Lessons from Wes Kao

Wes Kao is a prominent operator, marketing executive, and co-founder of Maven (the platform for cohort-based courses).[1] She previously co-founded the altMBA with Seth Godin.[2][3][4] She is best known for her frameworks on "Rigorous Thinking," "Spiky Point of View," and high-impact communication for leaders.

Here are the top 50 quotes and learnings from Wes Kao, categorized by her major frameworks.

On The "Spiky Point of View" (Marketing & Positioning)

A Spiky Point of View (SPOV) is Wes’s framework for differentiation. It advocates for standing for something distinct rather than blending in.

Definition of a Spiky POV: "A spiky point of view is a perspective others can disagree with.[5][6] It’s a way to signal to your tribe that you are one of them, while simultaneously signaling to everyone else that you are not for them." Source
Not Just Being Contrarian: "Spiky doesn’t mean being a jerk or being contrarian for the sake of it. It means having a perspective that is rooted in your expertise and experience." Source
The "Safe" Trap: "Most people feel safer saying things that everyone agrees with. But if you say what everyone else is saying, you have no advantage."
The 10% Disagree Rule: A good SPOV is something where reasonable people might disagree. If 100% of people agree with you, you aren't saying anything new.
Differentiation is Survival: "In a noisy world, fitting in is a failure state. Standing out is the only way to be heard."
Teachable Moments: "Your SPOV should teach your audience something. It shouldn't just be an opinion; it should be an insight that helps them see the world differently."
Brand vs. Performance Marketing: Wes argues that Brand Marketing (reputation, trust) acts as a multiplier for Performance Marketing (ads, direct sales). You cannot rely on performance hacks forever; you need a brand POV. Source
The "Middle" is Death: Avoid the "mushy middle" of content. Be specific, be opinionated, or be ignored.

On Rigorous Thinking & Leadership

Rigorous Thinking is the antidote to "Lazy Thinking."[7] It is about making decisions with intention and logic rather than autopilot.

Lazy Thinking: "Lazy thinking is making assumptions that you don’t even know are assumptions.[8] It’s having a black box of logic where 'suddenly it works'." Source
Rigorous Thinking Definition: "Rigorous thinking is asking critical questions about tactics, and having a systematic way of making decisions."[8]
The "What do you want me to do?" Trap: "Eliminate 'What do you want me to do?' from your vocabulary. Instead say, 'I would like to do this and here’s why it makes sense. Does this sound good to you?'" Source
Bring Solutions, Not Problems: Leaders value team members who bring a proposed solution along with the problem. It reduces cognitive load for the manager.[4]
Decision Fatigue: "When you ask your boss open-ended questions without a recommendation, you are assigning them homework. You are adding to their decision fatigue."
The "Look Good to Me" Default: "When managers say 'looks good to me,' it is often a lazy default. It usually means they haven't looked closely enough to find the flaws." Source
Standards are Infectious: If you accept mediocre work from your team, you are training them that mediocrity is acceptable. Raising the bar is uncomfortable but necessary.
Silence is Agreement: In a leadership context, if you see something wrong and say nothing, you have implicitly agreed to it.
Opt-Out vs. Opt-In Management: High-performing leaders often use "Opt-Out" management: "I am going to do X by [Date] unless I hear otherwise." This keeps momentum without waiting for permission.
The Cost of "Nice": "Being 'nice' often means avoiding difficult conversations. Being 'kind' means telling someone the truth so they can improve."

On High-Impact Communication

Wes focuses on how senior operators should communicate to get buy-in and drive action.

Strategy, Not Self-Expression: "Communication at work is about strategy, not self-expression. It’s not about venting your feelings; it’s about achieving a goal." Source
Avoid Negative Inception: "Don't plant negative ideas in people's heads. Instead of saying 'Sorry to be a pest,' say 'Following up on this.'" Source
The Danger of Apologizing: When you apologize for doing your job (e.g., following up), you lower your status and make the other person feel like you should be sorry.
The "Sales then Logistics" Framework: When pitching an idea, sell the value first before you talk about the logistics (how it will work). Most people get bogged down in logistics too early. Source
Signposting: "Executives skim. Use signposting (headers, bolding, bullet points) to guide them through your document so they can get the gist in 30 seconds."
Making the Implicit Explicit: "Conflict often arises because expectations were implicit. Make the implicit explicit to avoid misalignment."
The Question Behind the Question: "When a stakeholder asks a question, they often have a deeper worry. Answer the worry, not just the literal question."
Emotional Tone Setting: "You set the emotional tone of the conversation. If you are frantic, they will be frantic. If you are calm, they will be calm."
Writing is Thinking: "Writing isn't just a way to share ideas; it's a way to test if your ideas are actually good. If you can't write it clearly, you haven't thought it through."
Brevity is Confidence: "Long-winded explanations often signal insecurity. Confident experts can explain complex things simply and briefly."

