In 2024, Sean Smith walked away from investment banking and entrepreneurship to head straight into a world most professionals overlook: buying “boring” businesses instead of starting flashy ones.
Sean launched an investment fund to back acquisition entrepreneurs across North America, specifically those buying small and medium-sized businesses generating stable cash flow in unglamorous sectors like HVAC, commercial cleaning, and business services.
This conversation unpacks how ambitious professionals can become CEOs without climbing corporate ladders or risking everything on a startup, how to raise millions to acquire a business, and why Baby Boomer retirements are creating a trillion-dollar transfer of ownership that most people aren’t paying attention to yet.
Sean explains:
- Entrepreneurship through acquisition (ETA) versus traditional career paths
- Funded search vs. self-funded search: Pros, cons, and realities
- Raising and structuring capital for acquisitions
- Key criteria for investors
- What makes a business a strong buy
- Major lessons from Stanford research on what causes deals to fail
You’ll learn:
- Why buying a business can be less risky than starting one from scratch
- The two main models in entrepreneurship through acquisition: funded search vs. self-funded search
- How to evaluate whether you’re a fit to run a specific business
- What investors look for when backing acquisition entrepreneurs
Guest Background
Sean Smith is the Managing Partner at Search Fund Ventures and founder of the SMB Investor Network. He started his career in leveraged finance at CIBC Capital Markets, supporting over $11 billion in transactions including the Canada Goose IPO. Sean launched Search Fund Ventures in August 2024. The fund backs acquisition entrepreneurs buying small and medium-sized businesses across North America, focusing on mission-critical, cash-flowing companies in sectors like business services, healthcare support, and essential infrastructure.
Connect with Sean Smith on LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
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Additional Resources
Sean’s Fund https://www.searchfundventures.co/
Co-Investment Opportunities https://www.smbinvestornetwork.com/
Buy Then Build by Walker Deibel https://buythenbuild.com/
ETA Community https://searchfunder.com/
Scaling Up by Verne Harnish https://scalingup.com/
EOS (Entrepreneurial Operating System) https://www.eosworldwide.com/
About Business Unbound
Every week, your host, Florian Haufe, dives deep into conversations with visionary global leaders to bring you insights, inspiration, and the real stories behind success.
