Seeking the best startup and leadership advice tailored for CEOs? SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ---------------------------------------------- Are you curious about the journey of raising over $400 million in capital and navigating the path from startup to IPO? Tune in for this enlightening conversation! In this episode, host Mark MacLeod delves deep with Jack Newton, the co-founder and CEO of Clio, to explore the multi-faceted aspects of leading a legal tech company. Jack shares the inspiring story of Clio's origin, the pivotal moments in their fundraising journey, and the strategic decisions that led them to become a market leader. Discover insights into how Jack and his co-founder Ryan balanced their roles, the crucial importance of continuous learning, and how surrounding oneself with experienced team members can propel a company forward. ------------------------- Key moments: 04:15 The Origin Story of Clio 08:30 Importance of Product and Technology Expertise 11:45 Securing First Institutional Angel Funding 19:20 Growth Stage Power Dynamics 25:50 Transitioning from Venture to Private Equity 33:05 Choosing the Right Partners for Growth 40:50 Vertical SaaS and Customer Retention 46:30 Preparing for an IPO and Future Growth ----------------------- Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between. I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions. Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/ Connect on X/Twitter: https://twitter.com/markmacleod_ Contact Mark: https://markmacleod.me/