Podcasts about real ventures

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 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 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/

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/

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 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?

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?

In this engaging episode, we sit down with Mark Macleod, a seasoned CFO, VC, and angel investor whose career has significantly impacted high-growth technology companies. Mark takes us through his extensive experience, from his roles at FreshBooks and Real Ventures to founding SurePath Capital Partners. He shares invaluable lessons on the evolution of the CEO role, emphasizing the critical aspects of communication, team building, and financial management. In episode 10 of season 2, Mark explores the importance of maintaining boundaries and preventing burnout, offering practical advice on time management and self-care. He introduces the concept of the 24-hour rule for decision-making and discusses the necessity for CEOs to shift from working in the business to working on the business. Mark's insights on creating optionality for startups and navigating uncertain times provide listeners with robust strategies to enhance their leadership skills. As a coach to high-growth company CEOs, Mark brings a unique perspective on balancing professional demands with personal well-being. He highlights the importance of being authentic and designing roles that align with your strengths and passions. Mark's ability to distill complex ideas into actionable advice makes this episode a must-listen for anyone aiming to excel in leadership positions. This episode is filled with practical tips on preventing burnout, managing time effectively, and building high-performing teams. Tune in to gain Mark's wisdom on leading with intention and navigating the challenges of high-growth environments. . . . Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues. . . . TIME-STAMPED SHOW NOTES: [04:31] Career experiences and leadership, mistakes [07:55] The Importance of pausing and avoiding panic [11:45] The CEO's role in communication, vision, and values [14:18] Burnout and time management as a leader [21:58] Calendar audits = key to avoiding burnout. [23:53] Design your role for personal happiness [29:30] The roles and focus areas of a CEO [34:23] Dealing with uncertainty and layoffs [39:42] Be your authentic self to avoid burnout  

