The Team House Ep. 402 — From West Point to the 101st to 1 Million Subscribers | Preston Stewart
Podcast: The Team House
Host: Jack Murphy
Guest: Preston Stewart
Date: March 19, 2026
Episode Overview
In this episode, Jack Murphy welcomes Preston Stewart—a former Army officer, West Point graduate, and prominent military commentator on YouTube. The conversation explores Preston’s path from Midwestern upbringing and military family roots, through his West Point experience, deployments as a field artillery officer with the 101st Airborne, the veteran transition, and ultimately his surprising success as a global-minded, military-focused content creator and analyst. The episode balances firsthand perspectives on leadership, combat, and modern information warfare, with candid reflections on post-military life and the role of veterans and independent media in national security debates.
Key Discussion Points and Insights
Preston Stewart’s Early Motivation and West Point Journey
Branching, Fort Campbell, and Army Life
-
Branch and Post Selection (09:26)
- Explained the “ranking” system for choosing branches and duty stations. Chose Field Artillery as first choice.
- “You rank order at 1 through 20… my field artillery is my first choice. I was excited about that. I wanted to be a fire support officer.” (09:57)
-
Joining the 101st Airborne (2nd Brigade Combat Team)
- Arrival was anticlimactic: reported for duty while the unit was away at a training rotation.
- “There wasn’t [a reception]… I just have to find my way on post and just start looking around at different signs and asking random soldiers, where am I supposed to go?” (12:53)
-
Brigade Combat Team Structure and Deployment Tempo
- Outlines the integrated, modular nature of post-9/11 BCTs, readiness cycles, and the lack of large-scale division training as each brigade rotated independently into Iraq or Afghanistan. (14:25—15:51)
Afghanistan Deployments and Combat Experience
-
Role as a Fire Support Officer (FSO)
- “I loved it, man. That’s the reason I wanted to go field artillery… as a second lieutenant, I had a team… we were a part of that infantry company.” (16:32)
- Coordinated mortars, artillery, airstrikes, and helicopter gunships for infantry operations.
- Increasing digitalization in targeting and fire support: “At the schoolhouse, they were still teaching [map and plotting boards]… but then once you get into the field, it was all digital at that point.” (18:48)
-
First Afghanistan Tour: Kandahar, Zari District (2010–11)
- Deployed in the surge, vast AO—brigade covering Kandahar to Helmand.
- “When you went west of the city… all the way over to Helmand, was held by our brigade combat team. It was a big area…” (25:03)
- Described living in rough conditions, setting up outposts in Taliban territory, and close partnership with Afghan units.
- Field artillerymen often repurposed as infantry in tough fights (notably in the Arghandab Valley).
- “That was a serious fight, a very serious dismounted fight, and our artillery were there doing it… it was an artillery unit and guys will… figure it out and they’ll get the job done.” (26:49)
-
Nature of Combat and Challenges
- “You wake up and there’s some issue and you don’t know what the issue is… you’ve got to piece it together.” (23:03)
- Leadership stress, feeling of “not being forward enough,” and the burden of responsibility for lives:
- “As an officer, your job is not going to be very sexy a lot of times… my job was to be back a little bit and help kind of sift through the assets.” (29:42)
- Emotional difficulty when others are at direct risk and you’re at the command post: “It has to happen. But I felt sick to my stomach, like, is this what I’m going to be doing while these guys are out there?” (29:42—31:18)
-
Classic Air Assaults and “Mop Up” Operations
- “We spent the last 60 days doing air assaults across southern Afghanistan… special operations would go in and kick the hornet’s nest… and then we’d come in with a battalion size presence.” (33:11–35:43)
- Precariousness of suddenly being moved to unknown areas after “learning” a region.
Advising and Training Afghan Forces: Second Deployment (2012, Laghman)
Transition to Civilian Life
Building a New Career: Social Media, Content, and Military Analysis
-
Genesis of the YouTube Channel
- COVID downtime, interest in military history, and public hunger for accessible, clear explanation when the Ukraine conflict broke out.
- “I started making some content about military history because I like military history. And that was just doing well. People would watch it, which is crazy to see that.” (58:23)
-
Content Strategy: Focus on Current Events
- Creates updates on recent military developments, especially Ukraine, Iran, and Israel/Hezbollah.
- Engages directly with soldiers/units in-theater for interviews and fundraising.
