Who Is Eben Pagan?

The Pagan Paradox: How a Hippie Guitarist from the Oregon Woods Built a $100 Million Digital Empire Under Two Identities

Few online marketers and experts are as successful, influential, and enigmatic as Eben Pagan. He is a man of two distinct identities: one, a respected business guru and technology investor who has taught hundreds of thousands of entrepreneurs the art of wealth creation and productivity; the other, a controversial dating coach who operated under a pseudonym and became a foundational figure in the polarizing “pickup artist” community. This is the central paradox of Eben Pagan. He is a famously private man who has built two public, multi-million-dollar personas that seem, on the surface, to be mutually exclusive.

His success is staggering by any measure. Pagan claims to have sold over $100 million worth of products and services online, launching over 10 different brands and growing them to the seven-figure level from scratch, with four of those surpassing the $10 million mark. He is considered by many to be one of the “OGs” of digital marketing, building sophisticated online sales funnels back in 2001 when most of the business world was still focused on traditional advertising. To truly answer the question “Who is Eben Pagan?”, one must deconstruct both of his identities. The controversial tactics and systematic marketing engine perfected in the shadows of the “David DeAngelo” brand did not disappear; they became the foundational powerhouse for the mainstream success and legitimacy of the “Eben Pagan” empire. This is the story of that strategic evolution.

Part I: The Oregon Trail to Digital Gold: Forging a Founder

Humble Origins

Eben Pagan’s journey to digital mogul began far from the world of online commerce, in the “backwoods of Oregon” where he was raised by “hippie parents” from New York City. His early life was a portrait of counter-culture aspiration, not corporate ambition. He was a “long-haired rock n roll guitar player” who worked in a metal shop, made jewelry, and eventually dropped out of college to tour with a band. At the peak of his music career, he was earning just $75 a week, a reality that forced a pragmatic shift in his life’s direction.

Reasoning that wealth was often tied to real estate, the 22-year-old Pagan got his real estate license. The image he presented, however, was hardly that of a conventional agent. Driving a two-door Camaro and sporting a ponytail, he struggled to convince people to trust him with their property transactions. This initial failure proved to be a critical turning point.

The Catalyst for Change

His struggles in real estate led him to the world of self-help, sales, and marketing courses. While the emotional toll of traditional sales methods like cold calling and knocking on doors was challenging, he became captivated by the principles of direct response marketing—a system for selling that was less about personal charisma and more about repeatable processes. This discovery planted the seeds for his future business model, one that would rely on scalable systems rather than face-to-face persuasion.

Even as he found some success in real estate consulting, another personal challenge emerged. Despite having a good job, a nice car, and an apartment on the beach, he confessed that “girls wouldn’t talk to me”. He dove into the world of dating advice, attending seminars and reading books, but found much of the available material to be outdated, “weird and manipulative”. This personal frustration became the crucible for his first major business venture. Instead of accepting the existing solutions, he set out to solve the problem for himself by observing and codifying the behaviors of men who were “naturals” with women. This journey from personal pain point to systematized solution would become the defining pattern of his entire entrepreneurial career. His most significant successes were not born from a grand strategic plan, but from an intimate understanding of a widespread, emotionally charged problem that he himself had experienced and was determined to solve.

Part II: The Birth of David DeAngelo and the ‘Double Your Dating’ Empire

The Genesis of an Alias

In 2001, Pagan launched his first online business from his bedroom, but not as himself. He created the persona “David DeAngelo,” a name strategically chosen for its catchy, authoritative ring. This was not his first alias. In the late 90s, while studying under the dating coach Ross Jeffries, a proponent of Neuro-Linguistic Programming (NLP), Pagan went by “Sisonpyh”—hypnosis spelled backward—a nod to the psychologically-driven techniques he was learning. The creation of David DeAngelo was a deliberate branding move to establish a new authority in the nascent online dating advice space.

He locked himself in his bedroom for three weeks, wrote an e-book titled Double Your Dating, and built a website using Microsoft FrontPage, teaching himself the fundamentals of online business from scratch—from getting traffic to processing payments. On the very first day the site went live, it made a few sales. That immediate proof of concept was the spark that “realised something big was going on,” igniting an empire that would soon generate tens of millions of dollars annually.

