Why You Should Never Outsource Your Vision With Roy Coughlan Firing The Man podcast

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Why You Should Never Outsource Your Vision with Roy Coughlan

1d ago 44:22

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What does true entrepreneurial freedom look like? Roy Coughlan embodies this answer through his remarkable journey from washing cars at age 9 to building an empire spanning 20 companies across five countries.
Roy's entrepreneurial instinct emerged early. While other kids played, he delivered newspapers, washed cars, and by 14, had purchased his own lawnmower to start a neighborhood grass-cutting service. Despite formal education in construction management, Roy found corporate employment frustrating—watching dedicated colleagues mistreated and experiencing firsthand how companies reduced incentives for top performers.
The pivotal moment came when Roy spotted property investment opportunities in Poland. Gradually transitioning from his corporate role, he eventually made the complete leap to entrepreneurship—a status he's maintained for 18 years. This freedom allowed him to spend a month by his grandmother's bedside during her cancer battle and arrange his schedule around co-parenting his son—opportunities impossible within corporate constraints.
Through building his business empire, Roy learned crucial lessons about hands-on financial and legal management. "Don't outsource your legal side or accounting," he advises. "It's your business. You're the one that's going to suffer." This philosophy guided him through over 100 court cases and countless business negotiations.
Roy's journey eventually led him to podcasting, where he's established six successful shows, four reaching the global top 0.5%. His innovative approach uses podcasting as both a business itself and as a marketing tool—interviewing potential clients rather than making cold calls. His company VA World grew from his own need for reliable virtual assistant services, now helping entrepreneurs maximize productivity while maintaining proper oversight.
For anyone dreaming of entrepreneurial freedom, Roy's story offers inspiration and practical wisdom: develop a resilient mindset, never tolerate failure, and remember that entrepreneurship isn't just about financial success—it's about controlling your time, energy, and ultimately, your life.
How to connect with Roy?
Website: https://roycoughlan.com/

Podcast: https://podcasts.apple.com/us/podcast/speaking-podcast/id1443652346

YouTube: https://www.youtube.com/channel/UCk5CEEWZ2KgUTYJOTXNL8lQ

Facebook: https://www.facebook.com/roycoughlan

Linkedin: https://www.linkedin.com/in/roycoughlan/

Twitter: https://x.com/poleire
Spotify: https://open.spotify.com/show/5zg8fJBSvBCY0oWdoF7mkP#login

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Chapters

1. Why You Should Never Outsource Your Vision with Roy Coughlan (00:00:00)

2. Introduction to Roy Cullen (00:01:22)

3. Roy's Early Entrepreneurial Journey (00:05:04)

4. Firing the Man: Leaving Corporate Life (00:07:03)

5. Building 20 Companies: Key Business Lessons (00:11:51)

6. Podcasting Success Strategies (00:17:06)

7. Monetizing Your Podcast (00:21:55)

8. Virtual Assistants for Business Growth (00:29:16)

9. Fire Round & Final Thoughts (00:41:48)

271 episodes

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