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Scaling with Soul: How I Built and Sold a $25 Million Tech Company Without Being an A**hole
Before Co-founder and CEO Sharon K. Gillenwater exited Boardroom Insiders for $25M in 2022, she was a kid growing up in the turbulent '70s in sleepy Ocean Beach, California. A voracious reader and deep thinker often at odds with her working-class parents, she was determined to break from her surroundings-though she never thought her dreams would take her to the top of the tech food chain.
In Scaling with Soul, a swashbuckling memoir of resilience on the journey to becoming a CEO, Gillenwater traces her path from waitress to marketer to bootstrapping founder of an industry-leading software company-all despite false starts, sexism and an imploded first startup. In the process, she shares crucial lessons about how ambitious founders can learn to cultivate resilience without losing their soul.
Illuminating the myriad challenges inherent in tech startups and VC funding, and offering advice on how to beat them, Scaling with Soul is also a toolbox of nuts-and-bolts tech wisdom for ambitious on networking, scaling companies, navigating the politics of acquisitions and more.
Told in a voice guaranteed to galvanize, Gillenwater encourages readers to become tomorrow's leaders today and proves that entrepreneurship is a viable path to financial independence for all, no matter your gender or background.
In Scaling with Soul, a swashbuckling memoir of resilience on the journey to becoming a CEO, Gillenwater traces her path from waitress to marketer to bootstrapping founder of an industry-leading software company-all despite false starts, sexism and an imploded first startup. In the process, she shares crucial lessons about how ambitious founders can learn to cultivate resilience without losing their soul.
Illuminating the myriad challenges inherent in tech startups and VC funding, and offering advice on how to beat them, Scaling with Soul is also a toolbox of nuts-and-bolts tech wisdom for ambitious on networking, scaling companies, navigating the politics of acquisitions and more.
Told in a voice guaranteed to galvanize, Gillenwater encourages readers to become tomorrow's leaders today and proves that entrepreneurship is a viable path to financial independence for all, no matter your gender or background.
198 pages, Kindle Edition
Published May 21, 2024
3 people are currently reading
19 people want to read
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Displaying 1 - 23 of 23 reviews
April 13, 2025
Scaling with Soul by Sharon Gillenwater is a refreshing, human-centered approach to building a successful business in an often impersonal, numbers-driven world. In a space traditionally dominated by outdated sales tactics and a narrow view of success, Gillenwater emerges as a disruptor — not just in what she built, but in how she built it.
At the heart of her business philosophy is a deep respect for the individual. Rather than seeing C-suite executives as generic leads, she saw them as people — with likes, dislikes, problems, and personalities. This people-first approach led to the creation of Boardroom Insiders, a meticulously curated database that doesn’t just track business information, but captures the nuances that make high-level decision-makers tick. Gillenwater understood that the key to getting executives to attend high-value events wasn’t flashy invitations — it was crafting experiences that directly addressed their personal and professional interests.
One of the most compelling themes in the book is Gillenwater’s own journey — her vulnerability and honesty are striking. A standout moment is when she describes stepping on stage to pitch her product while wearing shoes that literally didn’t fit. It becomes a powerful metaphor for the imposter syndrome many women face in male-dominated industries — the feeling of playing dress-up, of filling shoes too big, of being visible and exposed in ways that feel uncomfortable and foreign. Yet she doesn’t back down. Instead, she transforms that discomfort into drive.
Gillenwater’s entrepreneurial grit shines through in her decision to spend an entire month — one August — cold-calling and emailing everyone she thought could help move her business forward. It wasn’t glamorous, but it was game-changing. That bold outreach helped her forge key relationships that shaped the trajectory of her company.
She also offers tactical insights for sustainable growth. A few key takeaways:
• Avoid one-off clients whose demands don’t align with your long-term vision or scalable offerings.
• Aim for recurring revenue, building predictable streams rather than chasing fragmented deals.
• Develop a defensible pricing model that reflects your value and sets a standard for your work.
A significant turning point came when Salesforce’s CEO credited his success to selling directly to other CEOs. That external validation opened doors for Gillenwater’s company, leading to exponential growth as others began to see the value in her executive-focused model.
But perhaps the most soulful part of Scaling with Soul is her leadership philosophy. Gillenwater believes in building a team the way she builds customer relationships — with care, attention, and a genuine desire to help people thrive. She invests in employee education, recognizes achievements with unexpected rewards, and aligns people with projects they love. Her willingness to shift roles based on her team members’ strengths and interests is a lesson in adaptive, empowering leadership.
This book is more than a business memoir — it’s a guide for entrepreneurs who want to scale with heart, clarity, and intention. Scaling with Soul is a rallying cry for leaders who believe success doesn’t have to come at the cost of humanity. Gillenwater proves that when you build a business around people — clients, team members, and yourself — the results don’t just follow. They flourish.
