The Startup CEO Show

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/-------------------------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.-----------------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 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/

In this enlightening discussion, Tobi Lütke, the visionary CEO and Co-founder of Shopify, shares insights into his unique leadership approach. He emphasizes the importance of continuous self-improvement and maintaining balance to combat burnout. Tobi reflects on his unexpected rise in tech, the role of motorsport in his life, and how it parallels business challenges. He advocates for the value of celebrating wins within startup cultures and explores the intricate relationship between personal happiness, ambition, and contentment.

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.------------------------------------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/

Russ Heddleston, former CEO of DocSend and a seasoned pro in tech acquisitions, shares his journey from VC funding to selling his company to Dropbox. He discusses the art of building relationships with potential buyers and competitors. The conversation explores product-led growth and capital efficiency. Russ also dives into the challenges faced during the acquisition process, emphasizing the importance of trust and adaptability in the tech landscape. Plus, he unveils a new initiative aimed at revolutionizing professional online identities.

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/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 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/Contact Mark: https://markmacleod.me/

🚀 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 Mark Faggiano, former co-founder and CEO of Taxjar, to discuss the journey from startup to successful acquisition and his current dedication to the Cure Alzheimer's fund. Mark Faggiano shares insights on navigating the e-commerce tax compliance landscape, fostering strong co-founder relationships, and making customer-centric decisions that drive growth. He also delves into the importance of profitability, independent control, and effective remote work strategies. Additionally, Faggiano talks about his commitment to Alzheimer’s research and ways to mitigate the risk of the disease through lifestyle choices.----------------------------------------------Connect with Mark Faggiano: https://www.linkedin.com/in/markfaggiano/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 special episode of The Startup CEO Show, host Mark MacLeod shares his extensive experience with venture-backed startup CEOs and discusses strategies to help CEOs lead their companies effectively without burning out. Mark dives into the importance of prioritizing health, fitness, mindset, and human connections, introducing frameworks such as the "CEO perpetual growth loop" and the "five factors of health" from Ben Bergeron. He also emphasizes the significance of living with intention and creating boundaries to ensure long-lasting leadership and satisfaction in life.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 sits down with Scot Chisholm to discuss the multifaceted journey of growing a startup and driving market penetration. Scot, the CEO and co-founder of Classy, delves deep into topics like forming strategic partnerships with heavyweights like Salesforce, navigating the complexities of fundraising from individuals to institutional investors, and the challenges associated with scaling from SMB to an enterprise-level organization. Scot also reflects on the evolution of Classy and its eventual acquisition by GoFundMe, sharing key insights that all startup CEOs can learn from.Learn More at https://scotchisholm.com/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/