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Scaling with Soul: How Sharon Gillenwater Built and Sold a $25M Tech Company Without Losing Herself
In this inspiring episode of the #WisdomOfWomen Show, I sit down with Sharon Gillenwater — co-founder and former CEO of Boardroom Insiders, a SaaS business intelligence platform she bootstrapped, scaled, and sold for $25 million — all without a single dollar of venture capital.
From waitress to exited tech entrepreneur, Sharon’s journey challenges Silicon Valley’s myth of what success must look like. She shares her three defining life moments, the heartbreak of a failed first startup, and the radical lessons that led her to build a profitable, purpose-driven company rooted in integrity, empathy, and courage.
You’ll learn how to trust your instincts over conventional wisdom, lead with heart, and grow your business without selling your soul. Sharon’s story is a masterclass in grit, grace, and grounded wisdom — and a roadmap for founders who want to do business differently.
Key Takeaways:
- Profitability and purpose aren’t opposites — they’re partners in sustainable growth.
- “Employee-first” leadership is the most effective customer strategy.
- Bootstrapping builds discipline, freedom, and true wealth.
- Founders must make every decision defensible — with clarity, not convention.
- Being someone’s first customer can forge partnerships that last for years.
- The best exits are built from day one: clean books, lean ops, clear leadership.
- Empathy and usefulness are a founder’s most underrated superpowers.
- Failure is not the end; it’s the foundation of your next great success.
Chapters:
00:00 – Welcome & Introduction
06:00 – Three Life Moments That Shaped Her Path
12:00 – The Dark Side of Venture Capital
15:00 – Rebuilding from the Ground Up
18:00 – Bootstrapping and Seed-Strapping
24:00 – Building the Tech Without a Tech Background
28:00 – The Art of the Exit
32:00 – Life After Exit & The Next Chapter
38:00 – Scaling with Soul Today
43:00 – Rapid Fire Round
Burning Questions Answered:
1.What really happens when you raise venture capital — and why might it kill your company?
2.Why is “employee-first” leadership the ultimate customer strategy?
3.How can founders recover from failure and rebuild stronger?
4.What does it really take to prepare for an exit that leaves you proud—and paid?
Favorite Quotes:
“You have to be in love with the problem, not the solution.”
“Put employees first—because they take care of your customers.”
“You can fail spectacularly—and still rise again.”
Guest Offers & Contact Information:
www.sharonkgillenwater.com
https://substack.com/@scalingwithsoul
https://www.tiktok.com/@sharonkgillenwater
https://www.linkedin.com/in/sharonkgillenwater/
https://www.youtube.com/@sharonkgillenwater/shorts
Buy Sharon’s book, Scaling with Soul: How I Built and Sold a $25 Million Tech Company Without Being an A**hole
From Women-Owned Bookstore: https://bookshop.org/p/books/scaling-with-soul-how-i-built-and-sold-a-25-million-tech-company-without-being-an-a-hole-sharon-k-gillenwater/21496638?ean=9781964377018&next=t
From Amazon: https://a.co/d/9LTOM4u
Follow the #WisdomOfWomen show for more inspiring stories and insights from trailblazing women founders, investors, and experts in growth and prosperity.
YouTube: https://tinyurl.com/yja3w7nh
Spotify: https://tinyurl.com/4tak8ajk
Amazon Prime: https://tinyurl.com/366syddj
Apple Podcasts: https://tinyurl.com/bdhananz
RSS Feed: https://feeds.captivate.fm/womengetfunded/
Coco Sellman, the host of #WisdomOfWomen, believes business is a force for good, especially with visionary women at the helm. With over 25 years of entrepreneurial experience, she has launched five companies and guided over 500 startups. As Founder & CEO of A Force for Good, Coco supports purpose-driven women founders in unlocking exponential growth and prosperity. Her recent venture, Allumé Home Care, reached eight-figure revenues and seven-figure profits in just four years before a successful exit in 2024. A venture investor and board director, Coco’s upcoming book, *A Force for Good*, reveals a roadmap for women to lead high-impact, high-growth companies.
