MasterClass with Tom

Abstract

In this MasterClass, you’ll learn how affiliate marketing can open pathways to financial independence—regardless of your background or circumstances. Through the story of “Tom,” a self-taught digital entrepreneur, you’ll discover how creative thinking, consistent effort, and a strong sense of purpose can turn simple online tools into sustainable income streams. Whether you’re preparing for release or building skills while incarcerated, this lesson shows how affiliate marketing aligns with the principles of self-advocacy, personal accountability, and success through merit.

Module 1: The Mission

Title: Partnering for Reform—Working with Tom

When I first began speaking with Tom, I didn’t know what kind of project we would develop together. He wanted to volunteer with our nonprofit, and when I told him more about our work and mission, he offered to help. I told him that we had a heavy lift ahead of us, as we would have to:

• Persuade cynical people to change the law, and change policies.
• Build a data-collection tool that shows how we’re preparing people for success upon release.
• Inspire people in prison to do the work necessary to advance the cause.

Tom asked about the challenges that I was having. I explained that our nonprofit reaches close to a million people in jail and prison. Every one of them has a story worth telling. But to bring real change—policy change—we needed to reach those people even earlier in the journey: before incarceration, when someone has just been charged or is hiring a lawyer. That’s where we could help them the most, teaching them how to memorialize their journey inside. If we could get more people working to prepare for success, and we collected data showing our work, we would be more effective at building arguments to persuade administrators to change the policies, and legislators to change the law. 

We needed to create a flywheel effect, building momentum. And that’s where we were falling short.

To told me about his expertise with affiliate marketing, and that he knows how to take abstract digital tools and transform them into systems that create real-world outcomes. I appreciated it when he volunteered time in developing a MasterClass on affiliate marketing, and then spent hours teaching me how to use affiliate marketing to grow our mission.

Together, Tom and I started to map out a digital campaign—not just to “market” our work, but to amplify our mission. And what began as a conversation turned into a collaboration.

“What if we could create a digital asset,” Tom said, “that’s simple, free, and so valuable that people want to share it?”

That question sparked the beginning of the Earning Freedom Playbook.

The Playbook as a Tool for Liberation

We designed the Playbook to serve as a self-advocacy workbook—a tool that would help people see the value of self-directed mitigation strategies. They could learn how to build a body of work that might make them a better candidate for the relief we wanted to see. For example, we wanted to create changes that would make all people in federal prison: 

• Eligible for work-release programs,
• Home confinement,
• Incentives that would help them get a higher level of liberty early.

Tom helped shape the vision for this asset. He guided how we structured it—not just in layout, but in how we would distribute it.

“Don’t just upload it,” he told me. “Build a system. Let the Playbook become a tool that would help the nonprofit begin a relationship. Use it to show how your nonprofit delivers value without asking for anything in return.”

Then he showed me how to:

• Create a landing page where people could opt-in and download the Playbook
• Set up triggers so we could track engagement
• Use that data to build trust with institutions, defense attorneys, and policymakers

This strategy would become my initial foray into digital advocacy.

Reaching the People Who Need It Most

Tom helped me reimagine how we find people—not in prison, but on the brink of it.

He asked me:

“What are they typing into Google when their world is falling apart?”

That led us to build content and campaigns around real search terms:

• What happens after I plead guilty?
• Do I have to go to prison?
• How can I prepare before sentencing?
• In what ways can I make myself more productive while in prison?
• How can I position myself for the earliest possible release date?
• What should I do to advance possibilities for success upon release?

If we could meet people in that moment—with empathy and education—we could help them develop self-advocacy skills that could potentially change their lives. And if people began to memorialize the steps they were taking, we would collect the data necessary to build arguments for reform.

I envisioned a multi-year project, requiring more work regularly. Tom volunteered to mentor and help me along the way.

From Outreach to Impact

Tom had extensive experience with affiliate models—Cost Per Click, Cost Per Acquisition. Yet in our case, we were not selling products. Instead, we wanted to broaden awareness. He showed us how we could:

• Set up systems that reward others (volunteers, partner organizations) for sharing the Playbook
• Use platforms like Google Ads, YouTube, and even TikTok to reach people with lived experience
• Track which outreach efforts resulted in downloads, signups, and lives changed

In a world where influence is measured in impressions and clicks, Tom helped us ensure every action counted toward something bigger.

Why This Matters to You

If you’re reading this MasterClass lesson, it’s likely because you’re working to transform your life. And that makes you part of this mission too. As you work through it, you may find opportunities to begin marketing yourself, or to build skills that will lead to multiple income streams once you go home. I always found it helpful to listen to leaders like Tom, which is why I’m grateful to him for volunteering time with us.

Tom helped me think about campaigns as a pathway to reform—one that invites people to take action, document their journey, and earn freedom through merit. That’s why I’m sharing this lesson with you: so that you can learn the same tools we used to build a movement.