At the heart of her business philosophy is a deep respect for the individual. Rather than seeing C-suite executives as generic leads, she saw them as people — with likes, dislikes, problems, and personalities. This people-first approach led to the creation of Boardroom Insiders, a meticulously curated database that doesn’t just track business information, but captures the nuances that make high-level decision-makers tick. Gillenwater understood that the key to getting executives to attend high-value events wasn’t flashy invitations — it was crafting experiences that directly addressed their personal and professional interests.
One of the most compelling themes in the book is Gillenwater’s own journey — her vulnerability and honesty are striking. A standout moment is when she describes stepping on stage to pitch her product while wearing shoes that literally didn’t fit. It becomes a powerful metaphor for the imposter syndrome many women face in male-dominated industries — the feeling of playing dress-up, of filling shoes too big, of being visible and exposed in ways that feel uncomfortable and foreign. Yet she doesn’t back down. Instead, she transforms that discomfort into drive.
Gillenwater’s entrepreneurial grit shines through in her decision to spend an entire month — one August — cold-calling and emailing everyone she thought could help move her business forward. It wasn’t glamorous, but it was game-changing. That bold outreach helped her forge key relationships that shaped the trajectory of her company.
She also offers tactical insights for sustainable growth. A few key takeaways:
• Avoid one-off clients whose demands don’t align with your long-term vision or scalable offerings.
• Aim for recurring revenue, building predictable streams rather than chasing fragmented deals.
• Develop a defensible pricing model that reflects your value and sets a standard for your work.
A significant turning point came when Salesforce’s CEO credited his success to selling directly to other CEOs. That external validation opened doors for Gillenwater’s company, leading to exponential growth as others began to see the value in her executive-focused model.
But perhaps the most soulful part of Scaling with Soul is her leadership philosophy. Gillenwater believes in building a team the way she builds customer relationships — with care, attention, and a genuine desire to help people thrive. She invests in employee education, recognizes achievements with unexpected rewards, and aligns people with projects they love. Her willingness to shift roles based on her team members’ strengths and interests is a lesson in adaptive, empowering leadership.
This book is more than a business memoir — it’s a guide for entrepreneurs who want to scale with heart, clarity, and intention. Scaling with Soul is a rallying cry for leaders who believe success doesn’t have to come at the cost of humanity. Gillenwater proves that when you build a business around people — clients, team members, and yourself — the results don’t just follow. They flourish.
June 1, 2024
Highly enjoyable read, 5-Stars and relatable tech founder's journey!
Scaling with Soul by Sharon Gillenwater is a refreshing take on the world of tech entrepreneurship. In a field often criticized for its cutthroat nature and ruthless pursuit of success, Sharon offers a different narrative: one of empathy, integrity, and sustainable growth.
Sharon's journey from a startup founder to the sale of his $25 million company is inspiring, not just because of the financial success, but because of the values she upheld along the way. Her voice is engaging, filled with personal anecdotes that provide a candid look into the challenges and triumphs of building a tech company. What sets this book apart is Sharon's emphasis on maintaining a humane and ethical approach to business, a theme that resonates throughout the chapters.
One of the most compelling aspects of Scaling with Soul is her honesty about the mistakes he made and the lessons he learned. She doesn’t shy away from discussing the darker moments of her journey, including times of self-doubt and the pressures of leadership. This vulnerability adds a layer of authenticity to his narrative, making his success story all the more relatable and inspiring.
In conclusion, Scaling with Soul is a must-read for anyone looking to build a business without compromising their values. Sharon Gillenwater's story is a testament to the fact that it is possible to achieve great success while staying true to oneself. His book is not only a guide to scaling a business but also a manifesto for a more compassionate and ethical approach to entrepreneurship.
I also enjoyed Sharon's TikTok videos which highlighted her journey and compelled me to follow her and buy her book. Highly enjoyable read 5-Stars and related to the tech founder's journey!
Scaling with Soul by Sharon Gillenwater is a refreshing take on the world of tech entrepreneurship. In a field often criticized for its cutthroat nature and ruthless pursuit of success, Sharon offers a different narrative: one of empathy, integrity, and sustainable growth.
Sharon's journey from a startup founder to the sale of his $25 million company is inspiring, not just because of the financial success, but because of the values she upheld along the way. Her voice is engaging, filled with personal anecdotes that provide a candid look into the challenges and triumphs of building a tech company. What sets this book apart is Sharon's emphasis on maintaining a humane and ethical approach to business, a theme that resonates throughout the chapters.
One of the most compelling aspects of Scaling with Soul is her honesty about the mistakes he made and the lessons he learned. She doesn’t shy away from discussing the darker moments of her journey, including times of self-doubt and the pressures of leadership. This vulnerability adds a layer of authenticity to his narrative, making his success story all the more relatable and inspiring.
In conclusion, Scaling with Soul is a must-read for anyone looking to build a business without compromising their values. Sharon Gillenwater's story is a testament to the fact that it is possible to achieve great success while staying true to oneself. His book is not only a guide to scaling a business but also a manifesto for a more compassionate and ethical approach to entrepreneurship.
I also enjoyed Sharon's TikTok videos which highlighted her journey and compelled me to follow her and buy her book. Highly enjoyable read 5-Stars and related to the tech founder's journey!
May 30, 2024
Gillenwater is an engaging writer with a good sense of humor, who shares stories about her life leading up to and her path to entrepreneurship. She's very candid about the uncertainty she felt and the mistakes she made while building her company. In addition to the business side of things, I like that she shares how being an entrepreneur impacted the rest of her life and relationships and how she managed it.
Gillenwater has led an interesting and entertaining life and because this is a memoir and not a dull advice book, you get to hear all about it while still learning a thing or two.
For me, Scaling with Soul is about how to be true to yourself and maintain your integrity in a brutal, capitalist society. Gillenwater succeeded in compassionate capitalism, which, in our society, is hard when you're a multimillion dollar company let alone a bootstrapping entrepreneur trying to make something from nothing.
And you don't have to be an entrepreneur to get something from Scaling with Soul. The book is also about the value of preparation, how to be a good manager and betting on yourself. Best of all, it's an entertaining read! I read it cover to cover in one sitting.
Gillenwater has led an interesting and entertaining life and because this is a memoir and not a dull advice book, you get to hear all about it while still learning a thing or two.
For me, Scaling with Soul is about how to be true to yourself and maintain your integrity in a brutal, capitalist society. Gillenwater succeeded in compassionate capitalism, which, in our society, is hard when you're a multimillion dollar company let alone a bootstrapping entrepreneur trying to make something from nothing.
And you don't have to be an entrepreneur to get something from Scaling with Soul. The book is also about the value of preparation, how to be a good manager and betting on yourself. Best of all, it's an entertaining read! I read it cover to cover in one sitting.
Read
July 29, 2024In Scaling with Soul, Sharon Gillenwater offers an insightful and refreshing perspective on entrepreneurship, blending practical business acumen with a strong ethical foundation. As the founder of a successful tech company that reached a $25 million valuation, Gillenwater draws from her personal journey to challenge the traditional notions of what it means to succeed in the business world. One of the standout themes of the book is the idea that success doesn’t have to come at the expense of one’s values. Gillenwater advocates for scaling businesses with soul, encouraging readers to integrate their personal values into their professional lives. This holistic approach not only benefits the bottom line but also enhances employee satisfaction and customer loyalty. Overall, Scaling with Soul is an inspiring and thought-provoking read that encourages readers to redefine success in a way that aligns with their values. Whether you’re an entrepreneur, a business leader, or simply someone interested in the world of startups, Gillenwater’s insights will resonate deeply and challenge you to consider how you can scale your own endeavors with soul. Highly recommended!
June 1, 2024
Entrepreneurship with Heart
Gillenwater's account of her personal journey is full of passion and deep commitment. She is clearly dedicated to helping her customers see the value they are missing in targeting C-level executives, while building a positive company culture from the ground up. There are actionable insights for entrepreneurs and corporate leaders and by the end, you feel like you made the trip with her. There are laugh out loud moments during her journey including an alarming recipe for how NOT to prepare polenta. Her self-deprecating manner is inspiring for the rest of us but she never makes it sound easy. A thoroughly enjoyable read!
Gillenwater's account of her personal journey is full of passion and deep commitment. She is clearly dedicated to helping her customers see the value they are missing in targeting C-level executives, while building a positive company culture from the ground up. There are actionable insights for entrepreneurs and corporate leaders and by the end, you feel like you made the trip with her. There are laugh out loud moments during her journey including an alarming recipe for how NOT to prepare polenta. Her self-deprecating manner is inspiring for the rest of us but she never makes it sound easy. A thoroughly enjoyable read!
July 25, 2024
"Scaling with soul" captures the tumultuous journey of the author as they navigate the challenges and triumphs of building and eventually selling their company, boardroom insiders. the narrative is infused with a palpable sense of anxiety and hope showcasing the profound impact the sale had on their life and the lives of their employees. the authors reflections on personal growth, faith, and the transformational power of taking bold risks make this book a compelling read for anyone interested in the human side of entrepreneurship. the vivid story telling and emotional depth highlights the complexity of scaling a business with integrity and heart.
July 23, 2024
This book is a great example of what happens when you have grit and determination as a woman in a man’s world. The backstory of Sharon’s upbringing and how she followed her own path is inspiring. Through all the trials and tribulations, she still persevered and was rewarded generously. Many times, we listen too much to the naysayers and get even more discouraged. Scaling with Soul will help direct you on your path offering great advice. This book will appeal to a wide range of audiences as it was well written, quick-witted and an easy read.
June 15, 2024
I loved this book...So well written and provides so many insights...Sharon's story is so relatable and authentic. Her frankness, vulnerability and courage shine through in this story about navigating the business climate in the nineties and early aughts in San Francisco, the epicenter of the dot.com boom/bust. Her perseverance, honesty, wisdom and integrity reaped many rewards including the sale of her company.
July 22, 2024
Gillenwater managed to create, manage and sell a company with humanity, empathy and soul. She never compromised her values, and her coworkers actually liked and respected her! So many business and entrepreneur books read like textbooks; this one is an inspiring story from someone who came up with and implemented ideas that solved problems and saved tons of time. The best part is how the author owns up to her mistakes and is not afraid to apologize for them. This is a great book.
July 29, 2024
“Scaling with Soul” by Sharon K. Gillenwater is a captivating memoir that traces her remarkable journey. Overcoming numerous challenges, Gillenwater offers invaluable lessons on cultivating resilience while maintaining integrity. Her story is not only inspirational but also provides practical advice on networking, scaling, and navigating acquisitions. This well-written and relatable book is a testament to the power of perseverance and serves as an essential guide for aspiring entrepreneurs.
July 30, 2024
Business mixed with pleasure
Witty, funny, and inspiring are words to describe the first couple of chapters I have read. The author is inspiring. Her message is to live the most fulfilling life possible and not let any obstacle get in your way. Very rarely do we get the “inside scoop” on one’s origin story. Truly remarkable that the author created and built what she did given the odds not being in her favor.
Excited to continue reading and learn any business tips!
Witty, funny, and inspiring are words to describe the first couple of chapters I have read. The author is inspiring. Her message is to live the most fulfilling life possible and not let any obstacle get in your way. Very rarely do we get the “inside scoop” on one’s origin story. Truly remarkable that the author created and built what she did given the odds not being in her favor.
Excited to continue reading and learn any business tips!
June 4, 2024
Laugh out loud page-turner! This is a must read! I could not put this book down and there were many parts that I read multiple times. Each chapter has unique tales that are hilarious and relatable. I highly suggest this for anyone who enjoys memoirs and great storytelling. I can’t wait for her next book!
July 23, 2024
Sharon K. Gillenwater's 'Scaling with Soul' offers invaluable insights into growing a business with purpose and integrity. Her emphasis on maintaining authenticity while expanding operations resonates deeply. The practical strategies provided are actionable and thought-provoking, making this book a must-read for entrepreneurs looking to scale sustainably.
July 24, 2024
How do we get ahead without being pushy or described as a bulldog? Sharon Gillenwater gives us a nice view of how. This book is clear and outlines how a "regular" person can navigate through these waters with ease and style. I recommend this book to anyone struggling to find your place in the world of self development and entrepreneur reasoning.
July 24, 2024
I was unsure about this book until I read the first three sentences of the prologue and got hooked! I love the author's way of educating the readers and telling an exciting story of their experiences. As a POC Female trying to start her own business right now, this book helped me put my foot in the right direction. It tells the highs and lows, which is realistic in business.
July 30, 2024
This quick-witted memoir/success story packs relatable and life-affirming insights to inspire others to take a chance on themselves. As a woman with a lot of ambition myself, I was inspired by Gillenwater’s journey and persistence through many challenges in order to reach her goals. It truly creates a narrative that if you put your mind to something, you can achieve anything.
July 22, 2024
I loved this take on a typically stiff topic. The author's story is really inspiring and the way she describes the steps she took to get where she is now was done so well. It's a refreshing look at the corporate world.
July 22, 2024
Sharon Gillenwater does not hold back in giving advice, or sharing what she went through in life and business. She explains what shaped her outlook, both experiences and the people she met along the way. No matter what stage you are at in business, you can find encouragement in this book.
July 23, 2024
A brutally honest rags to riches story in our modern day. The author is an excellent story teller who won't spare the uncomfortable details. Worth the read for those who need to be reminded of a success story.
July 24, 2024
The author truly encapsulates her journey of struggle and determination in the most witty and relatable ways! Her honesty and integrity makes the reader want her as both a mentor and friend. A sincere and extraordinary read!
July 22, 2024
I read many books about entrepreneurs and business. They can be dry at times but this is not that. Such a refreshing read due to the author’s tone and heart.
July 25, 2024
This book is honest. It takes the reader on a journey to open their mind when diving into being an entrepreneur. She offers insight while keeping her dignity.
August 19, 2024
Gillenwater has a relatable story and readable writing style. One of my favorite books of the "how to be successful" genre.
Displaying 1 - 23 of 23 reviews