Lenny's Podcast: Product | Growth | Career

How to build your product team from scratch, attract top product talent, go multi-product, and more | Rohini Pandhi (Mercury, Square)

Lenny's Podcast: Product | Growth | Career

Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss: • Key indicators that it’s time to hire PMs • How to build your early PM team • Why founders should initially take on the product manager role themselves • How to attract top PM talent • What she’s learned about going multi-product • A case for investing in quality • More — Skip the Mercury Personal waitlist: https://mercurytechnologies.typeform.com/lenny — Brought to you by: • Cloudinary—The foundational technology for all images and video on the internet • OneSchema—Import CSV data 10x faster • Airtable ProductCentral—Launch to new heights with a unified system for product development — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-build-your-product-team-from-scratch-rohini-pandhi — Where to find Rohini Pandhi: • X: https://x.com/rohinip • LinkedIn: https://www.linkedin.com/in/rohinipandhi — 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) Rohini’s background (05:00) The role of product managers at Mercury (09:51) Key indicators that it’s time to hire PMs (13:18) Building the product team at Mercury (19:53) Why you should avoid hiring PMs too early (22:26) The different flavors of product management (26:15) How to attract top talent (35:59) Advocating for quality in product development (44:10) Going multi-product (46:37) Organizational structure for multi-product success (50:57) Organizational culture for multi-product success (52:07) Customer obsession and product development (57:36) More lessons from going multi-product (01:05:57) Transparent Collective: supporting underrepresented founders (01:09:54) Lightning round — Referenced: • Immad Akhund on X: https://x.com/immad • Mercury: https://mercury.com • Square: https://squareup.com • Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7 • Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860 • What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html • Mercury Bill Pay: https://mercury.com/bill-pay • Zip: https://zip.co • Jira: https://www.atlassian.com/software/jira • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product • Gokul Rajaram on X: https://x.com/gokulr • Transparent Collective: https://www.transparentcollective.com • 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/16-reading-tips-from-naval-ravikant • Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking • Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses • Severance on AppleTV+: https://tv.apple.com/us/show/severance • Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent • Waymo: https://waymo.com • Adam Robinson on X: https://x.com/IAmAdamRobinson • Cyan Banister—From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More): https://tim.blog/2024/11/28/cyan-banister • Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson • Jobs at Mercury: https://mercury.com/jobs — Recommended books: • Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890 • The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314 • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367 • The Song of Achilles: https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627 — 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 Newsletter at www.lennysnewsletter.com/subscribe

Behind the founder: Drew Houston (Dropbox)

Lenny's Podcast: Product | Growth | Career

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about: • The three eras of Dropbox’s growth and evolution • The challenges he’s faced over the past 18 years • What he learned about himself • How he’s been able to manage his psychology as a founder • The importance of maintaining your learning curve • Finding purpose beyond metrics and growth • The micro, macro, and meta aspects of building companies • Much more — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Explo—Embed customer-facing analytics in your product • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox — Where to find Drew Houston: • X: https://x.com/drewhouston • LinkedIn: https://www.linkedin.com/in/drewhouston/ — 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 Drew and Dropbox (04:44) The three eras of Dropbox (07:53) The first era: Viral growth and early success (14:19) The second era: Challenges and competition (20:49) Strategic shifts and refocusing (29:36) Personal reflections and leadership lessons (40:19) Unlocking mindfulness and building support systems (43:14) The Enneagram test (50:35) The challenges of being a founder CEO (58:11) The third era: Rebooting the team and core business (01:22:41) Lessons and advice for aspiring founders (01:27:46) Balancing personal and professional growth (01:42:38) Final reflections and future outlook — Referenced: • Dropbox: https://www.dropbox.com/ • Y Combinator: https://www.ycombinator.com/ • Paul Graham’s website: https://www.paulgraham.com/ • Hacker News: https://news.ycombinator.com/ • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/ • Sequoia Capital: https://www.sequoiacap.com/ • Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/ • Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/ • TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/ • Dropbox viral demo: https://youtu.be/7QmCUDHpNzE • Digg: https://digg.com/ • Reddit: https://www.reddit.com/ • Hadi and Ali Partovi: https://www.partovi.org/ • Zynga: https://www.zynga.com/ • Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc • Dropbox Carousel: https://en.wikipedia.org/wiki/Dropbox_Carousel • Dropbox Is Buying Mega-Hyped Email Startup Mailbox: https://www.businessinsider.com/dropbox-is-buying-mega-hyped-email-startup-mailbox-2013-3 • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin • Intel: https://www.intel.com/ • Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore • Netscape: https://en.wikipedia.org/wiki/Netscape • Myspace: https://en.wikipedia.org/wiki/Myspace • Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) • Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/ • The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Ben Horowitz on X: https://x.com/bhorowitz • Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker • GitLab: https://about.gitlab.com/ • Automattic: https://automattic.com/ • Dropbox Dash: https://www.dash.dropbox.com/ • Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/welcome-command-e-to-dropbox- • StarCraft: https://en.wikipedia.org/wiki/StarCraft_(video_game) • Procter & Gamble and the Beauty of Small Wins: https://hbr.org/2009/10/the-beauty-of-small-wins • Teaching Smart People How to Learn: https://hbr.org/1991/05/teaching-smart-people-how-to-learn — Recommended books: • Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business: https://www.amazon.com/Guerilla-Marketing-Inexpensive-Strategies-Business/dp/0618785914 • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/ • Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821 • Zone to Win: Organizing to Compete in an Age of Disruption: https://www.amazon.com/Zone-Win-Organizing-Compete-Disruption/dp/1682302113 • Warren Buffett’s books: https://www.amazon.com/warren-buffett-Books/s?k=warren+buffett&rh=n%3A283155 • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239 • Invent and Wander: The Collected Writings of Jeff Bezos: https://www.amazon.com/Invent-Wander-Collected-Writings-Introduction/dp/1647820715/ • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE — 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 Newsletter at www.lennysnewsletter.com/subscribe

