Sales Tips for Technical Owners - ERP144

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

Evolve or Evaporate: Erik Boles on MSP Branding, Anti‑Commoditization, and Human‑Led MarketingOn the Evolved Radio podcast, Todd Kane interviews Erik Boles about why many MSPs look identical online and how that commoditizes them into “line items.” Erik shares his background from early internet businesses to VAR/MSP-era engineering, MX Logic, and early Pax8, explaining that customers care about outcomes and experience more than products or stacks. He argues brand is a result created by people, presence, and “lore,” and that templated marketing gets ignored due to pattern recognition and how the brain filters ads. He recommends MSPs differentiate through human-led communication, storytelling, and documenting real problems in plain business language, often via simple, authentic video rather than polished production. They discuss parasocial relationships, decision-making biases, AI-driven search/answers, and why personal brand should dominate corporate brand (about 95/5) to build trust and demand over time. Links mentioned: opsleader.co; vosa.co/erik; @erikbolz.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) - MSPs Becoming Line Items (00:15) - Meet Eric Bowles (01:44) - From Engineer to Brand Strategist (03:28) - Outcomes Over Product Demos (04:42) - Behavioral Psychology Roots (06:21) - Brand as a Result (08:37) - Pax8 Experience Differentiator (10:29) - Why Template Marketing Fails (12:35) - Neuroscience of Attention Filters (16:04) - Talk Human Not Geek (18:37) - Document Dont Create Content (19:45) - Define Sally Your Real Persona (20:35) - Authenticity Beats Perfect Video (23:15) - Communication Presence and Zoom Fatigue (25:31) - Stage Presence Basics (26:25) - Reps Over Perfection (27:28) - Authentic Content Wins (27:52) - Capture Client Call Gold (29:57) - Differentiating MSPs (31:13) - Emotion Drives Decisions (33:05) - AI Search Changes Buying (35:04) - Parasocial Trust Building (43:16) - Personal Brand First (46:14) - Human Led Marketing Era (47:50) - Where To Find Eric (48:52) - Just Do It Anyway (49:34) - Handling Online Hate (50:15) - Wrap Up And Thanks

Automation as Core Strategy: Aarin Bailey on RPA, AI, and Scaling MSP OperationsOn the Evolved Radio podcast, Todd interviews Aarin Bailey, COO at Webit Services and former COO at MSP Bots, about treating automation as a core MSP operating strategy. Aarin describes how his automation focus accelerated around COVID by chaining PowerShell scripts, later expanding into Python, GUIs, and modular systems connected via RESTful APIs, with much of the computation running outside the RMM on servers (including SQL and Python) while the RMM remains mainly a monitoring and job-push layer. They discuss whether RMM is a “zombie product,” the ongoing role of PSA/ticketing as a system of record, and managing complexity through separate modules and staff literacy in Python/RPA. Aarin explains build-vs-buy decisions driven by ROI and fit, cites automated triage/dispatch with ~98% accuracy and shifting token costs, argues AI should augment rather than replace humans, and emphasizes documentation, playbooks, and focusing on operational “bad” anomalies. They also cover client tolerance for AI, limiting client-facing AI after hallucinated ticket notes, skepticism about voice AI, and concerns about AI economics and subsidies.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) - Automation First Mindset (01:10) - Aaron Origin Story (05:04) - From Scripts to Platforms (05:41) - Beyond the RMM Beehive (08:35) - Is RMM a Zombie (12:14) - Managing Complexity Safely (14:33) - Build vs Buy ROI (19:39) - Token Costs and Pair Coding (23:49) - AI Security Reality Check (27:34) - Scaling with Playbooks (30:12) - Hunt the Bad Stuff (30:59) - Blueprints Before Automation (32:46) - Ticket Volume and Vision (33:32) - Saying No as Integrator (35:44) - Healthy Disagreement Dynamics (37:08) - Client Facing vs Backend AI (40:05) - AI Hallucinations and Guardrails (43:05) - Voice AI and Live Answer (46:06) - Costs and Subsidized AI Era (49:26) - Outcome First and RPA Focus (51:36) - Wrap Up and Thanks

