The Reality of Running a Creative Business: Imposter Syndrome, Spreadsheets & Staying Authentic

The Reality of Running a Creative Business: Imposter Syndrome, Spreadsheets & Staying Authentic

Join me for an honest conversation with Colin Gregory, founder of Sinclair Collective, about what it really takes to build a creative company in today's evolving content landscape.Colin is a filmmaker and director of photography who's been my go-to collaborator for nearly 20 years. In this episode, we dive deep into the messy reality of creative entrepreneurship—from dealing with imposter syndrome on major commercial shoots to learning to love spreadsheets as much as cinema cameras.Key Topics Discussed:•The art of collaboration: How to navigate creative differences on set without ego getting in the way•Balancing creativity and business: Why spreadsheets are just another form of art (even if you hate them)•Imposter syndrome: How self-doubt can coexist with confidence and actually fuel growth•The evolving content industry: Why 60-second commercials are dying and what's replacing them•AI in filmmaking: The tools we're actually using (audio cleanup, transcription, editing workflows)•Tolerance for uncertainty: Building the muscle to thrive in chaos and solve problems on the fly•Staying authentic: How honesty and vulnerability build stronger client relationships than pretending to have all the answersConnect with Colin:Website: sinclaircoilective.comInstagram: @sinclaircoilective#Filmmaking #Entrepreneurship #CreativeBusiness #ImposterSyndrome #ContentCreation #ProductionCompany #BusinessTips

Healing isn't a luxury. It's a business that works. Jamie Fanara.

In this episode of Makers & Misfits, Corbyn sits down with Jamie Fanara of Body Craft Wellness, a massage therapist and educator who has spent more than two decades helping people heal through intuition, purpose, and a whole lot of grit. Jamie shares how she built two thriving businesses almost entirely through word-of-mouth, why trusting your gut matters more than any business plan, and how to grow without losing your soul in the process. It’s a conversation about balance, burnout, and the magic that happens when you follow what feels right.

The Cinematographer Who Built His Career on Chaos-Tom Ciciura

Cinematographer, problem-solver, and Chicago workhorse Tom Ciciura joins host Corbyn Tyson for a brutally honest conversation about filmmaking, creativity, uncertainty, and surviving in an industry built on chaos. Tom talks about growing up on the south side of Chicago, how his mom literally found his first film job in the newspaper phone book, and how he worked his way onto sets for films, TV shows, and commercials across the Midwest. From cameras and location scouting to long nights, freezing shoots, and building a business around systems and efficiency — Tom’s story is a masterclass in grit. This episode dives into: • What it really takes to break into the film industry • How cinematographers think about story, light, and problem-solving • Chicago’s exploding production ecosystem • Building a production company from the ground up • The art of tinkering, craftsmanship, and staying curious • Managing uncertainty and the inner voice that tells you you’re not enough • Wild behind-the-scenes stories from the early days If you’re a filmmaker, creative, DP, agency person, or anyone obsessed with how things get made, you’ll love this conversation.

The Messy Magic of Creativity with Sarah Tyson

In this first episode of Makers & Misfits, I sit down with my wife, Sarah Tyson, the creative mind behind Burr Oak Floral. We talk about how she built her floral business from scratch, the challenges of pricing creativity, and what it’s like raising a house full of artists. This conversation is about more than flowers — it’s about the messy magic of turning passion into a profession and building a family culture that makes space for creativity.