All Episodes

August 23, 2024 66 mins

Sharon K. Gillenwater is a SaaS startup advisor, mentor, and coach for aspiring tech entrepreneurs. As a tech startup founder and executive, she built, scaled, and sold Boardroom Insiders — an award-winning Inc. 5000 SaaS business intelligence platform — for $25 million in 2022. Sharon recounts this journey in her book Scaling With Soul. After gaining experience in the tech and marketing space in San Francisco, she became an independent consultant working for major tech companies, including Cisco, Microsoft, Oracle, Adobe, Sun Microsystems, and Google. 

In this episode…

Founding a business with investments from venture capital may make the process easier initially, but when it comes time to sell the company, you may not receive your fair share of the equity. How can bootstrapping your company lead to greater returns upon exiting?

SaaS advisor and founder Sharon K. Gillenwater founded her VC-backed email newsletter company during the peak of the dot-com bubble. When the bubble burst, her investors dropped her business as a portfolio company despite Sharon’s attempts to restructure the business model. With this valuable lesson, she bootstrapped her next company, scaling it fast until she was approached by a private equity firm that offered to purchase the business. The exit process was grueling, but Sharon walked away with $9 million after a final sale of $25 million, a significantly higher personal return than if her company had been backed by VC. Bootstrapping your business allows you more control over each step of the process, from scaling to selling.

Join Rolando Rosas and Dave Kelly in the latest episode of What The Teck? as they interview SaaS startup advisor and founder Sharon K. Gillenwater about selling her bootstrapped tech company. Sharon discusses the rising number of bootstrapped tech companies, how bootstrapping differs from venture capital, and how to integrate your team into an exit by offering them a portion of the equity.

Mark as Played

Advertise With Us

Popular Podcasts

Bookmarked by Reese's Book Club

Bookmarked by Reese's Book Club

Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.