How is AI changing the way technology companies are bought and sold?

Mario Di Pietro, Co-founder and Managing Director of Origin Merchant Partners, joins Mario Nigro to discuss how AI is reshaping Canadian technology M&A.

In this episode:

• How AI is influencing the valuation of technology companies

• Why buyers, sellers, investors, and advisors are reevaluating long-term growth prospects

• The continued strength of technology M&A activity in Canada

• Why buyers are approaching transactions more cautiously amid market uncertainty

• The opportunities AI could create for Canadian technology entrepreneurs

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Justin Joffe of Legate Partners joins us to share insights from his journey as an entrepreneur turned CEO coach, and what he believes makes a successful CEO. The discussion focuses on the challenges facing first-time business leaders, who must be able to balance big-picture thinking with detailed analysis, depending on the situation. While there is no one formula for success, Justin emphasizes the importance of being level-headed, highly organized and responsive to daily developments. Also important is the ability to concisely articulate the company’s vision and values to create a sense of direction across the organization. Finally, Justin recommends that searchers and other prospective acquirors/CEOs look past the spreadsheet to understand the type of commitment that running a particular type of business will entail.

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Anish Singla of Tequity Advisors, a sell-side tech M&A boutique focused on $20m-100m transactions, joins Mario Nigro for an insightful look at the state of tech M&A. After record activity in 2025, buyer concerns about AI disruption vulnerability are impacting certain tech sub-sectors, notably lightly-embedded point solution SaaS businesses. Anish notes that AI has moved rapidly to the forefront of diligence processes, with potential buyers seeking information in the early stages of the process. This trend currently favours tech products that are embedded in customer workflows with proprietary data. Overall, however, while Anish foresees a period of adjustment, he remains bullish on tech M&A over the next few years.

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Tyler Lang of HDL Capital, a Toronto-based M&A advisory firm, joins Mario Nigro to discuss the latest trends in lower midmarket deals. One notable shift is the lengthening of typical deal timelines to 4-6 months post-LOI, up from 2-4 months just a few years ago, driven by increased lender caution and reliance on quality of earnings reports. He also highlights a trend of sellers holding unrealistic valuation expectations based on outdated market reports and, increasingly, AI-generated analyses. Despite macroeconomic uncertainty, Tyler remains optimistic, citing strong private equity interest and the continuing wave of “baby-boomer” exits.

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Ugo Dionne, President of M&A Club Canada, joins Mario Nigro to discuss his organization’s role in Canada’s M&A ecosystem. He explains how the Club, with 20 chapters across Canada, brings together M&A service providers for monthly meetings at which they can share deal opportunities, discuss trends, and build trust-based networks. Recent “hot topics” at M&A Club sessions include the challenge of getting business owners to prepare for exits earlier and the impact of tariff, interest rate, and geopolitical uncertainty on Canadian dealmaking. Ugo also highlights the Club’s new Academy, offering training programs in partnership with McGill University, and plans for international expansion to New York, London, and Paris.

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In this episode, Eric Ries joins Mario Nigro to discuss his latest book, Incorruptible. The book’s thesis is that the business world’s focus on shareholder primacy and profit extraction is inconsistent with the interests of the businesses themselves. Because purpose-driven companies outperform extractive companies, buyers should diligence intangibles such as ethos, pricing restraint and employee loyalty – not just balance sheets. In Eric’s experience, sellers of purpose-driven businesses often prefer bidders that commit to maintaining their legacy over higher bids from extractive buyers.

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Joining Mario Nigro for this episode is Mackenzie Regent, co-founder of Kalos, a boutique transaction advisory firm providing financial due diligence and valuation for midmarket deals across North America. They discuss how global uncertainty is affecting midmarket deals, where resources for diligence deep-dives are often limited. According to Mackenzie, recent systemic shocks are interrupting deal flow, but generally only briefly, because advisors have become adept at structuring earnouts and other valuation bridges that blunt the impact of global uncertainty.

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Jeffrey McCain of Woodward Capital joins Mario Nigro to discuss his firm’s evolution from traditional self-funded search into a broader investing platform participating across the capital stack (including LP positions in institutional funds and equity-gap situations). Jeff describes Woodward’s focus on trades-based businesses. HVAC, in particular, is attractive in light of the industry’s inherent stability, the frequency of succession-driven founder sales, and the ability to compound value through operational improvements. Jeff also provides an overview of the slightly different focus of JSM Capital, a new family office, which targets majority investments in infrastructure services platforms in the $5-15 million EBITDA range with a long-term hold strategy.

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George Sabbouh of Stifel Financial joins Mario Nigro for an enlightening discussion on the state of the deal market in Canada. After an uneven “K-shaped” recovery in 2025, George is seeing strong momentum in certain sectors – metals and mining, business services, infrastructure services, and waste management – amid continuing buyer hesitancy in tariff-exposed sectors such as manufacturing. Broader market trends include increasing diligence around AI disruption risk, which is emerging as a major concern in the marketplace. Looking ahead, Sabbouh expects 2026 to strengthen with easing rates, an IPO rebound, significant dry powder, and alternative exit tools such as continuation vehicles and dividend recaps.

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Ezio Bondi of Bondi Produce & Specialty Foods joins Mario Nigro to discuss the M&A-driven growth of his Ontario-based food distribution business. Ezio highlights the roles that operational discipline, early adoption of technology, and a clear integration playbook have played in Bondi’s success. In a fragmented produce-distribution market, Bondi’s M&A strategy leverages its roots as a small family-owned business to address potential sellers’ legacy-protection concerns. Mario and Ezio also discuss Bondi’s decision to fund acquisitions directly from its balance sheet – a reflection of its philosophy of control and capital discipline. Ezio remains confident in the resilience of the produce sector and sees significant opportunity as older owner operators look to exit over the coming decade.

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