Andy Sparks and the art of making yourself replaceable

Andy Sparks packed his California future into a Ford Focus. Everything that would not fit, he sold. He and two friends had started LaunchGram in Ohio after a startup weekend, collected a $50,000 accelerator grant, and headed west for 500 Startups. It had the familiar ingredients of a founder’s origin story: friends, a car, a little money, a large geographical commitment. Then came the less convenient ingredient. By the end of the program, they decided they had started the company for the wrong reasons and shut it down.

The trip taught him something the grant could not buy. Enthusiasm was enough to get him across the country. Making a company work required skills he had yet to acquire. He wanted an apprenticeship. He found one with Danielle Morrill, who had been Twilio’s first employee, and who would become his co-founder at Mattermark.

Years later, Sparks would make a curious argument about the work of a founding chief operating officer: being useful meant getting comfortable with becoming unnecessary. Build the thing. Find someone who can run it. Move on. For someone with a founder’s attachment to making things, that is an unusually demanding job description.

A business education, with a brewing manual

Before the Ford Focus came a trip to Barnes & Noble. At nineteen, Sparks and a friend began brewing beer, and he asked a bookseller for help. He left with Sam Calagione’s Brewing Up a Business, the Dogfish Head founder’s account of building a brewery. A book had supplied a way into an activity he wanted to try. That small transaction would become a recurring pattern.

He attended Ohio State, studied history, and gravitated toward people who wanted to start things. An early brewing venture gave way to less romantic work: folding clothes at Express, sometimes until three in the morning. A friend helped him get an internship at Columbus startup DOmedia. Data entry followed. Later, at an iPhone app development business, he tried design and sold development contracts. His education in technology arrived through assignments.

That route matters to the way Sparks now teaches. A new responsibility rarely arrives with the luxury of a semester to prepare. There is something to sell, somebody to hire, a meeting to run. You find useful instruction, try it, and discover the part you misunderstood. Books were an inexpensive way to borrow somebody else’s hard-won experience before paying for all of it yourself.

The job was to give away the job

At Mattermark, the early work was gloriously manual. Danielle wrote and spoke with investors. Sparks gathered company information by hand. Kevin Morrill helped turn the process into software. Before launch, Sparks asked whether he was a co-founder of this new undertaking. Danielle and Kevin told him he was.

His first team collected data about companies in venture portfolios. Once the operation became repeatable, it needed a more qualified head of data. Then came sales. By January 2014, the company wanted to test demand beyond venture investors. Sparks took on the work, then faced another handover. Doing a job well could make leaving it harder.

Eventually, his remit included offices, recruiting, customer support, finance, and human resources. Chief operating officer was a merciful abbreviation. His 2015 essay described founding COOs as people who should be “comfortable with firing themselves.” The phrase gets at an awkward bargain: a founder must care enough to build a function and resist making permanent ownership the reward.

The business accumulated an audience as well as customers. Mattermark Daily became a fixture for readers interested in venture capital and startups. Sparks later described a peak readership above 100,000, with more than half opening it daily. Yet the eventual sale was disappointing. An audience could be real, substantial, and insufficient to secure the outcome its makers wanted. He carried that distinction into his next attempts at publishing.

“comfortable with firing themselves”

Andy Sparks on founding COOs, 2015

The answer might be in chapter six

Holloway began with a complaint any determined internet reader could recognize. There was plenty to read, but finding a careful answer to a complicated question could still take hours. Books held sustained thinking. Search results often delivered fragments. Sparks and Joshua Levy wanted the depth to become easier to reach.

Levy had already helped create open guides to Amazon Web Services and equity compensation. People read them, suggested corrections, and asked questions. The collaboration offered a promising way to improve a substantial work after publication. Holloway added paid authors, an editorial operation, and a reading experience designed for long guides.

Sparks’s ambition was specific: someone searching for help with a problem should be able to arrive at the relevant part of a book. Chapter six ought to have a life beyond the table of contents. In a 2019 interview, he described a company that needed to understand both publishing and technology. Good software would not excuse a poor book. A thoughtful manuscript still needed a usable route to its reader.

