May 22, 2025 · 1h 19m · in-depth
How Wes Kao coaches founders to influence, lead, and get what they want | (Co-founder of Maven)
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In this interview, Maven co-founder Wes Kao shares practical communication models, leadership frameworks, and career strategies to help professionals influence stakeholders and operate in their zone of genius. Drawing on lessons from co-creating the AltMBA with Seth Godin, Kao explains how intentional preparation, upward management, and spiky points of view drive meaningful impact.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 16.1% of the talking time here. How this is scored →
Brett as informed peer 4.8 Guest teaching 6.0 Guest disagreement 2.7 Brett pushing back 2.0
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:13:40 Attack on defaulting to live calls
Wes forcefully dismisses the common impulse to 'hop on a call', arguing that doing so offloads cognitive labor and wastes colleagues' time when written clarity is needed.
Hardest push from Brett ▶ 22:06 Challenging the asymmetry of executive adaptationBrett directly challenges Wes's premise that executives must uniquely bend to eccentric founders, pointing out the inherent irony of fixed power dynamics.
Biggest teaching moment ▶ 17:00 Educating on true ideal outcomes vs feelingsWes explains to Brett how operators confuse emotional desires like 'feeling heard' with actual operational outcomes like getting a CEO to change a metric methodology.
Brett holds their own ▶ 24:10 Brett invokes Drucker's executive management principlesBrett demonstrates deep management expertise by citing Peter Drucker's classic work to frame how performance reviews mistakenly emphasize weaknesses over strengths.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Charisma, Authenticity, and Personality-Message Fit | 4 | 6 | 4 | 2 | Wes Kao immediately pushes back on conventional buzzwords around charisma and authenticity, offering her own framework of personality-message fit and treating personal traits as fixed constraints. | |
| Calibrating Baseline Communication and Reading the Room | 5 | 6 | 3 | 3 | Brett probes on whether reading the room is an innate talent or a learnable skill. Wes reframes perceived audience skepticism as usually stemming from poor upfront framing and ungrounded communication rather than lack of social intuition. | |
| Preparation as the Bottleneck to Clear Communication | 5 | 7 | 4 | 4 | Brett challenges the dynamic where underlings must bend to idiosyncratic founders, calling it ironic. Wes defends a pragmatic view of power dynamics, noting that trying to change a founder is an ineffective losing battle. | |
| Leaning into Strengths and Navigating Operational Weaknesses | 6 | 5 | 2 | 2 | Brett introduces Peter Drucker's core philosophy from The Effective Executive on doubling down on strengths over weakness-fixing. Wes validates the premise and shares her own career shift away from brand management logistics. | |
| Career Reflection, Unfair Advantages, and Avoiding Resentment | 6 | 6 | 2 | 2 | Brett highlights the societal inefficiency of poor job-to-talent matching and lack of career introspection. Wes expands on this by contrasting good struggle versus bad struggle and explaining the necessity of unfair advantages. | |
| Deconstructing Vague Feedback to 'Be More Strategic' | 6 | 6 | 2 | 2 | Wes deconstructs the common vague critique to 'be more strategic' and advises operators how to extract concrete meaning. Brett adds domain expertise by explaining how low-level tactical execution often fails to link to high-level company levers. | |
| Building the AltMBA and Iterating Educational Formats | 4 | 5 | 1 | 1 | Brett guides a narrative inquiry into the genesis of the AltMBA with Seth Godin. Wes explains the operational insights and low MOOC completion metrics that catalyzed cohort-based learning. | |
| Lessons from Seth Godin: High Standards and Fast Execution | 4 | 6 | 2 | 1 | Wes explains the cultural impact of working with Seth Godin, detailing how seemingly unreasonable deadlines forced radical problem reframing without sacrificing quality. | |
| Honing Craft, Audience Building, and Spiky Points of View | 4 | 6 | 3 | 2 | Wes details how building hype relies on subtle signals and a 'spiky point of view' rooted in personal irritation rather than generic customer polling. | |
| Workplace Communication vs. Public Speaking and Final Reflections | 4 | 7 | 4 | 1 | Wes tears down traditional public speaking frameworks as a flawed mental model for workplace communications, emphasizing that peer interactions are bi-directional debates among domain experts. |
Statements from this episode (15)
Kao: Low-emoting leaders should amplify enthusiastic wording over forced facial expressions
