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.
In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Darrell Heaps, co-founder and CEO of Q4 Inc., to explore the fascinating 18-year journey of building a successful investor relations platform. Heaps shares his experiences navigating different stages of growth, from bootstrapping to venture funding, going public, and ultimately becoming private equity-backed. He offers valuable advice on avoiding burnout as a long-term CEO, emphasizing the importance of setting challenging goals and constantly evolving. Heaps discusses how he's grown as a leader, including learning to delegate effectively and leverage diverse personality types on his executive team. He provides an inside look at the realities of taking a company public, including the challenges of managing stock price fluctuations and balancing investor relations with day-to-day operations. For founders considering an IPO, Heaps offers candid insights on the pros and cons, as well as key considerations around timing and scale. Tune in to gain wisdom from Heaps' nearly two decades of experience leading Q4 through multiple phases of growth and funding.-------------------------------------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 Casey Woo, founder of Operators Guild and Fog Ventures, to explore the evolving landscape of executive roles in the tech industry. Woo, a former military officer and six-time CFO, shares his unique perspective on how AI is reshaping the business world and creating new opportunities for multidisciplinary leaders he calls "scalers."The conversation delves into the changing nature of the CFO role, with Woo arguing that modern CFOs are becoming "mini CEOs" who need to be strategic partners rather than just number crunchers. He discusses how AI is making specialists vulnerable while elevating the importance of generalists who can synthesize information across disciplines. Woo introduces the concept of "scalers" - versatile executives who don't code or sell, but excel at solving complex business problems and leveraging AI for insights.Listeners will gain valuable insights into the future of executive leadership, the impact of AI on various roles, and the growing importance of business intelligence. Woo also shares details about Operators Guild, a community he founded for non-technical executives in tech startups. Tune in to learn how you can position yourself for success in this rapidly changing landscape.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 captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Rand Fishkin, co-founder and CEO of SparkToro, for a candid conversation about entrepreneurship, venture capital, and building successful businesses. Rand, best known for founding Moz and his influential role in the SEO industry, shares invaluable insights from his journey as a founder and thought leader.The discussion delves into the pros and cons of building a personal brand as a CEO, with Rand reflecting on how his own high profile impacted Moz both positively and negatively. He offers a refreshing perspective on the venture capital world, discussing why he now advocates for alternative funding models that prioritize sustainable growth over hypergrowth. Rand also provides a fascinating look at his current ventures, including SparkToro and Snackbar Studio, explaining how he's applying lessons learned from Moz to build more balanced, founder-friendly companies.This episode is a must-listen for entrepreneurs, marketers, and anyone interested in the realities of building and scaling startups in today's competitive landscape. Tune in to gain actionable advice from one of tech's most respected voices and learn why sometimes the path less traveled leads to greater success and fulfillment.-------------------------------------------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 insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Eli Portnoy, a serial entrepreneur with two successful exits under his belt. Portnoy shares his journey from his first venture to his current role as co-founder and CEO of BackEngine, offering a masterclass in navigating acquisitions and building thriving startups. The conversation delves into the psychological aspects of selling a company, the importance of building relationships with potential acquirers, and the challenges of transitioning from founder to employee post-acquisition. Portnoy's candid reflections on his experiences provide valuable lessons for aspiring entrepreneurs, emphasizing the rarity of acquisition opportunities and the need to carefully consider one's motivations when faced with an offer. The episode also explores Portnoy's current venture, Back Engine, which leverages AI to help companies maintain a strong connection with their customers as they scale. Listeners will gain actionable insights on fundraising, exits, and the evolving landscape of startup leadership in the age of AI. Tune in to learn from Portnoy's successes and challenges, and discover how to build a company with long-term vision while remaining open to transformative opportunities.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 captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Josh Pantony, co-founder and CEO of Boosted AI, to explore the cutting-edge world of artificial intelligence in finance. Josh, a veteran in the AI space, shares his journey from co-founding Maluva, an early competitor to Siri, to his current role revolutionizing Wall Street with AI-powered tools.The conversation delves into the technological breakthroughs that have made modern AI possible, including unsupervised training and attention networks, and how these advancements are reshaping the financial industry. Josh provides fascinating insights into the future of SaaS, predicting that AI will soon be able to auto-generate user interfaces and drastically reduce the cost of software development.He envisions Boosted AI becoming an integral part of every professional investment manager's workflow, ultimately accelerating wealth creation for society as a whole. Tune in to gain valuable insights from one of AI's pioneering minds and learn how these innovations may impact your own career and investments.