Deconstructing the ‘Double Your Dating’ Philosophy

The success of the brand was built on a compelling and controversial philosophy, a powerful marketing engine, and a suite of products designed to guide customers up a value ladder.

Core Tenet: “Attraction Isn’t a Choice”

The foundational principle of the entire DeAngelo brand was that attraction is not a conscious decision but a primal, biological response. This concept, repeated across all his materials, argued that one could not logically convince a woman to feel attraction; one had to trigger it on a subconscious level. This frame-shift was powerful because it moved the locus of control to the man, suggesting that attraction was a learnable skill based on specific behaviors, not inherent traits like looks or money.

The “Cocky & Funny” Method

DeAngelo’s most famous technique was “Cocky & Funny,” a communication style designed to project confidence, humor, and a lack of neediness—qualities he identified as key “attraction switches”. The method became a cornerstone of the pickup artist (PUA) lexicon. However, the concept was not without controversy, as Pagan later reportedly admitted to creating it without extensive field testing. He also introduced other memorable concepts like identifying and overcoming one’s “Inner Wuss” and using “Counterintuitive Behavior” to stand out.

The Marketing Engine

The true genius of the Double Your Dating empire was not just its content but its revolutionary marketing system.

• Education-Based Marketing: Pagan was a pioneer of what is now known as content marketing. Instead of a hard sell, he offered a free, high-value email newsletter. His stated goal was to create the “most valuable newsletter in the world on any topic and then to give it away for free”. This strategy built a massive and loyal email list—reportedly over 1 million subscribers—and established trust and authority long before asking for a sale.
• The Funnel and Back-End Sales: The Double Your Dating e-book was the low-cost entry point into his ecosystem. The real revenue, however, was generated on the back-end. He created a suite of approximately 20 higher-priced products, including multi-CD audio programs and DVD home study courses, that he sold to his established list of subscribers. He understood a critical business principle early on: “almost all of the money in a business is made after the customer buys their first item”.

This model was wildly successful. At its peak, the business was reportedly generating $20 million to $30 million in annual sales with a fully virtual team of 70 to 80 employees.

The David DeAngelo Product Suite

The following table outlines the evolution of the main products released under the(https://www.datingskillsreview.com/david-deangelo/), showing a progression from external techniques to a deeper focus on internal mindset.

Product Name	Approx. Year	Format	Core Concept
Double Your Dating eBook	2001	eBook	Foundational principles of attraction, “Cocky & Funny”.
Advanced Dating Techniques	2003	CD Program	Deeper strategies for seduction and empowering beliefs.
Mastery with Women & Dating	2004	DVD Program	A comprehensive 5-step learning formula and mastering emotions.
Deep Inner Game	2005	DVD Program	Focus on building internal confidence and a rock-solid mental foundation.
Man Transformation	2008	DVD Program	Evolved advice focusing on holistic personal development for men.

Part III: The Pivot: Becoming Eben Pagan, The Entrepreneur’s Mentor

The Strategic Transition

By 2007, the David DeAngelo brand was a massive success, but it was also confined to a controversial and niche market. Pagan executed a brilliant strategic pivot, transitioning to his real name to enter a broader, more legitimate, and ultimately more scalable market: business and entrepreneurship coaching. The first major step in this new direction was the 2007 launch of “Altitude,” a high-end course for entrepreneurs wanting to grow their businesses to the $10 million level.

This was not a reinvention of his methods, but a masterful rebranding. He applied the exact same marketing system he had perfected with Double Your Dating—a free content-driven email funnel leading to a tiered catalog of high-ticket information products—to his new brand,(https://ebenpagantraining.com/). The target audience changed from single men to ambitious entrepreneurs, but the underlying marketing machinery remained identical.

