

The Startup CEO Show
Mark MacLeod
The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week.
Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them.
This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions.
About Mark MacLeod
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.
Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them.
This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions.
About Mark MacLeod
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.
Episodes
Mentioned books

Jan 29, 2024 • 43min
How to know when it is time to sell your startup with Ben Jabbawy
Welcome to the Startup CEO Show, where we delve into the strategies and insights of successful entrepreneurs. In this episode, our host Mark MacLeod sits down with Ben Jabbawy, the mastermind behind Privy's remarkable journey to a $120 million exit. Ben Jabbawy is the co-founder and former CEO of Privy, a marketing automation platform that scaled phenomenally within the Shopify ecosystem. Starting from his parents' house, Ben grew Privy to 80 employees and $10 million in ARR, culminating in a $120 million exit in 2021. His insightful approach to market timing, distribution strategies, and capital efficiency has set a benchmark in the SaaS industry. Ben is now an active investor, sharing his wealth of experience with emerging entrepreneurs.Don't forget to subscribe for more insightful episodes like this. Drop your thoughts and questions in the comments below!Join the leading newsletter designed exclusively for the CEOs of high-growth startups and the VCs who back them.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/Contact Mark: https://markmacleod.me/

Jan 22, 2024 • 44min
From Near Bankruptcy to a $400M Exit: Kirk Simpson's Wave Odyssey
In this latest episode of the Start Up CEO Show, we dive deep into the dynamic world of startups, revealing the secrets behind successful entrepreneurship and innovative business strategies. Join us as we examine the intricate balance between risk and innovation, a critical aspect for any aspiring entrepreneur or business enthusiast.Our guest, Kirk Simpson, is a renowned figure in the startup ecosystem. With a career rich in entrepreneurial ventures, Kirk has navigated the challenging waters of the business world, transforming obstacles into opportunities for success. His journey is not just inspiring but also packed with valuable lessons for anyone looking to make their mark in the business world. In this episode, Kirk shares his insights on managing risks, fostering innovation, and the mindset needed to excel in the constantly evolving business environment.Don't forget to subscribe for more insightful episodes like this.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/Contact Mark: https://markmacleod.me/

Jan 17, 2024 • 38sec
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