On Managing Up & Career Growth

Advice on navigating corporate hierarchies and accelerating your career.

Managing Up is Not Kissing Up: "Managing up is about helping your boss help you. It is a partnership, not a subservient relationship." Source
No One is Coming to Save You: "Be your own mentor. Stop waiting for someone to spot your potential and groom you.[9] You have to take charge of your own growth." Source
The Osmosis Fallacy: "You can’t learn via immersion and proximity alone.[9] Learning is a result of deliberate thinking.[9] Just being in the room isn't enough." Source
Insecure Vibes are a Self-Fulfilling Prophecy: If you act like you don't belong in the room, people will treat you like you don't belong.
Reverse Imposter Syndrome: "The realization that 'Wait, these people in charge don't actually know what they are doing either.' Use this to give yourself permission to lead."
Don't Start at Entry Level (Mentally): "Starting at entry-level is a job title, not a mindset. If you think like a junior employee, you will stay one."
Turn Bugs into Features: In your career story, take your "weaknesses" or non-traditional background and frame them as unique assets (features).
Personal Credibility > Personal Brand: "Focus on personal credibility (being trusted to deliver) over personal brand (being known)."
Receiving Feedback: "When receiving feedback, stop trying to defend yourself. Just say 'Thank you' and process it later. Defensiveness kills your growth."
Asking for Feedback: Don't ask "Do you have any feedback?" (too vague). Ask "What is one thing I could have done differently to get a better outcome?"
The "Iceberg" of Context: Your manager has an iceberg of context you don't see. Assume there are factors you are unaware of before judging a decision.

On Education & Course Building (Maven)

Insights from co-founding Maven and altMBA regarding online learning.

Cohort-Based Courses (CBCs): "CBCs are about active learning, community, and accountability. They replace the 'content' focus of MOOCs with a 'transformation' focus."
The "Super Specific How": "Good courses don't just teach the 'Why' (philosophy); they teach the 'Super Specific How'—the step-by-step nuances of execution." Source
State Change Method: "Monotony causes audiences to tune out.[6] Use state changes (breakouts, polls, Q&A, slides off) every 10-15 minutes to reset attention." Source
Community as Curriculum: "In a cohort-based course, the other students are part of the learning material. Peer learning is often as powerful as instructor teaching."
Accountability is a Feature: "People pay for courses not just for information (which is free), but for the accountability to actually do the work."
Course-Market Fit: "Before you build a massive course, test your material. Validate that people actually want to solve this specific problem."
Completion Rates: "Self-paced courses have 3-6% completion rates. Cohort-based courses often have 80-90%+ because of the social contract."
Live vs. Async: "Use live time for discussion and feedback, not for lecturing. Lectures should be recorded (flipped classroom)."
Transformation over Information: "Don't ask 'What do I want to say?' Ask 'Who do I want my student to become?'"
Minimum Viable Testing: Don't build the whole product. Test the smallest piece that proves demand.
Shared Struggle: "Bonds are formed through shared struggle. Difficult assignments in a group setting create tighter communities than happy hours."

Advanced Managing Up Frameworks

51. The "Sales, Then Logistics" Framework
When pitching an idea, most people start with how it will work (logistics). This bores executives.

The Learning: Always sell the value (the "why") first. Once they are sold on the destination, they will care about the flight path. If you start with logistics, you invite them to poke holes in the process before they even want the outcome.
Source: Lenny's Newsletter

52. The "MOO" Rule (Most Obvious Objection)

The Learning: Before you present a plan, identify the Most Obvious Objection your manager will have. proactively state it and address it immediately.
Quote: "If you don't say it, they are thinking it. And if they are thinking it, they aren't listening to you. By saying it out loud, you neutralize the objection and show you’ve done your homework."

53. Context Loading (Combatting Context Switching)

The Learning: Executives are often in back-to-back meetings.[1] When they join your meeting, they are "cold." You must "load the context" for them in the first 60 seconds.
Tactic: Don't just dive in. Say: "As a reminder, last week we discussed X. Today, we are here to decide Y so we can unblock Z."