“If you are someone who's low emoting instead of trying to be, you know, high emoting, you should basically take that into account and turn up the enthusiasm in your words, in the actual content of your words, instead of relying on your facial expressions or to…”
Wes Kao: Most people over-index on explicit rather than implicit feedback
“I think that most people over index on explicit feedback. So we wait until, you know, our colleague complains about something. Or, you know, gives us very direct feedback before we're like, oh, okay, this was bothering them. Whereas if you took a step back and…”
Kao: Spending 15 to 30 seconds preparing clarifies business communication
“Literally, 15 to 30 seconds getting grounded on what am I really trying to say? What does this person need to know? What is my main point and what's potentially secondary? Spending a couple moments asking yourself these questions allows you to write a message …”
Kao: Frame recommendations under a founder's existing values, not new ones
“It is much better
To frame whatever it is you want to talk to them about or your recommendation under an existing umbrella of what they already care about, of values they already have, of ways that they already think the business should be run.”
Kao: Executives succeed when treating a founder's personality as a constraint
“I think that many pairings of execs and founders that work really well are when execs recognize that their founder can be spiky in different ways that might not really make sense, that they are really good at certain things and not as good as at other things.
…”
Kao: Employee feedback reflects issues simmering for a long time
“Knowing that being the person in power, you know, by the time anyone's speaking up to challenge you or to
Give you feedback.
This has probably been bothering them for longer than you knew.”
Kao: Competing outside natural strengths guarantees defeat to naturally talented peers
“Whatever it is you find extremely difficult and unnatural for you, there is someone out there who loves doing that and it comes extremely naturally for them. So if you are in a role that requires you to do this thing that you are not very good at and could not…”
Kao: Leaders react better to concrete proposals than defining abstract concepts
“It's much easier for most leaders to react to something you're putting in front of them to correct you basically to say, yes, that no, not that. Then it is to say, you know, teach me ways to be strategic or define what that means for me. Your leader Hasn't don…”
Kao: A business problem does not automatically warrant resources to solve
“Just because something is a problem doesn't mean it warrants resources to solve, or the resources that you are asking for to solve, and so You know, developing that sense of right sizing, of context, of, you know, is the juice worth the squeeze here to try to …”
Kao: Completion rates for asynchronous video courses were only 3% to 6%
“I started digging into the completion rates of video courses and realized that they were abysmally low. I think three to six percent is completion rate.”
Kao: Speed vs quality is a false trade-off in most situations
“Trade-offs like speed versus quality, you know, like people talk about that and throw that around, like, You probably have room or I had room to be faster and to produce better quality without starting to trade off on either. That in most situations, there's s…”
Kao: Online lecturers should introduce a state change every three minutes
“It's very hard for audiences to stay focused for an hour or two hours on Zoom, and so I shared a concept I called the state change method, about how every three to five minutes you should have a state change of some sort, whether that's switching from gallery …”
Kao: Building an audience requires a spiky point of view
“I think with an individual, but I would also say this works for companies, having a spiky point of view is really valuable. And so when I say spiky point of view, I don't mean stirring the pot with controversial statements just for the sake of it. I mean, Havi…”
Kao: The best founder content originates from internal pet peeves
“When I reflect on my own experiences and things that bother me, Pet peeves of mine. Things that I think are annoying. That's where a lot of my best stuff comes from. And I think, you know, that's kind of going full circle to what we started with, how important…”
Kao: Public speaking is a terrible mental model for workplace communication
“There was so much of communication that operators and founders do on a day to day basis where public speaking is actually a terrible mental model. If you think about it with public speaking, it's one directional. You're sage on stage. You have one speech which…”