<p><strong>Matt MacInnis </strong>is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.</p><p></p><p><strong>We discuss:</strong></p><p>1. Why “extraordinary results demand extraordinary efforts”</p><p>2. Why you should deliberately understaff projects, and how to know when you’ve gone too far</p><p>3. Matt’s transition from COO to CPO and what surprised him about leading product</p><p>4. The “high alpha, low beta” framework for evaluating people, processes, and products</p><p>5. When founders should quit their startups (hint: much earlier than VCs want you to)</p><p>6. How to fight entropy in your organization through relentless energy and intensity</p><p>—</p><p><strong>Brought to you by:</strong></p><p><a target="_blank" href="https://ai.dev/"><strong>Google Gemini</strong></a>—Your everyday AI assistant: <a target="_blank" href="https://ai.dev/">https://ai.dev/</a></p><p><a target="_blank" href="https://www.datadoghq.com/lenny"><strong>Datadog</strong></a>—Now home to Eppo, the leading experimentation and feature flagging platform: <a target="_blank" href="https://www.datadoghq.com/lenny">https://www.datadoghq.com/lenny</a></p><p><a target="_blank" href="http://gofundme.com/lenny"><strong>GoFundMe Giving Funds</strong></a>—Make year-end giving easy: <a target="_blank" href="http://gofundme.com/lenny">http://gofundme.com/lenny</a></p><p>—</p><p><strong>Transcript:</strong> <a target="_blank" href="https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths">https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths</a></p><p>—</p><p><strong>My biggest takeaways (for paid newsletter subscribers):</strong> <a target="_blank" href="https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation">https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation</a></p><p>—</p><p><strong>Where to find Matt MacInnis:</strong></p><p>• X: <a target="_blank" href="https://x.com/stanine">https://x.com/stanine</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/macinnis">https://www.linkedin.com/in/macinnis</a></p><p>• Email: <a target="_blank" href="mailto:
[email protected]">
[email protected]</a></p><p>—</p><p><strong>Where to find Lenny:</strong></p><p>• Newsletter: <a target="_blank" href="https://www.lennysnewsletter.com">https://www.lennysnewsletter.com</a></p><p>• X: <a target="_blank" href="https://twitter.com/lennysan">https://twitter.com/lennysan</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/lennyrachitsky/">https://www.linkedin.com/in/lennyrachitsky/</a></p><p>—</p><p><strong>In this episode, we cover:</strong></p><p>(00:00) Introduction to Matt MacInnis and Rippling</p><p>(04:38) The importance of extraordinary efforts</p><p>(08:37) The challenges and rewards of relentless effort</p><p>(10:11) Your job as a leader is to preserve intensity</p><p>(12:39) You learn far more from success than failure</p><p>(16:34) Transitioning to chief product officer</p><p>(19:54) Fixing product management at Rippling</p><p>(25:27) The “high alpha, low beta” framework</p><p>(28:55) The PQL framework</p><p>(35:16) Hiring frameworks and team dynamics</p><p>(36:52) A helpful interview tactic</p><p>(40:00) Leading as a COO vs. a CPO</p><p>(42:34) The reality of product-market fit</p><p>(46:38) The problem with venture capital</p><p>(49:29) When founders should quit their startups</p><p>(41:48) The immutable market</p><p>(54:13) Lessons from Notion’s success</p><p>(57:43) Investment strategies and narrative violations</p><p>(01:00:42) The power of compounding, power law, and entropy</p><p>(01:07:02) Maintaining intensity and fighting entropy</p><p>(01:11:33) The importance of feedback and escalations</p><p>(01:14:31) Rippling’s vision and success</p><p>(01:17:48) AI’s impact on SaaS and business software</p><p>(01:23:42) AI corner</p><p>(01:26:23) Final thoughts and lightning round</p><p>—</p><p><strong>Referenced:</strong></p><p>• Rippling: <a target="_blank" href="https://www.rippling.com">https://www.rippling.com</a></p><p>• Sunil Raman on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/sunilraman">https://www.linkedin.com/in/sunilraman</a></p><p>• Dan Gill on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/dangill">https://www.linkedin.com/in/dangill</a></p><p>• Carvana: <a target="_blank" href="https://www.carvana.com">https://www.carvana.com</a></p><p>• Brian Chesky’s new playbook: <a target="_blank" href="https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach">https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach</a></p><p>• Parker Conrad on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/parkerconrad">https://www.linkedin.com/in/parkerconrad</a></p><p>• Inkling: <a target="_blank" href="https://www.inkling.com">https://www.inkling.com</a></p><p>• Akshay Kothari on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/akothari">https://www.linkedin.com/in/akothari</a></p><p>• Notion: <a target="_blank" href="https://www.notion.com">https://www.notion.com</a></p><p>• Conway’s law: <a target="_blank" href="https://en.wikipedia.org/wiki/Conway%27s_law">https://en.wikipedia.org/wiki/Conway%27s_law</a></p><p>• Seeking Alpha: <a target="_blank" href="https://seekingalpha.com">https://seekingalpha.com</a></p><p>• Dennis Rodman’s website: <a target="_blank" href="https://dennisrodman.com">https://dennisrodman.com</a></p><p>• Dancing pickle emoji: <a target="_blank" href="https://slackmojis.com/emojis/456-dancing_pickle">https://slackmojis.com/emojis/456-dancing_pickle</a></p><p>• Pickle Rick: <a target="_blank" href="https://en.wikipedia.org/wiki/Pickle_Rick">https://en.wikipedia.org/wiki/Pickle_Rick</a></p><p>• SPOTAK: The Six Traits I Look for When I’m Hiring: <a target="_blank" href="https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html">https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html</a></p><p>• Geoff Lewis on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/geofflewis1">https://www.linkedin.com/in/geofflewis1</a></p><p>• Zenefits: <a target="_blank" href="https://en.wikipedia.org/wiki/TriNet_Zenefits">https://en.wikipedia.org/wiki/TriNet_Zenefits</a></p><p>• New banking records prove Deel paid thief who stole trade secrets from Rippling: <a target="_blank" href="https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling">https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling</a></p><p>• Workday: <a target="_blank" href="https://www.workday.com">https://www.workday.com</a></p><p>• Matic robots: <a target="_blank" href="https://maticrobots.com">https://maticrobots.com</a></p><p>• <em>Wall-E</em>: <a target="_blank" href="https://www.imdb.com/title/tt0910970">https://www.imdb.com/title/tt0910970</a></p><p>• Conviction: <a target="_blank" href="https://www.conviction.com">https://www.conviction.com</a></p><p>• Mike Vernal on X: <a target="_blank" href="https://x.com/mvernal">https://x.com/mvernal</a></p><p>• Sarah Guo on X: <a target="_blank" href="https://x.com/saranormous">https://x.com/saranormous</a></p><p>• No Priors: <a target="_blank" href="https://linktr.ee/nopriors">https://linktr.ee/nopriors</a></p><p>• Gemini: <a target="_blank" href="https://gemini.google.com">https://gemini.google.com</a></p><p>• ChatGPT: <a target="_blank" href="https://chatgpt.com">https://chatgpt.com</a></p><p>• Claude: <a target="_blank" href="https://claude.ai">https://claude.ai</a></p><p>• Bryan Schreier on LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/bryanschreier">https://www.linkedin.com/in/bryanschreier</a></p><p>• <em>Heated Rivalry </em>on HBO Max: <a target="_blank" href="https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c">https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c</a></p><p>• Fellow coffee maker: <a target="_blank" href="https://fellowproducts.com/products/aiden-precision-coffee-maker">https://fellowproducts.com/products/aiden-precision-coffee-maker</a></p><p>—</p><p><strong>Recommended books:</strong></p><p>• <em>Pale Blue Dot: A Vision of the Human Future in Space</em>: <a target="_blank" href="https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595">https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595</a></p><p>• <em>Conscious Business: How to Build Value Through Values</em>: <a target="_blank" href="https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020">https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020</a></p><p>• <em>Thinking in Systems:</em> <a target="_blank" href="https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557">https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557</a></p><p>• <em>The Effective Executive: The Definitive Guide to Getting the Right Things Done</em>:<em> </em><a target="_blank" href="https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459">https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459</a></p><p>—</p><p>Production and marketing by <a target="_blank" href="https://penname.co/">https://penname.co/</a>. For inquiries about sponsoring the podcast, email <a target="_blank" href="mailto:
[email protected]">
[email protected]</a>.</p><p>—</p><p><em>Lenny may be an investor in the companies discussed.</em></p> <br/><br/>To hear more, visit <a href="https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language">www.lennysnewsletter.com</a>