Business Under Fire | From Jail To An Artist 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
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