarding.

Cyril. What is your favorite way to relax? Pepper. Reading a book with a great Cabernet. Fire in the winter. Deck in the summer.

Cyril. What is the last music you downloaded in your iPod? Pepper. Dare I admit it, don’t have an iPod

Cyril. Best and worst quality? Pepper. A ridiculous (and sometimes annoyingly so) optimist. On the dark side I’ve have to admit that I have an interesting relationship with time. My mother once said that I was born late and that set me off in a bad direction. I don’t think it’ll surprise anyone when I state publicly that I am almost always late!

Cyril. Preferred actor and actress? Pepper. I’m certain Johnny Depp wants me to have his children. He’s beautiful, and talented. Denzel Washington, Harrison Ford, Cary Grant, Tommy Lee Jones. Strong beautiful men, and women interest me. Love Angelina Jolie and Helen Mirren, Annette Benning, Judi Dench, Meryl Streep. Can’t say I have a particular favorite.

Cyril. What are you afraid of? Pepper. Fire and the ocean. I love looking at the ocean, watching it, smelling it, but not being IN it. I’m not a very good swimmer and I’m absurdly afraid of sharks. Ridiculous as it sounds, read Jaws and then, after I was frightened out of my wits, went and saw the film! I just don’t go in the water. I was burned pretty severely as a child and have a fear of fire also. The whole fire and water thing is interesting though, don’t you think? Now if you asked me where I felt most comfortable I’d say having my two feet planted on earth. I’m a bird watcher and not afraid of flying and do it often, but have never dreamed about space and flying off into the air in search of life somewhere else. My fear of the ocean would preclude me from underwater exploration as much as I am fascinated watching the creatures that live there. I’m a tree hugger, love trees, and gardening and hiking, riding, love the creatures that inhabit it, many of the things associated with the earth. It gives me energy, grounds me and balances me. I appreciate and respect the life cycle, of four seasons, and am in awe each time the earth renews itself in the spring and then put’s itself to rest in the fall. It’s all magical to me.

Cyril. What is your type of biker? Intelligent and passionate. Pepper. I can spot a poser 100 meters away! Oh, and respect yourself enough to bathe. No dirty finger nails please.

Cyril. What is the person you would love to meet? Pepper. My father.

Cyril. Preferred motorcycle to ride? Pepper. Harleys. But I’m keeping my options open.

Cyril. We are having dinner together. Steakhouse, Italian, Thai, Sushi, French or Vegetarian? Pepper. Raw fish, Baby.

Cyril. Do you have any tattoos or piercings? Pepper. Two piercings in each ear. And one tattoo, sort of… Percy Lane stabbed me with his sharpened pencil in grade 6. He did it as a sign of affection. We never did hook up, but I always thought he was cute.

Cyril. If you would ask me to build a custom, which style? Pepper. Cruiser. FXR or FXD frame. Not too long, black matte paint w/gloss detail. Having said that… at a sport bike conference this weekend and looking seriously at street fighters.

Cyril. Which film made you cry? Pepper. Almost every film, and a few commercials! It’s a little embarrassing.

Cyril. Name five things you hate. Pepper. Bigotry; cruelty to children, and animals; loosing; ignorance; bullies. And uni.

Cyril. What is your best life achievement? Pepper. Putting my daughter on the planet.

Cyril. If you would be a season, which one? Pepper. Autumn

Cyril. What do you miss most at home when you are in a rally? Pepper. My bed. I have a Tempur-Pedic. I’d be a great spokesperson.

Cyril. What was the last book you read? Pepper. Winning by Jack Welch

Cyril. Where is your favorite vacation place? Pepper. Europe

Cyril. Do you have any guilty pleasures? Pepper. Oh yeah!

Cyril. Do you collect anything? Pepper. Boxes. I have loads of little boxes.

Cyril. What was your worst buy? Pepper. Hmmmm. Don’t have an answer for this one. Sorry.

