The Never Enough Newsletter
I’d be honored if you subscribed to my Friends Newsletter.
A brain dump of recommendations, mistakes, and things I’m thinking about. Check out past issues below.
Subscribe
Latest issue
August 19, 2026Are you guys hanging out without me?
On how money and success quietly wrecked my social life — and the rituals I built to become Friend Rich instead. Plus how to be more handsome, ways to make a million dollars, and all my new baby and home tech.
Read issueThe archive · 45
Newest first- Newsletter · MAY 27, 2026
Have babies with the wrong person…
On the birth of my daughter, why young people are obsessed with the prep work of dating but refuse to eat the meal, and why you should just have the freaking baby.
8 MIN READ - Newsletter · APRIL 29, 2026
I wasted my twenties...
What ADHD treatment, $16M of philanthropy, beta blockers, and the right contact lenses taught me about not spending decades trying to fix the wrong problem.
4 MIN READ - Newsletter · APRIL 9, 2026
I invited 150 people to an island…
Why I built an anti-conference event that prioritizes warmth over status, plus Mateina with Andrew Huberman, new AeroPress products, and pulse sensors for fighting better.
7 MIN READ - Newsletter · MARCH 3, 2026
I don't need help burying a body…
A short ask: upvote Deep Personality on Product Hunt and complete the karmic cycle for years of free writing.
2 MIN READ - Newsletter · FEBRUARY 11, 2026
My name was in the Epstein files…
How a Twitter notification ended up in the Epstein files, plus the ChatGPT prompt that led to Deep Personality, an accidental concrete company, and the cure for not being able to burp.
4 MIN READ - Newsletter · JANUARY 8, 2026
Divorce is awesome…
On unhappy marriages, the science of staying together for the kids, and why divorce is shameful when it shouldn't be.
4 MIN READ - Newsletter · DECEMBER 4, 2025
I own a misunderstood platypus…
Life lessons from Charlie Munger, why public markets misunderstand Tiny, and a year-end roundup of favorite books, music, and movies.
9 MIN READ - Newsletter · NOVEMBER 6, 2025
I lost ten million dollars doing something stupid.
The story of how I burned $10 million trying to compete with Asana, plus rituals for building friendships and the protest songs we're missing.
2 MIN READ - Newsletter · OCTOBER 27, 2025
Lonely Conglomerateurs in Maui
Hosting a small, family-friendly retreat in Maui for at-scale holdco operators—the rare role with its own set of headaches and almost no peer support.
2 MIN READ - Newsletter · OCTOBER 23, 2025
How I succeed by starting companies that (mostly) fail.
My recipe for starting a profitable business: a simple model, low competition, an obvious need, the right co-founder, and aligned incentives.
2 MIN READ - Newsletter · OCTOBER 9, 2025
Your business shouldn't do good.
Why charging less might be the most selfish thing you can do — a counterintuitive case for separating profit-maximization from philanthropy.
2 MIN READ - Newsletter · SEPTEMBER 4, 2025
I want you to hate me
On the courage to be disliked, escaping the prison of reputation, and why having 2% of people hate you is the price of an authentic life.
5 MIN READ - Newsletter · JULY 10, 2025
She pushed the needle into my arm…
What ketamine therapy taught me about emotional processing, plus a $3,600 keyboard, a 30,000-view paper-store reel, and the founding of download.
6 MIN READ - Newsletter · MAY 22, 2025
A crafty Dutchman pinned me down.
How I built an AI inbox triage that beats human assistants, plus Tiny's Q1 2025 results, the $150M fund explained, and finally good Canadian credit cards.
7 MIN READ - Newsletter · APRIL 30, 2025
Are you an Interesting Person?
On hating conferences, an open invitation to the third annual Interesting People event in Victoria, and what it actually takes to make others feel warm and gooey inside.
4 MIN READ - Newsletter · APRIL 25, 2025
I made $20,303 power washing driveways
How a college student's elevator pitch turned into PressurePros, plus the inversion habit that calms my cortisol every morning.
4 MIN READ - Newsletter · APRIL 4, 2025
A $3,600 keyboard and a $66 million dollar investment
Why we bought a majority stake in Serato, the story of Norbauer & Co's luxury keyboards, and the visionary-integrator pattern behind every great company.
4 MIN READ - Newsletter · MARCH 12, 2025
I got diagnosed with a brain disorder.
After a neurologist flagged my working memory in the 20th percentile, I went down the ADHD rabbit hole, got formally diagnosed, started Vyvanse—and finally felt the static turn off.
4 MIN READ - Newsletter · JANUARY 22, 2025
I committed email suicide.
How I escaped my inbox prison by deleting every email app and having my assistant copy important messages into Google Docs—plus PressurePros, Metalab nostalgia, Autobrush, and an AI that calls restaurants for me.
4 MIN READ - Newsletter · DECEMBER 31, 2024
Are you insane?
An annual New Year's life audit using YearCompass, plus PressurePros, the Apple Watch's surprisingly good Vitals feature, Vault for Canadian banking, and embracing your inner Dracula at night.
5 MIN READ - Newsletter · DECEMBER 9, 2024
Your parents put you down and never picked you back up.
On Tim Urban's tail end, the things that quietly disappear from our lives, and rediscovering dancing in middle age via a sober Sunday-morning rave.
2 MIN READ - Newsletter · OCTOBER 29, 2024
You should ignore your kids.
Modern parenting is a stress-induced crisis because we've abandoned how humans actually raise kids. The fix: schedule less, hover less, and let them get bored.
2 MIN READ - Newsletter · OCTOBER 8, 2024
My new favorite possession: a shotgun.
How forum became my deepest source of friendships, plus DBT for business nerds, an air-powered salt shotgun for flies, and an hour with Derek Sivers.
