We caught up with the brilliant and insightful Caleb Jahr a few weeks ago and have shared our conversation below.

Caleb, appreciate you joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

It has always been a dream of mine to make a living to support my family, Laura, my wife, and our three kids.

I have an entrepreneurial spirit and also a creative eye for video.

Present day I shoot a wide range of videos. I own and lead Jahr Wedding Films, a small wedding videography business. I’m also the Director of Photography for the Joshua Glover film, Liberty at Stake. And I do a lot of cooperate and freelance projects with agencies and business like Green Clock Films, Walker Media Agency, Blueplate, Event Essentials, and Lasting Legacies, to name a few.

It didn’t start out that way though.

My first wedding I ever led was for a friend. I asked him for $800 total, to shoot and edit his wedding film. That way if it turned out terrible, neither of us would feel too bad about it.

From there I worked my way up to be hired full time by Green Clock, a local video agency, and worked there for two and a half years. I learned a ton there and it helped me rocket into being a full time video freelancer.

It’s all about collaboration. I’ve learned a ton from working with other freelancers who are great and filming and lighting. Every time I do a shoot I learn something more.

Of course, being creative is only half of it. My wife Laura is an accountant, and has massively helped me to become organized with my taxes, rates, invoicing, and so on. The business would be no where near where it is now if it weren’t for her help with the finance and organization side of things.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

My name is Caleb and I love video. When I’m filming for a project or a client, it feels like it’s what I was meant to do. So many things in life have been a struggle, but being able to make a living shooting videos is both so rewarding and feels so natural.

Right out of high school I joined Youth With A Mission (YWAM) which is an international Christian Missions Organization. I staffed at a base in Mazatlan, MX where I worked in the kitchen for six months, cooking two meals a day for about 50-100 people, depending on the season.

After that I staffed a Discipleship Training School (DTS) where I co-led a team of 16 students to Amsterdam, Holland to do street evangelism, and to Lesvos, Greece, to work with refugees.

Fast forward a year and I married my best friend Laura, who I met in Mexico.

We moved to Madison because it was in between where my family lived, (Oconomowoc) and where her family lived, (La Crosse).

I didn’t have any idea of what I wanted to do with my career, so I was contemplating going to college, and also was working as a lot attendant at the Bergstrom Chevy dealership.

While I was working there, popular YouTuber and Vlogger Casey Neistat was the internet sensation at the time. He flew drones and video documented his every day life for all to see. Ever since I was a kid getting my first point and shoot camera at age twelve, I loved taking photos and videos. Seeing Casey do what he did shattered what I believed was possible with video and was deeply inspired by how he saw the world and how he incorporated video.

I saved up money to purchase my first DLSR camera, a Canon 70D, and a DJI Phantom 4 Drone.

I left the car dealership to pursue a career in real estate, and started vlogging to document my real estate journey.

Real estate never really took off for a newcomer in a city like Madison, but people did start to notice the vlogs. I had a couple different agents approach me about using the drone to highlight their real estate listings and it took off from there. I jumped full time into video for real estate agents in mid 2018 and did that until late 2019, when I was hired full time as the lead videographer at Green Clock Agency, a Madison video and marketing agency.

At Green Clock I learned the in’s and out’s of video, as well as the post production process and everything that goes into making a video, from start to finish.

Fast forward to end of 2021, and I was a bit burnt out. We had barely made it through the pandemic, and I wasn’t excited to be doing video like I had been when I first started. I spend a year working for a friend part time, filming weddings as a second videographer for a wedding company in Milwaukee and doing small video gigs here and there to make ends meat. I thought maybe, I would be done with video, and move on to something new. Nothing was off the table. I thought about getting my bachelors degree, going into the trades, or pursing whatever interested me at the time.

The problem was, nothing really interested me. I didn’t want another 9-5 job, and I’ve never been a very good student. I have too much energy and can’t sit still very long.

I had a friend who I was telling my process to, and she said something like, “video can be a really good career you know. You seem to be good at it and maybe you shouldn’t totally give up on it.”

That really got me thinking. What if she was right? What if I gave video one more try?

That conversation happened at the end of 2022, and beginning of 2023 I decided I was going to put all my energy into creating and building a wedding videography brand. It was one of the best decisions I ever made.

While I didn’t make that much money in 2023, it helped me build relationships with wedding professionals, build up my video portfolio, and start to get traction in the Madison area as a wedding professional. Money wasn’t the main focus for me in 2023, building a brand and a reputation was my main priority.

It also started to open the door to people seeing my video work and hiring me for video outside of the wedding sphere.

Fast forward to the end of 2024, I have a wonderful wedding video business (Jahr Wedding Films) that I love and get to pour my creativity into. I’ve loved working with every single one of my couples, who love their wedding videos and will get to relive their special day for the rest of their lives.

I also have a thriving freelance video business (Jahr Media) where I get to work with businesses from all over the state helping them make videos for marketing, advertising, and showcasing the products and services they offer to others.

My dad has even joined into the mix and he and I parter on specific projects where I need a good writer and director.

Let’s talk about resilience next – do you have a story you can share with us?

Money has never come naturally to me, it’s always been a grind. But I know that money would come in time, IF I was able to focus on the craft, do a good job, wow clients, and focus on the satisfaction or whoever was hiring me.

I often see so many new videographers try to get as much money out of the job as they can, but they lack the skills, knowledge, and equipment necessary to complete the job.

I knew that the videos I wanted to create needed to have a certain level of quality to them, but the cameras I needed to buy were thousands of dollars. And that didn’t include batteries, lenses, SD cards, tripods, and everything else that goes into making a quality video.

But despite not having the money to buy the gear I needed, I decided to get a credit card with no interest for twelve months. I thought, if I can work really hard and make great videos and serve my clients really well, this gear will pay for itself.

Sure enough, at the end of 2023 I paid back the $10,000 in gear I had put on the credit card, and I established Jahr Wedding Films as a viable option for couples looking to hire a videographer for their wedding.

Any resources you can share with us that might be helpful to other creatives?

I think the biggest thing that has helped me is collaborating with other freelancers.

It’s so easy to stay in your own little bubble as a freelancer, but if you can get out there and go to meetups, or just collab with other videographers, drone pilots, DP’s, gaffers, grips, and so on, you’ll learn so much more than you would if you just worked solo.

Contact Info:

• Website: jahrweddingfilms.com // calebjahr.com
• Instagram: @jahrweddingfilms // @calebjahr
• Facebook: https://www.facebook.com/jahrweddingfilms/
• Linkedin: https://www.linkedin.com/in/caleb-jahr-9082761ab/
• Youtube: https://www.youtube.com/@CalebJahr