How It Actually Works

The Newsletter

By Trevor McKendrick

I read every corner of the Internet to find the best material to answer the question: how does the world actually work?

What goes down in the room where it happens?

Sent every Monday

Read a previous email here


What Readers Are Saying

"Trevor is the Mike Rowe of Silicon Valley: a tough, no-nonsense, but positive 'get off your butt and achieve your dreams' message."
- Jason Crawford, Engineering @ Flexport and former cofounder/CEO of Fieldbook

"Trevor is a smart dude and a great writer. He's becoming the chief apologist and celebrator of Silicon Valley."
- Austen Allred, CEO & Founder @ Lambda School (YC S17)

"A great newsletter"
- Saku Panditharatne, CEO & Founder @ Asteroid

"Hey Trevor, I just wanted to say thanks! I've been reading your newsletter for several months now and truly enjoy it. It sparks a ton of great thought that helps me both personally and professionally."
- Tyler Wanlass, Head of Design @ Buffer

"Incredible newsletter & deeply sincere take on greatness. Thanks Trevor."
- Edouard Harris, CEO/Cofounder @ SharpestMinds (YC W18)

"How It Actually Works is the email I most look forward to getting every Monday. It’s a nugget of inspirational wisdom that helps me remember achieving excellence & making an impact takes resilience, and reality is a lot more messy than the glossy newsprint makes it seem.”
- Randall Bennett, CEO & Founder @ Vidpresso (YC W14, acquired by Facebook)

"Newsletters have largely replaced blogs for me, and Trevor's How It Actually Works is one of the best."
- Tommy Collison

"Reading this is part of my Monday morning rituals. Trevor's smart and logical perspective teaches me something each time I dive in.”
- Derek Andersen, CEO & Founder @ StartupGrind

"Trevor’s How It Actually Works newsletter is one of my favorites. As a writer and podcast host, Trevor gives me unique perspectives on familiar topics, in a format that grips my attention."
- David Perell, host of the North Star Podcast

"How It Actually Works always seems to have a new perspective to think about; it makes you reconsider ideas you thought were obvious and contemplate ideas you never thought of."
- Pearl Leff, Software Engineer @ LinkedIn

"I enjoy receiving Trevor's newsletter every Monday because I know it's going to contain something interesting to think about and fun links to check out. It's consistently good and one of the few newsletters I've directed Gmail to put into my Primary tab."
- Jonathan Bennett, CTO of My Body Tutor

"I read How It Actually Works because it's the best newsletter I've ever received. These days most newsletters are just glorified listicles or shallow marketing tools. HIAW is the total opposite - it's well-written, thought-provoking, and interesting. I always look forward to it in my inbox, and can't wait to read what Trevor has been thinking about all week."
- Nicholas Basile

"Yours is one of the few newsletters I regularly read"
- Emanuel Ferm

"Last week's email was excellent – really enjoyed reading from you (not just links). The words were on point."
- Tyler Vawser, VP of People @ Apptegy

"I have never liked newsletters because I hate having anything unimportant in my inbox. How It Actually Works is the only one I will not unsubscribe to. It's some of the most logical and practical material I have read."
- Matt Sutherland, CEO & Founder @ HQ

"Keep writing. I love your newsletters.”
- Brent Thomson, CEO & Founder @ Blip Billboards

"This was meaningful for me today, thanks man. (1 week later) Another great one man, love these more and more."
- Al Doan, Founder & former CEO @ Missour Star Quilt Co.

"My favorite weekly read. Inspires me to keep working."
- Dave Stevenson, CTO & Cofounder @ Simple Nexus

"Loved this article Trevor. It was a great reminder to me today"
- Kassidi Henrie, Founder @ Braid Workshop

"Surprisingly inspirational."
- Katelin Cannole

"This is some amazing writing, damn brother. I never read emails but this is a must now."
- Scott Paul, CEO & Founder at Wooly

"I really enjoyed this"
- Zarin Ficklin, Chief Design Officer & Cofounder @ HQ

"I like HIAW because I'm interested in how things work and because I feel that my own surfing across topics can be so random - so rabbit hole dependent; so tied to my own priors - and so it's great to see someone else's thought process."
- Anna Gát, CEO & Founder @ Ixy

