Oisin O’Connor and the business of coming back

Oisin O’Connor once had an unusually tangible way to judge the condition of his business: he could look around his co-founder’s apartment and count the boxes. Mike Flynn was considering packing up, moving home, and finding a job. An extra box meant the previous day had probably gone badly. Startup dashboards have since become considerably more elaborate. It is hard to imagine one more legible.

The story matters because Recharge’s later numbers can make the beginning look inevitable. O’Connor and Flynn founded the company in 2014. It eventually reached a valuation of $2.1 billion. Yet the recollection O’Connor offers of those early days concerns the possibility of leaving. Before subscriptions became a business worth financing, the two founders had to keep finding reasons to remain in the room.

He had already experienced ventures that failed and one that worked to a degree. At 30, broke and living with his parents, he took stock of what he could do and where he needed help. That admission gives the subsequent partnership its shape. He could see opportunities; he wanted someone who would pursue the details with him. The boxes belonged to a partnership that was still being tested.

A family accustomed to building things

O’Connor grew up in Los Angeles after his parents emigrated from Ireland. Both were architects. Building, design, and creative work were familiar activities at home, rather than mysterious occupations performed somewhere else. He has described a family containing several contractors, too. In that setting, the distance between imagining something and making it usable was part of everyday life.

His education included Santa Monica College and UCLA, where he earned a bachelor’s degree in economics. There was also a spell at Deloitte. A conventional professional job gave him something useful to compare against the work he actually wanted to do. He gravitated toward programming and entrepreneurship, with an interest in what technology could help other people accomplish.

One early venture, Empowered.org, pursued crowdfunding for communities and projects. It also supplied an inconvenient lesson: a worthwhile idea can arrive before a market is ready to support it. Ambition and timing have separate calendars. When O’Connor later went looking for another company to build, the choice of market had become a practical concern, carrying the weight of experience.

His own description of his upbringing adds another motive. Family success was connected to bringing other people along. That helps explain why independent merchants recur in his account of Recharge. The people selling products through the software are part of the purpose he gives the business, as well as the customers paying for it.

“I do my best thinking on the go and rarely sit still.”

Oisin O’Connor · mentorship biography

A barbecue, then six attempts

The meeting with Flynn happened at a barbecue in Santa Monica. The pair began asking people what they were seeing and which problems needed solving. Cold calls and LinkedIn messages became a form of reconnaissance. Among those they spoke with was Shopify’s Harley Finkelstein, who made the case for a future in which small entrepreneurs could sell physical goods online.

They started a development agency and launched roughly six products. Recharge came last. That sequence is a useful corrective to the polished founding moment: the eventual company was one experiment among several. The founders had chosen an expanding ecosystem and kept testing what they could contribute to it. A barbecue introduced the collaborators; repeated attempts gave them something to collaborate on.

Once Recharge found demand, they concentrated their efforts. Other products were sold or left running with less attention. Cash from those efforts helped fund the subscription business. The practical appeal was straightforward: an online merchant could offer repeat purchases without having to construct every piece of recurring billing alone. Software could take an awkward operational chore off the shopkeeper’s list.

There is a pleasing symmetry here. O’Connor was trying to establish a business that could keep going. The product he and Flynn settled on helped other businesses establish purchases that could keep going. Neither kind of continuity arrives merely because someone ticks a box.

Five years before outside money

Recharge was self-funded for more than five years before accepting outside investment. By May 2021, it announced $277 million in growth capital from Summit Partners, ICONIQ Growth, and Bain Capital Ventures, at a $2.1 billion valuation. Those figures marked a change in the resources available to the founders. They also came after a substantial period of making the operation work without that cushion.

The financing announcement described a cash flow positive company and more than $5.3 billion in transactions processed. Transaction volume measures the activity moving through the platform. The valuation records the price attached to the company in a financing. For a founder who had been working through one product experiment after another, those were substantial milestones, each measuring a different part of the company’s progress.