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/

Are you seeking invaluable tips on becoming a successful startup CEO?SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/----------------------------------------------In this episode, Mark MacLeod gets into an engaging discussion with Hiten Shah, the co-founder and CEO of Nira, exploring the myriad facets of leading and funding a startup. Hiten shares his experiences and philosophies, ranging from the necessity of aligning product development with customer feedback to the intricacies of venture capital and self-funding.Discover the profound insights on venture capital investment, the vital importance of investor-founder alignment, and Hiten's unique approach to product innovation and company culture. This episode is perfect for aspiring entrepreneurs and seasoned executives alike, who are eager to learn from someone who has walked the challenging path of startup success.-------------------------Key moments:05:10 How to Build a Startup from Scratch11:20 Advantages of Self-funding versus VC14:45 The role of Investors19:30 Strategies for Handling Risk and Investors29:10 Remote Work and its Impact on Company Culture32:40 Discussion on Customer Obsession37:50 Challenges of raising money and the timing of investment pitches.42:05 Understanding and Leveraging Investor Expectations.47:00 Accountability in Remote Work and Transparency in Business.----------------------------------------------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 the best Startup CEO Insights? SUBSCRIBE TO MARK MACLEOD'S NEWSLETTER: https://markmacleod.me/newsletter/ ----------------------------------------------In this episode, we're joined by former Dribbble CEO, Zack Onisko, who shares his insightful experiences from leading one of the few remaining independently owned social networks designed specifically for designers. Zack and host Mark MacLeod discuss his decision to step down, reflecting on a period of significant profitability and growth at Dribbble, achieved without the backing of venture capital. Making major career transitions, the impact of leadership on company culture, and the importance of aligning personal values with professional endeavors are some of the key topics of this episode. Join us for a compelling conversation that unveils the nuances of steering a tech enterprise through evolving landscapes and personal growth.-------------------------Key moments:00:00 Leaving Dribbble due to personal pursuits.05:42 Silicon Valley raised CEO reflects on growth.06:48 Talking to investors, company grew, profitable results.10:11 Technology has shifted startup landscape, lowering expenses.13:54 Email crucial for user acquisition and revenue.18:00 Transition from investment banker to coach amidst COVID.20:58 Transition from employee to successful entrepreneur for freedom.24:27 Self-driven urgency led to company's success.28:01 Learning from Andrew's entrepreneurial and investment approach.30:29 Transitioned from startup operator to capital management.36:43 Reinvesting profits to fuel company growth and acquisitions.40:52 Shifted managerial style, focused on building trust.42:10 Remote work offers efficiency and productivity benefits.46:58 Found your insights helpful, want to explore further.50:28 Joining Dribbble was a dream come true, looking to pursuit new ones-------------------------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, join us as Mark MacLeod welcomes special guest Amar Varma, co-founder and CEO of Mantle, for a captivating discussion. Discover how Mantle is revolutionizing private asset tracking through innovative AI integration and fresh approaches. Gain strategic insights from Amar as he explores market opportunities for startups and the transition to an enterprise-driven model. Explore the complexities of investment strategy and the transformative potential of AI, all while delving into Amar's invaluable firsthand experiences in the startup world.Don't forget to subscribe for more insights on how to become a successfull startup CEO!-----------------------Key moments:00:00 - 04:39 Reimagining market with fresh approach and AI.04:39 - 08:23 A dominant player in finance.08:23 - 13:03 Becoming investor after previous experiences with no regrets.13:03 - 16:25 Invest wisely, be mindful about timing and luck.16:25 - 20:26 Embracing feedback, self-awareness, and professional growth.20:26 - 23:54 Understanding my process and transparent communication23:54 - 26:46 Identify winners by DNA and winning consciousness.26:46 - 29:29:Obsessive people find success in various domains.32:00 - 37:14: Considering alignment before investing in overpriced companies. 37:14 - 41:05: AI progress with potential misuse concerning.41:05 - 43:11: Founder-led company going public. ------------------------------------------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 back to the Startup CEO Show with Mark MacLeod. In this episode, we dive deep with Jason Smith, CEO of Klue, into the gritty details of building and leading a tech company in the Competitive Enablement space. Connect with his story as we unravel the nuanced strategies of convincing C-suite executives of your product's value, the science of proving ROI through innovative attribution models, and the brave new world of AI's integration in business operations.Whether you're a startup CEO, a product marketer, or just someone passionate about the intersection of technology, leadership, and growth, this is an episode packed with wisdom you won't want to miss. So plug in and get ready to take notes - this is Startup CEO Show.---------------------Key moments:00:00 - 04:21 How AI is facilitating the transition from raw intel to insight.04:22 - 08:48 Networking and promoting innovative thinkers for change.08:50 - 14:01 In a world with competitive radar, investors see potential.15:35 - 19:01 Comparing sellers' adoption of clue for sales.19:21 - 22:00 Focusing on building culture and customer satisfaction.22:08 - 24:40 Productivity at home, missing human connection.24:43 - 29:50 Leaders learn from mistakes, delegate for growth.30:00 - 33:01 Experience navigating VC world during COVID challenges.33:10 - 36:10 Harnessing competitor data, leveraging AI for insight.36:14 - 38:01 Platform insight still needed for specific competitive edge.41:11 - 45:01 CEO key advices on managing and growing a SaaS company45:02 - 48:15 Balancing work and family life with focus.------------------------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 the Startup CEO Show, where we dive deep into the heart of startup leadership and growth. In this episode, join our host Mark MacLeod as he engages on a thrilling conversation with Notch's CEO, Jordan Huck, regarding the critical decisions and pivots that shape a startup's journey.We will explore the dynamic world startup leaders navigate daily and take a closer look at the challenges faced by companies as they brave new markets. We'll also focus on the relevance of sales and venture capital savvy in the Canadian startup scene.From discussing the emotional rollercoaster of passionate leadership to the cutthroat venture capital markets, we tackle the nuances of growth, value alignment, and the crucial need for personal growth outside one's comfort zone. Get ready to aprehend valuable lessons from a resilient startup CEO! And don't forget to subscribe for more insightful episodes like this.----------Chapters:00:00 - 8:50 How to face challenging times while building a startup09:00 - 18:00 Honest journey, relationship building, finance automation.18:33 - 30:00 Adaptation is vital for business survival.30:09 - 45:00 Raising venture capital fuels growth.46:20 - 48:00 Challenges drive success, belief in ethical 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/

