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May 2025
20m 43s

From Law School to Garbage Trucks: How A...

IBH Media
About this episode

Alfonso Guerreri, A Harvard-educated lawyer turned hands-on entrepreneur, founded RICI Contracting in 2022 and has since grown it into a full-service powerhouse. Today, RICI delivers construction, asphalt paving, snow & property maintenance, waste management, and facility services across Ontario. Alfonso shares how he parlayed legal training into strategic vision, weathered early food-truck misfires, and now innovates a once-old-school industry with sustainability, operational excellence, and client-first focus.

Key Discussion Points:

Law Meets Hard Hats: How a top-tier legal education taught Alfonso discipline, risk assessment, and negotiation skills he now applies to multimillion-dollar contracting bids.

Early Failures to Firm Foundations: The food-truck chapter that taught him to test market fit, manage debt serviceability, and pivot swiftly into construction.

Building RICI’s Service Portfolio: The step-by-step playbook for adding roll-off trucks, portable toilets, paving rigs, and snow-plow fleets—each driven by recurring revenue needs.

Ideally Niche Clients: Why focusing on property managers, REITs, and pension-fund portfolios ensures monthly billing reliability and repeat business.

Innovation & Sustainability: How Alfonso is modernizing a legacy sector through advanced equipment, AI-powered fleet surveillance, and eco-minded operational upgrades.

Scaling with Discipline: His criteria for debt-financed expansion, in-house versus subcontractor work, and turning low-risk jobs into entry points for higher-ticket contracts.

Key Takeaways:

  • Strategic Pivoting: Embrace early failures as fast-feedback loops that uncover scalable opportunities.
  • Debt Serviceability Test: Only invest in capital assets when your recurring cash-flows can safely cover the payments.
  • Client Lifetime Value: Lock in high-margin, recurring services for the same ideal customers rather than chasing one-off gigs.
  • Operational Excellence: Leverage technology, standardize processes, and build sustainability into every service offering.


Closing Thoughts:

 Alfonso Guerreri’s journey from articling desks to asphalt crews illustrates that true entrepreneurial grit lies in mastering finance-savvy expansion and relentless client focus. Tune in to discover how RICI Contracting is redefining Canadian facility services—one strategically financed roll-off bin at a time.



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