Podcasts about real ventures

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/

In this new episode of “Startup CEO Show,” we talk with Jordan Boesch, the dynamic co-founder and CEO of 7shifts, a comprehensive HR and team management platform tailored for the hospitality industry. Dive into the world of startup growth, leadership transitions, and the undeniable impact of user feedback on product development.Jordan Boesch's journey from a passionate developer to a visionary CEO is nothing short of inspiring. Hailing from Saskatoon, Jordan has scaled 7shifts from a nascent startup to a powerhouse with over 400 employees, all while maintaining a deep connection to product development and customer satisfaction. His unique approach to leadership, coupled with a relentless pursuit of excellence, makes this episode a must-watch for aspiring entrepreneurs and seasoned executives alike.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/___________________Connect with Jordan:https://www.linkedin.com/in/jordan-boesch/https://www.7shifts.com/Setting the table: https://www.amazon.ca/Setting-Table-Transforming-Hospitality-Business/dp/0060742755/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=1706900857&sr=1-1

Welcome to the Startup CEO Show, where we delve into the strategies and insights of successful entrepreneurs. In this episode, our host Mark MacLeod sits down with Ben Jabbawy, the mastermind behind Privy's remarkable journey to a $120 million exit. Ben Jabbawy is the co-founder and former CEO of Privy, a marketing automation platform that scaled phenomenally within the Shopify ecosystem. Starting from his parents' house, Ben grew Privy to 80 employees and $10 million in ARR, culminating in a $120 million exit in 2021. His insightful approach to market timing, distribution strategies, and capital efficiency has set a benchmark in the SaaS industry. Ben is now an active investor, sharing his wealth of experience with emerging entrepreneurs.Don't forget to subscribe for more insightful episodes like this. Drop your thoughts and questions in the comments below!Join the leading newsletter designed exclusively for the CEOs of high-growth startups and the VCs who back them.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 latest episode of the Start Up CEO Show, we dive deep into the dynamic world of startups, revealing the secrets behind successful entrepreneurship and innovative business strategies. Join us as we examine the intricate balance between risk and innovation, a critical aspect for any aspiring entrepreneur or business enthusiast.Our guest, Kirk Simpson, is a renowned figure in the startup ecosystem. With a career rich in entrepreneurial ventures, Kirk has navigated the challenging waters of the business world, transforming obstacles into opportunities for success. His journey is not just inspiring but also packed with valuable lessons for anyone looking to make their mark in the business world. In this episode, Kirk shares his insights on managing risks, fostering innovation, and the mindset needed to excel in the constantly evolving business environment.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/

Brenden Kumarasamy is the founder of MasterTalk, a YouTube channel dedicated to helping people improve their communication and public speaking skills. With a background in venture capital at Real Ventures and as an Associate Consultant at IBM, Brenden has helped many startups raise capital and navigate HR transformations in industries like telecommunications, construction, and steel manufacturing. As an experienced speaker and facilitator, Brenden emphasizes the importance of inspiring and captivating audiences when it comes to communication. He offers insights into presentation skills, storytelling, and what sets the best speakers apart from the rest. Tune in to hear more about mastering the art of communication with Brenden Kumarasamy.

GoodJob, the #1 pre-hire assessment software available in the marketplace today, announced a partnership with Merge, the Unified API for B2B integrations. As a result of this partnership, GoodJob's software now supports integrations with over 50 popular Applicant Tracking Systems (ATS), including Workday, SmartRecruiters, Lever and Greenhouse.  Recruiters, HR teams and business leaders can use GoodJob's software within their current ATS, allowing them to hire confidently and retain high-performing candidates. https://hrtechfeed.com/goodjob-partners-with-merge-to-integrate-with-over-50-applicant-tracking-systems-ats/ DALLAS — HireLogic, an artificial intelligence (AI) enabled hiring interview intelligence solution, today announced a $6M series A funding round led by Joseph P. Landy, former Partner and Co-Chief Executive Officer of Warburg Pincus. Existing investors from HireLogic's seed round also participated, bringing total funding raised to over $10M. This investment will be used to advance the capabilities of HireLogic's conversational analytics platform, expand go to market activities, and meet the demands of the firm's growing customer base. https://hrtechfeed.com/hirelogic-secures-6m-series-a-funding/ ATLANTA — LaborWorx, a tech-enabled staffing startup that helps construction and manufacturing companies connect with on-demand workers, has raised $4.2 million to continue its mission of solving the skilled worker shortage. https://hrtechfeed.com/laborworx-raises-4-2-million-for-skilled-worker-recruiting-platform/ CANADA - talent assessment platform Plum today announced details of its $6 million USD round of growth funding. Led by Pearson Ventures, other new investors include JFF Ventures and Strada Education Network. Existing investors Export Development Canada (EDC), Real Ventures, BDC Capital's Women in Technology Venture Fund, EduLab Capital Partners, and Impact Engine also participated. https://hrtechfeed.com/plum-raises-6-million-for-talent-assessment-platform/ ZipRecruiter® announced financial results for the quarter and full year ended December 31, 2022. Quarterly revenue $210.5 million, down 4% y/y Full-year revenue $904.6 million, up 22% y/y – fast approaching the billion dollar mark https://www.jobboardsecrets.com/2023/02/22/ziprecruiter-announces-fourth-quarter-and-full-year-2022-results/

