I didn’t set out to build a “reading challenge” this year. No quotas. No performative book stacks. Just books that showed up at the right time and stuck long enough to leave a mark.
What came out of 2025 was a mix of business fundamentals, personal operating systems, creative rebellion, and a steady undercurrent of motorcycles, outsiders, and people who choose the hard road on purpose.
Here’s the full list, month by month, and why each one mattered.
And yes, I definitely started a few books and bailed. Not wasting time on those here.
Never Split The Difference — Chris Voss
Still one of the sharpest negotiation books out there. Not about winning arguments. It’s about incentives, emotions, and leverage. Every serious operator should revisit it annually.
How to Win Friends and Influence People — Dale Carnegie
Old. Obvious. Still undefeated. This isn’t tactics. It’s human nature. Most people skip it because it feels basic, which is exactly why they need it.
The Art of the Deal — Donald Trump
Less real estate, more mindset. Bravado, momentum, narrative control. You don’t have to like the guy to understand why this shaped so many dealmakers.
How to Live an Extraordinary Life — Anthony Pompliano
A modern reminder that consistency beats intensity. Simple principles. Long-term thinking. Less noise. More ownership.
$100 Million Offers — Alex Hormozi
Pure signal. No fluff. Forces you to confront whether your offer actually deserves attention. Read if you sell anything. Especially if you think you’re already good.
From Under The Truck — Josh Brolin
Raw, unfiltered, and honest in the best way. Addiction, survival, and becoming yourself without the mythology.
The Algebra of Happiness — Scott Galloway
Short essays. Big truths. Career, money, family, regret. Galloway doesn’t sugarcoat the tradeoffs.
The One Thing — Gary Keller & Jay Papasan
A punch in the face for anyone hiding behind busyness. If you can’t name the one thing that moves the needle, this book fixes that.
Zen and the Art of Motorcycle Maintenance — Robert Pirsig
Not really about zen. Not really about motorcycles. It’s about quality, obsession, and what happens when you care a little too much about how the world works.
Whalefall — Daniel Kraus
Claustrophobic and intense. A survival story that doubles as a meditation on fear and reconciliation.
Hell’s Angels — Hunter S. Thompson
Journalism with teeth. Less about biker gangs, more about America’s obsession with outsiders.
Caught Stealing — Charlie Huston
Fast, violent, unapologetic. Pure noir energy. Sometimes you just want a book that moves.
Poems and Prayers — Matthew McConaughey
Surprisingly reflective. Not memoir, not self-help. Just questions and moments. Read slow.
Vagos, Mongols, and Outlaws — Charles Falco
An undercover look at biker gangs that reads like fiction but isn’t. Identity, risk, and the cost of living multiple lives.
Down and Out in Paris and London — George Orwell
Orwell before he became Orwell. Poverty, labor, dignity. Still painfully relevant.
Rebel Without a Crew — Robert Rodriguez
One of the best books ever written on making something from nothing. Grit beats permission. Constraints create creativity.
We Did Okay, Kid — Anthony Hopkins
A quiet reflection on aging, craft, and acceptance. No hype. Just earned wisdom.
Brand It Like Serhant — Ryan Serhant
Branding without the cringe. Tactical. Clear. Honest about the grind behind the glossy outcomes.
Notes on Being a Man — Scott Galloway
Direct, sharp, and uncomfortable in the right ways. Galloway takes aim at modern masculinity without turning it into a lecture.
Every book on this list nudged something. Some tightened up my operating system. Some cracked open old assumptions. Some just reminded me that life is short, weird, and better when you choose the harder path on purpose.
If any of these books find you at the right moment, good. If not, toss them aside and find the ones that do. The only bad reading list is the one you build for someone else.
On to the next chapter.