You may not be able to run ad campaigns from inside a prison—but you can understand the logic. You can prepare. You can learn how to build trust, spread value, and advocate for yourself or others—digitally or otherwise.

That’s what this course is about.

2. Cost Per Click (CPC)

The next model Tom taught me was CPC—Cost Per Click. In this model, the advertiser pays only when someone actively clicks the link.

“Clicks show interest,” Tom said. “And advertisers will pay more for actions than for glances.”

The difference? 

Tom went back to his earlier analogy of the billboard. He told me that I should think of concepts like CPM as a billboard, and CPC would be the flyer that someone picks up off a counter. By picking up the flyer, the person was showing intent. By clicking, a visitor is showing intent, taking the next step, wanting to learn more or get involved.

Tom told me that, depending on the topic, a single click might be worth anywhere from 10 cents to $10 or more. A CPC ad had more value than a CPM ad. I was happy to get that information, because it could help me be a good steward of our nonprofit’s capital. By placing a link strategically—especially if it’s tied to content that’s authentic and helpful—we could advance our mission. In our case, that meant creating blog posts or digital ads that asked things like:

• “Need help preparing for sentencing?”
• “Don’t know what happens next? Download the free Prison Professors Playbook.”
  
  • (But notice that when you click the link above, I am not harnessing the value. I wouldn’t have any metric of measuring intent.)

To collect data, instead of just providing a link that would give the person the asset, he wanted to send people to our opt-in page. The opt-in page would collect data (the person’s name and email). We would then provide the link to download the book. That person would be a step closer to becoming part of our community.

3. Cost Per Acquisition (CPA)

The third model was the most powerful: CPA—Cost Per Acquisition.

“This is where real campaigns are made,” Tom said. “You’re not paying for views or clicks—you’re paying for outcomes.”

CPA means you only pay a marketing partner (or affiliate) when someone completes a meaningful action—like submitting their email address, signing up for a newsletter, or downloading the Playbook.

In other words, I would define the result I wanted, and the system would only reward performance. This was where Tom and I really started to build. He showed me how to:

• Create a conversion trigger (e.g., “We’ll pay $1 for every defense attorney email collected”)
• Recruit affiliates or partners to share the campaign
• Set the budget and let the system grow organically

It was like having a digital street team—motivated not by salary, but by mission and measurable results.

Why These Models Matter

At this point in our MasterClass, you might be thinking:

• “That’s great, but I’m in prison. I can’t build websites or run ads right now.”

That’s true—for now. But that’s not the point. The point is to understand the logic behind how value flows online. Once you understand the difference between impressions, clicks, and conversions, you start thinking strategically. You start asking questions like:

• What am I offering that’s valuable?
• How do I build credibility before asking for anything in return?
• What result am I trying to create?

And most importantly:

• How can I apply this mindset—not just online, but in how I present myself to the world?

Tom helped me see that every outreach campaign—whether on Google or inside a federal prison—can be measured in outcomes. When we serve with intention, when we prepare with strategy, the results compound.

That’s the mindset I hope this module instills in you:
Learn to measure what matters. Learn how systems work. Then, start thinking about how you’ll build your own when the time comes.

Besides all of the above, this lesson should impress upon you to focus on things that you can do while you’re in prison. As we describe in all our lessons, although you may not have access to the internet while in prison, you can always work to develop skills that will accelerate your progress in the future. You can:

• Improve your vocabulary,
• Develop writing and reading skills,
• Become better at math,
• Improve your artistic skills,
• Focus on critical thinking, calculating the opportunity costs that come with every decision.

Step Three: Connecting with Affiliate Networks

Tom then introduced me to the world of affiliate networks—platforms that connect organizations like ours with publishers, bloggers, influencers, and everyday internet users who want to share our mission in exchange for a small commission. At first, I didn’t see how such relationships would benefit us, because we don’t sell anything.

“We’re not selling vitamins or software. We’re trying to get people ready for prison. Would anyone promote that?”

He said, “Many people have a problem with the social injustice of mass incarceration. It’s not fair that we lock so many people in prison, and we block some from getting incentives that others get. There was always a market that could help us spread our message. We just had to be creative.” He told me about several networks, including:

• ClickBank – a marketplace for digital products and educational content
• CJ Affiliate (formerly Commission Junction) – used by major brands to manage affiliate relationships
• ShareASale – a platform where small organizations can launch performance-based campaigns

By enrolling as an advertiser, we could invite others—nonprofits, influencers, even legal blogs—to help us distribute the Playbook. And because we could define the terms (e.g., $1 per verified email or PDF download), we maintained full control of our message, mission, and budget.

Step Four: Automating Follow-Up Communication

Tom helped me think beyond the first download.

“Every touchpoint should invite a deeper connection,” he said. “Otherwise, it’s a one-time exchange, not a relationship.”

He helped me set up an automated email sequence:

1. A welcome email thanking the visitor and offering context.
2. A follow-up message explaining our nonprofit’s mission and how they can get involved.
3. An invitation to share the Playbook with others who may need it.