----------------------------------------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, Mark MacLeod sits down with Craig Letton, founder and CEO of alcohol marketing platform hyble, for a raw and honest discussion about entrepreneurship, burnout, and building a successful global business. Craig shares the remarkable story of how he took over his parents' small print shop in Scotland and transformed it into a high-growth tech company serving major alcohol brands worldwide. He opens up about the immense challenges he faced along the way, including bootstrapping the business, navigating the pandemic, and executing a massive U.S. expansion that pushed him to the brink of burnout.Craig provides a candid look at the toll this took on his mental and physical health, and shares the strategies that helped him persevere and ultimately thrive. From tapping into his competitive athlete mindset to carving out time for self-care, his insights offer valuable lessons for any founder going through difficult times. The episode also explores Craig's approach to building an award-winning company culture based on authenticity, humility and continuous learning. Don't miss this must-listen conversation on navigating the 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/Contact Mark: https://markmacleod.me/
In this episode of the Startup CEO Show, Mark MacLeod sits down with Bryn Jones, co-founder and CEO of PartnerStack, to explore the world of B2B partnerships and scaling a successful SaaS company. As PartnerStack approaches its 10-year anniversary, Bryn shares valuable lessons from his journey as a competitive swimmer turned entrepreneur. He discusses how the discipline and resilience he developed as an athlete translated into building a thriving business. Bryn provides a candid look at the challenges of creating a new category in the partnership space, including navigating relationships with analysts and adapting to market volatility.The conversation delves deep into the intricacies of successful B2B partnerships, with Bryn emphasizing the importance of putting partners first and building relationships based on mutual value. He shares insights on identifying ideal partner profiles, setting up effective incentives, and the role of enablement in driving partnership success. Bryn also touches on the potential impact of AI in streamlining and optimizing partnership processes. The episode offers a wealth of practical advice for startups looking to leverage partnerships for growth, including the pros and cons of selling to early-stage companies.Perhaps most compellingly, Bryn opens up about the challenges of managing rapid growth and the importance of addressing underlying issues rather than simply chasing numbers. He reflects on the personal and professional lessons learned during PartnerStack's journey, including the value of trusting one's instincts as a leader. Tune in to gain a deeper understanding of how partnerships can drive business growth and the key factors that contribute to long-term success in the SaaS world.---------------------------------------------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 insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Justin Herlick, co-founder and CEO of Pine, a digital-first mortgage platform revolutionizing homeownership in Canada. Justin shares his journey from working on Wall Street to Silicon Valley, where he gained invaluable experience at fast-paced startups like Blend.He discusses how his time in San Francisco shaped his entrepreneurial mindset and inspired him to bring innovative fintech solutions back to Canada. Justin delves into Pine's mission to make homeownership more affordable and accessible, explaining how they're disrupting the traditional mortgage industry through technology and customer-centric approaches. He offers a fascinating look at the challenges of building a consumer-focused startup in Canada, including talent acquisition and fundraising hurdles.Justin's strategic insights on go-to-market strategies, building trust with customers, and creating a competitive edge in a bank-dominated market are invaluable for aspiring entrepreneurs. Don't miss this episode packed with lessons on intentional career building, startup growth, and transforming traditional industries through innovation. Tune in now to fuel your 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/
In this captivating episode of the Startup CEO Show, Mark MacLeod sits down with Clive Kinross, the CEO of Propel Holdings, a company that's revolutionizing lending for underserved consumers. Clive shares his remarkable journey from South African chartered accountant to successful entrepreneur, detailing the founding and growth of Propel Holdings. With over a million customers served and $2 billion in loan originations, Propel has become a game-changer in the financial industry. Clive discusses the company's innovative use of AI in credit assessment, allowing them to serve customers traditional banks often overlook. He emphasizes the importance of profitability, team loyalty, and maintaining a long-term perspective in business growth. Listeners will gain valuable insights into building a successful fintech company, navigating the challenges of going public, and maintaining a strong company culture through rapid growth.Clive's story is a masterclass in entrepreneurship, demonstrating how a background in accounting can be leveraged to create a thriving business. Don't miss this opportunity to learn from one of the most successful CEOs in the fintech space – tune in now!