Lyn Askin

Lyn Askin is a certified EOS Implementer® and Outgrow Advisor® who helps entrepreneurial companies (10-250 employees) transform owner-dependent businesses into scalable, systems-driven organizations. His expertise comes from lived experience—after a near-death health crisis in 2020 revealed his digital marketing agency couldn’t survive without him, Lyn implemented the Entrepreneurial Operating System (EOS), tripled revenue, increased profits 7x, and successfully exited the business in 2023.

Professional Background

Lyn’s career spans over 25 years in digital marketing and business transformation:

• Certified EOS Implementer®: Helps companies implement the Entrepreneurial Operating System framework
• Outgrow Advisor®: Specializes in helping business owners plan and execute successful exits
• Former Agency Owner: Built and exited Raxxar Digital Marketing after 18 years of operation
• Digital Marketing Expert: Deep expertise across SEO, PPC, marketing automation, website development, and lead generation
• Business Transformation Specialist: Proven track record of scaling service businesses from owner-dependent to self-sustaining

The Transformation Story

In 2020, Lyn faced a bilateral pulmonary embolism that landed him in the ICU fighting for his life. This near-death experience revealed a terrifying truth: his business was completely dependent on him, and if he didn’t survive, everything he’d built over 18 years would have to be shut down.

That wake-up call became the catalyst for implementing EOS at Raxxar Digital Marketing, resulting in:

• Revenue tripled over two years
• Profits increased 7x
• Team expanded from 10 to 27 employees
• Owner independence achieved: Successfully worked himself out of day-to-day operations
• Successful exit: The business was acquired in 2023, proving its value as a standalone entity

Areas of Expertise

EOS Implementation

• Vision alignment and strategic planning
• Leadership team development
• Accountability systems and traction tools
• Process documentation and systematization
• Data-driven decision making frameworks
• Issue identification and resolution systems

Digital Marketing

• Search Engine Optimization (SEO)
• Pay-Per-Click Advertising (PPC)
• Marketing automation systems
• Lead generation strategies
• Website development and optimization
• ROI-focused marketing campaigns

Business Scaling & Exit Planning

• Building systems-driven operations
• Reducing owner dependency
• Creating transferable value
• Exit strategy development
• Business valuation optimization
• Succession planning

Authority-Based Leadership

• Professional boundary setting
• Client relationship management
• Work-life balance strategies
• Leadership positioning in service industries
• Transparent communication practices

The EOS Framework

Lyn teaches and implements the six key components of EOS that transform businesses:

1. Vision: Aligning leadership teams on direction and strategy
2. People: Getting the right people in the right seats
3. Data: Creating scorecards for real-time business visibility
4. Issues: Developing systems to identify and solve problems permanently
5. Process: Documenting core processes that make businesses run
6. Traction: Building accountability and discipline to execute on vision

Service to Aviation Industry

Lyn brings his business transformation expertise to the aviation training industry, where many flight school owners face the same challenge he overcame: being the single point of failure in their business. He helps aviation entrepreneurs build scalable operations that can thrive independently of the founder, creating both better lifestyle outcomes and more valuable businesses.

Philosophy & Approach

Lyn’s approach is grounded in several key principles:

• Systems Trump Heroics: The best business owners work themselves out of daily operations, not deeper into them
• Document Everything: If it’s only in your head, it’s not a transferable process
• Transparency Creates Loyalty: Complete honesty with clients builds stronger, longer-lasting relationships
• Think Like a Buyer: Running your business as if preparing for sale forces better systems and documentation
• Leadership Development: You can’t scale past yourself without developing other leaders

Why This Matters for Flight Schools

The aviation training industry faces enormous opportunity with the ongoing pilot shortage, but growth amplifies problems. Lyn’s expertise helps flight school owners build businesses that serve them, rather than businesses that own them.

Whether working with 2 aircraft or 20, Lyn’s question is always the same: “If you disappeared tomorrow, would your flight school continue to thrive?”

His proven roadmap helps aviation entrepreneurs answer “yes” to that question with confidence.

Background & Credentials

• 25+ years in digital marketing and business development
• 18 years building Raxxar Digital Marketing before successful exit
• Certified EOS Implementer® through EOS Worldwide
• Outgrow Advisor® specializing in business exits
• Seven Figure Agency Program graduate and advocate
• Dan Kennedy school of marketing influence

Connect with Lyn

Lyn works with entrepreneurial companies ready to break free from owner-dependency and build scalable, systems-driven businesses. Whether you’re preparing for growth, seeking better work-life balance, or planning an eventual exit, his lived experience and proven frameworks provide the roadmap to transformation.

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Lyn Askin appeared on The Aviation Business Podcast in Episode 22: “From Near-Death to Seven Figures with EOS Implementer Lyn Askin,” sharing his transformation story and practical insights for building businesses that thrive independently of their founders.