Strategic Business Consulting for Regulated and Growth-Focused Companies
Strengthen Strategy, streamline operations & improve financial performance
Strategic Business Consulting for Regulated and Growth-Focused Companies
Strengthen Strategy, streamline operations & improve financial performance
Legitimus Enterprises is a strategic consulting firm founded in April 2024 by Matt Gilson, a strategic business leader with over eight years of experience driving growth, profitability, and operational excellence across the cannabis and financial industries. Legitimus empowers businesses and entrepreneurs by providing strategic guidance and services to succeed in dynamic and competitive environments. Our approach ensures our clients capitalize on opportunities, minimize risk, and drive sustainable growth with confidence.
As Founder of Legitimus and Co-Owner of Ski Shoppe Premium Cannabis, I bring an entrepreneurial mindset and hands-on leadership to help organizations strengthen their operations and grow their bottom line. During my career I've led strategic initiatives and portfolio operations for venture-backed companies, built scalable systems, and guided startups from concept to commercialization.
At Upstate Elevator Supply Co., a national Vermont-based wellness brand, I spearheaded the development of the first 100% Organic CBD capsules to enter the U.S. market in December 2019. Later in March 2023, I co-founded Inicio Capital, a cannabis investment fund that provides structured exposure to the fast-growing, complex and highly regulated industry.
Before launching my own ventures, I served as Director of Business Development for Kria Botanicals, a GMP certified extraction and formulation lab. I also served as Director of Cannabis Operations for Numerous Enterprises, a venture capital firm that oversees portfolio operations in California, Maine and Vermont.
My background gives me a unique edge: I understand regulated, complex, product-based businesses that need both operational structure and strategic clarity. With roots in the cannabis industry, one of the most regulated and complex markets in the world, I bring a systems-based approach that extends beyond cannabis to eCommerce & Direct-to-Consumer (DTC) brands, Consumer Packaged Goods (CPG) companies, financial services, and other growth-focused companies.
Help develop product lines, brand identity, and marketing approaches that align with consumer demand and regulations.
Identify new revenue opportunities, partnerships, and competitive positioning within emerging markets.
Provide Fractional COO / VP of Operations support, build leadership capacity and manage cross-functional initiatives.
Build financial models, forecasting, and pricing strategies to ensure sustainable growth.
Help investors, funds, and holding companies evaluate and manage assets.
Streamline end-to-end supply chain to improve efficiency, reduce costs, and increase profitability.
Guide businesses through local and state compliance laws, licensing applications, and ongoing compliance management.
Create and implement standardized operating procedures that ensure consistency, safety, and compliance.
Define mission, vision and values, indentify growth strategies, conduct market and competative analysis, and business model optimization.
Adult-use & medical multi-state operations, regulatory compliance, brand development, contract manufacturing, portfolio management, and vertical integration strategies.
eCommerce & Direct-to-Consumer (DTC) brands, Consumer Packaged Goods (CPG) companies, financial services, and other growth-focused companies.
Exercising Leadership: Foundational Principles
Foundations of Venture Capital
Core Concepts in Project Management
Certified Quality Improvement Associate (CQIA)
Process Improvement & Quality Fundamentals
Bachelor of Arts: Political Science, Sociology & Business Administration
United Kingdom Bilateral Exchange Program: School of Geography, Politics & Sociology