The goal wasn’t to flood people’s inboxes—but to accompany them on their journey, offering encouragement, structure, and ongoing support.

A System for Awareness and Action

At this point, Tom and I had moved beyond theory. We had:

• A digital asset: The Earning Freedom Playbook
• A landing page that delivered it
• Tracking tools to measure success
• A strategy to enlist partners and affiliates
• An automated system to continue the conversation

This wasn’t just a digital campaign. It was infrastructure for impact.

And more importantly, it was replicable. I started to imagine others—people like you, reading this from prison—who could one day take the same steps:

• Build content around your story or niche
• Offer real value to others
• Track your results with discipline
• Grow a following, responsibly and ethically

Even from inside, you can start practicing the mindset:

• “What am I offering?”
• “How do I deliver it clearly?”
• “How do I follow through?”
  
  

That’s how leaders think. That’s how reformers move.

Module 4: Driving Traffic with Purpose

Title: How Tom Explained the Role of Organic and Paid Attention

Once we built the Playbook, created a landing page, and set up our tracking system, I thought we were almost done.

But Tom shook his head.

“Now you have something worth sharing,” he said. “But unless people see it, it might as well not exist.”

That’s when he introduced me to one of the most important principles of affiliate marketing—and of digital advocacy in general:

Traffic is oxygen.

Without people visiting your content, there’s no one to download your Playbook, read your message, or take meaningful action. It’s like giving a powerful speech in an empty room. Tom showed me that there are two main ways to drive traffic to a digital asset: organic and paid.

Organic Traffic: Earning Attention the Hard Way (But the Right Way)

Organic traffic refers to people who find your content without paid promotion. These are the readers who click a link from a Google search, follow a post from social media, or hear about your work from someone else.

For Prison Professors, most of our early traffic came organically. I wrote blog posts, filmed videos, gave presentations in prisons—and slowly, people started sharing those resources with others.

Tom helped me understand that organic traffic is built on trust and relevance.

To earn it, he taught me to:

• Use real search terms that reflect what people are Googling in a moment of crisis:
  
  
  
  • “How to prepare for sentencing”
  • “What happens after a guilty plea”
  • “Can I reduce my prison time?”
  • “What steps can I take to prepare for success once I get out?”
    
    
• Create educational content that answers those questions clearly and with empathy
• Include internal links that connect each blog or video back to the Playbook opt-in page

He said, “Google rewards consistency, clarity, and authority. You’ve got all three—now you just need to put them to work.”

That’s how we began planning a series of blog posts, YouTube scripts, and even social media captions that could rank well over time—especially when paired with strong keywords and useful information.

And the best part? Once organic content starts generating traffic, it keeps working for you 24/7, long after it’s been published.

Paid Traffic: Fueling the Fire Strategically

While organic traffic grows over time, Tom explained that paid traffic is how you accelerate momentum—especially when you’re launching something new, like the Playbook. He walked me through how paid advertising works on platforms like:

• Google Ads – Show up at the top of search results
• Facebook/Instagram Ads – Target specific demographics or interests
• YouTube Pre-Roll Ads – Show a message before a video plays
• TikTok Ads – Reach younger audiences through short video formats

But he made one thing clear:

“If you’re going to pay for attention, make sure you’re prepared to keep it.”

That means:

• Your landing page must be clear and fast
• Your value proposition must be strong (“Free Playbook = Better Sentencing Prep”)
• Your tracking must be in place so you can see what’s working

Tom taught me how to set a daily budget, define a target audience (e.g., people searching for defense attorneys), and measure Cost Per Click (CPC) and Cost Per Acquisition (CPA) to stay efficient.

I realized that with just $10 a day, we could test different headlines, keywords, and designs—then scale up once we saw which one brought in the most downloads. He helped me understand that we were investing in impact.

Blending Both Strategies

Tom emphasized that the best digital campaigns use a blend of organic and paid traffic.

• Organic traffic builds long-term credibility
• Paid traffic builds short-term momentum

For example:

• We’d write a blog post answering “How can I prepare for federal prison?”
• At the bottom of the post, we’d link to the Playbook landing page
• Then we’d run a small paid ad promoting that blog post to people searching for “federal sentencing advice”

That way, paid dollars were used to amplify educational content, not just to “sell” a download.

“You’re leading with service,” Tom reminded me. “That’s what makes it sustainable.”

Lessons for Inside the Walls

If you’re inside prison reading this lesson, you might be thinking:

• “That’s great, but I don’t have money to run ads or access to the internet to build blog posts.”

And again, that’s true—for now. But here’s what you do have:

• The time and discipline to learn how attention works
• The ability to journal and outline future content ideas
• The power to study successful campaigns—even offline—and reverse engineer them
• The opportunity to craft your personal narrative in a way that will resonate later

Always remember that driving traffic requires communication skills. Communication is at the heart of advocacy, leadership, and transformation. Invest time today to develop those skills. You don’t need a digital ad budget to start thinking like a strategist. You just need to ask:

• Who is my audience?
• Where are they now?
• What would move them to take action?