Learn more about A Force for Good:
Website: https://aforceforgood.biz/
Are Your GROWING or PLATEAUING? https://aforceforgood.biz/quiz/
FFG Tool of the Week: https://aforceforgood.biz/weekly-tool/
The Book: https://aforceforgood.biz/book/
Growth Accelerator: https://aforceforgood.biz/accelerator/
View all episodes
By A Force for Good Inc.In this inspiring episode of the #WisdomOfWomen Show, I sit down with Sharon Gillenwater — co-founder and former CEO of Boardroom Insiders, a SaaS business intelligence platform she bootstrapped, scaled, and sold for $25 million — all without a single dollar of venture capital.
From waitress to exited tech entrepreneur, Sharon’s journey challenges Silicon Valley’s myth of what success must look like. She shares her three defining life moments, the heartbreak of a failed first startup, and the radical lessons that led her to build a profitable, purpose-driven company rooted in integrity, empathy, and courage.
You’ll learn how to trust your instincts over conventional wisdom, lead with heart, and grow your business without selling your soul. Sharon’s story is a masterclass in grit, grace, and grounded wisdom — and a roadmap for founders who want to do business differently.
Key Takeaways:
- Profitability and purpose aren’t opposites — they’re partners in sustainable growth.
- “Employee-first” leadership is the most effective customer strategy.
- Bootstrapping builds discipline, freedom, and true wealth.
- Founders must make every decision defensible — with clarity, not convention.
- Being someone’s first customer can forge partnerships that last for years.
- The best exits are built from day one: clean books, lean ops, clear leadership.
- Empathy and usefulness are a founder’s most underrated superpowers.
- Failure is not the end; it’s the foundation of your next great success.
Chapters:
00:00 – Welcome & Introduction
06:00 – Three Life Moments That Shaped Her Path
12:00 – The Dark Side of Venture Capital
15:00 – Rebuilding from the Ground Up
18:00 – Bootstrapping and Seed-Strapping
24:00 – Building the Tech Without a Tech Background
28:00 – The Art of the Exit
32:00 – Life After Exit & The Next Chapter
38:00 – Scaling with Soul Today
43:00 – Rapid Fire Round
Burning Questions Answered:
1.What really happens when you raise venture capital — and why might it kill your company?
2.Why is “employee-first” leadership the ultimate customer strategy?
3.How can founders recover from failure and rebuild stronger?
4.What does it really take to prepare for an exit that leaves you proud—and paid?
Favorite Quotes:
“You have to be in love with the problem, not the solution.”
“Put employees first—because they take care of your customers.”
“You can fail spectacularly—and still rise again.”
Guest Offers & Contact Information:
www.sharonkgillenwater.com
https://substack.com/@scalingwithsoul
https://www.tiktok.com/@sharonkgillenwater
https://www.linkedin.com/in/sharonkgillenwater/
https://www.youtube.com/@sharonkgillenwater/shorts
Buy Sharon’s book, Scaling with Soul: How I Built and Sold a $25 Million Tech Company Without Being an A**hole
From Women-Owned Bookstore: https://bookshop.org/p/books/scaling-with-soul-how-i-built-and-sold-a-25-million-tech-company-without-being-an-a-hole-sharon-k-gillenwater/21496638?ean=9781964377018&next=t
From Amazon: https://a.co/d/9LTOM4u
Follow the #WisdomOfWomen show for more inspiring stories and insights from trailblazing women founders, investors, and experts in growth and prosperity.
YouTube: https://tinyurl.com/yja3w7nh
Spotify: https://tinyurl.com/4tak8ajk
Amazon Prime: https://tinyurl.com/366syddj
Apple Podcasts: https://tinyurl.com/bdhananz
RSS Feed: https://feeds.captivate.fm/womengetfunded/
Coco Sellman, the host of #WisdomOfWomen, believes business is a force for good, especially with visionary women at the helm. With over 25 years of entrepreneurial experience, she has launched five companies and guided over 500 startups. As Founder & CEO of A Force for Good, Coco supports purpose-driven women founders in unlocking exponential growth and prosperity. Her recent venture, Allumé Home Care, reached eight-figure revenues and seven-figure profits in just four years before a successful exit in 2024. A venture investor and board director, Coco’s upcoming book, *A Force for Good*, reveals a roadmap for women to lead high-impact, high-growth companies.
Learn more about A Force for Good:
Website: https://aforceforgood.biz/
Are Your GROWING or PLATEAUING? https://aforceforgood.biz/quiz/
FFG Tool of the Week: https://aforceforgood.biz/weekly-tool/
The Book: https://aforceforgood.biz/book/
Growth Accelerator: https://aforceforgood.biz/accelerator/