"How It Actually Works has the ability to freeze time and compose simple events into a stunning Goldsworthy-like sculpture. Thanks for that!"
- Michal Fabinger, Assistant Professor of Economics at University of Tokyo

"Honestly, regularity and brevity is a big part of my appreciation for your weekly email."
- Benjamin Mercer

"I read How It Actually Works because it provides a new perspective and little titbits of current news and commentary that really resonate with me. And because I can compare my own mental model with yours."
- Prince Fefar

"The reason I look forward to Monday morning is your email. You have had some extreme successes in your life and have questioned many things. I like finding out what makes you 'tick'."
- Kathi Ware

"Your issues provide me a glimpse into the world of techies. Although not all your articles are technical, there is an insight to what your world encompasses. I enjoy your interpretations and reactions to the articles"
- Judy Hoyt

"I read How It Actually Works because I feel that it is one of the few things that imitates the way that my brain works when I take on a big project."
- Kevin Kononenko

"I like the mix of content sources and your commentary / lessons learned do a great job of telling me why I should care and what I will get out of the article."
- Trevor Bodily, founder of Room Choice

"What I like about your newsletter is that you communicate in a way that seems approachable as a friend, even though we've never met. The links you send are the stories that really resonate with me through what I am personally or professionally going through. The themes around balancing professional excellence with personal management are curated through your stories (I still tell the one about Larry Ellison's cat) and links to other sites. This is the only newsletter that I routinely forward to other friends to read since you touch on things that my peer group are all going through at the same time."
- Jason Gleason, CEO @ Eight Wire

"So happy Trevor is finally doing a regular email – I've found his insights super valuable for years. How It Actually Works is one of the only newsletters that goes to my real inbox. Love love love love."
- Eric Jorgenson, Zaarly

"I'm a huge fan of your newsletter How it Actually Works. I even created a shortcut​ in my inbox so as I don't miss a single one of your emails. Why is this? I read one of your emails titled "Efficiency is an excuse not to do the actual work" and it has transformed the way I approach how I do things. For example, I started working out using only push-ups in my bedroom while before I always thought I needed a gym membership first.
- Abdul Ngoko, Tanzania

"I’m very grateful for your emails. I love your consistency and your content. Your emails are part of the few I actually read and enjoy."
- Annette Phillips

"This is one of the best things I've seen in my inbox in a long time."
- Vinney Cavallo

"I read How It Actually Works because it's hand picked interesting stuff. Screw you algorithms!"
- Nick Walter

"Man, I really enjoy these emails. Probably the only newsletter I've stayed subscribed to for longer than two weeks. Good stuff!"
- Kevin Morrill

“Trevor writes about topics I wouldn’t find on my own in a way that's straight and to the point.”
- Carolyn Pope

"I wanted you to know that this week's newsletter was awesome."
- Ramsanthosh Reddy

"I can't remember how or when I signed up for this, but this is an awesome newsletter. Thanks Trevor."
- George Nuridzhanyan

"If you don’t subscribe… duh. Subscribe. Today’s email was awesome."
- Joshua Howland

"This is amazing!"
- Cameron Wiese

"How It Actually Works is one of the few weekly email newsletters that I actually look forward to. Trevor’s superpower is finding unique and insightful nuggets of wisdom, esoterica, and knowledge that are hiding right in plain sight, and sharing them in a fun and easy-to-read way. If you love learning new things, you’ll love How It Actually Works."
- Dan Loewenherz

"Trevor clearly has a passion for the details and it shows in his stories. He knows what actually happened and expertly weaves it into a compelling story, with lessons along the way."
- Ryan Jones

"How It Actually Works is great because it challenges my intuitions. Every week I get to evaluate my gut take on stories I thought I understood but look at with new information and perspective. Great way to start the week thinking in a new way."
- Nathan Dallon

"I just would like to thank you for your e-mails. "Future You Masturbating" specifically helped a lot in realizing certain aspects about myself that I wasn't fully aware of. I'll be looking forward to read more from you."
- Osama Alraddadi 

"You are a strategic, practical thinker and articulate simple life truths in a consumable way."
- Ken Frei

