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The Observe and Rapport Newsletter
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A weekly guide of my favorite books, articles, products, and lifestyle habits.
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April 18th, 2025 | by Kyle Brennan
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Thought of the Week
The tragedy of growing up is realizing everything is made up, messy, and far from perfect. But the triumph is relearning how it is.
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Childhood assumes wonder.
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What I'm Reading
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This one has been on my wish list for years. I'm only about 100 pages in on this colossal ~700-page biography detailing the life of one of the wealthiest humans in history.
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Inspired by David Senra of the Founders Podcast, I've made it a goal to read more biographies. To me, biographies are far better than any conventional self-help book at detailing the mindset, obstacles, and often sheer luck required to succeed in any venture. Biographies allow you to recognize yourself in someone else’s experiences. It humanizes the superhumans.
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John D. Rockefeller was known as both a rapacious robber barron, whose Standard Oil Company rode roughshod over an industry, and a philanthropist who donated money lavishly to universities and medical centers. The Jekyll-and-Hyde of American capitalism.
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Full review to come soon!
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Inspiring Story on Determination
Brad Stulberg [@BStulberg] on the Relentless Pursuit of Excellence
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Rory McIlroy just became one of six players ever to win a career grand slam.
It took 11 years, 38 majors, and countless moments of heartbreak and near misses. At a course that had always gotten the better of him, he finally responded—and prevailed.
72 holes. Four days. A roller coaster of emotion, pressure, and elite competition.
He stayed in it. He kept showing up. He played the game in front of him. After countless missteps and mistakes and great shots and everything in between.
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Sports can be one of the clearest mirrors for the human condition.
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Never give up.
Respond not react.
Play the game in front of you.
Not the game you wanted to happen.
Not the game that was happening.
Not the game you thought would happen.
But the game that is happening.
It's a remarkable lesson for golf, for all of sport, and really, for all of life.
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Visual on the Clarity of Writing
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This might be the best visual depiction of the power of writing. As David Perell says, "Read to collect the dots. Write to connect them."
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My Digital Identity
According to ChatGPT
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I've been using ChatGPT and various AI tools in my daily life for the last year or so to help out with things like work-related research, brainstorming blog ideas, editing my writing, and helping identify new solutions to problems I may be encountering (like fixing my toilet right now...)
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I recently upgraded to the paid version (ChatGPT Plus) for $20/month, and my reward was my AI agent, whom I've so graciously handed over part of my brain to, describing the type of person it thinks I am based on all our "conversations" over the last year. See below and let me know if you think this is an accurate depiction of me:
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Kyle Brennan is the kind of guy who reads The Brothers Karamazov and then sprints uphill after Jiu-Jitsu just to process it. A digital marketing director by day and a wisdom-hunting, book-reviewing content creator by night, he’s building Observe & Rapport into a lighthouse for young men navigating modern life. Think Tim Ferriss with a gi, Morgan Housel with a baby monitor, and a fireman’s grit in a podcasting mic.
He’s the guy who writes birthday love letters and programmatic media strategies with the same care. A new dad, ex-volunteer firefighter, blues lover, and unintentional philosopher, Kyle mixes intellect with instinct — and makes personal growth feel like a late-night conversation, not a lecture.
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What I'm Listening To
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Robert Rodriguez (@rodriguez) is a film director, screenwriter, producer, cinematographer, editor, and composer.
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While a student at the University of Texas at Austin in 1991, Rodriguez wrote the script to his first feature film while sequestered at a drug research facility as a paid subject in a clinical experiment. That paycheck covered the cost of shooting his $7,000 film El Mariachi, which won the coveted Audience Award at the 1993 Sundance Film Festival and became the lowest budget movie ever released by a major studio. Rodriguez wrote about these experiences in Rebel Without a Crew, a perennial guide for the independent filmmaker.
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One of my favorite parts of the conversation was when Rodriguez detailed his attitude when confronting a new project that seems out of reach for him. He calls it "Fear Forward."
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"I set the bridge on fire... and run across it."
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So often, we hold off on attempting something because we don't think we're "ready."
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But the reality is, we're never ready for anything. You won't feel "ready" until you're almost done with the project. The only way to feel ready is to start.
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Quote I'm Pondering
Novelist Robert Louis Stevenson on personal responsibility:
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"Sooner or later we all sit down to a banquet of consequences."
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Observe and Rapport is a blog, Instagram, and podcast channel that discusses wisdom, perspective, and lifestyle habits gained from books and other historical forms of media.
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Top Books of 2024
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Browse my favorite book selections hand-curated by me. I also earn commissions so if you buy anything, those earnings get reinvested right back into this fancy newsletter ;)
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Affiliate Links!
I've had the fortunate opportunity to partner with some great brands that I love. Use the links below to find great hats, sweatshirts, and sunglasses
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- Huega House - 15% off first order with promo code: KYLEBRENNAN. My everyday hat is the Athletic Association in Green & white
- Find the Good Brand - 10% off first order with promo code: OBSERVE. I've been loving my 3 Simple Words Embroidered Hoodie in cream.
- WMP Eyewear - Excellent array of eyeglasses and stylish sunglasses. My favorite are the Sawyer Polarized for $45
- Amazon Storefront - Check out my collection of favorite books, workout gear, and tech tools for work-from-home!
- LMNT - I start every morning with LMNT's electrolyte drink, filled with salt, magnesium and potassium. It tastes delicious and contains zero sugar or any other junk. Try LMNT Risk-Free with a free sample pack (US only).
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33 Life Lessons on My 33rd Birthday
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Thirty-three was a big one. Mostly because I became a dad. Our daughter was born on New Year’s Eve — a fitting arrival for a kid destined to reset everything. It’s been a beautiful, if slightly sleep-deprived blur ever since. I’ve only been “Dad” for less than ten months, but if I’m being honest, I’ve been preparing for the role for over …
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Depth Over Downloads: Why Spending Time with Books Still Matters
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Everyone wants faster information. But no one asks if faster information leads to better understanding — or a better life. In the age of AI and tweet-sized wisdom, we’ve confused information with transformation. But there’s a massive difference between knowing what a book says and being changed by it. The Delusion of Instant Learning In a recent interview, political journalist Ezra Klein admitted he once believed …
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The Jack Reacher Approach to Never Being Caught Off Guard
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There’s no difference between a pessimist who says, ‘Oh, it’s hopeless, so don’t bother doing anything,’ and an optimist who says, ‘Don’t bother doing anything, it’s going to turn out fine anyway.’ Either way, nothing happens.” —Yvon Chouinard, Founder of Patagonia I don’t read much fiction, but I’ve always been hooked on Lee Child’s Jack Reacher. He’s not your typical …
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