When you start answering those questions—on paper, in your journal, or in your Prison Professors Talent profile—you’re already building the foundation of a campaign.

Module 5: Choosing the Right Niche

Title: How Tom Helped Me Understand Where My Message Fits

Once we had the Playbook, the system, and the traffic strategy, Tom asked me a question that made me pause.

“Michael, who exactly are you trying to reach?”

I thought I had a clear answer: “Anyone going into the system.”

But Tom challenged me to dig deeper.

“You’re not speaking to everyone, and that’s a good thing. The most successful campaigns focus on a specific group—a niche—and serve them with laser precision.”

That’s when I began to understand what he was trying to teach me about one of the most important lessons in affiliate marketing—and in life:

• When you try to reach everyone, you often reach no one. But when you focus on your niche, you create impact.

Defining the Prison Professors Niche

Together, Tom and I workshopped the ideal audience for the Playbook. Not just “people in prison”—but more specifically, people who might help us connect with our audience. We identified several potential sub-niches:

• People who have just been indicted or charged
• Families searching for answers
• Defense attorneys who want resources for their clients
• People preparing for sentencing
• Individuals who want to prepare mitigation strategies
• Formerly incarcerated people interested in advocacy
• Those who work in prisons

Each group had different needs, different language, and different levels of awareness. So Tom guided me to pick one to start. We chose:

• Defense attorneys, or people who just hired a defense attorney and were looking for ways to prepare.

Why? Because that’s the moment when fear is highest—and motivation is strongest. They’re not looking for theories. They’re looking for help. And that’s exactly what our Playbook provides, offering them hope for a better future if they start preparing early.

Applying This Lesson to Your Journey

Tom explained that every effective campaign—whether for a product, nonprofit, or personal brand—starts by answering:

1. Who am I trying to help?
2. What is their pain point or problem?
3. How does my solution address it better than anything else?

That’s what defines a niche—not just demographics, but relevance. And this doesn’t just apply to nonprofits. It applies to you. If you're in prison right now, thinking about your reentry strategy or a future career in digital content, affiliate marketing, or advocacy—start here:

• Are you passionate about fitness? Maybe your niche is reentry fitness plans for people on home confinement.
• Do you love reading? Maybe you start reviewing books and linking to them with affiliate links.
• Have you studied the law while incarcerated? You might create a niche site helping people understand post-conviction remedies.

“The best niche is where your knowledge overlaps with someone else’s need,” Tom said.

Niche in Action: What We Built

Once we defined our niche, Tom helped me tailor every part of our campaign:

• Our headline on the landing page: “Charged with a federal crime? Download your free sentencing preparation workbook.”
• Our blog content focused on questions that people in that moment would ask
• Our ads targeted search terms like “how to prepare for federal sentencing”

That level of specificity made our campaign feel personal. Like it was written for the person reading it. 

Niche Thinking in Prison

Even if you’re not starting a website right now, you can start thinking like a niche builder. In fact, it may be the most powerful way to reframe your incarceration. Here are some prompts you can write about in your journal or Prison Professors Talent profile:

• What specific struggle have I overcome?
• What knowledge have I developed while incarcerated?
• Who would benefit from that knowledge on the outside?
• What would I say to someone five steps behind me in the same journey?

That’s how content is born. That’s how campaigns start. That’s how movements grow—one focused message at a time. And when the time comes, if you want to build something online, you’ll already have:

• A story
• A focus
• A strategy

You’ll be ahead of the game.

Tom’s Final Word on Niches

Before we wrapped up this part of our work, Tom left me with a line I’ll never forget:

“You don’t need to be famous. You just need to be known by the right people—for the right reasons.”

In today’s world, that’s how influence works. Not by casting the widest net, but by casting the right one—and showing up with value, consistency, and purpose.

That’s what we’re doing at Prison Professors. And that’s what I hope you’ll one day do, too.

Module 6: Ethical Campaigning and Avoiding Pitfalls

Title: What Tom Warned Me About When Building a Movement

After weeks of working together to build a values-based campaign around the Earning Freedom Playbook, Tom sat me down for a different kind of lesson.

“Michael, when you build something that works—people will try to copy it, distort it, or exploit it. You’ve got to stay grounded in your purpose.”

That conversation was a turning point. Up until then, we were focused on visibility—driving traffic, collecting emails, generating awareness. But now Tom was reminding me of something deeper:

• Integrity must scale with impact.

It doesn’t matter if you’re building a nonprofit campaign or a personal brand. The moment your message starts gaining attention, you’ll face a choice: Do you cut corners for short-term results? Or do you double down on ethical practices that create trust?

The Lure of Shortcuts

Tom had seen it all in the affiliate world—marketers manipulating clicks, exaggerating claims, or using “black hat” tactics to game the system. He warned me:

• Don’t buy fake traffic—bots might inflate your numbers, but they don’t change lives.
• Don’t bait and switch—if you offer something free, make sure it delivers real value.
• Don’t hide your intent—be transparent about your mission, who you’re helping, and how.

“The internet may forget,” he said, “but the people you serve won’t. You’re building trust—or you’re breaking it.”

And for an organization like Prison Professors, trust is everything. We’re asking people to open up, to reflect on their past, and to do the hard work of change. That means our campaigns must reflect the values we teach: accountability, authenticity, and long-term thinking.

Data Privacy and Respect

As we began collecting emails through our landing page, Tom also guided me through ethical data practices. He reminded me:

• Always get explicit consent before adding someone to a mailing list.
• Give people the option to opt out at any time—no guilt trips, no tricks.
• Never sell or share someone’s personal information—period.

He explained that email marketing laws like CAN-SPAM in the U.S. and GDPR in Europe were designed to protect users—and violating them, even unintentionally, could damage our credibility or worse. But even beyond compliance, he told me:

“You’re not collecting data. You’re building relationships. Treat that responsibility with care.”

Staying True to the Mission

One challenge we discussed was balancing scale with purpose. Tom warned me not to dilute the message just to appeal to more people. That’s how great campaigns lose their soul. Instead, he helped me define a set of non-negotiables:

• We serve, we don’t sell. Everything we offer must provide authentic value.
• We educate, we don’t exploit. Our content must uplift—not manipulate.
• We model the values we teach. If we preach accountability and transparency to incarcerated individuals, our outreach must reflect the same.

These commitments now live at the core of our campaign. They guide how we write, where we advertise, and who we choose to partner with.

Lessons for Life Beyond the Campaign

If you’re reading this from prison, I want you to know: these lessons don’t just apply to online marketing. They apply to every opportunity you’ll ever pursue.

• If you cut corners in a job, you’ll be remembered for your shortcuts.
• If you manipulate others for gain, you’ll lose trust faster than you gained it.
• But if you stand for something—and back it up with consistent action—you’ll build a foundation no one can take from you.

That’s what Tom showed me: that in a digital world full of noise, honesty cuts through louder than hype.

What Happens When You Get It Right

When we launched the Playbook campaign using Tom’s ethical framework:

• People downloaded it, shared it, and came back asking for more.
• Defense attorneys contacted us to request bulk copies for their clients.
• Other nonprofits began asking how they could collaborate and co-promote.

That’s what ethical campaigning creates: momentum built on mission. Not just clicks and conversions—but connections.

Final Words from Tom on Integrity

“Reputation isn’t built in clicks, Michael. It’s built in consistency.”

That’s what I carry with me from this part of our work. That in every system—digital or otherwise—your integrity is your brand.

And if you’re building something that truly matters, protect it fiercely.

Module 7: Execution Plan

Title: How Tom and I Designed a Campaign That Delivers Results

By the time Tom and I reached this point in our collaboration, we had:

• A clear mission: get the Earning Freedom Playbook into the hands of people who need it—especially early in the criminal justice process.
• A strong message: success after prison starts with preparation before prison.
• A simple, valuable offer: a free, digital self-advocacy workbook.
• The right systems in place: landing pages, conversion triggers, and analytics tools.
• A commitment to ethics and integrity that would guide every step of the journey.

Now came the final phase of our work together: execution.

“You’ve got the machine,” Tom said. “Now let’s make it move.”

This module lays out the exact structure we developed—so that even if you can’t build your own campaign today, you can learn the thinking behind it and start applying it to your personal journey.

Step 1: Define the Result

Tom always started with the outcome in mind.

“What does success look like—quantitatively?”

We decided on a very clear, trackable goal:

• Get 10,000 people to download the Playbook and opt in to receive additional self-advocacy resources.

This number wasn’t arbitrary. It represented:

• A benchmark we could report to policymakers
• A foundation of people we could serve, educate, and mobilize
• Evidence that there is demand for tools that help justice-impacted individuals prepare

Tom reminded me that every system we built—ads, emails, partnerships—had to be tied to this outcome.

Step 2: Build the Funnel

Tom used a word I hadn’t applied before: funnel. A “funnel” is the sequence of steps someone takes to go from not knowing who you are to taking meaningful action. Here’s what our funnel looked like:

1. Ad or Search Result – A person types “how to prepare for sentencing” and sees our message.
2. Landing Page – They click through to a clean, focused page offering the free Playbook.
3. Email Collection – They enter their name and email address to download.
4. Download Page – They receive the Playbook immediately.
5. Follow-Up Sequence – They get 3–4 emails over the next two weeks, offering additional tools, stories, and encouragement.
6. Engagement Opportunities – Eventually, they’re invited to join a newsletter, recommend the resource to others, or participate in future advocacy efforts.

This funnel wasn’t designed to pressure anyone—it was built to serve, educate, and build trust over time.