The Eben Pagan Training Ecosystem

Under his real name, Pagan built a comprehensive curriculum designed to address the key pain points of the modern entrepreneur. This ecosystem is built on several core pillars:

• Starting a Business: Courses like How To Be An Entrepreneur and the flagship Digital Product Blueprint teach the fundamentals of creating and launching an online business.
• Growing a Business: Advanced programs like Altitude and Accelerate are designed for established business owners looking to scale rapidly.
• Productivity: The highly successful Wake Up Productive course was a direct result of Pagan identifying a critical need among his business students. He discovered their biggest frustration wasn’t marketing, but time management, and created a product to solve it, which went on to generate nearly a million dollars in sales on its own.
• Wealth Creation: Programs like Self-Made Wealth focus on the mindsets and habits required for long-term financial success.

A Deeper Dive into the Eben Pagan Curriculum

Pagan’s courses are systematically designed to take an entrepreneur from idea to a scaled-up business. His most popular programs offer a detailed roadmap for each stage of the journey.

• Digital Product Blueprint: This flagship 90-day course is designed to teach entrepreneurs how to create and sell a high-demand information product. The curriculum is broken into six core modules, moving from ideation to execution:
  • Module 1: Orientation Fast Start: An overview of the system and the essential mindsets for success.
  • Module 2: Targeting Your Niche: A system for finding a profitable niche and creating an ideal customer avatar to ensure the product sells itself.
  • Module 3: Creating Your Product: Teaches seven frameworks for creating a high-quality product quickly, including strategies for naming and design to command a premium price.
  • Module 4: Building Your Marketing: A crash course in “Education-Based Marketing,” providing proven templates to create ethical and effective marketing materials.
  • Module 5: Launching Your Product: Covers techniques for generating traffic, securing promotional partners, and creating an irresistible offer.
  • Module 6: Email Mastery: Focuses on creating high-converting email follow-up sequences to turn leads into buyers.
• Virtual Coach: This 10-week program provides a comprehensive system for building a successful coaching practice. The course is structured in seven parts and includes training from Pagan and a faculty of world-class coaches:
  • Part 1: Your Personal Transformation: Focuses on the coach’s own development, teaching models for success in health, wealth, and relationships.
  • Part 2: Next Level Coaching: Provides tools, scripts, and frameworks for coaching clients effectively through major life changes.
  • Part 3: Attracting Your Clients: Teaches how to create a “client invitation” that automatically attracts ideal clients using proven marketing templates.
  • Part 4: Enrolling Your Clients: Covers how to present coaching services and offer long-term packages in a natural and compelling way.
  • Part 5: Social Media Mastery: A system for using social media, particularly Facebook, to build an email list and generate free traffic.
  • Part 6: Growing Your Business: Features special sessions from an elite group of high-paid coaches who have built six- and seven-figure practices.
  • The program has since evolved into Future Coach, which incorporates AI tools to help with tasks like defining a coaching niche, writing a bio, and creating ad copy.

• Wake Up Productive: This 90-day program is designed to help users double their productivity by installing key habits. The course is divided into three months, each with a specific focus:
  • Part 1: Orientation & “Fast Start” Sessions: Foundational principles and exercises to clear mental clutter and eliminate “energy robbers”.
  • Part 2: Month 1 – Inner Game of Productivity: Focuses on creating a personal success ritual and building “focus muscles”.
  • Part 3: Month 2 – Outer Game of Productivity: Teaches the “60-60-30” solution for getting more done and identifying the most valuable tasks.
  • Part 4: Month 3 – The Next Level of Productivity: Covers advanced concepts like “inevitability thinking” to guarantee outcomes and discovering one’s true purpose.

The ‘Opportunity’ Manifesto

In 2018, Pagan released the book Oportunity, which served as the culmination of his business philosophy. Endorsed by media personality Larry King, the book was based on interviews Pagan conducted with millionaires and billionaires, combined with his own frameworks for identifying and acting on opportunities in a rapidly changing world. It was the final step in cementing his public persona as a mainstream business thought leader.

Part IV: The Pagan Playbook: A Philosophy of Opportunity and Systems

Beneath the two personas lies a consistent and powerful philosophy of business and marketing. Pagan is, at his core, a systems thinker who translates complex human desires into scalable digital models.

