Steve O'Leary and the Machinery of Money

The assignment was to close the thing down. Early in his career at Shawmut Bank, Steve O'Leary sat in the asset-based lending group and was handed an equipment-leasing business marked for retreat. Then the portfolio committed a small act of insubordination: it performed. Credit losses stayed low. Gains appeared at the back end. In 1992, management asked O'Leary for a plan to return to the business it had asked him to leave.

“It was purely accidental,” he later said of his route into equipment finance. Accident, however, is only the opening scene. What followed required method. By the time Fleet acquired Shawmut in 1995, the portfolio had grown to roughly $400 million and was lending to middle-market companies across the country. A shutdown assignment had become a specialty, and the specialty became a career.

Equipment finance lives in the unglamorous, indispensable layer of business. It pays for the machine that cuts a component, the truck that reaches a worksite, the server that carries a service and the imaging system that opens a facility. The money matters because the object matters. A lender has to understand the borrower, the asset and the awkward possibility that one day the two may part company.

Build, sell, gather, repeat

O'Leary began at Shawmut in 1982, moved through Fleet Capital Leasing and AT&T Capital, then founded Eastern Capital, Eastern Bank's middle-market leasing subsidiary. Over eight years, that team grew its portfolio to nearly $200 million in net assets. The pattern was taking shape: enter a specialized corner, assemble people who can read both risk and machinery, and build enough operating discipline that the platform can survive scrutiny.

In June 2010, he joined NewStar Financial to establish an equipment-finance and leasing business for leveraged middle-market borrowers, with particular attention to private equity-owned companies. It was a combination of two dialects. Equipment lenders spoke about useful life, residual value and collateral. Leveraged-finance teams spoke about cash flow, capital structures and sponsors. O'Leary's platform needed fluency in both.

NewStar sold the equipment-finance business and related assets to Radius Bank in 2016 for approximately $140 million. The platform's net receivables were about $133 million. The sale closed one chapter without dissolving the relationships behind it. When former NewStar chief executive Tim Conway began discussing a new company with O'Leary, the idea was not to invent a team from introductions and résumés. It was to bring experienced colleagues back into the same room.

Clarus Capital launched in 2021 with O'Leary as chief executive, Conway as chairman and Michael Eisenstein as chief financial officer. BharCap Partners supplied a $300 million capital commitment. The firm opened its doors that August in Boston, focusing on tangible assets for leveraged middle-market and larger corporate borrowers. Many of the people joining had already worked with O'Leary. Trust arrived before the org chart.

A loan secured by something with a job

Clarus does not sell romance. It finances essential assets, usually in transactions large enough to need customization and small enough to reward attention. Its borrowers may be manufacturers, transportation operators, infrastructure-service companies or technology businesses. The common question is practical: which equipment allows this company to keep earning, expanding or releasing cash already tied up in assets?

That question became more valuable as banks reconsidered their appetite. In a 2024 industry roundtable, O'Leary described lenders facing tighter loan-to-deposit and capital constraints. Banks were reserving equipment loans for customers with broad relationships and accepting less leverage from new credits. The result, in his account, was a gap around asset-based lending and sponsor-finance customers. Independent lenders could step into it, provided they had durable funding of their own.

The new firm also had one modern luxury: no inherited technology stack. O'Leary said Clarus could design integrated systems without dragging old conversions or migrations behind it. By 2026, his boundary had become sharper. Clarus used technology to improve accounting, documentation and reporting. It used AI for research. It did not use AI to make credit decisions.

The distinction fits his career. A machine can arrange information about another machine. It cannot own the consequences of a weak structure or an overconfident forecast. Clarus's work with private equity-backed companies requires its team to deconstruct cash flows, test the durability of a business model and decide what leverage it can carry. Software can shorten the path to judgment. It cannot sign its name underneath it.

The billion, and what came after it

Clarus's numbers began to show the architecture. In late 2024, the firm closed its inaugural asset-backed securitization. Investors submitted more than $1 billion of orders, and the transaction gave the business long-term, fixed-rate funding against a portfolio of equipment loans and leases. For a lender whose assets typically carry fixed rates over several years, matching the funding matters. Otherwise, rising floating-rate costs can squeeze the margin between what a borrower pays and what the lender owes.

In April 2026, Clarus announced that it had passed $1 billion in total capital invested. The firm had financed companies backed by more than 40 private equity funds across manufacturing, technology, distribution, logistics and service industries. O'Leary called the figure evidence of the team's strength and of continuing demand for large-ticket equipment financing. He framed the strategy more plainly: be reliable and execution-focused.

Two months later came CLARUS 2026-1, a second securitization backed by more than $332 million of commercial equipment leases and loans. Combined issuance across the two transactions moved above $600 million. Wells Fargo Securities returned as structuring agent and bookrunner, with Bank of America Securities joining as co-manager.

The sequence matters more than any single announcement. Build a portfolio. Finance it for the long term. Broaden the investor base. Return to the market. In lending, growth cannot be separated from the quality of yesterday's decisions. Every triumphant closing becomes an asset that must keep behaving after the press release has disappeared.

Old colleagues, young talent

There is another portfolio O'Leary talks about: people. Clarus mixes equipment-finance professionals with leveraged-finance professionals, roughly half from each discipline. Its flat structure exposes younger employees to multiple parts of the business. The executive team, he has said, wants to build from within while continuing to hire at entry level.

This is more than pleasant corporate language. Specialty finance accumulates knowledge slowly. Someone has to learn why a dispersed pool of service equipment behaves differently from a single production line, why a sponsor's incentives matter, and which documentation detail will become urgent only when a borrower misses its plan. Mentorship is a transfer of pattern recognition. The flatter the organization, the shorter the distance that knowledge has to travel.

O'Leary's own education began with accounting at American International College, where he also played varsity baseball. The public outline of his career after graduation is institutional - banks, portfolios, acquisitions, capital commitments. Yet its recurring unit is the team. The majority of Clarus employees had worked with him before. At NewStar, Conway identified culture as the first condition for building the equipment-finance group. At Clarus, previous collaboration became an operating asset.

Patience is a form of speed

Asked what will separate independent equipment-finance firms over the next several years, O'Leary returned to consistency. Credit underwriting, repeated sponsor relationships and a patient approach to growth were his chosen differentiators. The answer is almost defiantly free of theatre. Money is the same color. Terms can be copied. A lender's behavior across a cycle is harder to imitate.

That is the useful idea hiding inside this specialized career. Patient growth does not mean idle growth. It means creating a system in which the next transaction improves the odds of the one after it. A careful close earns another call from a sponsor. A performing portfolio earns another audience with investors. A young analyst who sees the whole business becomes a more capable underwriter. Repetition becomes reputation.

O'Leary entered equipment finance because a business marked for closure refused to behave like a failure. Four decades later, he is still working with the same essential tension: assets age, markets turn, banks retreat and capital must decide where to stand. Clarus is his latest answer - a company built from institutional memory, financed for repeated use and measured by what keeps working.