From Near-Death to Seven Figures with EOS Implementer Lyn Askin

Live Recording: October 10, 10AM Central on Riverside

Episode Guest: Lyn Askin, EOS Implementer® & Former Digital Marketing Agency Owner

What if your business couldn’t survive without you? What would happen to your team, your clients, and your family if you suddenly couldn’t show up tomorrow?

For most flight school owners, this isn’t a comfortable question. But for this week’s guest, Lyn Askin, it became a life-or-death reality that fundamentally transformed how he built businesses—and now helps others do the same.

From Crisis to Clarity: A Near-Death Wake-Up Call

In 2020, Lyn Askin was running a successful digital marketing agency he’d built over 18 years. Then came the bilateral pulmonary embolism—a life-threatening condition that landed him in the ICU, fighting for his life.

But it wasn’t just the physical pain that terrified him. As he lay in that hospital bed, Lyn faced a devastating realization: if he didn’t survive, his wife would have to shut down the entire business, fire all the employees, and lose everything they’d spent nearly two decades building. His company was completely dependent on him—and that dependence could destroy it.

“I realized I hadn’t built a business,” Lyn shares in this powerful episode. “I’d just created a job that nobody else could do.”

That moment of clarity became the catalyst for one of the most dramatic business transformations you’ll hear about—and the lessons apply directly to flight school owners who find themselves in the same trap.

The EOS Transformation: From Owner-Dependent to Self-Sustaining

After his recovery, Lyn implemented the Entrepreneurial Operating System (EOS) in his agency, Raxxar Digital Marketing. The results were nothing short of remarkable:

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

Today, as a certified EOS Implementer® and Outgrow Advisor®, Lyn helps other entrepreneurial companies (10-250 employees) build businesses that thrive independently of their founders.

What You’ll Learn in This Episode

The Six Components That Transform Owner-Dependent Businesses

Lyn breaks down the EOS framework that saved his business and explains how each component applies to flight schools:

Vision: Getting your leadership team aligned on where you’re going and how you’ll get there

People: Ensuring you have the right people in the right seats doing the right things

Data: Creating scorecards that give you real-time visibility into business health

Issues: Developing systems to identify and solve problems permanently

Process: Documenting the core processes that make your business run

Traction: Building accountability and discipline to execute on your vision

Why Flight Schools Need This More Than Ever

If you’re a flight school owner who personally handles student consultations, steps in when instructors call out sick, manages the schedule, oversees maintenance, and puts out fires all day long—this episode is for you.

Many flight school owners have built their businesses on personal relationships, their instructional reputation, and hands-on involvement in everything. While this creates loyalty and quality, it also creates an unsustainable trap. You become the bottleneck to growth and the single point of failure.

Lyn explains how to break this cycle without sacrificing quality or losing the personal touch that makes your flight school special.

Digital Marketing Wisdom from 25+ Years in the Trenches

Before his transformation story, Lyn built deep expertise across every digital marketing discipline: SEO, PPC, marketing automation, website development, and lead generation systems. He shares critical insights on:

• Generating measurable ROI instead of vanity metrics
• Building marketing systems that run without constant oversight
• Creating authority positioning in crowded markets
• Automating client communication without losing the personal touch

Authority-Based Leadership for Service Businesses

Drawing from the Dan Kennedy school of marketing, Lyn discusses why maintaining professional boundaries and positioning yourself as an authority figure creates better client outcomes than being constantly accessible. For flight school owners who struggle with work-life balance because they’re always “on call” for students, this perspective is game-changing.

The Path to a Successful Exit (If You Want One)

As an Outgrow Advisor®, Lyn now helps business owners plan and execute exits. Whether you’re thinking about succession planning, selling to a management team, or attracting outside buyers, Lyn explains what makes a business valuable and sellable—and what scares buyers away.

Spoiler: A business that can’t run without its founder isn’t worth much to anyone.

Key Takeaways for Flight School Owners

Systems Trump Heroics: The best business owners work themselves out of daily operations, not deeper into them. Your job is to build the machine, not be the machine.

Document Everything: If it’s only in your head, it’s not a process. Your flight school’s procedures, scheduling systems, student communication protocols, and instructor training should all be documented and transferable.

Build Your Leadership Team: You can’t scale past yourself without developing other leaders. Identify who has the capacity to take on more responsibility and invest in their development.

Transparency Creates Loyalty: Lyn advocates for complete honesty with clients about business performance, even when it’s uncomfortable. This integrity creates loyal, long-term relationships with students and their families.

Think Like a Buyer: Even if you never want to sell, running your flight school as if you were preparing it for sale forces you to build better systems, stronger financials, and clearer documentation.

Why This Matters for Aviation Entrepreneurs

The aviation training industry is at a critical juncture. With the ongoing pilot shortage, there’s enormous opportunity for well-run flight schools to grow. But growth amplifies your problems—if you’re already overwhelmed at 30 students, what happens at 60? At 100?

Right Rudder Marketing’s vision includes helping flight schools become scalable, systems-driven businesses. Many flight school owners face the exact challenge Lyn overcame. Whether you have 2 aircraft or 20, if you disappeared tomorrow, would your flight school continue to thrive?

This episode provides a proven roadmap for building a business that serves you, rather than one that owns you.

Mark your calendar: October 10, 10AM Central Join the live recording: https://riverside.fm/studio/podcast-40nqk

Resources Mentioned

• Entrepreneurial Operating System (EOS): A complete business system for growth-oriented companies
• Seven Figure Agency Program: Coaching program for agency owners scaling to seven figures
• Raxxar Digital Marketing: Lyn’s former agency (successfully exited 2023)

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About The Aviation Business Podcast

The Aviation Business Podcast brings you conversations with successful aviation entrepreneurs, business leaders, and industry experts who share actionable strategies for growing flight schools and aviation businesses. Hosted by Right Rudder Marketing, each episode delivers insights you can implement immediately to train more pilots, increase revenue, and build the aviation business of your dreams.

Ready to transform your flight school’s marketing and operations? Visit rightruddermarketing.com to learn how we help flight schools implement proven systems that drive student enrollment and revenue growth.

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This episode is brought to you by Right Rudder Marketing—the digital marketing agency exclusively serving flight schools. Learn more at rightruddermarketing.com.