The Opportunity Mindset

Central to Pagan’s teaching is the “Opportunity Mindset.” He defines opportunity not as a lucky break but as “potential value” that can be cultivated. He believes we are living in a period of “Great Acceleration,” where the pace of technological and social change is creating an unprecedented explosion of online opportunities for those who know how to see them. His work encourages entrepreneurs to develop new mental models to perceive and act on these emerging possibilities.

This entire career arc is a masterclass in what could be termed “Identity Arbitrage.” Pagan astutely recognized that the David DeAngelo persona, while perfectly suited to the hyper-masculine dating advice market, would be a toxic liability in the mainstream business world. A single, unified brand could never have dominated both spaces. By creating the separate, “clean” Eben Pagan identity, he was able to leverage the capital, marketing expertise, and systems built by the DeAngelo empire without carrying over any of its reputational baggage. This wasn’t merely a name change; it was a sophisticated brand strategy that allowed him to arbitrage his identities, deploying the one best suited for each market to maximize his reach, influence, and revenue.

The Virtual Business Model

Long before remote work became mainstream, Pagan was a pioneer of the virtual company. Starting in 2001, he built his entire 80-person organization to be 100% remote, using then-nascent platforms like oDesk (now Upwork) to hire talent from around the world. His first virtual assistant was his friend and future marketing luminary, Dean Jackson. This forward-thinking approach to business structure afforded him immense freedom and flexibility, a lifestyle he now teaches to others.

Marketing as Value Exchange

Pagan’s marketing philosophy rejects aggressive, manipulative sales tactics in favor of building long-term relationships through value exchange.

• “Moving the Free Line”: This is a core concept where he advocates giving away such a massive amount of high-quality content for free—through e-books, newsletters, and videos—that prospects conclude the paid products must be exponentially more valuable. This builds immense trust and goodwill.
• Focus on the Back-End: His entire model is predicated on the idea that the first sale is only the beginning of the customer relationship. The majority of profit comes from subsequent sales to a happy, engaged customer base that has been nurtured over time through consistent, valuable communication.
• Psychology and Niche Targeting: He teaches entrepreneurs to develop a deep, empathetic understanding of their ideal customer avatar, including their emotional “hot buttons” and biggest frustrations. By targeting a narrow niche, a business can become the “only perceived option” for that specific group, effectively eliminating the competition.

Part V: A Network of Influence: Collaborators and Mentees

Pagan’s successful transition from a niche dating guru to a mainstream business expert is evidenced by his acceptance into the highest echelons of the marketing and personal development industries.

Connecting with the Titans

He has built a formidable professional network that includes some of the most recognizable names in business:

• Tony Robbins: Pagan has been interviewed by the world-renowned life and business strategist for his New Money Masters program, a significant endorsement of his expertise.
• Sir Richard Branson: He has worked with or connected with the Virgin Group founder, a fact he leverages to bolster his credibility.
• The Marketing Inner Circle: Pagan is deeply embedded with a group of legendary digital marketers. He has collaborated on products like the Print Persuasion Masterclass with Frank Kern (the “highest paid Internet direct response copywriter”) and Dean Jackson (founder of the I Love Marketing podcast). He is a frequent collaborator with Jackson and Joe Polish, founder of the exclusive Genius Network mastermind group.

Summits and Masterclasses: A Constellation of Experts

Pagan frequently leverages his extensive network by featuring other top-tier experts in his products and events, providing his students with a diverse range of perspectives.