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

Lenny's Podcast: Product | Growth | Career

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss: • The psychology behind why we avoid difficult conversations • Specific scripts for having five common difficult conversations • How to handle defensive reactions in the moment • The three questions you should end every meeting with • “The founder prenup” that every founding team should work through • Common leadership myths • Stories of failure from Alisa’s career — Brought to you by: • Eppo—Run reliable, impactful experiments • Rippling—Automate HR, IT, and finance so you can scale faster • Liveblocks—Ready-made collaborative features to drop into your product — Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn — Where to find Alisa Cohn: • X: https://x.com/AlisaCohn • LinkedIn: https://www.linkedin.com/in/alisacohn • Website: https://www.alisacohn.com • Podcast: https://www.alisacohn.com/podcast — 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) Alisa’s background (04:48) Having difficult conversations (12:48) Scripts for performance feedback (20:20) How to respond when someone is defensive or upset (25:07) Scripts for handling promotion disappointments (31:00) Scripts for handling terminations (35:44) The importance of positive feedback (38:49) Understanding your job as a leader (44:55) Recognizing your own blind spots (49:38) Three vital questions to ask in every meeting (55:57) The founder prenup (01:08:24) Failure corner (01:13:00) Final thoughts and lightning round — Referenced: • Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 • How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson • Joe Gebbia on X: https://x.com/jgebbia • Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425 • Core Values List: https://jamesclear.com/core-values • How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing • Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii • Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ • Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on — Recommended books: • From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375 • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of • Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473 — 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 Newsletter at www.lennysnewsletter.com/subscribe

Inside Gong: How teams work with design partners, their pod structure, autonomy, trust, and more | Eilon Reshef (co-founder and CPO)

Lenny's Podcast: Product | Growth | Career

Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss: • Gong’s unique approach to working with design partners • Their unique pod model • Why Eilon makes big decisions quickly • Lessons learned from being early in AI • The power of extreme focus • His “spiral method” for learning complex topics quickly • How to maintain quality while optimizing for speed — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Think Fast Talk Smart—Tools and techniques to help you communicate more effectively • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/inside-gong-eilon-reshef — Where to find Eilon Reshef:• LinkedIn: https://www.linkedin.com/in/eilonreshef — 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) Eilon’s background (04:20) The pod model (06:33) Working with design partners (09:13) Finding and coordinating design partners (13:12) Balancing customer feedback and vision (15:10) Gong's 95% feature adoption (17:05) The importance of autonomy and trust (23:30) How to implement this unique way of working (27:15) Speed and decision-making (31:47) Early AI adoption and lessons learned (35:50) Building effective AI teams (38:16) The spiral method for learning (41:36) Narrowing down the initial customer profile (44:24) Failure corner (46:35) Lightning round — Referenced: • Gong: https://www.gong.io • Cisco: https://www.cisco.com/ • How Gong builds product: https://www.lennysnewsletter.com/p/how-gong-builds-product • What is Montessori education?: https://amshq.org/About-Montessori/What-Is-Montessori • Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov • Amit Bendov on LinkedIn: https://www.linkedin.com/in/amitbendov/ • Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the • Nvidia: https://www.nvidia.com • Figma: https://www.figma.com • The Spiral Method: https://www.gong.io/blog/using-the-spiral-method/ • Webex: https://www.webex.com/ • L’Oréal: https://www.lorealparisusa.com/ • American Express: https://www.americanexpress.com/ • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Dishwasher basket: https://www.amazon.com/Munchkin-High-Capacity-Dishwasher-Basket/dp/B07ZPMYKKS/ • What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing • Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor • Hanlon’s razor: https://en.wikipedia.org/wiki/Hanlon%27s_razor • Sabich: https://en.wikipedia.org/wiki/Sabich#Ingredients_and_description • Careers at Gong: https://www.gong.io/careers — Recommended books: • Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM • “The Machine That Won the War”: https://www.goodreads.com/book/show/18402398-the-machine-that-won-the-war • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • The Ideal Executive: https://www.amazon.com/Ideal-Executive-Ichak-Kalderon-Adizes/dp/0937120030/ • Crucial Conversations: Tools for Talking when Stakes Are High: https://www.amazon.com/Crucial-Conversations-Tools-Talking-Stakes/dp/1260474186/ — 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 Newsletter at www.lennysnewsletter.com/subscribe