Sale and The JOLT Effect) Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss: • Why 40% to 60% of qualified sales opportunities are lost due to customer indecision • Why dialing up FOMO doesn’t work, and what to do instead • The “pings and echoes” technique to catch issues early • The JOLT method for overcoming indecision • Key lessons from The Challenger Sale • Practical examples of how to apply these principles to close more deals — Brought to you by: • Enterpret—Transform customer feedback into product growth • Webflow—The web experience platform • Heap—Cross-platform product analytics that converts, engages, and retains customers — Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon — Where to find Matt Dixon: • LinkedIn: https://www.linkedin.com/in/matthewxdixon • Website: https://www.jolteffect.com/ — 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) Matt’s background (01:57) The research behind Matt’s books (06:08) Insights from The JOLT Effect (10:15) FOMO vs. FOMU (18:18) An example of selling software (26:04) The JOLT method Step 1: Judge their level of indecision (29:41) The “pings and echoes” technique (34:49) Step 2: Offer a recommendation (38:36) Step 3: Limit the exploration (41:43) Step 4: Take risk off the table (45:58) When to hit the pause button with a customer (47:27) Insights from The Challenger Sale (49:07) An example of a challenger sale (55:23) Where to find Matt — Referenced: • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854 • The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102 • Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition • Tiger King on Netflix: https://www.netflix.com/title/81115994 • Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral • Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham • Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias • Omission bias: https://thedecisionlab.com/biases/omission-bias • Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant • Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect • Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision • Dentsply Sirona: https://www.dentsplysirona.com/ • “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE • Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html — 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. Get full access to Lenny's New
Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss: • A simple framework for choosing where to work and what to work on • The importance of “understand work” • The “adjacent users” theory and how it can help you drive growth • Advice for coaching product managers • Invaluable lessons from his time at Instagram, Facebook, and YouTube • Much more — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Mercury—The powerful and intuitive way for ambitious companies to bank • Vanta—Automate compliance. Simplify security. — Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba — Where to find Bangaly Kaba: • X: https://twitter.com/iambangaly • LinkedIn: https://www.linkedin.com/in/iambangaly/ • Instagram: https://www.instagram.com/iambangaly/ — 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) Bangaly’s background (06:31) Choosing where to work and what to work on (08:39) The impact factor (10:53) Evaluating the environment (15:53) The manager component (18:27) The skills part of the equation (23:49) Advice on finding a mentor (25:42) The power of “understand work” (31:17) Operationalizing understand work (37:55) Balancing understand work (41:25) Managing complex change (45:26) Effective management of product managers (51:35) The role of product managers as coaches and team leaders (54:52) Driving growth through flywheels and value proposition (01:03:14) Understanding adjacent users (01:08:41) The role of partnerships and SEO in Instagram’s early growth (01:16:08) The secret behind Instagram’s growth (01:25:37) Lessons from Facebook (01:29:15) Failure corner (01:31:58) Lightning round — Referenced: • Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey • Casey Winters’s blog: https://caseyaccidental.com/ • Ben Thompson’s newsletter: https://stratechery.com/about/ • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/ • Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E • What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html • Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/ • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/ • LeBron James: https://en.wikipedia.org/wiki/LeBron_James • Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant • Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski • John Calipari: https://en.wikipedia.org/wiki/John_Calipari • Stripe: https://stripe.com/ • Chief: https://chief.com/ • Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user • How the biggest consumer apps got t
Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore: • Why asking for what you want is so impactful • Three steps to effectively ask for what you want • Challenges that arise when people struggle to ask for what they want • Why hearing “no” is a normal part of the process • The “dream behind the complaint” technique for uncovering desires • Kenneth’s experience of being fired three times from Slack • How embracing fear and discomfort is key to getting what you want • Why discipline is overrated — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers • Webflow—The web experience platform • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger — Where to find Kenneth Berger: • X: https://twitter.com/kberger • Threads: https://www.threads.net/@kberger • LinkedIn: https://www.linkedin.com/in/kberger/ • Website: https://kberger.com/ — 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) Kenneth’s background (04:31) The importance of asking for what you want (06:36) Challenges that arise when people struggle to ask for what they want (08:09) A personal example of failing to ask for what you want (09:17) Signs this is a skill you need to work on (10:49) How to get better at knowing what you want (15:28) Why hearing “no” is a normal part of the process (17:29) Getting a “yes” vs. a “hell yes” (19:20) Step 1: Articulate what you want (24:07) Doing an integrity check (26:56) Step 2: Ask for what you want intentionally (30:45) Understanding your influence (34:48) Using complaints as inspiration (36:24) Internal family systems (38:00) Giving feedback (41:24) Step 3: Accept the response (45:22) Kenneth’s experience of being fired three times from Slack (57:30) Advice on being the first PM at a company or startup (01:04:58) Contrarian corner: anti-discipline (01:05:52) Lightning round — Referenced: • Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager • Internal Family Systems: https://ifs-institute.com/ • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • Leaders in Tech: https://leadersintech.org/ • The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup • DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man • Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/ • How to fire
Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss: • How Nubank builds a fanatical user base • Tactics for driving word-of-mouth growth • Measuring customer love through the Sean Ellis score • The importance of strategic clarity • The role of category design in creating successful products • Why companies should strive to be “fundamentally different,” not “incrementally better” • Nubank’s vision for an AI-powered banking future — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Mercury—The powerful and intuitive way for ambitious companies to bank • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal — Where to find Jag Duggal: • LinkedIn: https://www.linkedin.com/in/jagduggal/ — 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) Jag’s background (04:34) Nubank’s remarkable achievements (06:01) Nubank’s product development process (11:23) Nubank’s values (12:16) Building products people love fanatically (15:21) The Sean Ellis score (21:27) An example project using the Sean Ellis score (25:07) Picking up the phone and calling customers (28:20) The importance of starting small and iterating (30:42) Pushing back effectively (34:10) Uncovering pain points through customer research (37:53) An example of setting a clear hypothesis (42:01) Developing a strategy (52:16) “Be fundamentally different, not incrementally better” (53:10) Category design (57:37) Nubank’s founding story and goals for the future (01:00:46) Advice for adding new product lines (01:03:46) The future of fintech and banking (01:09:23) AI corner (01:12:34) Failure corner (01:20:24) Key takeaways (01:22:11) Lightning round — Referenced: • Nubank: https://nubank.com.br/en/ • Coinbase: https://www.coinbase.com/ • Robinhood: https://www.robinhood.com/ • SoFi: https://www.sofi.com/ • Affirm: https://www.affirm.com/ • Lemonade: https://www.lemfi.com/ • Bank of America: https://www.bankofamerica.com/ • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875 • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible • Sequoia Capital: https://www.sequoiacap.com/ • Churrascaria: https://en.wikipedia.org/wiki/Churrascaria • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/ • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/ • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket • Reid Hoffman o
Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss: • The most common traits among successful product managers • The 3 W’s framework for PM career growth • The Four A’s of leveling up in product management • The right way to push back as a PM • Common pitfalls that stall PM careers • Vikrama’s advice for transitioning into product management • Why intent alone is not enough — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Webflow—The web experience platform • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development — Where to find Vikrama Dhiman: • X: https://twitter.com/vikramadhiman • LinkedIn: https://www.linkedin.com/in/vikrama/ • Website: https://www.vikramadhiman.com/ — 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) Vikrama’s background (03:56) Three common traits among great PMs (07:09) The first W: What you produce (15:40) The second W: What you bring to the table (18:58) The third W: What’s your operating model? (20:36) Three traits that make you a great PM to work with (21:49) How to improve the quality and quantity of your outputs (23:26) The art of the pushback (26:55) Common factors that impede career growth (33:39) Vikrama’s personal reflections (39:33) Choosing which skill(s) to focus on developing (46:28) The ambiguity of the PM role (51:47) The 8 axis for PM growth (56:57) Contrarian corner: Why intent alone is not enough (59:30) Lightning round — Referenced: • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock • Gojek: https://www.gojek.com/en-id • SQL: https://en.wikipedia.org/wiki/SQL • Oracle: https://www.oracle.com/ • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/ • Workday: https://www.workday.com/ • Salesforce: https://www.salesforce.com/ • Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681 • Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555 • Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK • Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F • DramaBox: https://www.dramaboxapp.com/ • Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/ • Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF • 9 Best Hawker Centers in Singapore—and What to Eat There: https://ww
Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss: • Potential sources of power that startups should develop from an early stage • Common misconceptions among companies about the types of power they possess • How power relates to strategy • The difference between a moat and a power • Practical strategies for non-leaders to leverage insights about power and strategy in their work • AI’s impact on competitive advantages and barriers to entry — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer — Where to find Hamilton Helmer: • X: https://twitter.com/hamiltonhelmer • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/ • Website: https://7powers.com/ — 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) Hamilton’s background (04:08) When power becomes important (08:24) How strategy relates to power (12:09) How power informs strategy (14:46) The sequence of powers (21:13) Common misconceptions (24:39) Network effects vs. network economies (26:58) Uber’s success (29:16) Moats vs. powers (31:12) Strategies for non-leaders to leverage power and strategy (37:51) Advice on how to become a strategic thinker (39:27) AI’s impact on the seven powers (45:43) Why moving fast is not a power (50:24) Three things that create value in a company (51:16) The debt trajectory of the U.S. (56:35) Optimism for the future (59:25) Lightning round — Referenced: • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/ • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/ • Strategy Capital: https://strategycapital.com/ • Warren Buffett: https://www.forbes.com/profile/warren-buffett/ • Charlie Munger: https://www.forbes.com/profile/charles-munger/ • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6 • Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973 • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars
Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover: • What Annie learned from the late Daniel Kahneman • The power of pre-mortems and “kill criteria” • The relationship between money and happiness • The power of “mental time travel” • The nominal group technique for better decision quality • How First Round Capital improved their decision-making process • Many tactical decision-making frameworks — Brought to you by: • Vanta—Automate compliance. Simplify security. • UserTesting—Human understanding. Human experiences. • LinkedIn Ads—Reach professionals and drive results for your business — Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke — Where to find Annie Duke: • X: https://twitter.com/AnnieDuke • LinkedIn: https://www.linkedin.com/in/annie-duke/ • Website: https://www.annieduke.com/ • Substack: https://www.annieduke.com/substack/ — 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) Annie’s background (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness (09:15) The importance of unconditional love in parenting (15:15) Mental time travel and “nevertheless” (20:06) The extent of improvement possible in decision-making (24:54) Independent brainstorming for better decisions (35:36) Making sure people feel heard (42:41) The “3Ds” framework to make better decisions (44:49) Decision quality (55:46) Improving decision-making at First Round Capital (01:05:05) Using pre-mortems and kill criteria (01:10:15) Making explicit what’s implicit (01:10:55) The challenges of quitting and knowing when to walk away (01:19:23) Where to find Annie — Referenced: • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research# • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/ • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut • Cass Sunstein on X: https://twitter.com/CassSunstein • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market • First Round Capital: https://firstround.com/ • Brett Berson on X: https://twitter.com/brettberson • Renegade Partners: https://www.renegadepartners.com/ • Renata Quintini on X: https://twitter.com/rquintini • Roseanne Wincek on X: https://twitter.com/imthemusic • Josh Kopelman on X: https://twitter.com/joshk • Bill Trenchard on X: https://twitter.com/btrenchard • Linnea Gandhi on X: https://twitter.com/linneagandhi • Maurice Schweitzer on X: https://twitter.com/me_schweitzer • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/ • Quit: The
more | Kayvon Beykpour Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss: • The story of being let go from Twitter after Elon’s acquisition • How he turned Twitter’s stagnant culture around • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done • Why Periscope failed • Advice for building consumer products • When to copy, when to innovate — Brought to you by: • Enterpret—Transform customer feedback into product growth • OneSchema—Import CSV data 10x faster • Heap—Cross-platform product analytics that convert, engage, and retain customers — Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour — Where to find Kayvon Beykpour: • X: https://twitter.com/kayvz • LinkedIn: https://www.linkedin.com/in/kayvz/ — 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) Kayvon’s background (04:31) Getting Elon up to speed at Twitter (11:34) The story of being let go from Twitter after Elon’s acquisition (21:09) Changing the product culture at Twitter (29:44) Building