Victor Lopez on Fixing Broken MSP Financial Plumbing with AITodd interviews Victor Lopez, a former attorney and private credit professional at Blue Owl Capital who co-founded Flexpoint after seeing how clunky MSP financial tools were. Victor traces his "aha" back to Blue Owl financing Thoma Bravo's 2018 acquisition of ConnectWise, which led him to question why PSAs mix ticketing/project work with invoicing while still requiring separate accounting software.They discuss how most AI talk in the MSP industry centers on service delivery, but Victor argues owners should also apply AI to operations like accounts receivable/payable, collecting and making payments, payroll, and other non-revenue tasks that often fall on owner-operators (especially in sub-$1M MSPs). Victor describes AI agents, including voice AI for overdue invoice calls, and emphasizes human-in-the-loop controls, segmenting which customers are contacted, and escalation to a human to protect relationships while improving efficiency and owner quality of life.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 Victor Lopez (01:20) - From Law to Flexpoint (02:02) - ConnectWise Deal Spark (02:57) - Why PSA Billing Exists (05:35) - AI Beyond Tickets (08:13) - Operational AI Wins (14:09) - Agentic AI for AR (16:50) - Join Opsleader (17:26) - Controls and Oversight (22:09) - Voice Agents Calling Clients (28:27) - Owner Time and Quality (32:20) - Wrap Up and Takeaways

Preparing to Sell Your MSP: Emotions, Valuation, Deal Structure, and Exit Planning with Amy Babinchak Today on the Evolved Radio podcast, I welcome Amy Babinchak, a 22-time Microsoft MVP and author of "20 Questions Every Owner Asks Before Selling Their MSP," about planning an MSP sale years in advance. Babinchak describes the emotional impact of selling—often resembling grief—and stresses having a purpose and plan for life after the exit. They discuss avoiding pressure to "time the market," noting there is always demand for a well-run profitable business, and the need to prepare both operations and personal finances with a CPA, tax lawyer, financial planner, and business lawyer. The conversation covers deal structure tradeoffs (cash, time commitments, and total value), common earn-out/retention periods owners find miserable, valuation drivers like profitability, standardization, and running without the owner, typical multiples for small and mid-sized MSPs, and options for smaller firms such as selling a book of business or rare seller-financed sales to employees. 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 Amy Babinchak (01:12) - Why Plan Ahead (02:21) - Emotional Aftermath (04:15) - Life After Exit (06:44) - No Need To Rush (08:55) - Prep Business And Personal (10:16) - Build Your Sale Team (12:19) - Deal Structure Tradeoffs (16:45) - Know Your MSP Value (17:59) - How Buyers Value You (20:05) - What Buyers Value (20:48) - Opsleader Pro Break (21:24) - Realistic MSP Multiples (23:11) - Selling Small MSPs (25:15) - Books of Business Wins (27:03) - Buyer Options Overview (27:28) - Seller Financing to Team (31:00) - PE Size Thresholds (32:13) - Rollups and Stability (33:22) - Vetting PE Partners (37:33) - Legacy Over Price (39:15) - Book Wrap Up (40:55) - Final Takeaways

Ashley Cooper on Lovable, Local-First AI Apps, and Safe Agent Workflows for MSPsThe host interviews Ashley Cooper (COO at Cyber Drain, VP of Community at Rewst) about her use of Lovable and other AI coding tools to build small, local-first, deterministic apps and learn through prompting. Ashley describes receiving a Lovable contributor gift after ranking in the top 0.01% of users, her early failed attempt to rebuild community software, and her shift to rapid, browser-based prototypes like JSON-to-CSV converters, receipt/expense and food trackers, and a webhook-driven PSA time-entry timer. She explains her workflow moving from Lovable scaffolding to GitHub/VS Code with Copilot, plus experimenting with Bolt and tools like OpenClaw, emphasizing trust boundaries, least privilege, and treating agents like employees. They discuss prompt engineering using philosophical mental models, risks of unvetted "vibe-coded" SaaS, and advising MSPs to start with data readiness and education before deploying AI for clients.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.