Lenny's Podcast: Product | Growth | Career Lenny Rachitsky

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