Evolve or Evaporate: Erik Boles on MSP Branding, Anti‑Commoditization, and Human‑Led Marketing

On 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 Operations

On 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 AI

Todd 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