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.

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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.

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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.

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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/

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!

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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 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.

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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 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/

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/

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, host Mark MacLeod sits down with Tyler Denk, co-founder and CEO of Beehiiv, to explore the world of email marketing and the creator economy. Tyler shares the fascinating origin story of Beehiiv, which grew out of his experience building custom tools at Morning Brew. He explains how Beehiiv has become a leading all-in-one platform for creators and brands to grow their audience and monetize their content.

Tyler dives deep into Beehiiv's unique value proposition, combining website building, email newsletters, and monetization tools in one seamless platform. He discusses how this integrated approach sets Beehiiv apart from legacy email providers and allows creators to focus on what they do best. The conversation touches on the evolving role of AI in content creation, with Tyler offering nuanced insights on when AI can be helpful and when human creativity is irreplaceable.

One of the most compelling parts of the discussion centers on Tyler's leadership philosophy and operational strategies. He shares his commitment to radical transparency, describing how he writes detailed weekly emails to keep his team aligned and motivated. Tyler also reveals how Beehiiv raised its Series A in just six days and its Series B in two weeks, crediting his practice of sending comprehensive monthly investor updates. For aspiring founders and CEOs, this episode is a masterclass in building a high-growth startup with intention and focus. Don't miss Tyler's contrarian views on company size and his emphasis on deep work - tune in now to gain invaluable insights from one of tech's rising stars.