"That Sam Walton story hit home for me. It’s the unsexy bits that are interesting to me. Good issue this week, Trevor. Thanks."
- Russ Shanahan

"This is great Trevor. I love it when you write. Your examples of how we all Future Me Masturbate (did you make this term up?) pulled it all together... +1 to Trevor's newsletter. A must subscribe. Good stuff every time."
- Trent Mano

"I look forward to reading the newsletter every Monday. It exposes me to material that I wouldn't otherwise see."
- Connie Whitley

"I know we don't know each other, and I'm not sure if you read responses to your newsletter, but I've been getting your newsletter for about a month or so now. I just wanted you to know, I really enjoy reading it. I appreciate the work that goes into writing. I just wanted to say thanks, and keep up the good work."
- Michael Munsil

"Superb Trevor, well written and very insightful! Saving this to review every month."
- Jonathan Berkowitz

"Trevor, this is really great. Thanks."
- Austin Craig

"Loved this week's newsletter! I too recently noticed that biographies seem very predestined, that somehow their subjects were destined for greatness regardless of the near unlimited 'could've been' that exist in a career. I love the idea of the Abyss."
- Henry Brophy

"Damn Trevor I'm really enjoying your newsletter but today's issue was special. In two weeks I am leaving my current job to start my second company and I definitely feel deep into the Abyss. Thanks for putting words to it."
- Harrison Sanchez

"Thank you for saying this!"
- Alex Kuang

"Won't unsubscribe"
- Ryan Holdaway

"I like How It Actually Works because you are an excellent and concise writer. The links are also solid. I have been methodically eliminating most sources of non-information from my life, including “the news”, FB, Insta, and most of Twitter. This email is one of the few things I let in because it tends to be interesting without being overwhelming."
- Nick Farina, Founder of Meridian (acquired by HP)

"This is good stuff"
- Terry Feuerborn

"Hey man, kudos on the newsletter. I look forward to reading stuff I wouldn’t have found otherwise"
- Dallen Allred

"I read How It Actually Works for the same reason I listen to Tim Ferris‘ podcasts - your content exposes me to the thoughts and ideas of the people I want to be associated with and learn from in order to become a more intelligent and more worldly person."
- Chris Palmieri

"I have been reading your thoughts for some time now and have consistently found myself feeling inspired, confident, and enlightened. Thank you for continuing to share your fantastic insights, they have been truly helpful to me."
- Mike Tromba

"Nice inspiring stuff. Although given the ease of developing a site these days, creating is a great way to quickly test & see if you have potential customers to begin with. Now, to close my email and get back to building. No more distractions damnit! I was doing fine until I saw your newsletter come in!"
- Stefan Vonimhof

"Great email this week, Trevor. Loved it. Loving the past few week's content. Very thoughtful, personal."
- Jason Zook

What Haters Are Saying

"this writing is just.....not good stylistically....."
- Mike Isaac, The New York Times

"Is there anything more tiring and insipid than Silicon Valley bowing down in rapture at its electronic toys, "changing the world" by fucking up education across the country and praising moral dirtbags like Steve Jobs and Peter Thiel?"
- Brian Artese, Senior Lecturer of English, Kennesaw State University

"I AM DYING TO KNOW WHO'S NEWSLETTER THIS IS"
- Cassie Marketos, SVP at Kickstarter

"Wow tech guys who write for shit? Surely you jest"
- Blair Reeves, Product Principal at SAS Software

"it's so lazy!"
- Jackie Luo, Engineer @ Square

"The weirdest claim in this newsletter is that the work VCs are doing is more important than 'the Roman Empire, or the Industrial Revolution, or the Renaissance'"
- John Olmstead, Senior Software Engineer @ Credit Karma

"Broken record: these goons always claim to be "constantly changing the world" with their tech when in fact they are amplifying existing pathologies in our cultures and society. They're also doing all of this largely on advanced teletype emulators, which is hardly revolutionary"
- Eric Gade, COO @ Merriam Tech

"I subscribe to a lot of tech newsletters; from one, sent today, a criticism of media I've found increasingly common in SV ('the jealousy of the paper belt'). I mostly think it's a facile argument, but there's something a bit alarming about it, given the political environment"
- Anna Wiener, The New Yorker