Carlos Cashman and the business of buying the ordinary

Carlos Cashman was helping other people build valuable businesses, and the arrangement was beginning to bother him. At OrionCKB, his advertising agency, clients grew on the strength of campaigns his team ran on Facebook and Instagram. Some reached valuations of $50 million or $100 million. The agency received its monthly check. A perfectly respectable outcome, unless you were the person wondering why you owned the advertising relationship and somebody else owned the upside.

Cashman had spent years moving between software, marketing and startups. He could recognise the arithmetic. If the team knew how to bring customers to a product, perhaps it could do more than invoice the product’s owner. Perhaps it could become the owner. “I’m always looking for that lever,” he said. The remark supplies a useful entrance to his career: curiosity, followed fairly quickly by a question about how the business works.

The company that followed, Thrasio, made that question unusually consequential. Founded in 2018 with Joshua Silberstein, it bought businesses selling through Amazon and put them under shared management. Mundane products became the raw material for an ambitious company. The ambition would eventually run into the considerable work of managing what it had bought.

An education with room to improvise

Cashman graduated from MIT in 1994 with a degree in information systems engineering. His course of study combined computer science with management and information technology work at the Sloan School. He attended on an AT&T scholarship. Even the degree suggests an appetite for the space between disciplines: enough engineering to understand the machinery, enough business to ask who might pay to use it.

There were other kinds of arithmetic, too. He spent time as a professional blackjack player and card counter with a team of former MIT alumni. He also worked on film projects in New York. A casino table, a film production and a software company make an untidy career plan. They make rather better material for someone who prefers learning by doing.

In his early New York job hunt, Cashman tried CompUSA, which would not even interview him. He then used a paper phone book to identify companies within walking distance of his apartment and delivered printed résumés. One small startup had secured office space by giving the building superintendent a case of whiskey. The route into technology was, in this instance, decidedly analogue.

The companies before the company

Thrasio arrived after several rounds of building and selling. Cashman founded Opus360, a professional services automation software company that went public on Nasdaq in 2000 and was sold to Artemis International in 2001. The internet’s early commercial years gave him experience of a company passing through very different forms of ownership. The founder’s job could change even when the name on the door stayed familiar.

CourseAdvisor came next in 2005. It used search engine marketing in post-secondary education and was sold to the Washington Post two years later. His other work included Asset Performance Technologies, which supplied data and analytics for heavy industrial equipment, and ConstellationCK, an internet marketing business. These were different markets, with different customers and different practical demands.

By 2011, a University of Nebraska-Lincoln law-school event was inviting him to discuss questions including shareholder-management tensions and corporate decision-making. Later, his entrepreneurial history would also bring him into Berkeley’s roster of past startup guest speakers. The useful experience extended beyond having an idea. He had encountered the arguments that begin when an idea acquires shareholders.

The agency that made ownership tempting

OrionCKB supplied a more immediate bridge to Thrasio. Founded in 2013, the Boston social advertising agency focused on customer acquisition and lead generation. Its clients included Bombas, M.Gemi, Publishers Clearing House and Thumbtack. This was a business concerned with what an advertisement persuaded someone to do, rather than simply whether they had seen it.

Elite SEM announced its acquisition of OrionCKB in November 2017. The announcement described an agency offering advertising strategy, optimisation and analysis, with early ties to performance advertising software company Nanigans. Cashman’s next venture would draw on that practical familiarity with the machinery of online demand.

There was a recurring problem among smaller brands. They had products people wanted but insufficient money to test and expand paid advertising. In Cashman’s account, the first acquisition idea focused on independent ecommerce sites. Then Amazon became more interesting. A collection of separate storefronts meant a collection of different technical systems. Amazon sellers already worked within a common marketplace. That gave the proposed buyer a more consistent starting point.

A spatula is allowed to remain a spatula

The appeal of the Amazon business was wonderfully unromantic. Cashman wanted products with continuing demand, rather than fashion items dependent on a designer or accessories threatened by the next phone redesign. A spatula was his example of something whose purpose endured. Investors might discuss disruption all afternoon; dinner still needed turning over.

