#13 – From the Trenches - After Prison Show - From Prison to YouTube Empire (Joe Guerrero)

In this From the Trenches episode of the BMK Vision Podcast, Josh Peterson sits down with Joe Guerrero (creator of After Prison Show) for a leadership conversation that has nothing to do with “going viral” and everything to do with building a durable operating model when your starting point is disadvantage, uncertainty, and a world that changed while you were away. Joe’s story is extreme—seven years incarcerated, released into a smartphone-first economy, and forced to learn, earn, and adapt in public—but the core tension is familiar to every MSP owner: what happens when the market shifts faster than your identity, your systems, and your confidence? If you’re serious about building a business that can survive the next platform change, client loss, or talent shakeup, you’ll recognize the same strategic patterns BMK reinforces through Vision.

What makes this episode useful for MSP owners isn’t the category—prison reentry and YouTube—it’s the operating reality beneath it: Joe describes the moment “a thing you’re doing” becomes a business, the hidden tax of fame without structure, the leadership cost of hiring friends, and the way fear pushes owners into scattered diversification instead of focused advantage. There’s a clean lesson here for service firms: you don’t lose because you lack ideas; you lose because you can’t convert ideas into repeatable execution while noise—customers, competitors, critics, even your own ego—pulls you off the work that compounds.

Most MSPs don’t need more tactics. They need a better relationship with uncertainty. Joe’s path forces a hard question: are you building a business that gets stronger when the environment changes, or a business that only works when conditions stay familiar? The episode lands on a surprisingly practical conclusion—authenticity is not branding, and persistence is not a strategy—but both become powerful when they’re paired with discipline, focus, and a willingness to “do the next right thing” even when confidence is low.

What an MSP can learn from a “non-MSP” story

Great MSP leadership is mostly pattern recognition. Joe’s experience compresses patterns that take service firms a decade to learn: the shock of a new operating environment, the temptation to confuse attention with strategy, the fragility of growth without systems, and the personal identity crisis that follows when your business outgrows the version of you that started it.

The moment your “craft” becomes a business

Joe describes a turning point every MSP owner recognizes: the day you realize you’re not just delivering work—you’re running a business. That moment usually arrives through pain (taxes, cash flow, capacity, churn), and it forces a decision: keep improvising, or build structure.

• When “good money” still creates bad decisions without visibility
• Why hiring help doesn’t fix chaos if the model isn’t defined
• How fast success can hide operational weakness
• Why systems matter more when growth is emotional, not planned

The episode is a reminder that businesses don’t fail only from lack of demand—they fail because the owner can’t translate momentum into a repeatable machine.

Fear-driven diversification vs. focus-driven advantage

Joe’s most transferable insight is also the most uncomfortable: diversification often isn’t strategy—it’s anxiety. When you’re afraid your current engine could vanish, you reach for “more,” not “better.” MSPs do the same thing when they bolt on services, vendors, and delivery promises that dilute margin and confuse positioning.

The better move is often narrower: pick a lane you can win, build depth, and turn that depth into a defensible operating model instead of a constantly expanding menu of obligations.

What “authenticity” really means in professional services

Joe’s world is public, but the principle applies to every MSP: people buy trust before they buy capability. Authenticity isn’t oversharing—it’s clarity and consistency.

• Staying real without turning the business into a personality cult
• Learning to collaborate without losing control of your standards
• Hiring intentionally instead of emotionally
• Separating “what the audience wants” from “what the business needs”

For MSPs, this becomes a leadership discipline: you can be human and still run a tight machine. In fact, most teams trust you more when both are true.

A practical “anti-fragile” checklist for MSP owners

If you want a business that doesn’t collapse when conditions change, this episode points to a few non-negotiables:

• Build financial visibility so success can’t hide leakage
• Create roles and expectations before you “need” them
• Stop making fear-based expansion decisions
• Invest in marketing that earns trust, not just leads
• Design a model that can survive a platform change, a client loss, or a talent reset

In other words: don’t build a business that only works when you feel confident. Build one that keeps working when you don’t.

Episode highlights

• The real leadership challenge of adapting to a world that changed without you
• How a single insight (and relentless repetition) created breakout momentum
• When the “fun thing” becomes a business—and the taxes show up
• Why hiring friends tests leadership faster than hiring professionals
• Fear vs. winning: the mindset difference that reshapes strategy

About the guest: Joe Guerrero

Joe Guerrero is the creator of After Prison Show, a YouTube channel that documents prison realities, reentry, and the long arc of rebuilding a life after incarceration. He also runs Joe Does Stuff, where he shares entrepreneurship, renovation projects, and practical lessons from learning business the hard way.

Connect with Joe Guerrero on LinkedIn →

Frequently asked questions

What’s the MSP takeaway from a creator/entrepreneur story like this?
The category is different, but the leadership patterns are the same: turning momentum into systems, making decisions under uncertainty, and building a model that survives change.

How do I know if I’m diversifying for the wrong reasons?
If your expansion is primarily motivated by fear of losing what you have (instead of a clear thesis for winning), you’re likely buying complexity—not advantage.

What’s the biggest risk of “personality-led” marketing for MSPs?
If the brand becomes the owner, growth gets capped and trust becomes fragile. The goal is authenticity with operational consistency—so clients trust the firm, not just the face.

How should MSP owners think about hiring friends or “characters” clients love?
Treat it like any other role: define expectations, outcomes, and boundaries early. Popularity can’t substitute for accountability.

What’s the simplest way to start using video without overthinking it?
Start with your phone and a clear message: what you solve, who you solve it for, and how you think. Consistency beats production quality early.

How does BMK help MSPs build resilience into the business model?
By turning leadership intent into execution discipline—connecting people, process, and performance so the business isn’t dependent on heroics.

Related resources from Bering McKinley

• Solving common MSP profitability challenges with financial visibility
• The integration blueprint: building scalable operational systems

Want to continue the conversation?

If you’re an MSP owner who wants to build a business that holds up under real-world pressure—market shifts, margin compression, talent volatility—BMK can help you operationalize the fundamentals with the Vision operating system or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision