Dean Jackson and James Schramko Behind The Scenes

From business models to marketing strategies, James’s latest convo with Dean Jackson has it all. Tune in as they break down key insights on social clout, the power of retention, AI and automation, and why monetizing expertise is the next big opportunity for entrepreneurs.

Podcast: Download (Duration: 1:14:44 — 102.9MB)

In a long-overdue podcast episode, James reconnects with friend and marketing legend Dean Jackson. Their conversation, as always, is rich with insights and reflections, exploring everything from timeless movie metaphors to the seismic shifts happening in business and technology.

Ready to scale your online business but not sure how? Let’s talk about your next growth step

Table of contents:

1. The power of storytelling in business
2. A shift in movie-making and distribution
3. The Blumhouse model: lessons in business strategy
4. The business model shift: Free to paid and the backlash
5. The rise of AI and the idea economy
6. The role of collaboration currency
7. The power of email and timeless business strategies
8. Demonstrating ROI and building long-term relationships
9. Streamlining time and simplifying operations
10. Monetizing intellectual property: The hidden goldmine
11. The importance of true reach over vanity metrics
12. Less but better: The art of doing more with less
13. Final thoughts

The power of storytelling in business

James and Dean discuss how certain movies, like The Castle and Waking Ned Devine, serve as powerful metaphors for larger societal trends.

The Castle, in particular, represents the struggle between everyday people and big institutions, a theme that resonates strongly in today’s business environment.

The way stories shape how we view the world is just as relevant in marketing as it is in cinema. Business owners who master storytelling create stronger connections and brand loyalty with their audience.

Download The Smart Entrepreneur’s Playbook: How to Adapt, Innovate, and Thrive (and the PDF transcription)

A shift in movie-making and distribution

The conversation also touches on the evolution of Hollywood and movie distribution. With the dominance of streaming platforms, the traditional studio model is under pressure.

Dean laments the lack of new movies, noting that most releases today are either massive franchise films or remakes, leaving little room for original storytelling.

This shift mirrors what’s happening in business: the middle ground is shrinking. Just as indie filmmakers struggle to compete with blockbuster franchises, smaller businesses need to find innovative ways to carve out their niche in an increasingly competitive marketplace.

The Blumhouse model: lessons in business strategy

Dean highlights Jason Blum’s Blumhouse production model as a perfect example of smart business strategy. Blumhouse produces low-budget psychological horror films with a strict budget of $4.5 million per movie, allowing them to break even through streaming and foreign rights alone.

The upside? If a movie tests well, it gets a full theatrical release, potentially generating massive returns.

This strategy parallels the way businesses should approach risk and scalability. Instead of over-investing in untested products, companies should validate ideas on a small scale before going all in.

The takeaway? Low-cost, high-upside business models are the key to sustainable growth.

The business model shift: Free to paid and the backlash

James shares a real-world example of a friend transitioning a free Facebook group into a paid model. The backlash from entitled users highlights a common challenge business owners face: pricing their expertise. Many businesses start by offering free value to build an audience, but when it’s time to monetize, they encounter resistance.

This is a crucial lesson for entrepreneurs—setting the right business model from the start prevents unnecessary friction down the line. If customers aren’t willing to pay for your expertise, they may not be the right audience for your business.

The rise of AI and the idea economy

The discussion naturally flows into the role of AI in business. James and Dean note how AI is making execution more accessible than ever, shifting the balance of power towards those who can generate high-value ideas.

Dean’s VCR formula—Vision + Capability x Reach—illustrates this shift. Today, execution is commoditized, and success increasingly depends on pairing the right ideas with reach.

This means business owners must focus on developing intellectual property, proprietary processes, and unique insights rather than just grinding through execution. As automation takes over repetitive tasks, creativity and strategy will become even more valuable.

The role of collaboration currency

A new concept Dean introduces is collaboration currency—the assets businesses hold that can be leveraged for partnerships.

Businesses often overlook the excess capacity they have, whether it’s underutilized resources, time, or reach. Recognizing and exchanging these assets strategically can unlock new revenue streams and opportunities.

For example, James recalls how car dealerships cover operational costs through parts and service while generating most of their profits from car sales. This model of absorbing fixed costs and maximizing variable revenue can be applied across industries.

The power of email and timeless business strategies

In the ever-evolving world of digital marketing, where social media algorithms shift overnight and AI-driven tools dominate discussions, one strategy remains steadfast: email.

Despite the rise of new platforms, email marketing continues to be one of the most reliable and profitable channels for businesses. But not all emails are created equal.

