From Jail To An Artist | Business Under Fire S2 E13

On this episode of Business Under Fire, we sit down with Jacob Carroll, founder of Till Death Digital Media, a wedding photography and videography business based in Seguin, Texas — just 11 months into the game and already turning heads. Jacob's path here wasn't typical. Before picking up a camera, he spent years working as a correctional officer, starting as an 18-year-old control room operator and working his way up through general population, lockdown, psych units, and a prerelease parole unit. He opens up about growing up around the live music security industry, watching his mom battle addiction (and later become a substance abuse counselor herself), failing out of the police academy by two points, and how years inside a jail shaped — and jaded — his view of people. We talk about the leap from law enforcement to full-time creative entrepreneur, starting Till Death Digital Media the same day his daughter was born, landing his first paying client through a wedding planner connection, teaching himself videography through YouTube, and the biggest lessons from his first year in business — including why raising his prices actually helped him close more sales. We also get into his FAA Part 107 drone license, the DJI import ban, and how he's building his reputation through local think tanks, craft shows, and word of mouth in Seguin. If you're thinking about starting a creative business, working for yourself, or just want a raw conversation about life, jail, and entrepreneurship — this one's for you. TIMESTAMPS 00:00 – Intro: Meet Jacob Carroll & Till Death Digital Media 00:47 – Why "Till Death" Digital Media? 01:35 – 11 months in business (started the day his daughter was born) 02:26 – Background: growing up around live music security 03:07 – From Jimmy John's to the Sheriff's Office 03:35 – First job: control room operator in a county jail 04:39 – Talking to inmates through the intercom 05:00 – His mom's struggle with addiction and eventual recovery 07:45 – Promotion to correctional officer & the police academy 08:01 – Failing the police academy by two points 09:03 – Life inside the jail: the daily grind 11:19 – Working the prerelease parole unit 11:49 – Does the justice system actually rehabilitate people? 13:24 – Losing his creative spark working in corrections 13:59 – "Your reality is not my reality" 16:09 – Staying jaded vs. staying open 19:32 – Advice for anyone considering a career in corrections 19:56 – Starting a pressure washing business on the side 21:26 – What scares people about starting a business 22:05 – Getting the paperwork done & landing the first client 23:14 – Learning videography from YouTube 25:13 – What sets Jacob apart from other photographers/videographers 28:04 – His artistic background and how it shows in his work 31:07 – Becoming an FAA-licensed drone pilot 32:21 – What it takes to get a Part 107 license 33:01 – The DJI drone ban and its impact on the industry 38:04 – Biggest business lesson: closing sales 38:47 – Why raising his prices actually increased sales 40:07 – Marketing: Facebook ads, Instagram, and craft shows 41:33 – Becoming "the person of interest" in your local market 42:05 – Getting his work into local shops (Guadalupe Trading Company) 43:15 – The value of joining a local entrepreneur think tank 47:06 – Balancing family life with running a business 48:29 – The real difference between working for someone and working for yourself 50:00 – Hardest lessons from year one 50:49 – Jacob's goal: opening his own photography studio 51:52 – How to find and contact Jacob 53:26 – Outro CONNECT WITH JACOB CARROLL / TILL DEATH DIGITAL MEDIA 📍 Based in Seguin, TX — available to travel anywhere FOLLOW BUSINESS UNDER FIRE 🔔 Subscribe for new episodes 👍 Like this video if you enjoyed it 💬 Drop a comment — what part of Jacob's story hit home for you?