the “hide replies” feature (32:02) Sacred crows, taking bold bets, and reigniting growth (34:28) Aquihires and their impact (42:40) Tips for successful acquisitions and staffing (47:00) The limitations of frameworks like JTBD (53:20) Signs you’ve gone too far with a framework (57:44) Lessons from building Periscope (01:00:41) Reasons why Periscope failed (01:07:24) The challenges of implementing video at Twitter (01:12:05) Copying ideas in good taste (01:17:58) How to get better at building consumer products (01:19:51) What Kayvon is building (01:20:31) Lightning round — Referenced: • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3 • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/ • Elon Musk on X: https://twitter.com/elonmusk • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/ • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/ • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc. • Keith Coleman on X: https://twitter.com/kcoleman • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/ • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/ • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/ • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/ • Chris Sacca’s website: https://chrissacca.com/ • Facebook Live: https://www.facebook.com/formedia
Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss: • The benefits of building robust relationships, in life and work • The 15% rule, and how it will help you build better relationships • The power of vulnerability • Examples of how to practice vulnerability • Why mental models you build early in life hold you back later • The “three realities” and “the net” • The art of inquiry • Practical tips for avoiding defensiveness when getting feedback • The impact of long Covid on Carole’s life — Brought to you by: • Eppo—Run reliable, impactful experiments • CommandBar—AI-powered user assistance for modern products and impatient users • The a16z Podcast—Featuring conversations with the founders and technologists shaping our future — Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin — Where to find Carole Robin: • LinkedIn: https://www.linkedin.com/in/carole-robin/ • Email: carolerobinllc@gmail.com — 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) Carole’s background (05:17) The importance of building robust relationships (10:20) The “Touchy Feely” course at Stanford (13:29) An example of the in-class experience (17:19) Leaders in Tech: developing interpersonal competence (21:36) Progressive disclosure and the 15% rule (24:28) Appropriate disclosure (26:52) The power of vulnerability (34:57) Admitting mistakes and sharing feelings (37:08) Understanding mental models (42:57) The “three realities” framework (53:52) The power of feedback and personal change (58:47) The art of inquiry (01:03:27) How to get better at giving feedback (01:07:47) Exercises and continued learning (01:10:49) “Advice hinders relationships” (01:16:49) Failure corner: AFOG (01:20:30) Takeaways (01:21:51) Lessons from long Covid — Referenced: • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships • Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ • Leaders in Tech: https://leadersintech.org/ • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows • Steve Jobs: https://www.forbes.com/profile/steve-jobs/ • Sheryl Sandberg on X: https://twitter.com/sherylsandberg • Ursula Burns: https://www.forbes.com/profile/ursula-burns/ • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/ • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/ • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://pen-name.notion.site/Carole-Ro
Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss: • How to effectively take ideas from 0 to 1 at larger companies • How to craft a compelling vision • The importance of vulnerability and feedback • The role of intuition and product sense in making decisions • How to practically communicate your vision • How to balance collaboration and strong opinions • Advice for building a strong team culture • Pivoting with grace and enthusiasm • The current AI revolution and its impact on PM — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Lenny’s Talent Team—Hire the best product people. Find the best product gigs • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor — Where to find Mihika Kapoor: • X: https://twitter.com/mihikapoor • LinkedIn: https://www.linkedin.com/in/mihikakapoor/ — 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) Mihika’s background (04:29) Core attributes of great product managers (07:34) Crafting a compelling vision (12:12) The vision behind FigJam (18:25) Delivering a vision without design or engineering skills (21:52) Creating momentum (26:36) The importance of strong conviction (27:45) Direct communication (32:48) Building hype (42:20) Immersing yourself in user insights (47:16) Operationalizing user insights (50:33) Caring deeply about what you build (54:01) Finding passion in your work (57:00) Building a strong culture (01:07:07) Pivoting with grace and enthusiasm (01:11:48) Design Nation (01:13:15) Mihika’s weaknesses (01:16:07) Building new products at larger companies (01:20:50) Coming up with a great idea (01:22:49) The key to going from 0 to 1 (01:26:47) Spreading the idea across the company (01:29:15) Closing thoughts (01:32:11) Lightning round — Referenced: • Figma: https://www.figma.com/ • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/ • The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949 • FigJam: https://www.figma.com/figjam/ • Cognition: https://www.cognition-labs.com/ • Devin: https://www.cognition-labs.com/introducing-devin • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/ • Replit: https://replit.com/ • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/ • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/ • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625 • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/ • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/ • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/ • Config: https://config.figma.com/ • Dev Mode: https://www.figma.com/dev-mode/ • Asana: https://asana.com/ • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/ • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-fr