Step 3: Measure What Matters

Once the funnel was built, we used simple metrics to track our impact:

• Number of visitors to the landing page
• Email opt-in rate
• Download rate of the Playbook
• Email engagement (opens, replies, forwards)
• Follow-through behavior (e.g., sharing the resource, responding to our calls for input)

These were our accountability tools—a digital version of what we teach in our Straight-A Guide: track your progress, reflect, and adjust.

“If it’s not measurable, it’s not manageable,” Tom said.

Step 4: Activate Partners and Affiliates

We didn’t try to do it all alone. Tom helped me set up a basic affiliate structure—essentially, a referral incentive system—so other people could help promote the Playbook. Here’s how it worked:

• We gave trusted partners a custom link to our landing page.
  
  
• For each download or verified opt-in they generated, we offered a small reward—either a shout-out, future collaboration, or a budgeted CPA (Cost Per Acquisition) payout.

This turned our campaign into a community movement, not just a one-organization effort.

We invited:

• Legal professionals
• Advocacy organizations
• Formerly incarcerated influencers
• Students in criminal justice reform programs

And we gave them tools—social media captions, blog templates, graphics—to help them share the Playbook easily.

Step 5: Keep the Message Alive

Tom stressed the importance of consistency.

“Momentum isn’t built in a day. You need to show up over and over again.”

So we built a content calendar:

• Weekly blog posts answering common pre-sentencing questions
• Monthly newsletters featuring real stories of transformation
• Short-form video scripts for TikTok, Instagram, and YouTube

Each piece pointed back to the Playbook and invited engagement. This content strategy ensured we weren’t just running a one-time campaign—we were building a movement, brick by brick.

Lessons for Your Own Execution Plan

Even if you’re in prison and can’t launch a campaign today, you can build a campaign in your mind—and on paper. Start by asking:

1. What mission do I care about?
2. What message can I share?
3. What value can I offer others?
4. What steps can people take to engage with me or my work?
5. What systems can I set up—on paper now, online later—to support it?

Whether you’re building a business, launching a book, or advocating for change, the logic is the same.

• Define the result.
• Build the pathway.
• Measure what matters.
• Invite others to help.
• Stay consistent.

That’s what Tom taught me.

And that’s the strategy I hope you’ll one day apply—to your campaign, your story, or your legacy.

Vocabulary Development

10 Business-Related Words to Build Fluency and Confidence

One of the goals of this MasterClass is to strengthen your ability to communicate like a leader—especially when engaging in business, advocacy, or personal branding. The following vocabulary words appeared throughout the lesson. Each one is bolded where it first appears in the earlier modules and is defined here to reinforce understanding.

These terms not only expand your business vocabulary but also reflect the mindset and language of ethical entrepreneurship and digital strategy.

1. Impression: A single instance of an advertisement being displayed on a user’s screen.

• In affiliate marketing, impressions are used to measure visibility. When a campaign generates thousands of impressions, it means the message is getting seen—even if no one clicks. In life, impressions matter too—your actions, body language, and message make an impression whether you intend to or not.

2. Acquisition: The act of gaining something, typically a customer, user, or client.

• Cost Per Acquisition (CPA) campaigns reward affiliates only when a desired outcome is completed. In the context of nonprofit work, an acquisition might be someone signing up to receive the Playbook. In your personal development, it’s about acquiring trust, knowledge, or momentum.

3. Funnel: A strategic sequence of steps designed to guide someone toward a desired outcome.

• Tom taught you how to build a funnel that takes someone from discovering a resource to becoming part of a community. Funnels apply in many areas of life: education, advocacy, and even preparing for release. You guide others—or yourself—step by step.

4. Conversion: The process of turning a visitor or user into someone who takes action (e.g., clicks, signs up, downloads).

• Tom stressed the importance of conversion tracking. You can apply this thinking personally: what small actions (habits, lessons, journal entries) are converting into real growth?

5. Optimization: The process of making something as effective, functional, or useful as possible.

• Whether it's a webpage, routine, or release plan—optimization means continual improvement. In the campaign, you optimized content for maximum engagement. In prison, you optimize your time to strengthen your future.

6. Transparency: Openness and honesty in communication, especially regarding intentions or actions.

• In your campaign, you promised value without trickery. Transparency builds trust—online and off. If you’re building a narrative for release or clemency, transparency in your actions, mistakes, and growth can be your strongest tool.

7. Ethical: Following principles of right conduct, fairness, and moral responsibility.

• Tom emphasized ethical campaigning—no shortcuts, no tricks, no exploitation. As you build your reputation, remember: character compounds. In the digital world, in prison, or in business—ethics matter.

8. Analytics: The systematic analysis of data, usually to make informed decisions.

• From Google Analytics to self-tracking your journal responses, analytics teach you what’s working. Documenting progress—like tracking how many books you’ve read or lessons you’ve written—is a form of analytics too.

