Maven

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career. What you’ll learn: 1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in 2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings 3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning 4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure 5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it 6. The power of “signposting”—and why executives skim your docs without it 7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction 8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives 9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders 10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out 11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Where to find Wes Kao: • LinkedIn: https://www.linkedin.com/in/weskao/ • Website: https://www.weskao.com/ • Maven course: https://maven.com/wes-kao/executive-communication-influence — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Wes Kao (05:34) Working with Wes (06:58) The importance of communication (10:44) Sales before logistics (18:20) Being concise (24:31) Books to help you become a better writer (27:30) Signposting and formatting (32:05) How to develop and practice your communication skills (40:41) Slack communication (42:23) Confidence in communication (50:17) The MOO framework (54:00) Staying calm in high-stakes conversations (57:36) Which tactic to start with (58:53) Effective tactics for managing up (01:04:53) Giving constructive feedback: strategy, not self-expression (01:09:39) Delegating effectively while maintaining high standards (01:16:36) The swipe file: collecting inspiration for better communication (01:19:59) Leveraging AI for better communication (01:22:01) Lightning round — Referenced: • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto • Communication is the job: https://boz.com/articles/communication-is-the-job • Maven: https://maven.com/ • Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics • How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise • Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive • Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev • Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language • Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it • Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining • Swipe file: https://en.wikipedia.org/wiki/Swipe_file • Apple Notes: https://apps.apple.com/us/app/notes/id1110145109 • Claude: https://claude.ai/new • ChatGPT: https://chatgpt.com/ • Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1 • The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221 • Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/ • The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/ • Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A • 1,000,000: https://www.lennysnewsletter.com/p/1000000 — Recommended books: • On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/ • Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/ • On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375 • Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/ • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Wes Kao

Co-founder

Maven

This Week in Startups is brought to you by… Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at www.vanta.com/twist The Embroker Startup Program helps startups secure the most important lines of insurance, at a lower cost, and with less hassle. For guaranteed 10% off on premiums (& up to 20% depending on quote) go to www.embroker.com/twist. Brave is an internet privacy company on a mission to protect your personal info online. Try the Brave Search API at http://www.brave.com/jason Today’s show: Maven Co-Founder and CEO Gagan Biyani joins Jason to break down his startup's live, cohort-based education model (2:28). Then, Gagan dives into his past journeys at Udemy, where he was eventually fired but wound up revolutionizing online learning and going public (35:08), and Sprig, a food-delivery startup that went on to raise $60M and scale to $20M in revenue, but ultimately failed (47:36). * Time stamps: (0:00) Gagan Biyani, CEO of Maven, joins Jason to discuss the future of online learning. (2:24) Maven: the evolution of online learning. (3:23) Exploring Maven's elite courses offered by a diverse pool of passionate professionals. (6:57) Analyzing who is leveraging Maven for education and the cost dynamics of online learning. (10:30) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (11:36) How Maven's live cohort-based learning emphasizes accountability and interactivity for higher success rates. (13:15) Comparing the outdated cost structures of traditional education with modern alternatives. (23:10) Embroker - Use code TWIST to get an extra 10% off insurance at https://www.Embroker.com/twist (26:31) Unveiling the potential earnings for educators in the online learning marketplace. 28:27) The online educational landscape featuring insights on Coursera, Udemy, and others. (30:56) Brave - Try the Brave Search API at http://www.brave.com/jason (33:40) Jason built the “pit” at TechCrunch50, where he and Gagan first met. (35:08) How Udemy's early days were shaped by the Founder Institute and Adeo Ressi. (41:28) Gagan shares his personal story of being fired from Udemy and his lessons learned. (47:33) The trials, tribulations, and ultimate closure of the food delivery startup, Sprig. (53:39) Discussing the most effective methods for scaling and growing a product. (55:02) The world of fundraising and understanding the power law in venture capital. Check out Maven: https://www.maven.com Follow Gagan: https://twitter.com/gaganbiyani https://www.linkedin.com/in/gaganbiyani * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/fourApply for Funding: https://www.launch.co/applyBuy ANGEL: https://www.angelthebook.com Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Gagan Biyani

CEO & Co-founder

MavenSprig

For more than a decade, across numerous startups Gagan Biyani has helped lead the online education revolution. Now as the CEO of Maven, he's helping the world figure out how to reskill for the coming era of artificial intelligence. In this conversation, we talk about the growth in Maven's AI courses as well as how AI is transforming the platform and how they run the company.  The AI Breakdown helps you understand the most important news and discussions in AI.  Subscribe to The AI Breakdown newsletter: https://theaibreakdown.beehiiv.com/subscribe Subscribe to The AI Breakdown on YouTube: https://www.youtube.com/@TheAIBreakdown Join the community: bit.ly/aibreakdown Learn more: http://breakdown.network/

Gagan Biyani

CEO & Co-founder

MavenSprig

Wes Kao (@wes_kao) talks disrupting traditional education, what it's like to raise $25M, how to stay motivated as a founder, why cohorts are the gold standard of online learning, and how to apply the science of love to product-founder fit with Courtland (@csallen) and Channing (@ChanningAllen).

