The Startup CEO Show

Mark MacLeod
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Feb 12, 2024 • 45min

Execution Over Ideas: Mark Ang's Philosophy of Startup Success

We’re thrilled to bring you an insightful conversation with Mark Ang, the co-founder and CEO of Gobolt, a revolutionary logistics company transforming the way we think about delivery and sustainability. Mark's journey from a university side hustle to leading a major player in the logistics industry is nothing short of inspiring.Mark was recognized on the Forbes 30 Under 30 list, and he shares his unique perspective on scaling a business, the importance of sustainability in logistics, and the challenges of navigating the startup world. Gobolt, initially a summer storage solution for students, has evolved into a sustainable logistics powerhouse under Mark's leadership, emphasizing the critical role of adaptability and vision in entrepreneurship.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/
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Feb 5, 2024 • 45min

Building Trust and Embracing Change with Jordan Boesch

In this new episode of “Startup CEO Show,” we talk with Jordan Boesch, the dynamic co-founder and CEO of 7shifts, a comprehensive HR and team management platform tailored for the hospitality industry. Dive into the world of startup growth, leadership transitions, and the undeniable impact of user feedback on product development.Jordan Boesch's journey from a passionate developer to a visionary CEO is nothing short of inspiring. Hailing from Saskatoon, Jordan has scaled 7shifts from a nascent startup to a powerhouse with over 400 employees, all while maintaining a deep connection to product development and customer satisfaction. His unique approach to leadership, coupled with a relentless pursuit of excellence, makes this episode a must-watch for aspiring entrepreneurs and seasoned executives alike.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/___________________Connect with Jordan:https://www.linkedin.com/in/jordan-boesch/https://www.7shifts.com/Setting the table: https://www.amazon.ca/Setting-Table-Transforming-Hospitality-Business/dp/0060742755/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1706900857&sr=1-1
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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/
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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/
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Jan 17, 2024 • 38sec

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