The Startup CEO Show

Mark MacLeod
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The Startup CEO Show

The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week. Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them. This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions. About Mark MacLeod 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.

  1. From Clinic to 600 Employees: Jane App's Entrepreneurial Journey

    HÁ 2 DIAS

    From Clinic to 600 Employees: Jane App's Entrepreneurial Journey

    In this episode of the Startup CEO Show, Mark MacLeod engages in a deep and insightful conversation with Alison Taylor, co-founder and co-CEO of Jane App, a leading practice management and scheduling platform for healthcare clinics. Alison shares the remarkable journey of building Jane from a solution for her own healthcare practice to a thriving company with 600 employees and a global user base. Alison's unique perspective on growth, prioritizing customer and team satisfaction over rapid expansion at all costs, provides a refreshing alternative to the typical startup narrative. The conversation delves into the intricacies of maintaining a successful co-founder relationship, with Alison and her partner Trevor sharing the CEO role. She emphasizes the importance of values alignment and having a shared vision for the company's future. Alison also provides valuable insights into the advantages and challenges of building a tech company in Canada, advocating for the strength of the Canadian startup ecosystem and the importance of contributing to its growth. One of the most compelling aspects of the conversation is Alison's candid discussion of balancing the demands of running a fast-growing company with personal life. As a solo parent to three teenagers, she offers a unique perspective on the challenges faced by working parents, particularly women, in leadership roles. Alison provides thought-provoking insights into gender roles in the workplace and at home, emphasizing the need for true equality in both spheres. Don't miss this opportunity to learn from one of Canada's most successful tech entrepreneurs - tune in to the Startup CEO Show with Mark McLeod and gain invaluable insights that could shape your own entrepreneurial journey. ------------------------------------- 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/

    50min
  2. David Cancel: Lessons from HubSpot, Drift, and Beyond

    27 DE JAN.

    David Cancel: Lessons from HubSpot, Drift, and Beyond

    In this episode of the Startup CEO Show, host Mark MacLeod sits down with David Cancel, a five-time founder and tech industry veteran, to explore the secrets behind building successful startups. David shares invaluable insights from his experiences founding companies like Performable and Drift, as well as his pivotal role at HubSpot. The conversation delves into David's decision to sell Performable to HubSpot, a move that transformed both companies. David reveals how he rebuilt HubSpot's engineering team from the ground up while simultaneously scaling the business towards an IPO - a feat he likens to "changing a plane engine mid-flight." Listeners will gain a rare glimpse into the strategic thinking and bold decision-making that propelled HubSpot to its current $36 billion valuation. The episode also covers David's journey with Drift, exploring how he identified a massive opportunity in conversational marketing and built one of the fastest-growing SaaS companies in history. David offers candid reflections on work-life balance, the challenges of entrepreneurship, and the importance of continuous learning. Don't miss out on these hard-earned lessons from one of tech's most accomplished leaders - tune in now!

    52min
  3. Profitability vs Venture Funding: Lessons from ChartMogul's Success with Nick Franklin

    13 DE JAN.

    Profitability vs Venture Funding: Lessons from ChartMogul's Success with Nick Franklin

    The latest episode of the Startup CEO Show features an enlightening conversation with Nick Franklin, the visionary behind ChartMogul, a leading subscription analytics platform. Mark McLeod explores ChartMogul's evolution from a niche product to a comprehensive platform for B2B SaaS companies. Nick shares fascinating insights into the state of SaaS metrics, revealing that while core metrics like MRR and churn remain crucial, the rise of AI and metered billing is reshaping the landscape. The discussion touches on ChartMogul's unique position as a barometer for the SaaS industry, offering listeners a rare glimpse into industry-wide trends and benchmarks. Nick's journey from an illustration background to becoming a successful tech CEO is both inspiring and instructive, highlighting the importance of adaptability and continuous learning in the startup world. The episode also dives into the challenges of remote work, with ChartMogul embracing a distributed model long before it became mainstream. Listeners will appreciate Nick's candid reflections on the pros and cons of venture funding, and his decision to prioritize profitability over rapid, unsustainable growth. Don't miss this opportunity to learn from one of the industry's most experienced and thoughtful leaders. -------------------------- 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/ Contact Mark: https://markmacleod.me/

    1h
  4. From Nerd Olympics to Tech Entrepreneurship: Mike Serbinis' Story

    16/12/2024

    From Nerd Olympics to Tech Entrepreneurship: Mike Serbinis' Story

    In this captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Mike Serbinis, a prolific tech entrepreneur with over $1 billion in exits under his belt. Mike shares his incredible journey from engineer to CEO, including competing against Amazon with his e-reader company Kobo and his current venture League, a healthcare technology platform with over 20 million users. Dive into Mike's experiences in Silicon Valley, his approach to building and scaling companies, and how he's tackled immense challenges in the healthcare industry. Mike discusses the importance of going for "gold" in business, likening it to the Olympics where only the top performers are remembered. He also reveals his strategies for maintaining work-life balance while pursuing ambitious goals, including his weekly "Week Ahead" memos that have become a cornerstone of his leadership style. Tune in now to learn from one of tech's most successful founders and gain actionable insights to apply to your own entrepreneurial journey. -------------------------- 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/

    1h5min
  5. Building a Sustainable Smart Home Empire: The Ecobee Story with Stuart Lombard

    09/12/2024

    Building a Sustainable Smart Home Empire: The Ecobee Story with Stuart Lombard

    This episode of the Startup CEO Show delves deep into the world of sustainable business practices and corporate responsibility with Stuart Lombard, the visionary behind Ecobee. Mark MacLeod guides the conversation through Lombard's philosophy on building a company that not only succeeds financially but also makes a positive impact on the world. Lombard shares compelling examples of how Ecobee integrated sustainability into its core business model, from reducing packaging and optimizing shipping methods to negotiating better payment terms with suppliers. He explains how these practices not only reduced the company's environmental footprint but also improved its bottom line, challenging the notion that sustainability always comes at a cost. The discussion also touches on Ecobee's innovative "donate your data to science" program, which allowed the company to contribute to groundbreaking research in energy efficiency and senior care. Lombard's insights demonstrate how corporations can act as responsible citizens in their communities while driving innovation and growth. Don't miss this inspiring conversation that will change the way you think about business and sustainability. ------------------------------------- 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/

    49min
  6. Joel Gascoigne Discusses Fatherhood, Transparency, and Business Strategy at Buffer

    02/12/2024

    Joel Gascoigne Discusses Fatherhood, Transparency, and Business Strategy at Buffer

    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/

    59min
  7. The Importance of Persistence: Cody Ruberto's Path to Startup Success

    25/11/2024

    The Importance of Persistence: Cody Ruberto's Path to Startup Success

    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/

    50min
  8. The Power of Gratitude in Business: Insights from Indochino’s CEO

    18/11/2024

    The Power of Gratitude in Business: Insights from Indochino’s CEO

    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/

    53min
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Sobre

The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week. Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them. This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions. About Mark MacLeod 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.

Informações

  • Criado por
    Mark MacLeod
  • Anos de atividade
    2024 - 2025
  • Episódios
    49
  • Classificação
    Livre
  • Copyright
    © Copyright 2025 Mark MacLeod
  • Site do podcast
    The Startup CEO Show

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