Side Hustle Squad Ep 320: The Man Behind the Mic – Getting to Know Jason Triplett!
Host: Mike Garvey
Guest: Jason Triplett (JT), with Eric Triplett & Adam Fullerton
Date: March 26, 2026
Episode Overview
This episode takes a vibrant, freewheeling dive into the life and mindset of Jason Triplett—JT—a Marine Corps veteran, ex-musician, mining industry sales pro, and newly minted podcaster. Mix in some brotherly banter (with Eric Triplett, “The Pond Digger”) and sales wisdom, all against the backdrop of the Sponsor Games podcasting and creator event. Listeners get a candid look at side hustling, career pivots, relationship-driven sales, and the irreplaceable value of authenticity, grit, and fun in entrepreneurship.
Key Discussion Points & Insights
1. Who Is JT? – Background & Personality
- Long Beach Roots and Music Dreams:
- JT grew up in Southern California, tried to “find my way in this world” (02:57), leaning hard into music for a big part of his early years.
- “I made a lot of sacrifices in life to follow that dream. Never got to that level of rock stardom I wanted.” – JT (04:05)
- Played in Fallen Union for 11 years before the passion faded: “It wasn't fun anymore” (06:07).
- Marine Corps & Life Pivots:
- Joined the Marines (1996–2000) to straighten out his life, and credits the Corps for much-needed discipline (04:47).
- Returned to music after service, then shifted careers as interests changed (05:01).
2. The Journey into Podcasting
- From Music to the Mic:
- Left music behind and, encouraged by his brother Eric, started podcasting (07:34).
- Initial podcast was “In the Mind of Reels” (his motorcycle club nickname), but later rebranded as “In the Mind of JT” (09:20).
- “Eric was like, ‘You should have just kept it JT.’ Leave it to Eric to be brutally honest.” – JT on rebranding (09:30)
- JT’s current podcast is unapologetically broad: “Everything’s on the table—current events, politics, religion...” (54:22)
3. Insights from the Sponsor Games Event
- Taste of the Podcast/Creator World:
- JT, Eric, and Adam discuss how, even among marketing pros, few have actually hosted podcasts, making their hands-on experience unique (14:11).
- Book is the New Business Card:
- “It feels like everyone here has a book—maybe that’s the next step for us.” – Conversation (16:55)
4. Writing His Story – Memoirs of JT
- Family Legacy:
- JT has been privately writing his life story since 2017—“I want to document... some of the cool shit I’ve done” (17:59).
- Now considers using AI to help format and finish his memoirs (20:15).
5. Mining Equipment Sales as a Main Hustle
- Territory & Job:
- Sells mining equipment across CA, NV, AZ, now focusing on parts & service rather than big machines (11:20).
- Emphasizes personal relationships as key to sales—“If someone likes you, they're most likely gonna buy from you” (31:20)
- “Sometimes you know you’re not going to sell anything, you’re just there to build the relationship” (34:24)
- Trust & Authenticity:
- Open about not always having the answer—“I learned early on: say you don’t know and find out” (28:49).
- Adam gives sales language tip: use “transparent” instead of “honest” (29:12–30:19).
6. Sales Tactics, Gatekeepers, and Building Rapport
- Bypassing Gatekeepers:
- Early Fastenal days taught JT to park around back, talk with maintenance staff, and enter through “the back door” to get to decision-makers (39:27–41:25).
- Adam shares a similar story: sometimes you just “walk in like you own the place” (43:04).
- Relationship Wins:
- JT’s best customers trust him so much they’ll hand him a competitor’s quote to beat (49:35).
- “You sure you want to give me that? Yeah, call me.” (50:39)
- $30K sale thanks to trust and pricing transparency (50:47).
- JT’s best customers trust him so much they’ll hand him a competitor’s quote to beat (49:35).
- Pricing & Mindset:
- Will intentionally undercut on margin just to win business—“I’d rather quote low and get the sale than nothing at all” (53:00).
7. Lessons From Missed Side Hustles
- Trying & Dropping Mobile Detailing:
- JT jumped into mobile detailing on Eric’s suggestion, spent $7K on supplies... and realized quickly, “Manual labor is not one of them [my skills]” (23:56).
- Self-Assess & Pivot:
- Knows to stick to what fits his personality—“I like to use my mind, make suggestions, be personable in sales. Manual labor is not it, bro.” (23:58)
8. The Human Side of the Sale
- Empathy & Personal Connection:
- “You let them talk... they want to use you as a vent, their psychologist. Info is power: next time, ask about their kid, and they’ll remember you.” (33:08)
- Small Gestures, Big Impact:
- Bringing breakfast sandwiches for the site entry guards led to valuable tips (“M-SHAW’s here, don’t come on site!”) and prevented substantial fines (46:53).
Notable Quotes & Memorable Moments
- On Music Dreams:
- “I sacrificed a lot... to pursue, go that route. Some successes, but nothing crazy. I started realizing I’m just not in love with that anymore.” – JT (05:34)
- On Podcasting:
- “My partner wanted to do one episode a month. I’m like, ‘No, let’s do this like a couple times a week!’” – JT (07:39)
- On Sales & Authenticity:
- “If someone likes you, they're most likely gonna buy from you.” – JT (31:20)
- “I learned early on: don’t try to bullshit. Just say, ‘I don’t know, but I can get you the answer.’” – JT (28:49)
- On Learning from Mistakes:
- “I’ve done so much stupid over the years, and Eric’s just like, nothing surprises him anymore.” – JT (21:55)
- On Sales Tactics:
- “You don’t go through the front. You go through the back, dude. Maintenance guys are the key.” – JT (39:27)
- On Pricing:
- “I’d rather sell you something at a low margin than not get the sale at all.” – JT (52:53)
Standout Segments & Timestamps
| Segment | Timestamp | |-----------------------------------------------|-------------| | JT’s Background – Marine & Musician | 03:20–06:40 | | Pivot to Podcasting, Rebranding Struggles | 07:23–09:49 | | Inside Sponsor Games: Podcasters & Creators | 13:45–17:12 | | On Memoirs: Documenting a Family Legacy | 17:12–20:17 | | Sales Job: Mining Equipment & Strategy | 11:20–12:13/28:04–34:00 | | Sales Language Tip: “Honest” vs “Transparent” | 29:11–31:00 | | Gatekeeper Hacks: Entering Through the Back | 39:26–41:25/43:04–44:30 | | Real-Life Sales Win via Relationships | 49:35–50:52 | | Side Hustle Failure: Detailing Business | 23:36–24:31 | | Building Empathy in Sales | 33:08–34:24 | | The Value of Small Gestures | 46:53–47:56 | | JT’s Podcast Info/Where to Find Him | 53:41–54:45 |
Final Takeaways
- Success in business is less about a perfect system, more about knowing yourself, owning your mistakes, being transparent, and giving a damn about people.
- Side hustles are about experimentation—some work, some don’t, but each offers lessons.
- Relationship-building and persistence yield the biggest wins in sales, even in the grittiest industries.
- Personal stories and authenticity connect, whether in the field or behind the mic.
Connect with JT & The Crew
- Facebook: JT Space Triplett
- Instagram & TikTok: @JTRoxYou
- Podcast: In the Mind of JT (YouTube & podcast directories)
- Topics: Everything’s on the table—current events, politics, religion, and more!
This episode fuses real talk, industry insight, and plenty of laughs—a must-listen for anyone hustling on the side, especially those who value honesty, relationships, and a bit of irreverence on their entrepreneurial journey.