#27: The Art of Photography, Vision, Rejection & Timeless Storytelling

#27: The Art of Photography, Vision, Rejection & Timeless Storytelling

December 03, 2025 59 min
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🤖 AI Summary

Overview

This episode dives into the life and philosophy of Squint, a renowned photographer and filmmaker whose work captures the essence of sports, culture, and entertainment icons. From his early start in Palo Alto to photographing legends like Nas and Steph Curry, Squint shares insights on storytelling, resilience, and the art of photography. He reflects on overcoming rejection, rediscovering black-and-white photography after personal loss, and the importance of relationships and love in his craft.

Notable Quotes

- No one's going to govern my income ever. Like, I'm not going to be limited to that. I'm going to do what I'm called to do at any cost. - Squint, on the impact of losing his father and shaping his career.

- I haven't lost in Monopoly in almost 20 years. But the wild part is, when Steph wins, he wins for the world. - Squint, on Steph Curry's selflessness and competitive spirit.

- You get so much further in life by showing love. If I love you, I’m going to do everything in my power to see you better than myself. - Squint, on the power of love and its role in his life and work.

🎥 The Beginnings of a Visual Storyteller

- Squint’s journey began at age five with his mother’s 110 camera, sparking his love for photography.

- By age eight, he was working at a local TV studio, progressing from camera operator to producer over a decade. This early exposure instilled discipline and shaped his approach to storytelling.

- At age 12, he wrote a list of dream subjects to photograph, including Nas, Kobe Bryant, and Michael Jordan. He completed this list decades later, marking a full-circle moment in his career.

📸 The Art of Photography

- Squint emphasizes capturing emotion and intimacy in his images, often focusing on subtle moments like the eyes or body language.

- He prefers black-and-white photography for its timeless quality, noting how it evokes mystery and longevity compared to color.

- His cinematic background influences his framing and composition, ensuring each shot feels dynamic and intentional.

🚫 Rejection as a Superpower

- Squint views rejection as a tool for growth, citing his ability to adapt and find alternative paths when faced with obstacles.

- He shared a story of being denied access to shoot The Killers but pivoting to capture a unique shot from a balcony, turning rejection into opportunity.

- His resilience stems from a mindset shaped by his upbringing in Palo Alto, where failure was seen as a stepping stone to success.

🏀 Building Trust with Icons

- Squint’s relationship with Steph Curry evolved through mutual connections and consistent work. He earned Steph’s trust by capturing moments that reflected his discipline and selflessness.

- The creation of the coffee table book Shot Ready was a dream come true for Squint, blending Steph’s career milestones with his own artistic vision.

- Squint’s approach to working with high-profile figures centers on genuine care and building meaningful relationships beyond the lens.

❤️ Legacy, Loss, and Love

- Losing his father during college profoundly impacted Squint’s life, leading him to drop out and take on family responsibilities.

- For eight years, he avoided black-and-white photography, a medium his father admired, until rediscovering it as a way to honor his memory.

- Squint’s philosophy revolves around love—whether in his craft, relationships, or fatherhood. He prioritizes being present and creating a legacy rooted in kindness and impact.

AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.

📋 Video Description

Before becoming the photographer trusted by the world’s biggest icons, Squint built his path on discipline, creativity, and a lifelong commitment to mastering storytelling. Raised in Palo Alto and shaped by years inside a TV studio before he turned 18, he grew from a kid with a camera into a filmmaker and cinematographer behind iconic portraits of Nas, Michael B. Jordan, Dave Chappelle, Draymond Green, and Steph Curry. As co-creator of the New York Times bestselling book Shot Ready, his black-and-white, emotionally driven style reflects a belief that great photography comes from patience, intention, and truly seeing people.

In this conversation, he breaks down the ingredients of a powerful photograph, motion, eyes, framing, intimacy, and explains why rejection became his greatest superpower. He shares how he wrote a list of dream subjects at age 12 and photographed every name on it, how fatherhood reshaped his purpose, and why staying in the Bay Area defined his career more than any move to LA or New York. Squint reflects on rediscovering black-and-white photography after losing his father and earning Steph Curry’s trust through consistency, humility, and discipline.

A grounded masterclass in photography, vision, resilience, and legacy, showing what it takes to create work that endures. This episode is a reminder that great art is built on love, discipline, and showing up, especially when the world tells you no.

Follow Squint - Instagram: https://www.instagram.com/iamsquint
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 Introduction & how Squint became a visual storyteller
3:48 First camera at age five
5:17 Running a TV studio at eight
6:44 Deciding at ten to do this forever
8:09 The list he wrote at age 12
9:46 Shooting Nas for the first time
12:12 How he processes rejection
13:46 The Killers story
16:30 Identity vs his work
18:47 What makes a great picture
20:31 Reading emotion through the eyes
22:37 Atmosphere vs the subject
26:13 Black and white vs color
28:41 Training his eye
32:59 Mastering relationships in the industry
35:32 Showing people how he sees them
48:53 Steph Curry’s discipline & ego
50:20 Losing his father & rebuilding
56:01 What makes a great dad

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Hashtags:
#PhotographyMasterclass #VisualStorytelling #BlackAndWhitePhotography #CinematicPortraits #ShotReady #StephCurry #CreativeDiscipline #IconicImages #ArtOfSeeing #LegacyAndPurpose #CreatorsJourney