• Unsplash Journey: From Viral Hit to the Ultimate Exit with Mikael Cho
    Sep 30 2024

    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/

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    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! 🌟

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    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!

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    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/

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    48 mins
  • Modernizing Canada’s Business Banking: Rob Khazzam’s Vision
    Sep 23 2024

    Seeking ground-breaking insights on startup growth and leadership excellence?

    🚀 SUBSCRIBE to Mark MacLeod's newsletter for exclusive tips and updates: https://markmacleod.me/newsletter/

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    Ever thought, "This meeting could be an email"? We've got you covered!

    Meet Fellow: The AI Meeting Assistant that transforms your meetings by connecting to your calendar and productivity tools. Transcribe, summarize, and centralize your meetings like never before!

    ✨ Discover the future of productivity: https://fellow.app/

    -------------------------

    Join host Mark MacLeod as he dives deep with Rob Khazzam, CEO of Float, in an unmissable conversation about redefining finance, navigating the fintech landscape, and leading high-growth startups.

    Rob shares his journey from Uber to fintech innovation, emphasizing the blend of intense execution and strategic foresight required for sustainable growth. Learn about best practices for hiring, building resilient teams, and leveraging financial strategies for long-term success. Plus, Rob offers a candid look at the Canadian market's potential and challenges, bringing you unmatched insights into fintech's future.

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    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/

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    55 mins
  • Values-Driven Leadership: Gusto’s Core Philosophy with Josh Reeves
    Sep 16 2024

    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 Josh Reeves, Co-founder and CEO of Gusto, to discuss Gusto’s values-driven approach, the intricacies of scaling an SMB, and the long-term vision for Gusto.

    Josh delves into critical topics such as Gusto's UI simplicity, building a warm customer experience, and maintaining company culture. He shares his unique leadership style, the importance of aligning values in hiring, and how he promotes a culture of kindness and honest feedback at Gusto.

    ------------------------------------------------------

    Connect with Mark on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

    Stay updated on X: https://twitter.com/markmacleod_

    Get in touch with Mark: https://markmacleod.me/

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    57 mins
  • Tobi Lütke: The Infinite Game of Leadership
    Sep 9 2024

    Unlock unparalleled wisdom on leadership and innovation!

    🚀 SUBSCRIBE TO THE STARTUP CEO SHOW NEWSLETTER: https://markmacleod.me/newsletter/

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    Transform your meeting productivity with Fellow, the ultimate AI Meeting Assistant. Fellow transcribes, summarizes, and optimizes your meeting workflow, seamlessly integrating with your calendar and productivity tools.

    Enhance your efficiency now at https://fellow.app/

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    In this riveting episode of The Startup CEO Show, host Mark MacLeod dives deep with Tobi Lütke, CEO and Co-Founder of Shopify.

    Together, they navigate the complexities of constant self-improvement, the philosophy of infinite games, and the critical importance of learning loops. Tobi shares his journey from startup founder to CEO, the vital role of motorsport in his life, and his unorthodox perspectives on business excellence and personal contentment.

    Prepare to revolutionize your approach to leadership with Tobi's unique insights on balancing burnout, fostering a winning culture, and pursuing ambition beyond comfort zones.

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    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/

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    51 mins
  • From Burning Man to a $100M IPO with Nicholas Reichenbach
    Sep 3 2024

    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 Nicholas Reichenbach to discuss the journey of Flow Alkaline Spring Water, from its unique inception to becoming a public company.

    Nicholas dives into key topics such as building strategic partnerships, the challenges of raising capital in Canada, and driving sustainable business practices. Learn how Flow distinguished itself in the competitive water market, the importance of long-term vision, and the role of serendipity and positive energy in startup success. Nicholas also shares his experiences with celebrity endorsements and the impact of maintaining strong entrepreneurial leadership.

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    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/

    Show more Show less
    51 mins
  • DocSend's Roadmap: From VC Funding to Dropbox Acquisition with Russ Heddleston
    Aug 19 2024

    Looking for expert insights on startup success and leadership strategies for CEOs?

    🚀 Subscribe to Mark MacLeod's Newsletter: markmacleod.me/newsletter

    ------------------

    Tired of meetings that should've been emails?

    Fellow's AI Meeting Assistant is your solution—transcribing, summarizing, and streamlining your workflow by connecting with your calendar and productivity tools.

    Enhance your productivity today: fellow.app

    ------------------------------

    In this episode of The Startup CEO Show, host Mark MacLeod interviews Russ Heddleston, former CEO of DocSend, to explore the nuances of startup acquisitions and creating market value. Russ shares his experience selling to Dropbox, navigating competition, and making strategic business decisions. Discover how building relationships with potential buyers and competitors can influence acquisition outcomes. Russ also discusses product-led growth, capital efficiency, and his new ventures focused on leveraging LLMs.

    ------------------

    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/

    Show more Show less
    49 mins
  • Optimizing Life: Fitness, Health, and Startup Success with David Hauser
    Aug 12 2024

    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 David Hauser to discuss optimizing routines, building processes, and achieving startup success.

    David, a multi-time founder, angel investor, and author, delves into crucial topics such as the importance of morning routines, building a high-performing team, integrating values into company culture, and sending regular updates as a predictor of entrepreneurial success. Learn how to apply discipline and data-driven marketing across various industries, as well as insights into bootstrapping versus raising venture capital.

    ----------

    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/

    Show more Show less
    56 mins
  • Mindful Leadership with Cameron Wenaus
    Aug 5 2024

    Seeking valuable insights on startup success and leadership strategies for CEOs?

    🚀 SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/

    -----------------------------------------------

    How often do you think about improving your company's culture and efficiency?

    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 Cameron Wenaus, the co-founder and CEO of Retreat Guru, to discuss building trust within a company, embracing emotional sharing, and integrating mindfulness into business practices.

    Cameron dives into the importance of personal check-ins in leadership meetings, the impact of feeling safe in a work environment, and shares various resources and methods for beginning mindfulness meditation. The conversation also explores the challenges of managing resource limitations, the value of mission-aligned stakeholders, and how spiritual growth intersects with running a startup.

    -----------------------

    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/

    Show more Show less
    56 mins