Cyril. What was the most embarrassing thing you have ever made? Pepper. Meatloaf.

Cyril. What is the best thing you can cook? Pepper. A cheese plate with grapes, salami and crusty French bread

Cyril. When was the time you were really angry? Pepper. When I was offered a “choice” between leaving and being let go at the rally department because they didn’t like my politics. And they got to put out the press release!

Cyril. What is your perfect weekend when you are at home? Pepper. Sleeping in; digging in the garden; hike in the woods; ride on a warm sunny day; sitting on the deck watching the sunset and birds feed, with a good glass of wine and a Dirt cigar; hot tub; and being made love to at least once.

Cyril. What is your preferred rally? Pepper. Sturgis. The first time I set eyes on the Hills I fell in love and I’ve never recovered. Ok, loved the TTs on the Isle of Man, so I guess I’m conflicted.

Cyril. What is the worst question a journalist asked you? Pepper. This one, Silly Goose!

For all curious minds. How Pepper was called Pepper? Her given name is Priscilla. People always wanted to shorten her name like Pris, Prissy, Cilla, Cilly, Percy, Pepsi, PM (!). A school friend was moving away and wanted to write to her. She always mispelled her name, which frustrated her and made her promise she wouldn’t anymore. Rather than learning how to spell correctly her name she decided to find a new one. She thought of things that began with a P that reminded her. Out of all the names she has been called, the name Pepper stuck. Might be because she was known to be sassy, passionate and opinionated, speaking her mind…

Zipper's

33 Responses to “The Secret Life Of Pepper Massey”


  1. 1 Roberto Jan 19th, 2011 at 8:13 am

    Another great lady of the industry.

  2. 2 Wiz Jan 19th, 2011 at 8:58 am

    So Pepper, You remember me writing to you about the high prices and rip-offs at the rally that hurts the intent of the celebration of motorcycling that we enjoy.Like the guy that was traveling through the Hills during Sturgis and called a motel in Rapid to get a room. “Are you here for the Rally?” asked the motel owner. “No” was his reply. “It will be $70.” “How much if I was here for the Rally?” he asked. “$90.” was the reply. WTF!! You’re a Groovy gal and you are invited to run away to the Casba with me, Laura Klock, that Simmons gal, an’ every other strong woman Cyril has interviewed! I know we would have some STIMULATING conversations in the hot tub, what with four or five of you all ‘an me!! YUK-YUK!! There are 7 power centers on the planet like Stonhendge, the Andes, the Pyramids of Egypt, etc. Did you know that South Dakota has two of ’em? Of course there is PaHa SaPa [The Black Hills], but the other one is on the eastern end called Gitchie Manitou. Natives have been bringing their dead to this area for over 10,000 years! The Burial Mounds date back to the times of Atlantis and the Axtecs! I am blessed to live here, much Power if you respect it, much misery if you don’t! Maybe we can get together sometime to discuss how we can improve life for all. Are you a South Dakota ABATE member? We have one of the strongest ABATE’s in the nation! Other states ask us how we do it. One of the things we do is assemble members from all over to the opening of the State Legislature [which is this Friday, by the way]. Can’t swing a dead cat and not hit black leather in the Capitol building! We are a force to be reconded with. You see, not only do we have a responsablity to the bikers of South Dakota, but since we play host to the world’s largest gathering of like minded, two-wheeled, individuals on the planet, we are reponsible to the world! A challenge we don’t take lightly. Thank you for your efforts in this cause. We can DO IT!! Wiz

  3. 3 Darin Maltsberger - Instructor @MTI Jan 19th, 2011 at 9:29 am

    We are blessed to have her here in South Dakota. She is an inspiration to many young ladies looking for careers in the motorcycle industry.
    -Darin

  4. 4 Richard Trenz Jan 19th, 2011 at 10:34 am

    Can we still forward Sturgis complaints to her? I have a lot and I am not the only one.