He also became an author. The Holloway Guide to Raising Venture Capital brought together practical detail, scenarios, references, and contributions from more than fifty-five people. Forbes included him in its 2019 30 Under 30 Media list. Public recognition sat beside the ordinary labor of researching, drafting, editing, and deciding whether an explanation actually helped.

A succession plan for a different life

In September 2020, Sparks announced that Levy was taking over as Holloway’s CEO. He wanted to spend more time researching, writing, and helping co-founders understand how to work together. The decision had developed through conversations with Levy during the summer. He was leaving an operating role to pursue work he had discovered while doing it.

The announcement described the peculiar feeling of starting another writing project while still running the company. Attention was moving before the title did. Rather than keep treating the new interest as something to squeeze into evenings, the two founders arranged a change of leadership. Sparks enrolled in the Hudson Institute’s coaching program; his professional profile records certification in September 2021.

Coaching brought him back to a familiar situation from a different chair. Founders were learning unfamiliar jobs while being responsible for everybody else doing theirs. He could help with practical questions because he had held operating roles himself. He also had to learn how to help without assuming that his previous answer would fit somebody else’s company.

Put the calendar next to the promise

Much of his management writing begins with a small, inspectable mismatch. A founder says hiring is the priority. The calendar has barely any time reserved for it. Sparks’s response is practical: identify the priorities, allocate time, protect it, and check what happened. A declaration becomes more useful when it has an appointment attached.

He applies similar care to the weekly conversation between a manager and a direct report. His guide to one-on-ones treats them as a place to exchange information, learn, and coach. Preparation matters. So does leaving room for the other person’s concerns. The recurring meeting earns its space by making work clearer, rather than merely proving that two calendars overlap.

His sales writing asks founders to notice what stage their company has reached before importing a leader from a larger organization. Someone skilled at executing an established sales process may struggle when the assignment is to discover the process. A recognizable résumé can conceal a poor match between the task and the experience.

The coaching practice now runs mostly through phone or Zoom conversations, generally every two weeks. Sparks reports more than sixty people coached and over 1,800 hours of work, with fifteen to twenty clients at a time. The work remains particular: a hiring choice, a disagreement, a decision that has become harder to make alone.

The unread books have an argument

Sparks’s reading habits leave room for apparently inefficient behavior. He buys books before he is ready to read them. They sit around the office, catching his eye. Some become less interesting. Others become irresistible. In a February 2025 essay, he described the accumulation as a way of letting curiosity choose its next assignment.

That essay also announced a move from San Francisco to Columbus, Ohio, with his wife, Kate. They ran remote businesses. Friends from his Ohio State years lived within walking distance of each other in a historic neighborhood. The choice favored nearby friendship and the daily shape of life. After years in a city associated with opportunity, he was choosing which opportunities deserved to organize his days.

His interest in physical places kept growing. In May 2025, he wrote about reading Christopher Alexander’s The Timeless Way of Building while away facilitating a client off-site. It sharpened an ambition to make homes and, eventually, neighborhoods. He described that ambition as something to explore. The appeal was recognizable: gather people, use accumulated skills, make a place where something worthwhile can happen.

Leave room for the wizard

Management Craft gives his teaching another form. The library gathers competencies and tools for people growing teams from one person to one hundred. Sparks combines operational experience with research, then works on making the material usable. Its wizard imagery leaves a little mischief in an occupation well supplied with frameworks.

By March 2026, he was writing enthusiastically about using AI to make designs and build things he had previously needed other people to implement. He described dictating ideas, working through drafts, and consulting his accumulated notes. The attraction was creative independence: being able to try an idea and see it take shape.

There is a useful continuity here. The teenager looking for a brewing manual, the operator handing over a department, and the coach building a management library are all trying to shorten the distance between wanting to do something and knowing how. The tools have changed. So has the size of the undertaking.

In his essay Keepers, Sparks wrote about the close friends he had found through work. An enterprise might end; the people could remain. That is a less tidy measure of a career than a funding total, but it explains why he keeps returning to the work of making things with others. Eventually, somebody else can take the job. With luck, you still have somebody to call.