The Startup CEO Show

Welcome to another episode of The Startup CEO Show!This week, we have a special video edition featuring Joel Gascoigne, founder and CEO of Buffer, known for its revolutionary approach to transparency and remote work. Our host, Mark MacLeod, dives deep with Joel into the intricacies of managing a startup during times of growth and decline, the strategic changes that Buffer has embarked on, and the personal journey of leadership.Joel shares his unique experience of managing 12 direct reports and transitioning to an asynchronous communication model to foster deep work and reduce meeting overload. He reflects on overcoming challenges, such as plateauing growth and navigating the pandemic's impacts with a renewed focus on supporting entrepreneurs and small businesses. We also explore the dynamics of co-founder relationships, raising and managing investor expectations, and Buffer’s return to a bootstrap model after a strategic VC buyout.Joel's insights into the long-term strategic vision, maintaining company culture, and embracing transparency offer invaluable lessons for startup CEOs and leaders striving to sustain growth while preserving core values. Plus, we touch on how fatherhood has influenced Joel's productivity and work-life balance.Tune in to glean actionable strategies for managing your startup more effectively and authentically.------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!----------------------------------Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Stay updated on X: https://x.com/markmacleod_Get in touch with Mark: https://markmacleod.me/

In today's episode of the Startup CEO Show, we dive into the incredible journey of Cody Ruberto, the founder and CEO of Uride. Mark MacLeod sits down with Cody to explore how he overcame financial obstacles early in his startup journey, leveraging angel investment and creative problem-solving to build a successful rideshare company. Cody shares revealing insights on expanding Uride into underserved markets, the importance of staying close to customers, and navigating the challenges of competition and market dynamics.We'll hear how Cody's athletic background in soccer laid the foundation for resilience and leadership, and how he channels continuous learning and self-improvement into driving business success. From battling aggressive competitors to establishing ethical business practices, Cody's story is one of perseverance, innovation, and a relentless drive to make a global impact. Don't miss this episode as we uncover the strategies, challenges, and inspiring journey behind Uride's mission to solve transportation issues in small towns and cities around the world. Tune in, subscribe, and prepare to be motivated by Cody Ruberto’s remarkable entrepreneurial expedition!------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!----------------------------------Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Stay updated on Twitter: https://twitter.com/markmacleod_Get in touch with Mark: https://markmacleod.me/

In this episode of the Startup CEO Show we're diving deep with Drew Green, the visionary CEO of Indochino, a transformative men's fashion brand known for their custom suits. Drew unpacks their unique strategies—like extending payment terms and adopting an appointment-based retail model—and shares invaluable insights on cash flow management, strategic partnerships, and leveraging media and CRM tools for efficient customer engagement.We'll also explore how Indochino navigated the tumultuous landscape of the COVID-19 pandemic, strategically expanded their retail footprint, and tapped into the wedding market, which now represents a significant portion of their business.Stick around for an enlightening conversation about resilience, innovation, and staying ahead in the competitive world of custom apparel.------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!----------------------------------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/

In this episode of The Startup CEO Show, host Mark MacLeod interviews Mike Katchen, Co-founder and CEO of Wealthsimple. Discover how Wealthsimple has transitioned from a single-product company to a multi-product leader in financial services.Listen in for tips on maintaining control, leadership strategies, working within regulatory frameworks, and evolving with client needs. Plus, learn how Mike's personal growth, fitness routines, and mental health strategies contribute to his effective leadership.Join us for an episode filled with practical advice and inspiring stories from one of Canada's top startup leaders!------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!----------------------------------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/

On this episode of The Startup CEO Show, Mark MacLeod and Amar Varma discuss everything from the role of artificial intelligence in business to navigating complex political climates -such as US election day- as a CEO. Amar offers his expertise on creating sustainable growth, overcoming business hurdles, and building successful teams in today’s fast-paced world. Whether you’re looking to innovate in your field or adapt to new challenges, this episode is packed with actionable insights for leaders and entrepreneurs alike.------------------- Looking to elevate your leadership game with actionable strategies?🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter----------------------Boost team productivity and streamline meetings with Fellow, the AI Meeting Assistant that transcribes, organizes, and integrates seamlessly with your calendar. Learn more: https://fellow.app/-----------------------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/

