About the Show
Technology affects every business. Most people just don’t know how to talk about it yet.
Trailhead Tech Talk is a monthly podcast built for small business owners, operators, and managers who want to understand the technology they rely on every day — without the jargon, the hype, or the sales pitch.
Each episode, we dig into one tool, one trend, or one technology question that shows up in real businesses across New England. Sometimes it’s a solo conversation. Sometimes we bring in a guest — a business owner who learned a hard lesson, an expert who cut through the noise, or someone doing something interesting with everyday tools.
The goal is simple: leave each episode with something useful you can apply to your business.
Who It’s For
You don’t need a technical background to get value from Trailhead Tech Talk. If you run or help operate a small business and you’ve ever wondered:
- “Should we be using a different tool for this?”
- “Is our Wi-Fi actually good enough?”
- “What even is a data backup, and do we have one?”
- “Our vendor is recommending something — how do we know if it’s the right call?”
— then this show is for you.
Episodes
Episodes are on the way. Subscribe or check back soon — new episodes drop monthly.
Your Business Already Has an IT Department — You Just Don’t Know It
Every small business is managing technology whether they realize it or not. In the debut episode, Justin breaks down what that actually means, why it matters more than most owners expect, and the first question every business should be asking about their technology setup.
The Email That Almost Broke the Business
Business email fraud costs small businesses billions every year — and most attacks start with one convincing message. In this episode, Justin breaks down the most common email threats hitting New England businesses right now, how to spot them before they cause damage, and the no-cost steps every organization can take this week to reduce their exposure.
🎙 Paired with the free Email Security 101 webinar on June 12 — register free →
Live Webinar: Email Security 101
Episode 02 goes deep on email threats — and on June 12, 2026 at 12:00 PM ET we’re hosting a free live session covering the same ground interactively. Ask questions, get a practical checklist, and learn how to check your own domain for spoofing vulnerabilities. Open to all New England small business owners — free to attend.
Sponsor Trailhead Tech Talk
Reach small business owners and operators across New England who are actively making technology decisions. Host-read sponsorships available as pre-roll, mid-roll, episode, and season packages — starting at $50/episode.
Want to be a guest or suggest a topic?
If you have a technology story worth telling, a question worth exploring, or expertise that would help small business owners — we’d love to hear from you.
Get a Free Intro Call