Alan Matthews and the resignation that became Rapid7

The resignation did not go according to plan. Tas Giakouminakis walked into Alan Matthews’s office intending to leave his job as chief technology officer at another Matthews company. Matthews remembers refusing the resignation. They sat down with a blank sheet of paper and began considering what to do next. The conversation eventually became part of Rapid7’s origin story. Human resources departments generally prefer a more predictable exit procedure.

Matthews told that story in 2015, by which time a disagreement about one person’s next move had acquired a considerable corporate afterlife. Rapid7 had been founded in July 2000. He had served as its CEO and become its chairman. The paper had long since filled up.

The scene is useful because it puts a working relationship at the center of the story. A colleague wanted a change. Matthews wanted to keep working with him. There was a business to consider, and there were people whose next chapter might be written together. Much of Matthews’s subsequent thinking concerns the difficulty of making that arrangement worthwhile.

“Rapid7 began when my CTO, Tas Giakouminakis, walked into my office and tried to quit.”

Alan Matthews, 2015

A programmer before the pitch

Before the companies came the code. From 1976 to 1979, Matthews worked in the United Kingdom as a programmer and designer on IBM’s VM operating system. His early professional life belonged to the machinery beneath other people’s work: the systems that made computing possible before a sales presentation could make it sound simple.

His career subsequently crossed into television and finance. He developed a computer graphics lab at HBO/Time Warner, wrote mortgage-backed securities software at First Boston, and consulted to Merrill Lynch’s investment banking group. These were distinct environments, with distinct demands. Their common material was software, built for institutions that needed it to do something particular.

Matthews places his move from the United Kingdom to New York in 1980. Years later, writing about money, he used that arrival as a reference point for how much everyday prices had changed. It is a programmer’s sort of autobiographical detail: establish the starting conditions, then consider what happens when the numbers move.

By the time cybersecurity entered the picture, he had experience moving between industries. The blank sheet in the resignation story therefore carried an unusual advantage. Matthews and his colleague could consider a different business without first having to discover whether they could work together.

The office, the train, the company

Rapid7’s founding has another everyday setting attached to it: New York’s express 7 subway. The company’s name recalls the line traveled by founders Tas Giakouminakis, Chad Loder, and Matthews. An office conversation and a train journey make a pleasingly unceremonious beginning for a business concerned with computer security.

John Devine also belongs to Matthews’s entrepreneurial history. The two had worked together on other businesses, and accounts of Rapid7’s beginnings place Devine in that founding circle. In a later interview, Corey Thomas recalled Matthews, Devine, Giakouminakis, and Loder as founders who wanted cybersecurity to become easier to consume.

That recollection matters because security software has to be used by somebody. Finding technical weaknesses is part of the work. Helping an organization understand and act on them is another. A product can have an impressive vocabulary and still leave its customer wondering what to do on Monday morning.

The people around Matthews provide another view of his role. H. D. Moore, creator of Metasploit, later described the acquisition relationship as resting on personal commitments and a handshake, with risks for both parties. His public recommendation credits Matthews with honoring those commitments. In a business built around assessing vulnerabilities, someone else’s account of reliability carries a certain symmetry.

Five years in the CEO’s chair. Ten at the board.

The job titles have precise boundaries. Matthews served as Rapid7’s chief executive from April 2004 to July 2009. He became chairman in July 2008, so the roles overlapped for a year. His employment with the company continued until October 2009; his board service lasted much longer.

It is tempting to compress a founder’s career into a single continuous reign. Matthews’s dates tell a more interesting story about changing responsibilities. The company kept developing while his relationship to its daily operation changed. Founding, managing, and chairing a business are connected jobs, each with its own point of view.

In July 2015, Rapid7 priced its initial public offering at $16 a share. By the closing on July 22, the offering included 7,417,500 shares, following the underwriters’ full exercise of their option. The company received approximately $110.4 million after underwriting discounts and commissions, before estimated offering expenses.

Those numbers mark a change in the company’s circumstances. A conversation between colleagues had become an enterprise with public shareholders. Matthews was chairman during that transition. There is enough achievement in that fact without asking the stock market to explain his personality.

The board continued changing too. In 2016, Matthews welcomed Marc Brown and Tom Schodorf as directors, pointing to the experience they brought in business development, operations, and taking products to market. He also thanked departing director Christopher Young. It was the language of a company assembling capabilities for its next stage.

Matthews’s own board chapter ended on June 12, 2018. He chose not to stand for re-election; the company said his decision did not arise from a disagreement. The dates close a formal responsibility while leaving the founding history intact. A company can carry its beginnings forward without keeping everyone in the same seat.

Four words with a workload attached

For Matthews’s account of how people should work together, turn to the four terms he put in the title of a 2016 hiring essay: trust, honesty, respect, and investment. They are comfortable words until someone has to practice them in a difficult meeting.

He asks for reliability in what people promise, candor about facts, and respect for the abilities of colleagues. Investment includes the unglamorous contribution of time and sustained effort. The argument links someone’s character to the practical business of completing work with other people. A polished résumé has limited value if its owner cannot be relied upon.

“Be that person first and describe it second.”

Alan Matthews, on hiring and character

There is a demanding side to this outlook. Respect does not excuse a person from knowing their job, and honesty requires more than pleasant agreement. Matthews wants colleagues who can contribute something real and recognize what others contribute. The formula is short; the daily implementation is likely to occupy the rest of the calendar.

The future an employer is selling

His 2014 essay on building belief treats growth as a way to create room for employees: more responsibility, more learning, and more possibilities for advancement. He describes a team becoming capable of something larger together. That ambition depends on convincing people that their effort has a future attached to it.

He is particularly interested in the development of sales leaders and communication between departments. The argument keeps returning to training, repeatable work, and people understanding what happens elsewhere in the business. Belief may sound airy. In his account it needs a calendar, a customer, and someone prepared to teach the next colleague.

In a 2022 essay, Matthews returned to those themes and the changes that expansion imposes on employees. A larger organization brings additional management and responsibilities. People must keep learning as the space around their job grows. The prospect can be rewarding and uncomfortable at the same time; a new layer of management may arrive before anyone has finished enjoying the old arrangement.

He also makes employee prosperity an employer’s responsibility. His provocatively titled 2015 essay about needing $40 million in the bank uses personal arithmetic to argue for thinking about money at scale. Read as a statement of managerial ambition, it asks whether a business can offer people a materially different future. It is an expectation he places on the person building the company.

Still leaving room on the page

There are smaller details around this working life. Matthews lists a commercial multi-engine instrument rating, volunteer service with People Making a Difference, and schooling at Hurstpierpoint College. He describes the school as “Hogwarts without spells!” One suspects the timetable was less accommodating than the comparison suggests.

His public account also looks beyond software. He has written about visiting the Galápagos after reading Jonathan Weiner’s The Beak of the Finch, and announced plans to leave Miami Beach for Uruguay. The announcement describes a prospective change, another place to go after years in New York, Boston, and Miami.

To former Rapid7 colleagues, he has offered thanks and a reminder to keep learning, accompanied by a joke about taking turns as pigeon and statue. It is a suitably undignified image for a former chairman. The titles come with dates. The relationships, and the next conversation about what to do, have a less orderly ending.