Being an investor in the early stages of companies has a lot of responsibility. You know the money you are putting in is a vote of confidence, but your role is even more important, you become a sounding board, a mentor, and in the best cases, a friend to the founder. Our guest today is Sam Haffar, Partner at Real Ventures, and he knows this road very well.This was a great chat and it was wonderful to hear Sam's perspective on investing and the markets.And we also have reactions to the week's news with John Ruffolo.About Sam Haffar:Sam Haffar is Partner at Real Ventures, where he works with founders on all aspects of their business from organizational development and product strategy to series A fundraising, growth, and scale initiatives.He began in the Silicon Valley startup world barely before he graduated from university and then joined the founding team at Chegg, a leading education technology company that went public in 2013.In this episode we discuss:(0:00:56)  News roundup with John Ruffolo talks Thoma Bravo acquiring Magnet Forensics, preventing hollowing out Canada, ChatGPT's threat to white collar workers, and activist investors(0:19:03)  Sam Haffar's journey to becoming an investor(0:22:39)  Where Sam gets his drive(0:25:21)  On becoming an extrovert(0:27:57)  How Sam came to the Canadian tech scene(0:32:14)  Coping with imposter syndrome as an early investor(0:36:14)  Processing the emotional rollercoaster of being an early-stage investor(0:43:10)  Staying grounded when things may look a bit too rosy(0:48:57)  How founders can deal with adversity(0:52:00)  Backing founders super early(0:54:43)  Work-life balance with young kids at home(0:57:56)  What keeps Sam passionate about this space(1:01:07)  His vision as a content creator in the space(1:04:18)  Content creators he admires(1:06:23)  How he supports his portfolio as they growFast Favorites:*

Episode 87 is with Hamzah Nassif, Parnter at Real Ventures! Real Ventures is an early-stage venture firm focused on serving daring entrepreneurs with the ambition to create successful, global companies. Since 2007, Real Ventures has dedicated itself to building the Canadian startup ecosystem on the belief that people, not money, build game-changing companies. Real Ventures manages $325 million across five funds and its active portfolio of 100+ companies is currently valued at $10 billion. An engineer first and investor second, Hamzah began his career working on Qualcomm's first-generation multiprocessor chipsets in Boulder, Colorado. After 9 years of engineering study and work in the US, he moved halfway across the world to work with startups in the frontier and emerging markets of the Middle East. We talk to Hamzah about his career journey thus far, from engineer to Partner. He details the Investment thesis of Real ventures, the day to day of a partner and board member, the importance and role of the board, and much more. Real Ventures https://realventures.com/ Timestamps 2:20 - Intro 12:50 - Defining Product-Market Fit 14:50 - It's Ok To Be Wrong 17:30 - Convertible Notes & SAFEs - Pros & Cons 25:25 - Advice for Founders to Protect Themselves Financially 26:50 - How to Run a Tight Fundraising Process 28:00 - Why Do Boards Members Exist? 33:38 - Providing Feedback as a Board Member 35:50 - Guidelines for Board Members 38:10 - Day to Day of a Partner at Real Ventures 42:00 - Real Ventures 48:00 - Future Trends of A.I. 53:00 - Risks of Consolidated Power in Tech Companies 57:00 - Lightning Round