Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4)

The episode opens with Wes Kao making a claim that frames much of what follows: most people assume their boss has to manage them, and they feel a little resentful at the idea of managing their boss in return, since the boss is paid more, is the manager and carries more responsibility. Kao does not say this view will wreck a career; she concedes a person can keep thinking this way and still be fine. Her counter-claim is that people who do manage their boss tend to be appreciated more, get more opportunities and earn more trust.

Host Lenny introduces Kao as co-founder of Maven, the cohort-based learning platform he used to build his own product management course, and as someone who helped Seth Godin start the altMBA, as well as helping David Perell, Tiago Forte, Scott Galloway and Morning Brew build cohort-based courses. He previews the topics: a concept he calls the super specific who (the transcript says "who"; the later discussion in the transcript is of a "super specific how"), the state change method and better meetings, managing up, better writing and saying no. The mismatch is a transcript-level inconsistency, not something the speakers resolve.

Two sponsor reads follow. They are advertisements, not part of the interview: Modern Treasury, which is described as an operating system for moving and tracking money with APIs for payment flows, and Berbix, an identity verification service based on government ID and a real-time selfie. Neither is discussed further by the guest.

Lenny frames Kao's route as untraditional for the show's guests and asks for an overview. Kao says she began in corporate retail at the Gap headquarters in San Francisco, in a rotational training program across Old Navy, Banana Republic and Gap, which she calls a great foundation in business fundamentals. She treats the common question of whether to start at a big company or a startup as one she answered by going big first and then moving to progressively smaller companies, ending with founding her own over the past 15 years.

Her argument for the big-company start is specific: seeing inside a company that had been around for 40-plus years was, in her words, fantastic training that set her up for tech and later roles. She then lists later steps as a beauty company that was acquired by Shiseido, an ad tech company that was acquired by Snap, and a cross-country move from San Francisco to New York to work with Seth Godin. The transcript offers no further detail on these roles, and no evidence beyond her own account for how the big-company start affected later outcomes.

Kao describes the three years with Godin as transformative and says they co-founded the altMBA. She gives scale figures from her own telling: from an idea between the two of them to thousands of students, 45 countries, 500 cities, and a team that grew from two people to more than 60 around the world. These numbers are her recollection on the show and are not independently checked in the conversation.

After the altMBA she consulted for a couple of years with course creators who wanted "mini versions" of it. She says that work proved to her that the cohort-based format was special and could be used by experts in other industries and functions. It also exposed a practical problem, which she calls a janky tech stack: course creators had to toggle between half a dozen tools to run a live-plus-asynchronous course, and she was shocked nobody had tackled this.

That observation led to Maven. Kao says she and co-founder Gagan Biyani were brainstorming the future of education, were surprised the problem was unsolved, and both believed cohort-based courses are the future. The transcript contains an inaudible stretch (marked "[inaudible 00:07:02]") in the middle of the sentence about experts wanting to teach; her stated conclusion is that teaching these courses is technically too hard now but need not be.

Lenny, a long-time Godin reader who recently unsubscribed from the daily email because it was overwhelming, asks how Kao connected with Godin and what he is like to work with. Kao explains that in 2014 Godin posted a blog entry seeking a special projects lead to help him decide what to do next, shortly after he had sold his previous company, Squidoo, which she says he had worked on for about eight years.