54. The "Middle" is the Critical Loop

The Learning: Most people are good at "Closing the Loop" at the end of a project. But the most dangerous time is the middle.
Insight: You must "re-close the loop" and "re-sell" the project midway through. Stakeholders forget why they agreed to something.[2][3] Remind them of the strategy during the messy middle to keep momentum and prevent them from changing their minds.
Source: Wes Kao's Newsletter

55. Incepting Positive Ideas (Avoid Negative Inception)

The Learning: Never plant a negative seed that wasn't there.
Example: Instead of saying "I know this might be annoying..." (which makes them think it is annoying), say "I'm excited to share this update..." or simply state the update. You define the emotional reality of the interaction.

56. "Start Right Before You Get Eaten by the Bear"

The Learning: In storytelling or updates, cut the preamble. Start at the moment of highest tension or relevance.
Quote: "Minimum Viable Backstory. Executives don't need the history of the world. They need to know what matters now."
Source: Wes Kao Blog[4]

57. Drafts over Descriptions

The Learning: Never ask for feedback on a raw concept if you can show a "Shitty First Draft" (SFD).
Insight: It is infinitely easier for a manager to critique a rough mock-up than to visualize a description. Bringing a draft reduces their cognitive load and gets you faster approval.

Nuanced Communication Tactics

58. Density of Insight > Brevity

The Learning: "Concise" doesn't mean "short." It means "high density of insight."
Quote: "You can have a 300-word email that is fluffy and wasting my time, and a 1,000-word memo that is gripping and necessary. Don't optimize for word count; optimize for value per word."

59. The "Yellow Spot into the Sun" (Framing Weaknesses)

The Learning: If your project has a flaw or risk (a "yellow spot"), don't hide it.[5][6] Frame it as a central feature or a conscious trade-off (turn it into the "sun").
Why it works: It shows you are in control of the risk rather than a victim of it.

60. Signposting for Skimmers

The Learning: Senior leaders skim. If your document is a wall of text, they will miss the point.
Tactic: Use "Signposting"—explicit headers like "The Recommendation," "The Risk," and "Next Steps." Bold the single most important sentence in every paragraph.

61. Answer the "Worry," Not Just the Question

The Learning: When a leader asks a specific, narrow question, they are usually anxious about a larger issue.
Tactic: Answer the literal question, but then address the underlying anxiety. "You asked about the budget for X. The number is $5k. But I suspect you're asking because you're worried about Q4 burn—rest assured, this is factored into our savings."

62. State Your Confidence Level

The Learning: Don't present guesses as facts. Explicitly state your confidence interval.
Script: "I am 90% sure of this data," vs. "I have low confidence in these numbers, but it's the best we have right now." This builds massive trust because you aren't bluffing.

63. The "Opt-Out" Deadline

The Learning: To move fast, use negative consent.
Script: "I plan to ship this on Thursday at 5 PM. If you have edits, please let me know by then. Otherwise, I will proceed." This prevents projects from stalling while waiting for a "yes."

64. Separate "FYI" from "Action Required"

The Learning: never mix these. If an email is FYA (For Your Action), say so in the subject line or the first sentence.
Quote: "Ambiguity creates anxiety. If I don't know if I need to do something, I have to re-read your email three times. That is a tax on my time."

Career & Self-Management

65. "No One Is Coming to Save You"

The Learning: This is a core Wes Kao philosophy.[2] In a startup or high-growth company, there is no "training department" coming to map your career.
Action: You must define your own role, ask for your own feedback, and create your own curriculum.

66. Reverse Imposter Syndrome

The Learning: Realize that everyone else is figuring it out as they go, including the CEO.
Insight: "Use this not to lower your opinion of them, but to raise your opinion of yourself. You are just as capable of solving the problem as they are."

67. Turn "Bugs" Into "Features" (Personal Brand)

The Learning: If you have a non-traditional background (e.g., you were a teacher before tech), don't hide it.
Application: Position it as your unique advantage. "Because I was a teacher, I am better at explaining complex product roadmaps to stakeholders than a traditional PM."

68. The "Osmosis Fallacy"

The Learning: You don't learn just by sitting next to smart people. You learn by doing the work and getting critiqued.
Quote: "Passive exposure is not learning. Deliberate practice is learning."[7]

69. Emotional Tone Setting

The Learning: As a leader or operator, you are the thermostat, not the thermometer.
Insight: If you come to a meeting frantic, the team becomes frantic. If you bring calm intensity, the team focuses. You control the "vibe" of the room more than you think.

70. "Make the Implicit Explicit"

The Learning: 90% of workplace conflict comes from unspoken expectations.
Rule: If you expect an update every Friday, say it. If you expect a draft 24 hours before the meeting, say it. Do not assume people know your "unwritten rules."

Key Resources & Links

Newsletter: Wes Kao's Newsletter (Substack)
Website: weskao.com[10]
Maven: maven.com
Twitter/X: @wes_kao

Sources