9. Leverage: The strategic use of resources or relationships to maximize results.

• Tom showed you how to leverage partners, platforms, and content. In prison, you can leverage time, mentors, and self-discipline to open new doors. Leverage doesn’t mean manipulation—it means intentional use of advantage.

10. Engagement: The level of interest, interaction, or participation someone shows in a message, product, or cause.

• Whether it’s measuring how many people read an email or how many people complete a course, engagement is key. In your own journey, how engaged are you with your goals, your growth, your accountability?

Bonus Challenge
Use each of these words in a sentence that applies to your own life. For example:

“I’m working to optimize my daily schedule so I can complete five reading assignments per week.”

You can use your Prison Professors Talent profile to demonstrate this vocabulary in action—strengthening both your language skills and your self-advocacy profile.

Self-Directed Reflection Questions

10 Socratic Prompts to Deepen Your Self-Understanding and Growth

These open-ended questions are designed to help you internalize the lessons from this MasterClass, while also practicing critical thinking, written communication, and strategic planning. Each question aligns with principles from the Straight-A Guide, and can serve as prompts for your personal journal or your Prison Professors Talent profile.

Your responses can become evidence of growth—valuable for stakeholders, future employers, or those reviewing your progress toward release.

1. Values

• What core values will guide the message you want to share with the world—and how do those values influence your decisions today?
  Think about honesty, service, integrity, resilience, or anything else you want to model.

2. Goals

• If you had to define one specific outcome to pursue right now (like the Playbook download goal), what would it be, and what steps would move you toward it?
  SMART goals are Specific, Measurable, Achievable, Relevant, and Time-bound.

3. Attitude

• How can a shift in mindset—from “what I can’t do” to “what I can create”—influence your future, even while incarcerated? Consider how Tom’s strategic thinking applies to your present situation.

4. Aspiration

• What kind of positive impact would you like to make in your community after your release—and what message would you want to be known for? You don’t need internet access to begin building your brand or legacy.

5. Action

• What daily habit or small action can you take—starting now—that aligns with the mission you want to lead later? Reading? Writing? Teaching others? Practicing structured thinking?

6. Accountability

• How will you track your progress and hold yourself accountable, even when no one else is watching? Can you develop a weekly goal-setting or reflection system?

7. Awareness

• What are some current trends or problems in society that you think you could help solve using your lived experience? In advocacy, business, or education—what issues matter to you?

8. Authenticity

• What stories or messages can only you tell because of your unique background—and how can you tell them honestly and respectfully? Remember Tom’s advice: lead with value, not hype.

9. Achievement

• What success have you already achieved during your incarceration that you may not have recognized—and how can you build on it? Completing a book, mentoring someone, learning a new skill—they all count.

10. Appreciation

• Who or what in your life today deserves your gratitude—and how can you express that appreciation in a meaningful way? Gratitude builds character and strengthens your leadership message.

Challenge:
Choose three of these questions and write out your answers in your journal or in a personal profile on Prison Professors Talent. Each answer becomes part of your documented transformation.

Absolutely. Here are three carefully selected business-related books that directly reinforce the principles and strategies in this MasterClass. Each one aligns with Tom’s teachings and your mission to help justice-impacted individuals use preparation, self-advocacy, and merit to transform their lives.

Supplemental Reading

Books to Deepen Your Understanding of Strategic Communication, Digital Branding, and Focused Discipline

1. Crush It!: Why Now Is the Time to Cash In on Your Passion

By: Gary Vaynerchuk

Summary:

In Crush It!, entrepreneur Gary Vaynerchuk teaches readers how to build a personal brand and monetize it through digital platforms—starting with what you already love. The book emphasizes the importance of authenticity, passion, and delivering real value to an audience before ever asking for anything in return. Vaynerchuk believes that anyone can succeed in the digital economy by focusing on a niche and staying consistent.

This book echoes Tom’s message: when you align your work with your passion and your values, you don’t need gimmicks—you need purpose.

Key Quote:

“Love your family, work super hard, live your passion.”

Connection to Tom’s Lesson:

Tom taught us that the most powerful campaigns come from personal experience. Crush It! validates that idea. Whether you’re building a digital asset or documenting your growth from inside prison, the key is to lead with value, speak from experience, and stay consistent.

Deep Work: Rules for Focused Success in a Distracted World

By: Cal Newport

Summary:

Deep Work is a guide to mastering focus in an age of distraction. Newport makes the case that the ability to do high-quality, undistracted work is one of the most valuable—and rare—skills in our economy. He outlines a framework for eliminating distraction and increasing output, especially for people looking to create content, learn new skills, or build a legacy.

This book is ideal for individuals in prison: no internet, no social media, no interruptions. The perfect place to practice “deep work.”

Key Quote:

“Clarity about what matters provides clarity about what does not.”

Connection to Tom’s Lesson:

Tom emphasized the importance of discipline, simplicity, and strategy. This book teaches how to channel your energy into one important goal at a time. Whether it’s writing your story, designing a campaign, or preparing for reentry, the ability to focus deeply is a superpower.

