The Startup CEO Show

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/Connect on X/Twitter: https://twitter.com/markmacleod_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/Connect on X/Twitter: https://twitter.com/markmacleod_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/Connect on X/Twitter: https://twitter.com/markmacleod_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/Connect on X/Twitter: https://twitter.com/markmacleod_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/

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/

Unlock unparalleled wisdom on leadership and innovation!🚀 SUBSCRIBE TO THE STARTUP CEO SHOW NEWSLETTER: https://markmacleod.me/newsletter/----------------------------------------------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/----------------------------------------------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.---------------------------------------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 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/Connect on X/Twitter: https://twitter.com/markmacleod_Contact Mark: https://markmacleod.me/

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/

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/

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/

🚀 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/Connect on X/Twitter: https://twitter.com/markmacleod_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/Connect on X/Twitter: https://twitter.com/markmacleod_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/Connect on X/Twitter: https://twitter.com/markmacleod_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 Andrew Gazdecki, to discuss the intricacies of startup acquisitions and building market value. Andrew, the CEO of acquire.com, delves into crucial topics such as building trust with buyers, preparing your business for sale, and the importance of being diligence ready. Learn how to streamline the acquisition process with data rooms, templates, and financial recasting. Andrew also shares his experiences and insights on bootstrapping SaaS businesses, navigating private equity markets, and leveraging strong brand narratives for maximum impact.-----------------------------------------------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/

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 Katherine Regnier, founder and CEO of Coconut Software, for an insightful discussion on growing a business while staying true to your values. Discover Katherine's thoughts on raising funds, focusing the company's direction, and prioritizing customer perspectives while navigating sales cycles in the financial sector. Tune in to understand how flexible work policies impact productivity and employee satisfaction, and gain wisdom on transitioning from founder to CEO.--------------------------------------------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/