Bootstrapping To $25 Million with Sharon K. Gillenwater

My Perfect Failure

MPF Discussion with Sharon K. Gillenwater

Bootstrapping To $25 Million with Sharon K. Gillenwater
About Sharon
Sharon K. Gillenwater is a tech founder who built, scaled, and sold Boardroom Insiders for $25 million in 2022. She shares her journey in her book, Scaling With Soul: How I Built & Sold a $25 Million Tech Company Without Being an A**hole, aiming to make entrepreneurial success accessible to all. Sharon
grew up in a working-class family, became the first in her family to earn a
college degree, and found her passion for tech and business in San Francisco.
In 2008, she founded Boardroom Insiders to address a need she identified among her clients, evolving her consulting work into an executive profile database and SaaS platform. Sharon’s leadership grew the company to a point of acquisition, achieving a $25 million exit. She now consults as a SaaS advisor, mentors aspiring entrepreneurs, and speaks professionally on her experiences. Sharon lives in San Francisco with her husband and pets, and she enjoys travel and strategy games.
In this episode of My Perfect
Failure, Sharon Gillenwater shares her remarkable journey from startup
culture in 1990s San Francisco to a $25 million exit with her company, Boardroom
Insiders. A true entrepreneur, Sharon started her career at small, nimble
companies where she discovered the thrill of making an impact. This ignited her
passion for entrepreneurship and shaped her belief in the power of
bootstrapping.
We explore Sharon’s experiences with venture capital, the benefits of bootstrapping, and her decision to prioritize customers over funding rounds. Sharon's transparency on her $25 million exit will inspire anyone curious about self-funded growth. Her insights into cultivating “raving fans” and navigating a sale process offer a real-world look at building and selling a company from the ground up.
Key Takeaways:
1. The Power of Bootstrapping: Why Sharon chose to bypass VC funding to keep control of her company and stay customer-focused.
2. Lessons from a $25 Million Exit: Sharon breaks down the reality behind her viral TikTok video on the financial outcome of her exit.
3. Crafting an Exit Strategy: Insight into creating a plan that fits your goals, whether it’s selling, going lifestyle, or selling to employees.
4. Finding Focus and Resilience: Tips for staying grounded and resilient as an
entrepreneur, especially when scaling up.
5. Demystifying Entrepreneurship: Sharon’s advice on navigating startup jargon and prioritizing what truly matters.
Social Links to Sharon
Website:
https://www.sharonkgillenwater.com/
Order Scaling with Soul:
https://www.amazon.co.uk/Scaling-Soul-Million-Company-Without/dp/1964377021/ref=sr_1_1?crid=1KMY6N0Q8DPHL&dib=eyJ2IjoiMSJ9
YouTube: https://www.youtube.com/channel/UCD4ba8Fngv0XYJXjXwEHI0g
TikTok: https://www.tiktok.com/@sharonkgillenwater
Course Recommendation Discussed during discussion
Section : https://www.sectionschool.com/
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