Building a StoryBrand: Clarify Your Message So Customers Will Listen

By: Donald Miller

🔎 Summary:

Donald Miller teaches a proven framework for crafting clear, engaging messages that connect with audiences. The StoryBrand method positions your audience as the hero and your organization (or offer) as the guide. Whether you’re selling a product, spreading a message, or growing a nonprofit, this book helps simplify your pitch so it resonates with the people you’re trying to reach.

Miller’s approach is especially useful for campaigns like the one Tom helped build around the Earning Freedom Playbook.

Key Quote:

“People don’t buy the best products. They buy the ones they can understand the fastest.”

Connection to Tom’s Lesson:

Tom pushed for clarity, focus, and relevance in the campaign. Building a StoryBrand reinforces that lesson: if your message is confusing, people won’t act. Whether you’re asking a stakeholder for a second chance or asking a visitor to download a workbook, clear beats clever.

Straight-A Guide Alignment

How This MasterClass Reflects the Ten Core Modules of the Straight-A Guide

As you know, I built the Straight-A Guide while serving 26 years in federal prison. It was my way of creating structure—so that no matter the situation, I could keep moving forward with discipline, purpose, and integrity. I’ve used this framework in every part of my life since coming home, and I teach it in every course we offer through Prison Professors.

This MasterClass is no exception. In fact, the campaign I built with Tom reflects each of the ten modules in the Straight-A Guide. Let me show you how.

1. Values – Define Success by What You Stand For

Tom and I never talked about building this campaign to generate revenue. That wasn’t the mission. From the beginning, we aligned around values—reaching people early in their journey through the justice system, offering free resources, and amplifying the message that people in prison can earn freedom through merit. Those values—service, honesty, transformation—guided every decision we made.

2. Goals – Clarify the Target and Plan the Steps

I’ve always believed that clarity brings power. So Tom and I set a clear, measurable goal: get 10,000 people to download the Playbook. From there, we reverse-engineered the plan. We built a landing page, mapped out the funnel, and developed the content. We didn’t guess our way through—we followed a blueprint. You can do the same with your own goals, no matter where you are.

3. Attitude – Choose the Mindset That Leads to Growth

I didn’t know anything about digital marketing when I started this journey. But instead of saying, “I can’t,” I said, “I’ll learn.” That mindset—the same one I had to adopt when I entered prison at 23—still carries me forward today. If you’re reading this lesson from inside a cell, I want you to remember: your mindset determines your direction.

4. Aspiration – See a Better Future and Build Toward It

This wasn’t about building a website. It was about building a movement. Tom and I weren’t thinking small—we were thinking about reaching thousands, maybe even millions, with a message that could save someone’s life. That kind of vision—that aspiration—is what I want you to cultivate. Whether you want to mentor others, launch a business, or reunite with your family stronger than before—you need a picture of the future you’re working toward.

5. Action – Do the Work, Step by Step

We didn’t talk about doing it—we built it. Every day, Tom and I took the next step: write copy, test ads, revise the landing page, follow up with partners. Small, consistent actions created real momentum. That’s the same formula I used to write books from prison, complete courses, and build a reputation. Whatever your vision is, start with one action. Then take another. Then repeat.

6. Accountability – Measure Progress and Stay Honest

Tom taught me how to measure outcomes—clicks, downloads, email opt-ins. That’s the same principle I teach in all of our courses. If you say you want something, show the steps you’re taking to get it. Track your progress. Document your work. Build a record. That’s what accountability looks like, and it’s how you prove to yourself—and others—that you’re serious about success.

7. Awareness – Pay Attention to Opportunities

Throughout this process, I had to stay alert. What was working? Where were people coming from? What content connected most? I used analytics to stay aware—but even inside, without access to those tools, you can train this habit. Pay attention to patterns in your thoughts, routines, and relationships. Adjust when something isn’t working. Awareness allows you to stay on course, even when life throws you off balance.

8. Authenticity – Be Real, Be Consistent

Everything Tom and I created was built on honesty. No hype. No gimmicks. Just value. The people who download our Playbook don’t get a pitch—they get help. And that’s how I want you to show up, too. When you’re honest about your past and consistent with your future actions, people take notice. Authenticity builds credibility—and credibility builds opportunity.

9. Achievement – Recognize Your Progress

It would be easy to move on to the next project without acknowledging the success of this campaign. But we need to pause and recognize the milestone. From nothing, we built a working system that reached thousands. You should do the same in your life. Finished a book? That’s an achievement. Helped a younger guy stay out of trouble? That’s an achievement. Document it. Celebrate it. Stack your wins.

10. Appreciation – Acknowledge the Help and the Journey

This MasterClass wouldn’t exist without Tom’s generosity. He volunteered his time, his knowledge, and his belief in the mission. I’m grateful for him—and for every one of you who’s putting in the work. Whether you’re inside or already free, appreciation will keep your heart in the right place. The journey is hard, but it’s also a gift.

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