Outsourced CFO’s (OCFO) Founders Conference brought South African founders together to explore the shift from hustle-led entrepreneurship to structured, scalable growth. Through practical insights on systems, technology, capital, and risk, the event highlighted how intentional frameworks enable sustainable, resilient businesses.
-- Outsourced CFO’s (OCFO) Founders Conference, held on 27 November 2025 at The Cape Town Club, brought together founders, executives, and advisors for an evening of practical insight, peer discussion, and shared experience. Hosted in partnership with The Cape Town Club, Zoho, Bridgement, and Thirst, the event combined thought-provoking conversations with a guided whiskey tasting and blending session, creating a relaxed setting for meaningful engagement.
The event forms part of OCFO’s annual programme aimed at supporting founders navigating the next phase of their business journey. As companies grow, the challenges founders face shift from starting and surviving to structuring and sustaining. OCFO co-founder Louw Barnardt noted that helping entrepreneurs recognise and prepare for this transition was a key focus of the evening’s discussions.
“Most founders do not fail because they lack ambition or work ethic,” said Barnardt. “They struggle because the business outgrows the way it is being run. Founders Conference was about giving entrepreneurs the thinking tools and frameworks they need to build companies that scale without chaos.”
The evening’s keynote sessions reflected this theme by focusing on practical systems, modern technology, and smarter decision-making rather than motivational rhetoric.
Dillon Jearey, entrepreneurial coach and certified Bloom Growth facilitator, opened with a keynote on moving beyond founder-driven hustle. He unpacked the frustrations that emerge when businesses grow without a clear operating framework, including declining profitability, bottlenecks, and constant overwhelm. Jearey emphasized that these challenges are structural rather than personal and demonstrated how implementing a Business Operating System can create alignment, accountability, and momentum across leadership teams.
Technology and artificial intelligence featured prominently as tools for leverage rather than disruption. Purpose-led entrepreneur Mosa Nyamande challenged founders to rethink AI not as a replacement for human intelligence but as an amplifier of it. Drawing on familiar cultural references, he encouraged entrepreneurs to “augment themselves” by using AI to extend their decision-making and execution capacity.
That theme was reinforced by digital advertising strategist Denzel Masuku, who explored how data-driven and AI-powered advertising is reshaping customer acquisition in South Africa. His session highlighted the importance of intent, trust, and full-funnel thinking in an environment where ad costs are rising and competition is intensifying. Masuku offered founders a practical roadmap for using automation and data to drive sustainable, predictable growth rather than short-term spikes.
Risk and governance formed another key pillar of the evening. Jessica Spira addressed the misconception that investors care only about rapid growth, arguing instead that sustainable scale depends on sound controls and a mature approach to risk. Through a real-world cyber breach case study, she illustrated how thoughtful risk architecture, including appropriate insurance, protects continuity and credibility while strengthening investor confidence.
Capital strategy was explored further during a panel discussion featuring representatives from Bridgement and Launch Africa, alongside OCFO leadership. The panel reframed funding as a strategic toolbox rather than a binary choice between debt and equity. Speakers addressed common misconceptions, including the belief that debt signals distress or always requires collateral, and emphasized the importance of matching the right type of capital to specific business needs.
“Equity is flexible, but it is permanently expensive,” said Barnardt during the discussion. “Debt, when used correctly, preserves ownership and accelerates growth. The strongest companies are intentional about their capital stack and disciplined about how and when they raise.”
Beyond the content, Founders Conference was intentionally designed as an experience. Hosted at the historic Cape Town Club, the evening included a guided whiskey tasting and blending session that encouraged informal discussion and connection among attendees.
For Barnardt, the success of Founders Conference lies not only in attendance but in the quality of conversations it sparked. “Founders Conference was created as an annual touchpoint for founders who are serious about building businesses that last,” said Barnardt. “Each year, we focus on the real challenges entrepreneurs are facing as they scale, and bring practical insight that helps them move forward with clarity. Founders need spaces where they can step back from the noise, think clearly about their businesses, and learn from peers who are facing similar challenges,” he said. “What we saw again at Founders Conference this year was a community of entrepreneurs ready to build with intention, structure, and long-term thinking.”
As South Africa’s founder ecosystem continues to mature, OCFO’s Founders Conference reflected a growing emphasis on clarity, structure, and well-defined systems. It points to a broader move toward building businesses designed for long-term, resilient growth.
For more information about Outsourced CFO, or to speak to one of the team, please visit www.ocfo.com.
About the company: Outsourced CFO is a global financial advisory firm supporting more than 1,300 organisations across over 25 industries. From its roots in South Africa, the company has expanded internationally and now boasts a presence in Cape Town, London, and New York. Outsourced CFO provides a complete suite of services including outsourced CFO support, accounting, compliance, strategic financial guidance, and talent placement. By combining deep financial expertise with modern technology, the firm helps entrepreneurs and high-growth companies gain clarity, raise capital, and build sustainable businesses.
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