Director) Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss: • Why founders need to adopt the mindset “Just don’t die” • The most common reason startups fail • When to pivot, and characteristics of a good pivot • The concept of “tar pit ideas” and examples of bad startup ideas • Why investors say no to startups • The importance of market size in investment decisions • The pitfalls of founders over-delegating • Effective ways to talk to customers • 20 ideas Dalton is looking to fund — Brought to you by: • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups — Where to find Dalton Caldwell: • X: https://twitter.com/daltonc • LinkedIn: https://www.linkedin.com/in/daltoncaldwell/ — 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) Dalton’s background (04:41) The value of simple advice (07:04) Dalton’s advice: “Just don’t die” (08:39) Knowing when to stop (11:45) Deciding to pivot (14:26) Characteristics of a good pivot (17:53) Knowing when to pivot (19:03) Zip’s journey and finding a market (21:22) Why Dalton says to “Move towards the mountains and the desert” (23:45) Tar pit ideas (26:49) Understanding why investors say no (29:14) The importance of market size (32:16) Avoiding over-delegation and hiring senior people too early (36:43) Why startups fail (40:30) Effectively talking to customers (45:17) Examples of startups hustling to talk to customers (48:01) Patterns of successful startups (52:05) YC’s Request for Startups (55:37) Early days of Silicon Valley (01:05:33) Contrarian corner: growth hacking for early startups (01:09:28) Failure corner (01:11:15) Closing thoughts (01:12:22) Lightning round — Referenced: • Y Combinator: https://www.ycombinator.com/ • Tiger Woods’s website: https://tigerwoods.com/ • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17 • Brex: https://www.brex.com/ • Retool: https://retool.com/ • Segment: https://segment.com/ • Mixpanel: https://mixpanel.com/ • Whatnot: https://www.whatnot.com/ • Andreessen Horowitz: https://a16z.com/ • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/ • Zip: https://ziphq.com/ • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/ • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/ • Foursquare: https://foursquare.com/ • Razorpay: https://razorpay.com/ • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/ • Lenny Bogdonoff on LinkedIn: https://ww
David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss: • How GitLab operationalizes transparency • The philosophy behind recording and sharing team meetings on YouTube • Their extensive public employee handbook • GitLab’s core value of having “short toes” • Challenges and advice for doing remote work well • Strategies for ensuring effective communication in a remote work environment • GitLab’s breadth-over-depth strategy • The company’s unique approach to AI • The value of using humor in high-stakes conversations — Brought to you by: • Orb—The flexible billing engine for modern pricing • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way — Where to find David DeSanto: • X: https://twitter.com/david_desanto • LinkedIn: https://www.linkedin.com/in/ddesanto/ • Threads: https://www.threads.net/@david.the.beard — 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) David’s background (04:20) Maintaining an epic beard (05:29) Why GitLab publicly shares team meetings (09:49) The GitLab Handbook (11:30) GitLab’s issue tracker (14:29) How to successfully build a culture of transparency (18:11) Benefits of operating with transparency (19:55) The value of building in public (21:53) How GitLab implements their core value of kindness (25:16) What it means to have “short toes” (27:41) Other core values (32:16) Common reasons for not fitting in at GitLab (34:42) Advice for remote teams (42:04) Advice for getting into product (43:52) Advice for PMs who are struggling in a remote world (48:25) Specific tools that help with remote work (53:13) Time zones and remote work (57:18) Breadth-over-depth strategy (01:04:14) AI at GitLab (01:13:11) GitLab’s products and solutions (01:14:54) Lightning round — Referenced: • GitLab: https://about.gitlab.com/ • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4 • The GitLab Handbook: https://handbook.gitlab.com/ • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/ • Y Combinator: https://www.ycombinator.com/ • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/ • Salesforce: https://www.salesforce.com/ • GitLab values: https://handbook.gitlab.com/handbook/values • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure • GitLab direction: https://about.gitlab.com/direction/ • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7 • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • HubSpot: https://www.hubspot.com/ • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-mar
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