2 MIN READ - Newsletter · SEPTEMBER 10, 2024
Are you a rat or a frog?
Why I work best from cafes (with the right soundscape), a stupid little personality meme that won't leave me alone, and a new forum for fellow conglomerateurs.
3 MIN READ - Newsletter · AUGUST 30, 2024
An innovative use for rectal thermometers.
Self-driving cars feel like magic until they don't, a WSJ review of Never Enough that made me shriek, and the UCSF sauna study we're funding to treat depression.
4 MIN READ - Newsletter · AUGUST 16, 2024
Never tell, always storytell.
What Matt Dicks taught 80 entrepreneurs about story over 48 hours, plus Nick Gray's friend funnel and how negotiating software bills bought Tiny shareholders six Porsches.
2 MIN READ - Newsletter · JULY 5, 2024
I'm going to be a douche.
Asking you to buy my book, a pop-up desk that fixed my cafe-hunch, and why driving a different route to work makes time slow down.
4 MIN READ - Newsletter · JUNE 18, 2024
I couldn't burp...
How a Reddit forum and a Botox shot in Chicago cured the acid reflux I'd had for a decade. Plus Brent Beshore on control, and the perfect overnight bag.
3 MIN READ - Newsletter · JUNE 5, 2024
Delete 95% of your email.
Why awareness creates stress, how I used Freedom to gray out the entire news cycle, plus my favorite annual letters and Tiny's second one.
4 MIN READ - Newsletter · MAY 27, 2024
I started wearing makeup.
How I accidentally bought tinted sunscreen and started looking better, why my calendar is undefeated, and a saying that sums up most ruined lives.
3 MIN READ - Newsletter · MAY 18, 2024
What was that like for you?
Six words that kill small talk, why scaling a business pulls you away from the thing you love, and a Will Durant passage on the persistence of life.
3 MIN READ - Newsletter · MAY 5, 2024
I used to dress terribly.
Hiring a personal stylist, then graduating to ChatGPT as my pocket fashion advisor. Plus the Vision Pro moment that finally clicked, and the perfect pair of jeans.
3 MIN READ - Newsletter · APRIL 27, 2024
I don’t respond to long emails.
The custom GPT that finally gets my long-email backlog answered, why I only build software for price-insensitive customers, and a small Zuckerberg confession.
2 MIN READ - Newsletter · APRIL 21, 2024
Getting fucked over can pay off…
How a $20,000 TED ticket I couldn't afford unlocked my entire career, plus an AI pin that records every conversation and a Vancouver penthouse for sale.
2 MIN READ - Newsletter · APRIL 12, 2024
You are probably a jerk in some way.
I hired a psychologist to do a 360-review on my entire life. The report was a shit sandwich, and it changed everything—from my marriage to my masks at work.
2 MIN READ - Newsletter · APRIL 6, 2024
When you die, your stories die with you.
Why I commissioned a 50,000-word book about my dad's life, a Waymo ride that converted me, and a Daniel Kahneman rule for over-committers.
3 MIN READ - Newsletter · APRIL 1, 2024
My hairline is receding and I’m going gray.
38 lessons from 13,952 days on earth, plus a terrifying air-quality story from DHH and why I finally caved on executive recruiters.
3 MIN READ - Newsletter · MARCH 25, 2024
After years, I finally took the pill...
Why I delayed taking an SSRI for a year, the 23andMe trick that helped me pick the right one, and how Vortioxetine quietly turned the volume down on my anxiety.
4 MIN READ - Newsletter · MARCH 18, 2024
If you got poo on your arm, would you wipe it?
On the writing skills that built MetaLab and Tiny, Chuck Feeney secretly giving away $8 billion, the case for a Toto Washlet, KreAlkalyn creatine, and the launch of The DTC Index.
2 MIN READ - Newsletter · MARCH 8, 2024
Never Enough - March 8th, 2024
A $5,000 titanium keyboard from Ryan Norbauer, the launch of Tech Source for SaaS expense management, Teenage Engineering's CM-15 mic, our Mateina partnership with Andrew Huberman, and why kids need risky play.
2 MIN READ - Newsletter · MARCH 1, 2024
Never Enough - March 1, 2024
MetaLab's first major rebrand in years, an Inc. profile, the Atoms habits app launch with James Clear, Once.com from 37signals, Readwise Reader, and Prince Harry's surprisingly good memoir.
2 MIN READ - Newsletter · FEBRUARY 23, 2024
Never Enough - February 23, 2024
Zofran for stomach flu, the Cuzen Matcha machine, Texts.com for messaging, Raycast's Dash Off extension, and a sugar-free protein ice cream recipe for the Ninja Creami.
2 MIN READ - Newsletter · FEBRUARY 16, 2024
Never Enough - February 16, 2024
Two books that counterbalance each other on AI, SuperWhisper for dictation, Priscilla and The Killer in theaters, the Dyson Solarcycle Morph, and a voice-note journaling workflow.
2 MIN READ - Newsletter · FEBRUARY 9, 2024
Why I'm Starting a Newsletter
The first issue of Never Enough. Why I bid $57,000 to have lunch with Bill Ackman, and why I'm now starting a weekly newsletter to share what I'm learning.
2 MIN READ
Why subscribe
Honest, not polished
I write the way I think — first drafts, real numbers, the deals I lost. No corporate gloss.
Things I’m actually doing
What I’m investing in, the books I’m reading, the tools I’m using, the stuff I’m getting wrong.
No pitch, no ads
Nothing to sell you. Nothing sponsored. Just an email roughly monthly. Unsubscribe whenever.
Still here?
Drop your email. I’ll send something roughly monthly.Unsubscribe whenever — I won’t take it personally.
(I will take it personally.)