  5. 5 Larry R Jan 19th, 2011 at 11:06 am

    Great lady! Thanks for sharing Pepper and Cyril.

  6. 6 gina woods Jan 19th, 2011 at 11:31 am

    Pepper is intelligent, fun, inspiring to all and just an all round “groovy” chic as Wiz says! Truely deserves all the alcolades and happiness in life! Congrats on your continued success Pepper Girl!!
    XO Gina

  7. 7 Steve Hog Radio Producer Jan 19th, 2011 at 4:16 pm

    Briefly met Pepper at 2009 NCOM where we were both awarded Silver Spoke Awards. She has a lovely daughter.

    If you’re reading this Pepper, Ill be in touch. We need to get you on the show!

    Thanks Cyril for your great interview.

  8. 8 David Jan 20th, 2011 at 12:30 am

    From what I read in the interview Pepper seems to be a very nice but confused lady.

    Wiz…..Lets hope you only can converse and not influence anyone over “improving life for all” sounds pretty socalistic or progressive to me, because if they didn’t earn it(or help themselves) then your taking it from someone else and giving it to them and who does that really help.You can give a man a fish or teach him to fish. Charity or helping is a whole different matter.

    SSDD; David

  9. 9 Fred Jan 20th, 2011 at 7:20 am

    Great ladies in the biz. Interesting interview.

  10. 10 ROGUE Jan 20th, 2011 at 8:41 am

    I am very happy that Ed and Wil put togother the book BIKER CHICKZ of North America and Pepper was one of the great women too be in it.
    I have had the pleasure of knowing and being a friend of Pepper for some time.
    Hopefully those of you that have not met her in person will have a opportunity to do so. You will come away a better person for knowing her.

  11. 11 LeftTenant Jan 20th, 2011 at 9:50 am

    4300 worldwide firefighter riders recognize Pepper as a celebrated Honorary Member of Wind & Fire MC. Sister Massey’s commitment to service in the motorcycling community and to childrens charities is a driving inspiration for many (certainly for me). Great interview, Cyril. Great topic!

  12. 12 Dave Davis Jan 20th, 2011 at 10:49 am

    Cyril, thanks for sharing one of the “great ones” with the world through your interview. Sorry Pep, you are no longer a secret!

  13. 13 gene the gm Jan 20th, 2011 at 11:28 am

    David….. You obviously have never met Pepper. She is far from confused. She knows exactly where she is heading and has the intestinal fortitude to reach her goals at all risk.

    I have never seen her without a smile on her face and a cherry outlook. It must be the “almost annoying optimism” she projects. It is not an act. She is truly happy to be here.

    Pepper, you are always welcome in Dallas. Come see us..Your pal, gene

    see ya in Sturgis..

    (P.S. I meant CHERRY not CHEERY. There is a slight difference)

  14. 14 Walt Lumpkin Jan 20th, 2011 at 12:11 pm

    Only met Pepper once (Daytona, thnx BeeB) but what her friends say about her personality was evident with just a few minutes of casual conversation. And David give her a break, John Wayne was her childhood hero.

  15. 15 Carlos Jan 20th, 2011 at 1:37 pm

    Met Pepper 3/4 years ago in Sturgis. Sounded very nice.

  16. 16 Cris Sommer Simmons Jan 20th, 2011 at 2:47 pm

    Proud to call her my sister and there is no confusion with this lady!

  17. 17 Patrick Breen Jan 20th, 2011 at 9:14 pm

    if you are lucky enough to get to know this woman’s heart you will find it strong, loving, kind, passionate, caring and full of – FIRE! They don’t come any better or full of life. I know – because I’m one of the lucky ones. Her contributions to this industry originate from this heart. Congratulations on recognition well deserved!!

    P.S. The only confusion surrounding this woman is from those who have never met anyone like her.