- “A lot of the videos, even three or four days later, they’re just not all that relevant because things have changed.” (61:26)
- Benefits of networking via social media:
- “Content is networking in so many ways.” (62:37)
-
Comparing Pay and Growth: Viral Moments
- Sometimes windfall growth and income:
- “With… shorts on YouTube… a couple of those went viral and made like $7,000 in a month.” (60:08)
- Growth spikes linked to world events—surges in subscribers during crises (88:52).
- “Get into war and conflict, start a couple wars. Problem solved. Easy enough.” (89:50)
Reflections on the Modern Information Environment
-
Complexity and Challenges of War Reporting
- Jack Murphy: “Our government doesn’t necessarily do a great job of… explaining how the military works, explaining combat to a civilian audience, and sometimes even to the military itself.” (63:56)
- Attempting simplicity and accessibility, striving to balance jargon for both military and public audiences.
- “Instead of saying JTAC or fob, let’s open that up a little bit and explain the guy that talks aircraft onto targets…” (64:44)
-
Disinformation and AI in Modern War
- Discussed the proliferation of fake images and deepfakes in Syria, Gaza, Iran, and the difficulty in verifying information.
- “If you’re doing that, we’re in trouble. The vast majority of people aren’t spending that much time on it… can’t tell the difference.” (77:21)
- Noted deliberate censorship and info gaps (e.g., Israel asking citizens not to share missile impacts)—creating openings for propaganda/AI fakes.
-
Skepticism Toward Official Narratives
- Reflection on the Iraq WMD fiasco:
- “I always wonder if there is more of an independent media… would more people have been able to flesh that out and say, ‘This doesn’t make sense’…” (79:36)
- Worries about escalation with Iran and the ease with which war might be entered today, without public buy-in or explanation.
- “If they don’t really need our support to do it, what does it matter if we catch them?… The American people say we’re not on board—what does that even matter?” (82:20)
Military Technology: Artillery, Drones, and Lessons from Ukraine
Reflections on Service, Transition, and the Veteran Community
Notable Quotes & Memorable Moments
Timestamps for Important Segments
| Time | Topic / Quote |
|-----------|-------------------------------------------------------------------------|
| 03:20 | Preston’s path to West Point, impact of 9/11 |
| 05:46 | West Point punishments (“hours”) |
| 09:57 | Explaining branch selection, choosing Field Artillery |
| 12:53 | Arriving at Fort Campbell, anticlimactic unit reception |
| 16:32 | Describing FSO role, responsibility, and love for the job |
| 23:03 | “Wake up and there’s some issue…” — deployment problem-solving |
| 25:03 | Scope of 101st involvement in Afghanistan |
| 29:42 | First combat, tension of command post vs. “outside the wire” |
| 33:11 | Air assault “mop-up” operations, classic 101st “airmobile” missions |
| 43:50 | Training Afghan army on D-30 howitzers; limits of capability |
| 50:59 | Transition struggle—civilian resumes and job search |
| 58:23 | Launching a YouTube channel during COVID, accidental career |
| 62:37 | “Content is networking in so many ways” |
| 70:30 | Lessons from Ukraine: drones changing artillery’s role |
| 77:21 | AI and deepfakes—“If you’re doing that [squinting at video] we’re in trouble.” |
| 79:36 | Value of independent media in conflict escalation moments |
| 86:02 | Reflecting on the value of veterans |
Where to Find Preston Stewart
- YouTube: Preston Stewart
- Socials: @PrestonStewart (Twitter/X, Instagram, TikTok)
Closing Thoughts
This episode offers a grounded, deeply personal view into the life cycle of a post-9/11 Army officer—from youthful idealism and the “rush” of deployment, through the grind and ambiguity of advising, the jarring transition back to civilian life, and finally public relevance in a new role—educator and explainer for a global audience in a world where independent, apolitical military analysis is more in demand (and more contested) than ever. The conversation is candid, emblematic of a veteran generation still adapting and still striving for purpose.
“I love what I do every day. I’m excited about it. And going to a drill weekend meant two days of sitting in a random classroom… and I couldn’t do this. It was starting to bleed into getting phone calls on Tuesdays to knock something out for the army—like, no, I’ve got other stuff I’ve got to do.”
—Preston Stewart (57:20)
“This is like going back to the winter of ‘03, trying to wonder, like, which way is this going to go.”
—Preston Stewart, on watching today’s confrontation with Iran (81:03)
Note:
This summary omits all advertisements, intros/outros, and focuses only on the substantive discussion between Jack Murphy and Preston Stewart. For an accessible and engaging account of military service, transition, and the modern information battleground, this episode is not to be missed.