--------------------------------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 Sameer Dhar, co-founder and CEO of NiaHealth, to explore the intersection of entrepreneurship and personal health. Dhar shares his journey from diabetes researcher to investment banker to healthcare innovator, highlighting how his experiences shaped NiaHealth's mission to bring proactive, evidence-based healthcare to the masses. The conversation delves into the challenges of Canada's healthcare system and how NiaHealth is working to complement and alleviate pressure on public healthcare through personalized diagnostics and actionable insights. Dhar emphasizes the importance of empowering individuals with consumer-friendly health information, allowing them to take charge of their wellbeing in ways previously unavailable. The episode offers valuable insights for entrepreneurs on balancing the demands of building a company with maintaining personal health, drawing parallels between running a successful business and managing one's physical wellbeing.Tune in to discover how you can leverage the latest in health technology to enhance your performance and quality of 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/
In this episode of the Startup CEO Show, Mark MacLeod welcomes Glen Coates, former CEO of Handshake and current VP of Product for Core at Shopify. Glen takes listeners on a journey through his entrepreneurial experiences, from founding Handshake to his current role at Shopify.He shares candid insights about the challenges of building a B2B e-commerce platform, including the complexities of serving businesses with thin margins and intricate needs. Glen's transition to Shopify provides a unique perspective on what makes the company a magnet for talented founders. He offers fascinating glimpses into Shopify's culture of innovation, driven by CEO Tobi Lütke's relentless pursuit of cutting-edge technology.The conversation takes an exciting turn as Glen discusses the rapid advancements in AI and their potential impact on e-commerce. He shares intriguing examples of how Shopify is integrating AI into its platform, including a multilingual AI assistant that's revolutionizing customer support. The discussion also touches on the evolving landscape of AI and its implications for businesses of all sizes.Don't miss out on these invaluable insights - listen now and gain a competitive edge in the rapidly evolving world of e-commerce and technology.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 welcomes Dax Dasilva, the founder and CEO of Lightspeed Commerce, for a wide-ranging discussion on leadership, spirituality, and building a billion-dollar tech company. As Lightspeed celebrates its 20th anniversary, Dasilva reflects on the company's journey from a small team in Montreal's Gay Village to a global leader in commerce solutions. He shares how his personal growth, including his conversion to Judaism, has intertwined with Lightspeed's evolution, providing him with the spiritual foundation to navigate the challenges of scaling a tech company.Dasilva offers unique perspectives on creating an inclusive workplace culture, emphasizing the importance of allowing employees to bring their authentic selves to work. The conversation delves into Lightspeed's funding journey, from bootstrapping to venture capital to going public, with Dasilva providing valuable insights on each stage. He also discusses the company's acquisition strategy and the complexities of integrating multiple platforms. Dasilva opens up about his experiences with burnout and the importance of physical health in maintaining leadership stamina. The episode concludes with Dasilva explaining his decision to return as CEO and his vision for Lightspeed's future. This conversation is a goldmine of wisdom for entrepreneurs, offering a rare glimpse into the mind of a leader who has successfully balanced growth, innovation, and values over two decades.Tune in now to gain invaluable insights from one of Canada's most successful tech entrepreneurs.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 Tyler Denk, co-founder and CEO of Beehiiv, to explore the world of email marketing and the creator economy. Tyler shares the fascinating origin story of Beehiiv, which grew out of his experience building custom tools at Morning Brew. He explains how Beehiiv has become a leading all-in-one platform for creators and brands to grow their audience and monetize their content.Tyler dives deep into Beehiiv's unique value proposition, combining website building, email newsletters, and monetization tools in one seamless platform. He discusses how this integrated approach sets Beehiiv apart from legacy email providers and allows creators to focus on what they do best. The conversation touches on the evolving role of AI in content creation, with Tyler offering nuanced insights on when AI can be helpful and when human creativity is irreplaceable.One of the most compelling parts of the discussion centers on Tyler's leadership philosophy and operational strategies. He shares his commitment to radical transparency, describing how he writes detailed weekly emails to keep his team aligned and motivated. Tyler also reveals how Beehiiv raised its Series A in just six days and its Series B in two weeks, crediting his practice of sending comprehensive monthly investor updates. For aspiring founders and CEOs, this episode is a masterclass in building a high-growth startup with intention and focus. Don't miss Tyler's contrarian views on company size and his emphasis on deep work - tune in now to gain invaluable insights from one of tech's rising stars.
