Evolved Radio

Brian Gillette took his first MSP job as VP of Sales and had to ask what MRR stood for. Three years later that company had grown from about $700K to over $2 million in recurring revenue, and he did it without a marketing budget. Before MSPs, he was an actor in LA, which is where he learned to hear no at audition after audition and keep his self-worth out of it. Today he runs Feel-Good MSP, hosts The MSP Sales Podcast, and wrote How to Sell a Shitload of Managed Services (Without Selling Your Soul). His approach, the Feel-Good Close, is built for technical owners who hate the idea of being a salesperson. We’re talking about why fear-based selling stopped working for MSPs and what replaces it when the person running the process would rather be fixing a server. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. (00:00) - Brian’s MSP Origin Story (01:34) - Prospecting Tiers Ranked (04:25) - S Tier Video Outreach (06:07) - Stop Selling Features (08:49) - Turning Tech Into Outcomes (10:51) - Different vs Better (13:02) - Magic Trick Differentiation (18:34) - Handling We Have IT (22:28) - Curiosity Over Persistence (24:20) - Beyond Fear Based Selling (26:16) - Risk Without Fearmongering (28:04) - Stewardship Over FUD (28:59) - Trust Beats Dirty Tactics (30:36) - Talent Versus Grit (33:42) - Sales As A System (36:55) - Technical Founder Mindset (38:57) - Networking SOPs That Work (41:57) - Three Cs For Rapport (43:35) - Smooth Sales To Onboarding Handoff (47:39) - One Action For Next Week (49:26) - Closing Advice And Encouragement

MSPs and accounting firms have a lot of shared DNA. My guest today thinks that accounting is paving the way for MSPs in AI adoption. Peter McCarroll has spent over 30 years in public accounting, and he's been helping other firm owners rethink how they price and deliver their work as AI takes over the routine stuff. His view is that accounting is the canary in the coal mine for professional services, with MSPs next in line.Today we're looking at what's already happening in his industry and what MSP owners can learn from it before it reaches them. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

Today we're talking about something every MSP is running into right now: how do you let your team actually use AI without turning your ticket data into someone else's training set.My guest today is Callen Sapien. Callen is currently building Synthreo, an AI infrastructure platform built specifically for MSPs and SMBs, and before that he was Chief Strategy Officer over at MSPbots.Here's how I've been framing this one. We spent a decade dragging our clients to the cloud. Then we spent a decade dragging them to security. And now our clients are dragging us into AI, whether we're ready or not.So today Callen and I are digging into how you actually give your whole team AI superpowers without blowing up your PII exposure in the process.This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. (00:00) - AI Risk for MSPs (01:10) - Ticket Data and PII (03:18) - Three Safety Buckets (05:56) - Zero Data Retention (14:00) - Shadow AI in SaaS (15:54) - Protecting Process IP (19:41) - From Prompts to Agents (22:31) - Cloud vs Local Models (26:01) - Hallucinations and Guardrails (29:15) - Batching and Delegation (37:34) - Managed Intelligence Opportunity (41:21) - Synthrio Approach and Portability (44:13) - Governance and Back to Basics (46:49) - Wrap Up and Contact

We've got a repeat guest on the show today. Alex Dow is back. Co-founder of Mirai Security, and currently an enterprise security architect for a large financial firm, and honestly one of my favorite people to talk security with. Alex has done federal security work, and securing the actual Olympics, now then a security consulting firm.If you've been listening a while, you might remember Alex from way back in episode 11 and then again in episode 96.Today's round three, and we're going fully nerd-out mode on the OpenAI/Hugging Face hack. Walking through the signals and understanding how this type of attack was seen from a defensive side.The timeline visualization of the Hugging Face attack that Alex referenced.This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. (00:00) - Welcome Back Alex Dow (00:50) - What Happened in the Hack (02:22) - Mythos and AI Hype (06:05) - Throughput Beats Creativity (08:04) - Sandbox Escape Explained (11:02) - Swarm Agents and Breadcrumbs (14:13) - Reward Hacking and Alignment (19:30) - Four Days Undetected (21:27) - Blue Team Limits and Guardrails (25:28) - Detecting AI in the Noise (30:50) - Using Your AI Against You (34:30) - Honeytokens and Deception (37:22) - Zero Trust as a Baseline (38:59) - AI Botnets and Key Theft (43:01) - Wrap Up and Takeaways

Josh Hobein, manager of cybersecurity and automation at Centrex IT, discusses how MSPs can be run like five-star restaurants by prioritizing service, empathy, and experience over mere SLA “checkbox” performance. Drawing on his background in restaurant management, he explains how hospitality skills translate to tier-one helpdesk and why culture is defined by what leaders tolerate, requiring top-down standards, accountability, recognition, and sometimes letting misaligned people go; Centrex’s ESOP model also supports ownership and buy-in. On security, he describes a simplified five-stage maturity model built from cyber insurance requirements and CIS controls (favoring CIS for its programmatic implementation groups) to help non-technical owners understand progress via a roadmap. He cautions against fear-only security selling, advocating education-based conversations, and emphasizes business-decision-focused tabletop exercises (including IRGame.ai) plus the importance of cyber insurance and minimum security baselines.Check out a scene from The Bear that demonstartes what choosing excellence looks like. This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP. (00:00) - Meet Josh Hobein (00:41) - Michelin Star MSP Mindset (02:25) - Hospitality to Helpdesk (04:39) - Service That Wins Loyalty (06:56) - Beyond SLAs With XLAs (09:36) - Leading Culture and Standards (13:06) - From IT to Restaurants Back (19:13) - Frameworks Without Jargon (22:11) - Five Stage Security Maturity (23:28) - Maturity Model Roadmap (24:57) - Fear vs Education Sales (26:00) - Dark Web Scan Reality (29:02) - Trust Through Assessments (30:17) - Cyber Insurance Minimums (32:26) - Walking Away From Risk (33:04) - Waivers and Enforceability (34:41) - Minimum Standards and Compromises (36:28) - Tabletops for Executives (39:13) - Roleplay High Stakes Decisions (41:15) - Practice Like a Restaurant Rush (42:16) - Next Monday Action Steps (43:39) - Closing and Resources