  18. 18 David Jan 20th, 2011 at 10:44 pm

    LIke I said I never have met her just reading the interview and you can reread it a draw your own conclusions. I’m not going to analize my statement here.

    SSDD; David

  19. 19 gina woods Jan 20th, 2011 at 11:30 pm

    Rogue,
    Good for you for spreading the “good:” word about WOMEN IN MOTORCYCING – thank you for your support and recomendations, thats how so many of these wonderful women got in the book !!
    LOVE ya baby! Congrats again Pep

  20. 20 Duhl Jan 21st, 2011 at 1:49 am

    We could all use a little more pepper, such a wonderful asset to the banquet.

  21. 21 Pepper Massey Jan 21st, 2011 at 8:39 am

    Thanks, Cyril, for including me in this process. Truly an honor to be asked.
    And thanks to those of you who took a moment to jot down a comment – positive or negative, you’re passionate enough about our lifestyle to put your time and energy into it.
    Me, I just dig it that I get to hang out with all of you guys!

  22. 22 john reed Jan 21st, 2011 at 11:17 am

    I have known Pepper for many years,
    Its easy to wind her up and easier to make her laugh,
    both gives me a lot of pleasure.
    I am very fond her

  23. 23 Cindy Erato Jan 21st, 2011 at 11:59 am

    This women is a spitfire and a great friend! Go Pepper!

  24. 24 Richie Finney London Jan 21st, 2011 at 1:16 pm

    Proud to call Pepper a very dear friend! ;}> X

  25. 25 burnout Jan 21st, 2011 at 4:59 pm

    My first trip to Sturgis Pepper was the first person I met. Class. peace

  26. 26 Wiz Jan 22nd, 2011 at 6:33 am

    David, I try to teach people how to fish. “The Lord helps those that help themselves.” I work at an Alcohol and Drug treatment center and I tell them “We won’t give you the fish, we will give you the pole, line, hook, sinker, even the worm, but YOU gotta go to the RIVER!!” We don’t do anything, they do if they want it. We just show them how. That’s what I’m takin’ about Baby!! Nothing is accomplished without effort. I don’t like all this video lottery stuff because people want to get rich without earning it. I hope you catch my drift. Thanks, Wiz

  27. 27 jim breen Jan 23rd, 2011 at 1:37 pm

    Sounds like my baby bro is a lucky man, hope to get too know Ms. PEPPER better this summer @ the reunion…

  28. 28 nicker Jan 23rd, 2011 at 4:42 pm

    Cyril,
    Great interview.
    “Who’s Who” in M/C is a great idea!
    Thanks much.

    David, Wiz, & Pepper,
    As i recall, the Dr’s oath goes something like “…first do no harm…”

    The way i see it, before heading down the path where “… I might make a difference….” a good start is by not making a mess of your own life.
    Because that inevitable messes up other people.

    So, just as in teaching fishing, it’s something more than helpful if you’re “first an accomplished angler” yourself (a problem with many do-gooders).
    In my experience there is absolutely nothing more worthless or counter productive than “bad help.”

    Just a thought
    -nicker-

  29. 29 Mutch Jan 23rd, 2011 at 6:57 pm

    The nicest person in America – what am I talking about? – the world – probably too good for it, bit like Vincent only with two ears, cute ears

    Mutch x
    London England

  30. 30 Wiz Jan 24th, 2011 at 4:18 am

    Nicker. The “Blind leading the Blind” kinda thing, Huh? Come to think of it I see that scenario in our current Federal Government. YUK-YUK!! Wiz

  31. 31 Rick Jan 25th, 2011 at 12:42 am

    Great interview. Pepper seems like a wonderful person and a blast to be around. Love her answers.

  32. 32 Micah McCloskey Jan 27th, 2011 at 3:45 pm

    Pepper you are a true motorcycle enthusiast and it has been my pleasure to know and work
    with you. I wish you the best in the comming years. Cyril did you justice. Great article

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