I built and sold a $25 million tech company | Sharon Gillenwater | Episodes 13 |

Summary

In this episode of Finance for Founders, host Samuel Ajala interviews Sharon Gillenwater, co-founder and former CEO of Boardroom Insiders. Sharon shares her journey from her upbringing in California to building a successful tech startup that sold for $25 million. She discusses the challenges she faced, including her experiences with venture capital, the lessons learned from her early ventures, and her current endeavors in supporting other entrepreneurs. The conversation highlights the importance of resilience, integrity in business, and the often-overlooked stories of entrepreneurs outside the Silicon Valley narrative. In this conversation, Sharon Gillenwater shares her journey from facing job loss after the dot-com crash and 9/11 to becoming a successful freelancer and eventually founding Boardroom Insiders. She discusses her experiences in big tech marketing, the importance of C-suite engagement, and the challenges of transitioning from consulting to a SaaS business model. Sharon also reflects on the emotional rollercoaster of exiting her business and the lessons learned along the way. In this conversation, Sharon Gillenwater shares her journey through the complexities of selling her business, the emotional challenges she faced during the transition, and the lessons learned along the way. She emphasizes the importance of due diligence, choosing the right banker, and the excitement and pain of closing a deal. Sharon also discusses the emotional rollercoaster post-sale, the significance of building a supportive network, and key lessons for aspiring entrepreneurs, particularly around product market fit and the value of community.

Takeaways

• Sharon's upbringing as an only child fostered her independent thinking.
• Boardroom Insiders was born from a consulting practice addressing tech sales challenges.
• Raising venture capital can lead to unforeseen challenges and risks.
• The venture capital experience taught her to be cautious about external funding.
• C-suite engagement is crucial for tech companies selling to larger organizations.
• Building a robust database was key to the success of Boardroom Insiders.

Chapters

00:00 Introduction to Sharon Gillenwater
04:56 Sharon's Upbringing and Its Impact on Entrepreneurship
11:51 The Journey of Boardroom Insiders
17:53 Lessons from Early Ventures and the Venture Capital Experience
30:07 Resilience and the Path Forward
34:59 Current Endeavors and Future Aspirations
39:21 Navigating Life's Challenges: From Job Loss to Freelancing
42:46 Building Expertise in Big Tech Marketing
45:48 C-Suite Engagement: Strategies for Success
49:13 The Birth of Boardroom Insiders
56:49 Understanding the C-Suite: Insights from Events
01:01:19 Transitioning from Consulting to SaaS
01:11:18 The Emotional Journey of Exiting a Business
01:22:20 Navigating the Due Diligence Process
01:24:23 Choosing the Right Banker
01:25:51 The Excitement and Pain of Closing a Deal
01:27:52 The Emotional Rollercoaster of Selling a Business
01:30:41 Celebrating the Sale
01:33:27 Transitioning Post-Sale
01:36:34 Finding New Purpose After Exit
01:39:05 Building a Network and Sharing Knowledge
01:55:29 Key Lessons for Aspiring Entrepreneurs


Keywords

#entrepreneurship #tech #startups #venture capital #resilience #business lessons #Boardroom Insiders #Sharon Gillenwater #scaling business #integrity in business #women in tech #Sharon Gillenwater #entrepreneurship #freelancing #big tech marketing #C-suite engagement #Boardroom Insiders #SaaS #business exit #event marketing #startup challenges #due diligence #business sale #investment banking #emotional transition #entrepreneurship #networking #product market fit #women in business #startup advice #business exit