Improbable Possibilities

An Entrepreneur’s Quest
Linda E. Rawlings


Ever wonder what it takes to succeed?

Improbable Possibilities by Linda Rawlings is a captivating memoir that weaves together the untold stories of an extraordinary woman’s entrepreneurial journey.

Rawlings, best known as the co-creator of Otis Spunkmeyer, Inc., takes readers on a roller-coaster ride through the unexpected twists and turns of her career.

From the trading floors of Wall Street to founding multiple businesses, including a manufacturing company for Otis Spunkmeyer ovens, a unique airline promoting the brand’s cookies, and even a dance company, Rawlings’ journey is as unpredictable as it is inspiring.

This is a book about more than just business. It’s about resilience, creativity, and the courage to pursue multiple passions, even when they don’t always align. Rawlings recounts her experiences with grace and humor, sharing not only the highs but also the challenges of navigating three marriages, business failures, and triumphs.

For readers who enjoy memoirs based on true stories, Improbable Possibilities is an unflinching look at what it takes to succeed in business while staying true to your personal and professional goals.

It’s a book about making bold decisions, embracing change, and finding the possibilities that lie beyond the expected. A must-read for anyone interested in entrepreneurial spirit, life’s unpredictability, and the art of transformation.

Discover the untold stories behind entrepreneurial success.

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Linda E. Rawlings

Linda Rawlings was born in Wethersfield, Connecticut, but has lived in California, Singapore, Hong Kong, Toronto, Sydney, and Las Vegas. Newport, Rhode Island is her home— for now. She has undergraduate degrees in Fine Arts and Mathematics (Bates College) and master’s degrees in Business and in Journalism (UC Berkeley). Her writing has appeared in Heterodoxy, The Oakland Tribune, and Newport Life Magazine.

Rawlings’ diverse San Francisco entrepreneurial adventures include Robert C. Brown and Company, investment advisors; Otis Spunkmeyer, the cookie company; Triple 888 Manufacturing, the sheet metal company that manufactured ovens for baking Otis Spunkmeyer cookies; and Sentimental Journeys, the DC-3 airline that promoted Otis Spunkmeyer Cookies. Her other entrepreneurial activities include founding and producing New Shoes, Old Souls Dance Company, producing Yoga Garden Dancers, and working with Heterodoxy magazine and George magazine. While in Hong Kong, Rawlings helped develop MANA!, a food brand, and founded Flying East LLC, a business incubator.

Improbable Possibilities is her first book.

Author website

“Improbable Possibilities” by Linda E. Rawlings, book cover.

“Luna”, Cowell Theater, San Francisco.

“You’ve Got The Love”, Cowell Theater, San Francisco.

“Simple Thoughts”, Cowell Theater, San Francisco.

Linda E. Rawlings with Ken Rawlings at Otis Spunkmeyer, California, 1988.

Carmel-By-The-Sea.

Lindsey, Linda and Logan Rawlings.

North Gate Hall, UC Berkeley.

“

Rawlings, who created the California-based Otis Spunkmeyer baked goods company with her husband, Ken, in the 1970s, presents the stories she’s accumulated over decades of dealing with everybody from shipping to sheet metal companies to celebrities. The author, who describes herself as a baby boomer with an old soul, opens with an account of her youth in Connecticut, and in a series of chapters filled with quotes from rock music, she charts her own growth in the industry from rather modest beginnings.
There’s also a good deal of storytelling ability;
those characters entertainingly fill these pages.
A LIVELY, COLORFUL MEMOIR OF
CORPORATE AND PERSONAL GROWTH.

KIRKUS REVIEWS
“

Throw spaghetti on the wall and see what sticks is Rawlings’ mantra, as she takes us through her adventurous personal odyssey and business life by “observing, investigating, and creating possibilities.” Experiencing Rawling’s life and psychological journey, each chapter drew me onward to the next. An enticing biographical tale that will keep you turning the pages.

Rafe CohenPresident, Galaxy Theaters, Los Angeles, CA
“

Improbable Possibilities shares Rawlings’ life, which is sometimes a roller coaster and sometimes a magic carpet ride. And what a ride: The famous cookie company, the classic airplanes. Always in motion, always creative, and never bound by conventions, her story takes many unexpected turns that will surprise and delight the reader. The energy of this amazing and accomplished woman is there on every page. And her story is not over.

Robert ArnoldPresident, Chandelle Winery, Glen Ellen, CA
“

The chocolate chip cookie is a mainstream food that's been associated with a surprising array of offbeat personalities. Though perhaps not as well-known as Famous Amos, Debbi Fields or David Liederman, Otis Spunkmeyer co-founder Linda Rawlings is arguably even more interesting. Reading Improbable Possibilities is like sitting down with spiked coffee and cookies and catching up with your most adventurous and entertaining friend.

Carolyn WymanAuthor, “The Great American Chocolate Chip Cookie Book”
“

As we age, being seen as vital can be a challenge. Creating space for artists over 40 to dance were doors Linda opened; kept opening; and keeps opening with Improbable Possibilities. For folks in San Francisco, for me, and for herself. Linda’s advocacy and philanthropic support for moving bodies, at any age, is a glorious gift.

Wayne HazzardExecutive Director, Dancers’ Group, San Francisco, CA
“

Aptly named, Improbable Possibilities chronicles the author’s journey from investment trainee to business mogul, entangling with JFK Jr., Clint Eastwood, and John Chambers. Life changes, but she hasn’t. She’s still my kindergarten friend from our one-roomed Little Red Schoolhouse.

Robert GentinoLaw Offices of Robert Gentino, Esq., Los Angeles, CA
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Thank you very much for sending me your book. I remember Ken very well, as well as the Otis Spunkmeyer Company. It has been a long time since the days at Bear Stearns, of which I remember many of them fondly. All the best.

George R. RobertsCo-founder: KKR, New York, NY