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Sean Kelly to discuss the importance of founder well-being and its impact on business performance.Sean, the founder of Family Fund, explores crucial topics such as treating founders like elite athletes, avoiding the pitfalls of hustle culture, and the significance of health, wealth, and freedom for entrepreneurs. Learn about the essential steps for maintaining mental clarity, fostering continuous learning, and strategic growth in consumer brands. Sean also shares his approach to investment and community building, along with insightful examples from his extensive experience in the health and wellness space. Don’t miss this conversation packed with strategies to optimize your business and personal success._______________________________🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/How many times a day do you think "This meeting could have been an e-mail"?----------------------------------------------------------Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!

In this episode of The Startup CEO Show, host Mark MacLeod sits down with Steve Bajuvez, to uncover the power of customer support as a strategic advantage.Steve, a former FreshBooks employee with 14 years of tenure, shares the transformative impact of spending time in support roles for new hires and how it shifts their perspective and understanding of the product. Discover the unique support strategies at FreshBooks, the importance of empathy and problem-solving in support roles, and how Steve led his team to foster a culture where every member could shine. Learn about the balance between creating memorable customer experiences and the "effortless experiment" aimed at reducing support calls by solving issues proactively.---------------------------------------------Seeking valuable insights on startup success and leadership strategies for CEOs?🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/-----------------------------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!---------------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/

Seeking valuable insights on startup success and leadership strategies for CEOs?🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/----------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!---------------In this episode of The Startup CEO Show, host Mark MacLeod engages with Daniel Saks in an insightful discussion on leadership transitions and the future of AI in business.Daniel, who navigated a successful transition from CEO to president and board member at AppDirect, talks about the importance of leadership changes for company growth. He shares his experiences with technology startups, the role of AI in enhancing business productivity, and his vision for agentic AI. Learn from Daniel's perspectives on building market value, overcoming industry challenges, and leveraging digital tools for optimal operational efficiency.--------------------Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Stay updated on Twitter: https://twitter.com/markmacleod_Get in touch with Mark: https://markmacleod.me/

Seeking valuable insights on startup success and leadership strategies for CEOs?🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/----------------------------------How many times a day do you think "This meeting could have been an e-mail"?Fellow is the only AI Meeting Assistant that transcribes, summarizes, and centralizes your meeting workflow by connecting to your calendar and existing productivity tools.Go to https://fellow.app/ and discover the best way to enhance productivity today!------------------------------------In this episode of The Startup CEO Show, host Mark MacLeod sits down with Mikita Mikado, co-founder and CEO of Pandadoc, to explore the journey of transforming a startup into a thriving business with over $100 million in revenue.Gain inspiration from Mikita's reflections on his entrepreneurial mission, his commitment to paying it forward, and the impact of therapy and emotional health on his leadership journey.--------------Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Stay updated on Twitter: https://twitter.com/markmacleod_Get in touch with Mark: https://markmacleod.me/

Looking to master the art of startup leadership and ace your CEO role? You're in the right place! 😎🔗 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER FOR EXCLUSIVE INSIGHTS: https://markmacleod.me/newsletter/------------------------------------Exhausted by endless meetings? Feel like some could be just emails?Meet Fellow – the AI Meeting Assistant that changes the game by transcribing, summarizing, and organizing your meeting workflow. It's time to let AI supercharge your productivity! 🚀Discover Fellow at https://fellow.app/ and take your efficiency to the next level! 🌟-------------In this must-watch episode of The Startup CEO Show, Mark MacLeod interviews Mikael Cho, CEO of Unsplash, as they unravel the mysteries of startup success.Mikael dives into the roller-coaster ride of Unsplash's journey, sharing hard-earned wisdom on overcoming challenges, iterating quickly, and managing cap tables. Get inspired by tales of skyrocketing growth, strategic acquisitions, and the art of aligning investor expectations. Mikael also sheds light on balancing work and personal life, all while keeping the entrepreneurial flame burning bright. 🔥Don't miss out on expert strategies for optimizing your startup adventure!--------------------Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/Stay updated on Twitter: https://twitter.com/markmacleod_Get in touch with Mark: https://markmacleod.me/