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

• Origins and Military Aspirations

  • Preston describes a background familiar to many post-9/11 soldiers:
    • “I was a sophomore in high school when the 9/11 attacks occurred… at that period in my life trying to decide what’s next and the military just jumped out.” (03:20)
  • Both grandfathers were veterans; he grew up "playing army" and aspired to service.

• Choosing West Point

  • Negotiated with parents: they wanted him to go to college; he wanted to join the military.
    • “We found this middle ground of what if I can go to college and do the military?” (03:20)
  • He worked a “post-grad” year to meet West Point’s standards, entered in 2005 during intense Iraq War years.
  • The academy’s harsh schedule:
    • “They would take away your time was the punishment… you literally just march back and forth in a line for 50 minutes and then they give you a 10-minute break and then you do it again. It’s just a waste.” (05:46)

• Cadet Life: Academic and Athletic Rigor

  • Required participation in sports, high general fitness level, and the culture of intramural and club competition.
    • “Everyone’s a good athlete that’s there… we’d go out play intramural football and [the guys] we’re going up against were four-year varsity lettermen in their high school.” (06:47)
  • Shoutouts to West Point rugby and the tight-knit nature of such sporting communities, including documentaries and books capturing their legacy.

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)

• Role Shift: Advisor to Afghan Artillery

  • Whole deployment focused on coaching/training Afghan National Army in use of D-30 (Russian 122mm) howitzers.
    • “Trying to explain to the gunner that you’re not going to see the target… to the forward observer that you’re not going to see the gun. We had a very, very hard time getting that to really mesh.” (43:50)

• Cultural and Educational Hurdles

  • “Most of the time, by the time we left, they were using them in direct fire and just slinging rounds into the sides of hills.” (44:53)
  • Afghan mechanics were ingenious with vehicles, but less able to grasp abstract indirect fire concepts, e.g., indirect fire, forward observation, etc.

• Systemic Issues

  • Afghan officers would prioritize showing off hardware in city centers, not tactical placement.
  • “It seemed like they were doing things for us… checking the box while we’re there. And if we weren’t showing up, then they weren’t showing up.” (48:15)

Transition to Civilian Life

• Leaving Active Duty and the Struggles of Transition

  • “It was weird… You don’t know what you don’t know, it’s the first job I’d ever had.” (50:59)
  • Challenge of translating military experience to civilian resumes—what matters to a hiring manager vs. what means something to you.
    • “My first resume write-up was talking about number of fire missions we called in southern Afghanistan… it means nothing to anyone else.” (50:59)

• Early Civilian Jobs and National Guard/Reserve Service

  • Bounced through insurance sales (miserable), then to a software company:
    • “My boss… would just, this one’s on you, hey, can you figure this out?… It was a breath of fresh air.” (52:50)
  • Returned to the National Guard for the sense of purpose and camaraderie:
    • “Configuration software might not go live on Thursday. So went back into the National Guard at that point… checked a lot of the boxes of being back with soldiers.” (54:50)
  • Eventually, phased out of service as civilian career flourished.

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

• Changing Nature of Artillery

  • Artillery increasingly threatened by drones; frontlines now so deep artillery can’t be close enough without being destroyed.
    • “The kill zone has gotten too big… to get howitzers close enough to be able to hit Russians, they’re in drone range and get taken out.” (70:30)
  • Ukraine repurposing artillerymen as drone operators, sometimes in classic “call-for-fire” style but now with UAVs.

• Future of Large-Scale Warfare

  • US likely to fight differently—if forced into the same style of war as Ukraine/Russia, “we failed somewhere along the lines” due to loss of air superiority.
  • The greatest concern: how adversaries will adapt and the proliferation of cheap, deadly drone-based IEDs.
    • “IEDs are flying at you… we aren’t ready to deal with that yet.” (73:22)
  • AI making its mark in both kinetic and informational/psychological warfare.

Reflections on Service, Transition, and the Veteran Community

• Value of Veterans in Society

  • “If I was going to start a business tomorrow, I’d want to hire veterans… I know they’d be able to figure it out and would run through a wall…” (86:02)

• Changing Veteran Demographics and Recruitment

  • Fewer veterans as time passes from major wars; looking forward, questions about what draws people into service without a galvanizing event like 9/11.
  • The importance of honest “good reviews” from veterans to sustain the institution and inspire future volunteers.

Notable Quotes & Memorable Moments

• On Cadet “Hours”:

  • “You’re in your full dress uniform with a rifle and you literally just march back and forth in a line for 50 minutes and then they give you a 10 minute break and then you do it again. It’s just a waste.” (05:46, Preston Stewart)

• On the Emotional Stress of Command:

  • “You just don’t want to let anybody down… It felt like a pinch point. So it made me focus even harder. I loved it. It was favorite job.” (18:33, Preston Stewart)

• On Transitioning Out:

  • “Trying to move back into the civilian workforce and not really knowing what I should be looking for… The nightmare of moving your military service onto like a civilian resume…” (50:59, Preston Stewart)

• On Independent Media in War:

  • “This is networking. Content is networking in so many ways.” (62:37, Preston Stewart)
  • “I always have in the back of my mind our buildup to the Iraq invasion. I think that’s one of our defining moments for our generation… would more people have been able to say, ‘This doesn’t make sense’?” (79:36, Preston Stewart)

• On Lessons from Ukraine:

  • “Gotta stay adaptable… we’ve got to be able to change. The kill zone has gotten too big… if you can’t move the howitzers forward, they’re repurposing artillerymen to serve in that same general role with drones.” (70:30, Preston Stewart)

• On Modern Info Ops:

  • “I hope I’m not checking out, but… if I see a video on social media of a strike in Iran or Israel, I just assume it’s not real at this point. I can’t trust it.” (77:53, Jack Murphy)

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.