EP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies

From dog genetics to bootstrapping to an eight-figure exit , Conor Tomkies has done it all. As the founder of Support Ninja, Conor scaled a bootstrapped business into a middle eight-figure success story, managing thousands of employees worldwide. After selling to private equity, Conor is now building Operator Equity and Entrepreneur Cooperative, empowering founders to scale and exit with purpose. Conor Tomkies shares how he leveraged strategic legal and operational efficiencies to save millions during acquisitions. He highlights his founder-first approach with Operator Equity, focused on scaling SaaS businesses using EOS, and discusses the startup shift from venture-backed moonshots to sustainable, profitable growth. ----------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here:⁠ https://web.thunder.vc/list-of-investors-vcs-for-founders⁠ Get the latest fundraising insights, news, and tips:⁠ https://blog.thunder.vc/funding-101⁠  Here's what you'll find in this episode: 00:00 Introduction 00:37 Dog genetics and the birth of Support Ninja 02:54 Bootstrapping vs. raising venture capital 05:30 Lessons from selling to private equity 10:14 Why EOS is a game-changer for scaling companies 18:34 Operator Equity’s focus on SaaS and ecosystem synergy 27:00 Common founder mistakes and the value of recurring revenue 30:45 The rise of moonshots and the future of venture capital ABOUT CONOR TOMKIES Conor Tomkies is a serial entrepreneur, investor, and post-exit founder with a passion for creating scalable businesses and empowering other entrepreneurs. He founded Support Ninja, a bootstrapped outsourcing company that scaled into a middle eight-figure success story and sold it to private equity. Now leading Operator Equity, Conor focuses on acquiring and scaling SaaS businesses using the Entrepreneurial Operating System (EOS), helping founders navigate successful exits with a streamlined 45-day process that prioritizes simplicity and a human touch. Conor is also the co-founder of Entrepreneur Cooperative (ECo) and host of the Made It Podcast. Through ECo, he has built a community where seasoned founders share experiences, collaborate, and gain insider strategies for navigating business sales and life beyond the exit. It’s the network every entrepreneur wishes they had when starting out, focused on meaningful growth, impactful exits, and supporting the next generation of founders. Connect with Conor: Website: operatorequity.com Entrepreneur Cooperative: entrepreneurcooperative.com X (formerly Twitter): @conortomkies_ ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.