Not Boring (with Packy McCormick)

Acquired approaches Not Boring as a company with an unusual structure: one person at its center. At the time of the interview, the hosts describe Packy McCormick's newsletter as roughly eighteen months old, already prominent on Substack, and developing into a media and investment business. They cite about 88,460 subscribers during the conversation and frame its growth as a challenge to both the media and startup-investing models. Those rankings and growth comparisons are the hosts' assessment at that moment, while the more durable point is the combination they identify: a creator building distribution and investing activity around his own work.

The format depends on Packy's recognizable voice. The hosts describe it as whimsical and playful, but the interview later grounds that style in a pairing of comedy with research: he says his school essays were carefully researched and funny, and that readers need both information and entertainment to keep up with his prolific output. The opening also shows how the business is tied to his public identity. Packy is not sure whether to call himself a writer, author, or founder, and chooses 'founder' as a broad label for a project whose shape is still changing. That flexibility is an asset for an early media business, but it also means the product and the person are closely linked.

The interview traces the voice back to childhood experiments in publishing. Packy recalls making miniature newspapers from Post-it notes at age six, inspired in part by his father's work with the Miami Herald, and creating a comic booklet called Golden Memories Of a Young Boy's Life. In school, he sometimes welcomed disciplinary writing assignments because he could turn them into jokes for the class. The same pattern persisted in his essays: he wanted research and rigor without giving up humor. This origin story does not prove that an early habit predicts a scalable company, but it explains why writing and audience attention felt like natural work rather than a later marketing tactic.

Packy attributes his work ethic to both parents, who combined demanding jobs, education, and family life. The story that stands out is a report card with mostly strong grades and one C+: his father was angry less about the grade than about Packy's claiming that the class was going well. He says the lesson was honesty as well as effort, and connects it to being willing to acknowledge mistakes in his writing and public commentary. The episode hints at an important trust mechanism for a creator business: readers may tolerate changing interests or wrong predictions when the writer is candid about them. At this point in the conversation, that principle is still a personal ethic, not yet a formal editorial system.

The lesson from Packy's report card became a way to think about mistakes: his father objected less to one C+ than to the months of claiming the class was going well. Packy says he started taking French seriously afterward and carried the idea of honest self-assessment into his writing. The hosts connect that stance to a public tweet about crypto losses and to Packy's willingness to admit that his own ideas are often wrong. For a newsletter built around judgment, that admission is not a side note; it is part of the relationship with readers.

Packy's early career moved through institutions that looked very different from the independent media business he would later build. At Duke he joined debate and an a cappella group, and after graduating in 2009 he entered investment banking during the recession. His first experience was on Bank of America's energy trading desk, where he says ex-Enron employees and the distinction between physical and financial trading made the environment unusually intense. After the Bank of America–Merrill Lynch combination, he rotated into public finance, working on municipal bonds for New Jersey and the Pennsylvania Turnpike. He performed well, but says he was aiming for business school rather than a long career in finance.

A side business and a failed education plan pushed him toward operating work. While in finance, Packy built ThrowGo, a party-bus service connecting New York with the Jersey Shore and the Hamptons. He treated it as a serious entrepreneurial project and wrote about it in business-school applications, though he later described it as 'startup light.' Stanford rejected him, Chicago admitted him, and he paid a deposit before deciding not to attend. After discovering Breather on AngelList, he tried to defer, was refused, and chose to pursue the job instead. His account shows how a small venture could provide practical operating experience even when it was not itself a venture-scale business.

The Breather hiring process valued evidence of execution over a polished finance résumé. Packy had to create the role description for New York general manager, interview with an Uber operator, and compare two hotel lobbies for a co-founder with a design background. He won the job by one point, then became Breather's first US employee. The episode's broader point is that his early work was deliberately unglamorous: selling landlords on short bookings, managing spaces, and taking on practical problems. Packy says those responsibilities helped him build the judgment and experience he brought to the next stage, even though the work was difficult and the company itself had uncertain prospects.

Breather offered a different bet from the business-school route Packy had planned. He had paid a deposit for Chicago, but the school would not let him defer after he found the early-stage company on AngelList. He decided that practical experience with a paying employer was preferable to two more years without income and with added debt. Breather's six-person Montreal team needed a first US employee, so Packy wrote the job description for the New York general-manager role and went through an improvised hiring process that tested his judgment and initiative rather than just his résumé.