In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Matt Turck, General Partner at FirstMark Capital, for a wide-ranging discussion on venture capital, AI, and the startup ecosystem.As the first VC guest on the show, Turck offers a unique perspective on board dynamics, content creation, and the evolution of the tech industry. He shares his experiences as an early AI investor and discusses the current state of enterprise AI adoption, highlighting the challenges and opportunities in the space. Turck emphasizes the importance of founder quality and market timing in startup success, drawing on his years of experience backing unicorn companies. The conversation also touches on the global nature of tech innovation, with Turck expressing bullish sentiments on European entrepreneurship and the spread of Silicon Valley's model worldwide. Tune in to hear Turck's thoughts on the future of SaaS, the AI revolution, and what it takes to build a successful startup in today's rapidly changing landscape.-------------------------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, Mark MacLeod sits down with Joanna Griffiths, the visionary founder and CEO of Knix, a revolutionary women's clothing brand. Joanna shares her remarkable journey of building Knix from its inception in 2013 to becoming a major player in the intimate apparel industry.She discusses how she identified a gap in the market for leak-proof underwear and turned it into a thriving business that has expanded into bras, activewear, and swimwear. Joanna provides fascinating insights into the challenges of being a female founder in a male-dominated industry, including her experiences pitching to investors who often struggled to understand her product. She also reveals how she navigated fundraising while pregnant with twins and closed a round just days before giving birth. Listeners will be inspired by Joanna's determination, innovative approach to product development, and commitment to creating a brand that truly serves women's needs.Don't miss this opportunity to learn from one of the most successful female founders in the direct-to-consumer space - tune in now!----------------------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 captivating episode of the Startup CEO Show, host Mark MacLeod sits down with Dan Park, co-founder and CEO of Clutch, to discuss the rollercoaster journey of building Canada's leading online used car marketplace. Park shares the highs and lows of Clutch's growth, from rapid expansion fueled by venture capital to a near-death experience that forced massive layoffs. He offers a candid look at how Clutch weathered the storm, pivoted to profitability, and emerged stronger on the other side.Park dives deep into Clutch's mission to disrupt the traditional used car buying experience in Canada by offering full transparency, reconditioning every vehicle, and allowing customers to complete the entire purchase online. He explains how Clutch's vertically integrated model and focus on customer experience sets it apart in an industry not known for trust or convenience. Listeners will gain valuable insights into building a venture-scale business in a mature market, balancing growth with unit economics, and staying motivated through extreme challenges.The conversation also explores key lessons Park brought from his time leading Uber Eats Canada, including the importance of operational focus and rapid iteration. His perspective on fundraising cycles, investor expectations, and navigating macro headwinds will resonate with many founders. Don't miss Park's inspiring story of turning setbacks into comebacks - tune in now to the Startup CEO Show.--------------------------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 enlightening episode of the Startup CEO Show, host Mark MacLeod welcomes Andrew D'Souza, the innovative co-founder and CEO of Boardy, for a deep dive into the world of AI-driven networking and entrepreneurship. D'Souza, known for his previous success with Clearco, shares candid reflections on his journey from building a unicorn company to exploring the frontiers of AI technology. The conversation offers listeners a rare glimpse into the mind of a serial entrepreneur, covering everything from the challenges of hypergrowth to the intricacies of navigating investor relationships in today's competitive landscape.Andrew introduces Boardy, an AI super connector that's redefining how professionals network and collaborate. He explains the groundbreaking technology behind Boardy, including its use of advanced voice models and AI to facilitate meaningful connections. The discussion explores the potential for AI to unlock hidden value in human interactions and reshape our understanding of work and productivity. Andrew's vision for Boardy goes beyond traditional AI assistants, imagining a future where AI entities play a more integral role in society, with their own agency and autonomy.The episode delves into the impact of AI on various industries, with a particular focus on SaaS companies. D'Souza challenges CEOs to rethink their competitive advantages in light of rapidly evolving AI capabilities, offering valuable insights for business leaders navigating this technological revolution. The conversation also touches on the broader implications of AI for the job market and workforce development, with D'Souza presenting an optimistic view of AI's potential to enhance human creativity and self-expression. The episode concludes with a thought-provoking discussion on the Canadian tech landscape and the cultural challenges faced by ambitious entrepreneurs.Tune in now to gain invaluable insights from one of tech's most forward-thinking leaders.
