the tension between success and comfort, and how being yourself is the greatest risk of all—and the only one that pays off long-term.

If you’re a photographer, videographer, planner, or designer who’s felt stuck between playing it safe and playing full out, this one’s going to hit deep. It’s not about the camera or the venue. It’s about the mindset it takes to stay real, keep growing, and build a brand with soul.

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About Chris Jespersen

A sought-after filmmaker with a larger-than-life personality, Chris Jesperson is a destination wedding cinematographer and founder of Storybox Cinema, who truly loves his work and clients. He’s passionate about people and parties and approaches filmmaking with joy and a grateful heart.

As a destination cinematographer, Chris travels the world with his team––capturing events in some of the most beautiful places around the world, from New York to Phuket, London, Sea Island, Italy, Montenegro and beyond.

Passionate about entrepreneurship, Chris is a mentor to many. He offers his insights and expertise to other small business owners across the country at business education events such as Engage and Wedding Pro workshops.

Key Takeaways

1. Risk Is the Real Job—Especially in Luxury

Chris reminds us that creativity without risk is just repetition. Whether it’s a new angle, a bold drone shot, or an entirely new way of showing up, the job is to keep pushing the edge—especially when the stakes are high.

2. Playing Small Has a Cost—And It’s Often Invisible

Staying safe might feel smart in the moment, but over time it erodes your confidence, dulls your creativity, and slowly disconnects you from the work that lights you up. The cost of playing small? Regret.

3. Being Yourself Is the Ultimate Risk—And the Ultimate Advantage

In a world obsessed with performance and polish, showing up as your full, unfiltered self is scary—but it’s also what builds the deepest trust and most lasting relationships. People don’t just hire talent. They hire you.

4. The Long Game Changes Everything

When Chris shifted from short-term wins to long-term relationships, everything changed. The energy, the bookings, the clarity. The fastest way to grow your business? Think 10 years ahead—and act like you’re already there.

5. Opportunity Lives on the Other Side of Service

Getting in the room takes courage—but staying in the room takes humility. Chris built his brand by dancing when no one else would, writing hand-written notes, and asking, “How can I help?” before asking for anything in return.

Episode Timestamps

[00:00] Intro banter and the first impression that sealed a friendship

[02:30] From YouTube tutorials to global weddings: Chris’s unexpected start

[06:00] How risk-taking shaped his business—and why we’re all more nervous than we admit

[10:45] Dancing as a metaphor for business (and confidence)

[19:25] The “passport story” — how Chris bet everything on one shoot

[27:00] Why your biggest wedding is the time to take the biggest risk

[32:00] How to actually see (and seize) opportunity when you’re in the room

[37:00] The long game mindset—and why it’s the best-kept secret in luxury

[41:00] The ultimate risk: being yourself

[44:30] Identity, imposter syndrome, and stretching into your next season

[50:00] Building a team culture around creativity and curiosity

[53:00] How to reignite your passion when the work gets too easy

Resources and Links

Visit Storybox Cinema website.

Follow Chris on Instagram

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