Welcome back to the Startup CEO Show, where we delve into the minds and experiences of successful startup leaders! In today's episode, we're joined by Aydin Mirzaee, CEO of Fellow.app, a company on a mission to make meetings more productive. Tune in as Aydin shares his journey from bootstrapping his first startup to a stellar exit, and the shifts in his entrepreneurial approach since diving into the world of venture capital. Our host, Mark MacLeod, explores practical tips from Aydin on schedule management, energy audits, and embracing the unconventional. For an insightful blend of big-picture dreaming and operational tactics, this episode is a must-listen for every high-growth CEO out there! And don't forget to subscribe for more insightful episodes like this!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 back to the Startup CEO Show! In this episode, we're diving into the inspiring journey of Kyle Braatz, founder and CEO of Fullscript. From competitive hockey to shaking up the healthcare industry, Kyle's path exemplifies the crossover between sports and entrepreneurship, highlighting the power of teamwork and competitive spirit.We'll uncover the inner workings of building a billion-dollar company, Fullscript, which is revolutionizing whole person medicine by championing natural alternatives. Kyle shares the strategic choices that set Fullscript apart – shunning venture capital, focusing on a niche market, and prioritizing capital efficiency and organic growth.Stay tuned as we skate through the highs and lows of startup growth, strategic investment decisions, and the qualities of empathetic leadership with Kyle Braatz. Whether you're a budding entrepreneur or an established CEO, you won't want to miss the wisdom Kyle drops on this episode of the Startup CEO Show.Don't forget to subscribe for more insightful episodes like this.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/

How do you transform doubt into focus and determination? Janet speaks to us about her career journey from Procter and Gamble to Staircase Ventures, being a competitive long distance runner, and maintaining focus and determination when people say “it cannot be done!” Janet Bannister is the Founder and Managing Partner of Staircase Ventures. In 2004, Janet launched Kijiji.ca and grew it to become one of the most visited websites in Canada. Before Kijii, Janet spent four years at eBay in Silicon Valley where she helped transform eBay from a Collectibles to a mainstream marketplace. She started her career as a Brand Manager at Procter & Gamble and then joined McKinsey & Co. where she was an Engagement Manager. She also founded and built a successful consulting business and was CEO at a venture-backed start-up prior to joining Real Ventures. Janet has won numerous awards and recognition including Venture Capital Journal's 2021 “Women of Influence in Private Markets”, Pitchbooks' 2021 “Female Founders & Investors to Know”, and American Bankers' 2019 “Most Influential Women in Payments”.

In this new episode, our host Mark MacLeod sits down with Robbie Bent, the visionary co-founder and CEO of Othership, a transformative space that combines sauna, ice baths, breathwork, sound, and community to redefine wellness in urban settings. Bent's innovative approach to tackling loneliness and fostering genuine connections in major cities through unique physical experiences is nothing short of revolutionary.Robbie Bent's story is not your average entrepreneurial tale. With a background marked by personal challenges, including a battle with substance abuse, Bent's mission with Othership is deeply personal. His commitment to creating a healthy, inclusive space where individuals can meet, heal, and grow together is the foundation of Othership's rapid growth trajectory. Bent's insights into the power of community, health, and wellness as tools for transformation are both inspiring and instructive.Don't forget to subscribe for more insightful episodes like this.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/

We're thrilled to bring you an insightful conversation with Mark Ang, the co-founder and CEO of Gobolt, a revolutionary logistics company transforming the way we think about delivery and sustainability. Mark's journey from a university side hustle to leading a major player in the logistics industry is nothing short of inspiring.Mark was recognized on the Forbes 30 Under 30 list, and he shares his unique perspective on scaling a business, the importance of sustainability in logistics, and the challenges of navigating the startup world. Gobolt, initially a summer storage solution for students, has evolved into a sustainable logistics powerhouse under Mark's leadership, emphasizing the critical role of adaptability and vision in entrepreneurship.Don't forget to subscribe for more insightful episodes like this.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/