Podcast Notes Playlist: Latest Episodes

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

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Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation

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Where to find Matt MacInnis:

• X: https://x.com/stanine

• LinkedIn: https://www.linkedin.com/in/macinnis

• Email: [email protected]

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Matt MacInnis and Rippling

(04:38) The importance of extraordinary efforts

(08:37) The challenges and rewards of relentless effort

(10:11) Your job as a leader is to preserve intensity

(12:39) You learn far more from success than failure

(16:34) Transitioning to chief product officer

(19:54) Fixing product management at Rippling

(25:27) The “high alpha, low beta” framework

(28:55) The PQL framework

(35:16) Hiring frameworks and team dynamics

(36:52) A helpful interview tactic

(40:00) Leading as a COO vs. a CPO

(42:34) The reality of product-market fit

(46:38) The problem with venture capital

(49:29) When founders should quit their startups

(41:48) The immutable market

(54:13) Lessons from Notion’s success

(57:43) Investment strategies and narrative violations

(01:00:42) The power of compounding, power law, and entropy

(01:07:02) Maintaining intensity and fighting entropy

(01:11:33) The importance of feedback and escalations

(01:14:31) Rippling’s vision and success

(01:17:48) AI’s impact on SaaS and business software

(01:23:42) AI corner

(01:26:23) Final thoughts and lightning round

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Referenced:

• Rippling: https://www.rippling.com

• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman

• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill

• Carvana: https://www.carvana.com

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• Inkling: https://www.inkling.com

• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari

• Notion: https://www.notion.com

• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law

• Seeking Alpha: https://seekingalpha.com

• Dennis Rodman’s website: https://dennisrodman.com

• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle

• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick

• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html

• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1

• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits

• 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

• Workday: https://www.workday.com

• Matic robots: https://maticrobots.com

• Wall-E: https://www.imdb.com/title/tt0910970

• Conviction: https://www.conviction.com

• Mike Vernal on X: https://x.com/mvernal

• Sarah Guo on X: https://x.com/saranormous

• No Priors: https://linktr.ee/nopriors

• Gemini: https://gemini.google.com

• ChatGPT: https://chatgpt.com

• Claude: https://claude.ai

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier

• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c

• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker

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Recommended books:

• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595

• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

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Lenny may be an investor in the companies discussed.

• Mind Pump Fit Tip: Stress is Making You Fat! Here's how and how to fix it. (2:28)

• The most effective anti-inflammatory. (26:04)

• Hip thrust king! (28:19)

• Baby sumo. (31:27)

• Kids do the darndest things. (34:13)

• The delicate dance of getting your kids to do things they don't want to do. (36:48)

• Carnival genetics. (39:24)

• Effects of ultra-processed foods on kids. (41:32)

• American culture and consumption. (43:18)

• The importance of having a healthy microbiome on your skin. (49:42)

• #ListenerCoaching call #1 – How to structure the workout when hitting two or more muscle groups in the same workout. (55:38)

• #ListenerCoaching call #2 – How do you know when a low HRV score means you actually need to back off training, versus when it's just reflecting daily stress, hormones, or life chaos? (1:04:46)

• #ListenerCoaching call #3 – How to balance work/life, while trying to be an inspiring entrepreneur. (1:12:15)

• #ListenerCoaching call #4 – How can I continue to incorporate all of the things I love without losing muscle and strength gains, while also seeking optimal overall health outside of aesthetics (I deal with quite a bit of body dysmorphia)? (1:24:26)

Related Links/Products Mentioned

• Get Coached by Mind Pump, live! Visit https://www.mplivecaller.com

• Visit Fatty15 for an exclusive offer for Mind Pump listeners! ** You can get an additional 15% off their 90-day subscription Starter Kit with code MINDPUMP **

• Visit Caldera Lab for an exclusive offer for Mind Pump listeners! **Code MINDPUMP20 for 20% off your first order of their best products. **

• MAPS 15 FORTY PLUS 50% half from Dec. 14-20th. Code DECEMBER50 at checkout.

• Mind Pump Store

• Purpose in life and stress: An individual-participant meta-analysis of 16 samples

• Gratitude enhances health, brings happiness - Harvard Health

• The importance of friendships in reducing brain responses to stress in adolescents exposed to childhood adversity: a preregistered systematic review

• Ultra-processed foods threaten brain health in kids and teens, review warns

• Australia's social media ban for kids under 16 goes into effect

• 'We fear people will end up in financial trouble.' Americans will spend a record $20 billion via buy-now-pay-later during the holidays.