• Entrepreneurial Mastery Summit: His 2025 online summit showcases the caliber of his connections, featuring over 45 leading business minds, marketers, and visionaries. The speaker list is a who’s who of the industry, including memory expert Jim Kwik, motivational speaker Lisa Nichols, Chicken Soup for the Soul co-creator Jack Canfield, Shark Tank investor Daymond John, biohacker Dave Asprey, marketing expert Ryan Deiss, and high-level entrepreneurs Dan Sullivan and Joe Polish.
• Business Growth Mentors: This course is built around 32 in-depth audio interviews Pagan conducted with highly successful entrepreneurs. The series offers a look inside the minds of business leaders from various industries. Featured mentors include Vishen Lakhiani, founder of MindValley; Eric Ries, author of the bestseller The Lean Startup; Jeff Walker, the creator of the “Product Launch Formula”; and Tony Hsieh, the late CEO of Zappos.com.
• Print Persuasion Masterclass: This advanced copywriting course is a collaboration with four individuals Pagan describes as “copywriting legends”. The masterclass features exclusive interviews and lessons from:
  • Frank Kern: Widely considered one of the greatest internet marketers, responsible for massive multi-million dollar launches like “Mass Control”.
  • Craig Clemens: A millionaire copywriter who Pagan calls his “‘secret’ copywriting weapon” that helped build his dating company to over $25 million in sales.
  • John Carlton: A legendary direct response copywriter known as a “mentor of mentors” in the field.
  • Dean Jackson: Founder of the I Love Marketing podcast, known for his ability to create effective marketing angles “off the cuff”.

A Legacy of Mentees

Perhaps the most powerful proof of his impact comes from the testimonials of his students, many of whom have become highly successful entrepreneurs in their own right.

• Marie Forleo, founder of a digital empire focused on female entrepreneurs, calls Pagan one of her “earliest marketing mentors” and says, “I’ll never forget how much he’s taught me about growing an online business and I’m forever grateful”.
• Laura Roeder, founder of multiple successful software companies, credits Pagan’s teaching with allowing her to “skip over about 10 years of mistakes that I would have made on my own!”.
• Other notable students provide specific, quantifiable results of his mentorship. Nick Unsworth went from being $50k in debt to selling his business for $550,000 within two years of Pagan’s guidance, while Christian Mickelsen grew his business more than tenfold.

Part VI: The Legacy and the Controversy

No examination of Eben Pagan is complete without addressing the controversies that shadow his career, primarily stemming from his David DeAngelo persona.

The PUA Connection and Criticism

While some defenders are careful to distinguish DeAngelo’s self-improvement focus from the more misogynistic elements of the PUA community, his book Double Your Dating was undeniably a foundational text for a generation of men in that world. The community has been widely criticized for fostering an objectifying, “romance-as-combat” mentality, where interactions with women are framed as a game to be won. Over time, DeAngelo’s advice, particularly the “Cocky & Funny” technique, has been described as dated and potentially counterproductive. Some former followers have even noted that Pagan himself later acknowledged that some of his early material was flawed, developed before he had more real-world experience.

The “Guru” Business Model Scrutiny

Pagan’s business model also faces the broader skepticism directed at the “make money online” guru industry. Critics sometimes describe the model as a “legitimate Ponzi scheme,” where the primary business is teaching others how to build the same kind of business, creating a self-perpetuating cycle of selling courses. The marketing often sells the dream of an easy, automated path to wealth, while the reality for students requires immense effort, resources, and often, a pre-existing level of expertise to succeed. While Pagan has verifiable testimonials from high-profile successes, the outcome for the average student remains, as with most online courses, largely unquantifiable.

His intensely private nature has only added to the mystique. He rarely grants interviews, and at one point, the disappearance of his YouTube channel fueled speculation among his followers.

Conclusion: The Man Behind the Brands

Eben Pagan’s story is a study in paradox. He is the reclusive teacher and the public guru; the hippie guitarist and the master capitalist; the controversial dating coach and the respected business mentor. His journey from the Oregon woods to a $100 million digital empire is a testament to his unique ability to identify deep-seated human problems and build elegant, scalable systems to solve them.

His legacy is twofold. On one hand, he is an undeniable pioneer of the digital information product industry. The marketing funnels he built in the early 2000s became the blueprint for a generation of online entrepreneurs, and his philosophies on value-based marketing continue to influence the industry today. On the other hand, that legacy is inextricably linked to the controversial origins of the David DeAngelo brand, raising enduring questions about the ethics of persuasion and the sometimes-blurry line between empowerment and manipulation.

Ultimately, who is Eben Pagan? He is a master systems-builder who transformed his own personal struggles into profitable enterprises. He is a brilliant marketer who understood, perhaps better than anyone, that in the fluid reality of the digital world, identity itself can be the ultimate strategic asset. He is the man who proved you can be whoever the market needs you to be, and build an empire on it.