Direct Investment

Greenleaf maintains a network of relationships with other investment funds, brokers, lenders, business owners and professional advisors like lawyers and accountants. We leverage our professional network to open doors and create opportunities for entrepreneurs. Though we approach transactions with a corporate development mentality, we are flexible in the type of investment we will consider.

Our business partners are refreshed by Greenleaf’s creativity and flexibility when structuring transactions. Some firms approach private equity according to their Golden Rule – the one with the gold makes the rule. We know we will be a business partner and our relationship must continue beyond closing. Greenleaf works to create a transaction structure that promotes fairness and an opportunity for all parties to participate in future value creation.

Investment Criteria

Market Focus:
Lower middle market companies with $1 million – $50 million in revenue.

Transaction Type:
Typically minority equity investments in the form of common or preferred stock, and/or convertible notes. Will consider mezzanine debt and other structures on an opportunistic basis. Greenleaf will take controlling equity interests in certain situations, particularly in the Testing, Inspection and Certification (TIC) industry.

Industry Focus:
Greenleaf will consider all opportunities, with a preference for companies within the TIC industry.

Greenleaf considers TIC opportunities on a nationwide basis. For non-TIC opportunities, we have a preference for Midwest-based companies.

Within the TIC industry, Greenleaf provides owners flexibility to continue, exit, or reduce their workload. For non-TIC opportunities, Greenleaf seeks to partner with passionate, proficient managers who intend to continue after closing.

Investment Structure

Greenleaf’s investments take the form of equity, convertible notes, or preferred stock. The firm will consider full sales, controlling interests, and minority investments. We have a preference for established businesses but have invested in start-ups and early stage ventures.

Greenleaf primarily targets investments in the Testing, Inspection, and Certification industry. TIC sub-industries include elevator inspection, boiler inspection, HVAC testing, fire suppression inspection, and other building inspections. In the past, Greenleaf has pursued additional TIC opportunities including underground mapping or pipeline & sewer inspections.