• Visit Seed for an exclusive offer for Mind Pump listeners! ** Code 20MINDPUMP for 20% off your first month of Seed's DS-01® Daily Synbiotic. **

• Mind Pump #2469: Compound Before Isolation Lifts are the Best, Except When They're Not (Listener Live Coaching)

• Online Personal Training Course | Mind Pump Fitness Coaching ** Approved provider by NASM/AFAA (1.9 CEUs)! Grow your business and succeed in 2025. **

• Mind Pump #2560: How to Break Free from Destructive Body Image Issues

• Mind Pump Podcast – YouTube

• Mind Pump Free Resources

People Mentioned

• Bret Contreras PhD (@bretcontreras1) Instagram

• Christopher M. Naghibi (@chrisnaghibi) Instagram

• Kyle P (@mindpumpkyle) Instagram

Full Show Notes: https://bengreenfieldlife.com/lnraw06/

Welcome to RAW—my unfiltered solo podcast (hosted on LIFE Network), where you get the real, behind-the-scenes version of my life: the biohacking experiments I’m running on myself, the protocols I’m building and breaking, the tools and tech I’m stress-testing before anyone hears about them, the ideas in physiology, performance, and longevity I’m diving into, the beliefs I’m questioning, the routines I’m refining, and the unconventional stuff I’m actually doing day to day—no gloss, no script, just a direct line into what I’m thinking, testing, discovering, and living in real time.

In this episode, we go deep into the “RAW” terrain of jaw mechanics—think controversial, awkward, and a tad nerdy, but game-changing for health. It all starts at a cocktail party when a Sherlock Holmes-style dentist spots red flags just by looking at his mouth. Cue a year-plus journey into bioesthetic dentistry, mindfully chewing food, and mastering “mewing” (tongue and jaw posture that even changes your face shape).

What’s the big actionable win? Stop ignoring your mouth! Rethink your mechanics, posture, and oral hygiene—ditch the fluoride, embrace hydroxyapatite toothpaste, train your tongue to suction to your palate, and breathe through your nose like a pro. Bonus: mouth taping is not just for sleep geeks.

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See omnystudio.com/listener for privacy information.

Jimmy Soni, CEO and editor in chief of Infinite Books, is back on Infinite Loops. We discuss what's broken in traditional publishing and how we're fixing it. We also dig into Jimmy's forthcoming book on Kobe Bryant, why the world needs more "problem authors," and why our goal is to make our authors millionaires.

We explore why most industries optimize for prestige instead of outcomes, how digital distribution has reshaped attention, and why authors — and creators more broadly — have more leverage than they realize.

Important Links:

Infinite Books: https://www.infinitebooks.com/

Jimmy's X: https://x.com/jimmyasoni

Substack: https://newsletter.osv.llc/

Books Mentioned:

The Founders by Jimmy Soni

A Mind at Play by Jimmy Soni

The Dao of Kobe by Jimmy Soni (Upcoming)

What Works on Wall Street by Jim O'Shaughnessy

Invest Like the Best by Jim O'Shaughnessy

How to Retire Rich by Jim O'Shaughnessy

The 4-Hour Workweek by Tim Ferriss

The Almanac of Naval Ravikant by Eric Jorgenson (transcribed as "Naval Akan")

Dispatches from Grief (Upcoming)

Mamba Mentality by Kobe Bryant

Slow Horses by Mick Herron

The Boys in the Boat by Daniel James Brown

Launch into the new year with the best ideas learned from the stories of 2025. I've gone through 70+ lessons that I took from the stories of the last 12 months and picked the 8 that I think are the most powerful for you to apply in your life.

Listen, and then go forth and conquer the year.

Sign up for 'BTMC: Protagonist Edition', where you get EXTENDED VERSIONS of the episodes to take you even deeper into the story with more scenes, more lessons, and more of everything that makes the show what it is, as well as access to all of the Character Analysis episodes. Sign up link below:

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We love us some MC Escher. Turns out his story is pretty fascinating too. Tune in to this classic episode and find out all about it with Josh and Chuck.

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