From Side Hustle to Sent Ones – The Birth of Penitent Media

It started small. Really small.

Nate was already stretched thin: running an e-commerce business by day, being a husband and dad by night, and squeezing in video edits for a little YouTube channel called Sidehustle Survivalist whenever the house finally went quiet. Bear was grinding a 9-to-5 at Dell while quietly building his own channel on the side, waiting for the right door to open. Ian had the itch too, but his path was still forming.

Then the workload exploded: five long-form videos a week and three shorts a day. What began as a favor turned into a full-on demand. Bear stepped in. Late-night calls, shared Google Drives, and a growing conviction that this wasn’t just a gig; it was a call.

The Holy Spirit kept nudging: Leave the corporate safety net. Go all in.

So we did.

Penitent Media was born (three friends, zero safety net, and a stubborn belief that excellent work and unashamed faith could coexist in a noisy digital world).

The clients came faster than we expected: Ritchie Bros. (Canada’s heavyweight auction giant), Red Rock Canyon Adventure Park, Rotating Acres Farm with their unreal goat-milk and tallow products, plus a growing list of creators who could make the content but didn’t have time to edit or post it. We built the website, claimed the handles, formed the LLC, and got to work.

But remote editing and social media management only took us so far. We wanted to be on the ground: capturing live events, telling stories that actually move people, filming moments that outlive a news cycle.

That’s when Ian came on as partner and co-founder. With his live-audio and video expertise, Penitent went from screen-only to boots-on-the-ground overnight. Suddenly we were running multi-camera rigs at Native Wings Like an Eagle youth events, documenting raw testimonies for Journey of Our One Life, and serving ministries like Grafted Church, E15 Initiative, and Refuge Ruckus.

We’ve never wanted to be just another media company in an oversaturated market. From day one the goal was simple: amplify voices worth hearing, tell stories that matter, and do it all with excellence that points back to the One who called us out of cubicles and into this wild ride.

Penitent Media is still growing (fast). But the heartbeat hasn’t changed: repentant people using redeemed gifts to serve those who have something true, good, and beautiful to say.

The sky isn’t the limit anymore. By God’s grace, we’re already reaching further.