In this milestone 50th episode of The Startup CEO Show, host Mark MacLeod reflects on 25 key lessons from his 25 years in the startup world. Drawing from his extensive experience as a CFO, venture capitalist, and advisor, Mark shares invaluable insights on timing, market dynamics, fundraising, and leadership. He emphasizes how timing and luck play a crucial role in startup success, citing examples like Tungle's fortunate Series A raise just before the 2008 financial crisis. MacLeod also delves into the challenges of operating in hot markets, the potential of disrupting established industries, and the pitfalls of poor market selection. He shares candid thoughts on the venture capital industry, board dynamics, and the importance of founder self-awareness. Throughout the episode, Mark peppers in anecdotes from his work with successful companies like Shopify, providing listeners with a rich tapestry of startup wisdom.Tune in to gain insights that could shape your entrepreneurial journey and potentially save you from costly mistakes.----------------------------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/
The Startup CEO Show takes a deep dive into the world of conscious entrepreneurship in this enlightening episode featuring Shrad Rao, the visionary former CEO of Wagepoint. Host Mark MacLeod guides listeners through a fascinating discussion that bridges Eastern spirituality with Western business acumen. Rao, fresh from stepping down after over a decade at the helm of Wagepoint, shares his journey of building a successful tech company while maintaining a strong spiritual foundation.The episode explores the emotional landscape of transitioning out of a long-held CEO position, with Rao candidly discussing the mix of exhilaration and grief he experienced. He reveals his unique approach to leadership, emphasizing the importance of caring deeply for employees and creating a culture of experimentation and growth. Rao's insights into conducting personal "culture calls" with potential hires and his philosophy on parting ways with employees compassionately offer valuable lessons for leaders at all levels.MacLeod and Rao delve into the power of intuition in business decision-making, discussing how to balance analytical thinking with gut instincts. The conversation takes an introspective turn as both share their experiences with Eastern spiritual practices and how these inform their leadership styles. Rao's perspective on the intersection of creativity and technology, inspired by figures like Steve Jobs and Warren Buffett, provides a fresh take on innovation in the tech industry.This episode is a must-listen for entrepreneurs and leaders seeking to infuse their business practices with mindfulness and compassion while driving success.----------------------------------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, 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/
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!
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/
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/
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/
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/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?
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._______________________________
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?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
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Seeking ground-breaking insights on startup growth and leadership excellence?
Seeking valuable insights on startup success and leadership strategies for CEOs?
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Seeking valuable insights on startup success and leadership strategies for CEOs?
Looking for expert insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking valuable insights on startup success and leadership strategies for CEOs?
Seeking the best startup and leadership advice tailored for CEOs?SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ----------------------------------------------Are you curious about the journey of raising over $400 million in capital and navigating the path from startup to IPO? Tune in for this enlightening conversation! In this episode, host Mark MacLeod delves deep with Jack Newton, the co-founder and CEO of Clio, to explore the multi-faceted aspects of leading a legal tech company. Jack shares the inspiring story of Clio's origin, the pivotal moments in their fundraising journey, and the strategic decisions that led them to become a market leader. Discover insights into how Jack and his co-founder Ryan balanced their roles, the crucial importance of continuous learning, and how surrounding oneself with experienced team members can propel a company forward. -------------------------Key moments: 04:15 The Origin Story of Clio08:30 Importance of Product and Technology Expertise 11:45 Securing First Institutional Angel Funding 19:20 Growth Stage Power Dynamics 25:50 Transitioning from Venture to Private Equity 33:05 Choosing the Right Partners for Growth 40:50 Vertical SaaS and Customer Retention 46:30 Preparing for an IPO and Future Growth-----------------------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/