Sean Smith is the Managing Partner at Search Fund Ventures, a firm dedicated to backing acquisition entrepreneurs and independent sponsors. In this role, he oversees the deployment of capital into “mission-critical” small and medium-sized businesses while mentoring searchers through the complexities of buying and operating companies.
Background
Sean’s career began in the high-stakes world of investment banking in New York City. After graduating from university, he joined CIBC Capital Markets in their Leveraged Finance and Debt Capital Markets group. During his tenure from 2016 to 2018, he gained rigorous transactional experience, supporting over $11 billion in deal volume, including high-profile transactions such as the Canada Goose IPO. This period honed his ability to analyze complex capital structures and understand the financial levers that drive enterprise value.
Seeking a more hands-on entrepreneurial challenge, Sean left banking to co-found Tangerine House, a co-living community for creatives based in Brooklyn. As Chief Operating Officer, he bootstrapped the business, managing everything from property leasing to brand partnerships with major companies like Jägermeister. His leadership helped scale the venture to a successful exit in 2019, when it was acquired by Treble. This experience gave him a visceral understanding of the risks founders face, particularly the psychological weight of personal guarantees and operational accountability.
Following his exit, Sean joined Applico, a strategic advisory and investment firm, where he advanced from Associate to Vice President. There, he played a pivotal role in building the firm’s buy-side M&A practice, advising large enterprises on acquiring platform businesses and supporting the firm’s venture capital investments. His time at Applico bridged the gap between his institutional finance background and his entrepreneurial operator skillset, eventually leading him to identify a significant opportunity in the “Entrepreneurship through Acquisition” (ETA) space. In August 2024, he launched Search Fund Ventures to bridge the capital gap for searchers looking to acquire enduring small businesses.
Core Expertise
Sean is a specialist in Entrepreneurship through Acquisition (ETA), with a specific focus on the “self-funded” search model. He is known for his disciplined investment philosophy that favors “boring,” recession-resistant businesses over flashy startups. His expertise lies in identifying companies with mission-critical service offering, such as commercial cleaning or HVAC, that possess recurring revenue and low customer concentration.
Beyond deal sourcing, Sean provides deep value in the due diligence phase, particularly in “vetting the buyer.” He argues that while financial diligence is a science, assessing a potential CEO’s emotional resilience and discipline is an art. He advises searchers on structuring deals that align incentives without creating excessive fragility, often cautioning against capital structures that leave no room for error. His approach combines the rigor of institutional finance with the empathy of a former operator who has lived through the stresses of meeting payroll and managing growth.
Academia
Sean holds a Bachelor of Arts in Economics and Political Science from New York University. His time at NYU provided the theoretical foundation for his future career in finance, placing him at the center of the global financial hub and facilitating his entry into top-tier investment banking.
He is also a proponent of continuous professional education, citing the importance of frameworks like EOS (Entrepreneurial Operating System) for small business management. While he does not hold an MBA, his career trajectory exemplifies the “apprenticeship” model of high finance and entrepreneurship, learning directly from deal execution and business operations rather than solely through classroom theory.
Key Perspectives that Sean Shares on the Podcast
Sean challenges the conventional wisdom that entrepreneurship requires a “zero-to-one” invention of a new product. He argues that buying an existing, profitable business is a viable and often superior path for ambitious professionals. He highlights that the “career risk” of searching for a business is often overstated; even searchers who fail to close a deal typically land high-caliber roles in private equity or consulting, having gained a “mini-MBA” in real-world dealmaking during their search.
A recurring theme in his conversation is the double-edged sword of personal guarantees. Sean offers a nuanced view, noting that while personal liability creates powerful discipline for a new CEO, it can also create divergent incentives between the operator and their investors when a business faces headwinds. He advises searchers to be deeply self-aware about their risk tolerance and to match their search criteria, specifically the size and complexity of the target business, to their actual management experience rather than just their financial ambition.
A Quote from this Conversation with Sean:
“You can become an entrepreneur, you can become a CEO of a business without needing to start it or without rising up the ranks in an organization.”