The seller, meanwhile, could be facing a job that had expanded beyond one person’s capacity. Advertising, inventory, supply chains, creative work and legal obligations all needed attention. Thrasio’s proposition was to bring specialists together and spread their expertise across acquired brands. A business built by one or two people could become part of a larger operating organisation.

Cashman said the initial possibility had seemed quite modest: buy four or five businesses and have a worthwhile company. The larger opportunity was conditional on finding enough suitable sellers and operating their businesses well. That second condition matters. Buying a product listing transfers ownership. Improving a business requires people to make thousands of decisions after the purchase agreement has been signed.

When the shopping list became a strategy

By December 2021, Thrasio had completed more than 150 acquisitions and raised over $3.4 billion in capital. An idea that once involved a handful of businesses had acquired a very different scale. Each new purchase enlarged the portfolio, while also adding products, suppliers and operating details that had to be understood.

Cashman described a difficulty that funding headlines tend to conceal: raising money at an acceptable price. Early investors had needed convincing that the model was stable. Later, rival aggregators could raise large sums to pursue similar opportunities. Being early brought attention and imitation, along with the obligation to keep making the underlying operation work.

He also talked about building a place where employees could develop and test ideas. “My goal is to create a culture where innovation can thrive,” he said. It is an aspiration with particular weight inside an acquisition business. The organisation is continually absorbing other people’s work. Keeping initiative alive requires more than providing a new reporting structure and a larger email directory.

The dates that complicate the growth chart

On May 2, 2022, Thrasio announced that Greg Greeley would succeed Cashman as chief executive in August. Cashman would remain a director. Greeley brought experience from Amazon and Airbnb. The announcement framed the handover as preparation for another stage of growth, with Cashman endorsing the incoming leader and the people building the company.

The company’s subsequent history belongs in any account of its founder. Thrasio and affiliated businesses filed for Chapter 11 protection on February 28, 2024. The court confirmed a reorganisation plan that June. These dates put a firm boundary around the earlier enthusiasm. A rapid acquisition programme had produced a substantial business, and that business later required a financial restructuring.

Thrasio announced its emergence from Chapter 11 on June 18, 2024. Stephanie Fox, previously chief operating officer and the company’s first employee, became CEO. The stated priority was profitability and a focus on selected brands. For a company associated with the speed of its purchases, this was a pointed change of emphasis: concentrate attention on the products already in the house.

The next inventory is human

Cashman’s current work includes Corbo, where he is co-founder and chairman. The company builds software intended to retain useful context about relationships from email, calendars and meeting notes. Its team includes co-founder and CEO Ryan Christensen and co-founder and advisor Jay Chakrapani. The object being organised has changed from consumer products to the details people forget about one another.

Christensen has described the familiar frustration of knowing there is a suitable person somewhere in your network, without being able to remember who. A conversation may be buried in an old message, a meeting transcript or a recollection of coffee. Corbo’s proposed answer is to make that context retrievable without asking users to maintain another contact database.

There is a connection here to Cashman’s earlier work, although it is an interpretation of the career rather than a claim about his private motives. Again, useful information exists in scattered places. Again, the proposed business brings it together so somebody can act on it. The difference is intimate: a forgotten introduction, rather than an overlooked product listing.

“I’m always looking for that lever.”Carlos Cashman · 2021

What survives the next venture

Cashman’s public career resists the neatness of a single startup biography. There are industrial analytics and education leads, advertising campaigns and everyday household goods. There are public markets, acquisitions and a restructuring. A motorcycle trip across the country even appears in the account of his years after Opus360. The chronology has room for a detour.

His name is also attached to angel investing and advisory work, roles that put him on the other side of a founder’s pitch. That breadth helps explain why Thrasio’s origin reads less like a sudden revelation than an accumulation: technical training, repeated company building, a working knowledge of advertising, and a small commercial irritation that would not go away.

The monthly check was the beginning of the question. Thrasio supplied an answer on a scale far beyond the original handful of brands, along with the complications that followed. Corbo now asks a smaller, recognisable question about remembering people. Cashman has changed what he is trying to organise. The habit of looking closely at a familiar inconvenience remains visible.