One of the most effective strategies in email marketing is the “slipping away email,” designed to re-engage customers who are on the verge of canceling their subscription or disengaging from your business.

James describes this email as a safety net, a last touchpoint that helps customers see the value they’re leaving behind. With an 86% open rate and millions in recovered revenue, this approach highlights the massive impact a simple, well-crafted email can have on a membership or subscription business.

Customer retention is often overshadowed by the rush to acquire new leads, yet the difference between a three-month customer and a seven-year loyalist is substantial. Instead of exhausting resources chasing new prospects, businesses can focus on keeping existing customers engaged, eliminating the need for constant reinvention and expensive ad campaigns.

Demonstrating ROI and building long-term relationships

Beyond re-engagement emails, ensuring customers recognize their return on investment (ROI) is crucial. If customers don’t see the value in what they’ve subscribed to, their enthusiasm dwindles quickly.

Dean explains how positioning customers as “self-sustaining members” helps them understand that they are essentially playing with house money—they’ve already received more value than they paid for. This mindset removes buyer’s remorse and strengthens long-term loyalty.

James echoes this philosophy in his business model, aiming for new members in his coaching program to generate $10,000 in revenue within their first month. This tangible return removes doubts, making them far more likely to stay engaged and continue their subscription.

Streamlining time and simplifying operations

Time is the most valuable resource for entrepreneurs, yet many spend it inefficiently.

James shares how he helped a client shift from offering free 40-minute strategy calls to only taking calls from paying customers. The impact was immediate—more focus on existing customers, reduced burnout, and an increase in profitability.

Another example is hiring strategically. Instead of drowning in administrative tasks, businesses can bring in team members to handle production, marketing, and operations, often at a fraction of the cost. One client of James’s reduced podcast production costs by 75% while doubling output simply by restructuring their team. These optimizations allow businesses to scale without adding complexity.

Monetizing intellectual property: The hidden goldmine

Many service-based businesses don’t realize that their methods and expertise can be repackaged into scalable models.

As Dean points out, countless businesses have valuable intellectual property (IP) they overlook—strategies, systems, or insights that could be licensed or productized.

An example is a client who initially offered a service but later built a membership community around it, creating a sustainable business model that didn’t rely solely on client work. By shifting focus from direct service to knowledge-based products, they unlocked an entirely new revenue stream.

The importance of true reach over vanity metrics

In a world where social media followings can be bought and engagement can be artificially inflated, the real power lies in genuine influence.

Many online personalities boast large audiences but see minimal engagement. True reach isn’t just about numbers—it’s about holding real influence over an audience that trusts you.

Email lists remain one of the strongest assets in this regard. Unlike social media, where visibility is controlled by algorithms, an email list gives you direct access to your audience. James and Dean both emphasize that email marketing is their most consistent and profitable channel, proving that despite its age, email remains the foundation of digital business.

Less but better: The art of doing more with less

A recurring theme in this discussion is efficiency. The “less but better” approach—focusing on the 20% of activities that generate 80% of results—leads to higher profitability with less stress.

James shares that his own business has grown by 30% in profit simply by eliminating unnecessary tasks and refining his focus.

Instead of chasing every new trend, businesses should double down on strategies that consistently deliver. Whether it’s optimizing pricing, refining customer experience, or leveraging strategic partnerships, the key is to work smarter, not harder.

Final thoughts

Ultimately, business success isn’t about mindlessly chasing the latest fads. James and Dean’s conversation underscores the importance of adaptability yes, but also points out the need to leverage timeless strategies.

Leveraging storytelling, embracing AI and understanding pricing dynamics can position business owners for long-term success. However, email marketing, retention-focused customer relationships, strategic hiring, and efficiency-driven models are principles that have stood the test of time.

Ultimately, the biggest lesson is this: the world is changing fast, but the fundamentals of value creation, strategic positioning, and audience engagement remain timeless. Those who master these will continue to thrive, no matter what disruptions come next.

As James and Dean demonstrate, businesses that balance the basics with innovation will continue to thrive, no matter what changes come next.

Imagine a business that grows without needing you every day. Discover how to scale smarter, with recurring leverage

Liked the show? Enjoy all the episodes when you subscribe on Apple Podcasts

Grab your FREE copy of Work Less, Make More! James went from working a full-time job to running a profitable business, having the freedom to travel, surf and spend time with family, and in his book you will find everything you need to know about how you can actualize the life you want, so you too can finally work less, and make more!