The founders’ letter put the next stage in operational terms: more investment in products, support, and the teams taking those products to market. Money expanded the available choices. It also increased the importance of choosing. An early company may struggle because it cannot afford enough experiments. A larger one can struggle to decide which experiments deserve the attention.

The meeting that keeps its place on Friday

For O’Connor, a recurring appointment supplies some discipline. He has described reserving Fridays for merchant calls, filling the calendar with conversations about their goals. It is a revealing habit for someone selling subscription software: the customer relationship gets its own subscription to the chief executive’s time. A calendar invitation is a modest object to place beside a billion-dollar valuation, but it is easier to act on.

In a 2024 reflection, he said those Friday calls remained part of his routine. The point was continuity. Growing companies generate plenty of internal explanations for what customers want. A regular conversation with someone actually running a brand gives those explanations a chance to encounter resistance. The merchant can bring a question that does not fit neatly into the presentation.

His 2023 conversation with Brandon Amoroso also addressed listening beneath a customer’s stated request, changing the organizational structure as a company grows, and finding people suited to each stage. These subjects belong together. Hearing a useful complaint achieves little if the company cannot organize itself to respond. Conversely, hiring more people cannot rescue work aimed at the wrong problem.

That interview also considered company culture and deliberately distinctive job postings. As a founder hands responsibilities to other people, decisions about who joins become decisions about how the business will behave. The customer calls keep one part of the work close; the hiring choices determine who will carry the rest.

A mentor who would rather keep moving

There is a more literal explanation for the movement in O’Connor’s working life. In a Santa Monica College mentorship biography, he described himself as someone who thinks best on the go and rarely sits still. His invitation to prospective mentees included a warning to be ready to move. Anyone expecting a solemn conference-table audience might do well to bring comfortable shoes.

That biography lists hiking, surfing, Manchester United, and Settlers of Catan among his interests. It also records mentoring people at different stages, from would-be entrepreneurs to founders dealing with fast-growing businesses. He credited business mentors and professional coaches with helping him in turn. The exchange fits his account of the cold calls that helped him and Flynn find their direction.

Remote work introduces another version of the same question: how do people stay connected while working apart? Recharge adopted remote work early. O’Connor has argued that it encourages judging people by their results. The appeal is concrete for a founder who has built with constrained resources: useful work has to be visible in what gets done, wherever the person happens to be sitting.

An hour reserved for being a beginner

In a later LinkedIn post, O’Connor described carving out an hour each morning to experiment with AI. He used the time to code workflows, try automations, and explore tools. The language was unusually playful for a chief executive discussing his schedule. He wanted room to build and break things, and to recover the feeling of learning in his early twenties.

He connected that personal practice to Recharge’s first AI hackathon. Projects included preparing for merchant check-ins from internal information, handling subscription changes through conversation, and retrieving answers from company documents. The examples are revealing because their ambitions are so recognizable. Each begins with a task someone already needs to finish.

For O’Connor, experimenting personally supplied a way to develop judgment about how the organization should work. A chief executive can read a briefing about new tools; actually trying them produces different questions. Which tasks become easier? Where does a promising demonstration turn awkward? His morning hour creates a small space in which he can encounter those questions before asking everyone else to answer them.

The next return visit

In April 2026, Recharge announced that Skio was joining the company. Together, the platforms reported serving more than 20,000 brands and processing over $20 billion in annual gross merchandise volume. The announcement said both platforms would continue operating, with further product decisions to follow. For O’Connor, it brought another subscription business into a company that had itself begun among several product experiments.

By September’s ChargeX East event in New York, he was opening a discussion about a further shift: merchants increasingly wanting software to help run retention work alongside them. The proposed direction included helping customers, explaining business performance, and assisting with operations. It extended the old recurring-billing problem into the ongoing work of giving people reasons to return.

The scale has changed substantially since the apartment and its accumulating boxes. The useful habits remain small enough to recognize: ask someone a question, test an idea, take a walk, call the customer again. O’Connor’s career contains expensive milestones, but it is those repeatable actions that give the story its texture. The next order, like the next attempt, still has to be earned.