Wes Kao

Co-founder

Maven

Wes Kao has worked with Seth Godin (where she co-founded the altMBA and served as executive director), David Perell on his Write of Passage course, Professor Scott Galloway on Section4, and Morning Brew. Currently, she’s the co-founder of Maven, a cohort-based learning platform where I taught my own course. Wes is passionate about telling stories that stay true to the creator’s intentions while keeping your audience listening. In today’s episode, you will learn how to use state changes to keep your audience engaged, how to communicate more clearly by focusing on the how more than the why, how to manage up for success, and how to communicate your priorities to set a boundary. — Find the full transcript here: https://www.lennyspodcast.com/persuasive-communication-and-managing-up-wes-kao-maven-seth-godin-section4/#transcription — Where to find Wes Kao: • Website: https://www.weskao.com/ • Twitter: https://twitter.com/wes_kao • LinkedIn: https://www.linkedin.com/in/weskao/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Modern Treasury: https://www.moderntreasury.com/ • Berbix: https://www.berbix.com/start • Makelog: https://www.makelog.com/lenny — Referenced: • The Super Specific How: How to make your cohort-based course more rigorous: https://www.weskao.com/blog/super-specific-how • It Was the Best of Sentences, It Was the Worst of Sentences: A Writer’s Guide to Crafting Killer Sentences: https://www.amazon.com/Was-Best-Sentences-Worst-Crafting/dp/158008740X • Guide to Better Business Writing (HBR Guide Series): https://www.amazon.com/HBR-Guide-Better-Business-Writing/dp/142218403X • Seth Godin’s blog: https://seths.blog/ • The Minto Pyramid Principle: Logic in Writing, Thinking, and Problem Solving: https://www.amazon.com/Minto-Pyramid-Principle-Writing-Thinking/dp/0960191038 • Doctor Foster: https://www.amazon.com/Doctor-Foster/dp/B01DT0WQ2C • Suzy Batiz: https://www.suzybatiz.com/ • Amanda Natividad’s Marketing 201 course: https://maven.com/amandanat/content-marketing • Dr. Marily Nika’s course:  https://maven.com/marily-nika/technical-product-management — In this episode, we cover: [03:39] Wes’s early career [07:08] How to land a job with Seth Godin [09:56] What makes Seth Godin stand apart [14:50] Wes’s framework for better writing: the super-specific how [18:08] Writing and teaching without the BS [21:45] State changes: how to keep your audience engaged when teaching [25:51] The data of “eyes light up” moments [29:27] What managing up can do for you [32:51] How to manage up effectively [34:17] Lenny’s template for proactive communication [36:19] The skills you need to communicate clearly through writing [43:50] How to protect your bandwidth (without having to say no to your boss) [47:32] How Lenny sets priorities and communicates them [48:24] Lightning round! — Production and marketing: https://penname.co/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Wes Kao

Co-founder

Maven

Gagan Biyani is the CEO and Co-Founder @ Sprig, on a mission to build the world's largest restaurant providing healthy and sustainable food. Sprig has attained funding from the likes of Greylock Partners, Accel and Battery Partners. Prior to Sprig, Gagan was the Interim Head of Marketing @ Lyft, where he wrote the first Lyft new market launch playbook and launched Lyft LA. Before that Gagan, was the Co-Founder and CEO of the world's largest online teaching and learning marketplace with the founding of Udemy. In Today's Episode You Will Learn: 1.) What was the origin story for Sprig? What was the aha moment? 2.) Question from Josh Elman: What lessons have Sprig and Gagan learnt from Chipotle, both in terms of their growth and their food? 3.) What are the coolest things that Gagan has learnt about foods that have learnt and not worked from user and product testing? 4.) On TWIST Gagan stated that the food delivery market is a winner take all market , so what makes Gagan believe that and what will ensure that Sprig is the startup that will be victorious? 5.) How do Sprig address expansion theory? Are they the Uber or the Lyft in terms of aggressive market expansion? How do Sprig choose which new market to enter? Is there a scientific approach? 6.) From having raised 9 rounds of VC and angel funding, what are Gagan's biggest tips and takeaways to anyone entering the VC or funding process? Items Mentioned In Today's Episode: Gagan's's Fave Book: The Tragedy of Great Power Politics As always you can follow The Twenty Minute VC, Harry and Gagan on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!

Gagan Biyani

CEO & Co-founder

MavenSprig