Harry O'Connor
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Harry O'Connor

Founder, CEO @ multiple digital marketing agencies
5.0
(100 reviews)
2 x Agency Founder | 25+ Years Experience | 6 Businesses Built | 8 Years Mentoring | 300+ Mentees
United Kingdom Active yesterday Usually responds in a few hours

Services

$990 / month

60 min calls reserved weekly slot + priority access + hands-on support for serious mentees only

4 calls per month (60min/call)

Unlimited Q&A via chat

Expect responses in 24 hours or less

Hands-on support

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Only 2 spots left!

About

I help agency founders, freelancers, and digital professionals win higher-value clients, increase income, and reduce stress.

Why work with me?

✅ Agency founder and founder of six separate businesses
✅ Experience comes from owning and running businesses, not from an employee role
✅ 25+ years in business; 300+ mentees and 1,000+ agency clients worldwide
✅ Hands-on experience of real business life; clients, deadlines, and growth pressure
✅ Practical mentoring only; no theory or generic motivation
✅ Agency clients include AliExpress, Engel & Volkers, and the Ministry of Defence
✅ Top 1% mentor on MentorCruise with 100+ five-star reviews

I work with a maximum of 15 mentees at any one time and I am usually close to capacity; save to Wishlist to be notified when a space opens.

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● Recent Mentee Wins

• Added $5K MRR after two sessions
• Moved from $1K projects to $18K builds in 3 months
• Signed a first $10K per month client after one session
• Grew from $2K to $10K per month micro-agency within a year
• Increased average project value by 50% at a 25-person agency
• Referred a paid speaking engagement at a top UK university to a mentee
• Referred over six figures in paid client work directly to mentees

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● Who This Is For

• Freelancers who want better-paying clients
• Agency founders stuck at a revenue or confidence ceiling
• Senior digital leaders who want clearer direction and leverage

If you want reassurance or motivation, this probably isn’t for you. If you want straight, practical guidance from someone who has done it, this will help.

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🔥 Non-Executive Director (NED)

My Pro Plan allows you to hire me as your NED. It costs less than a junior hire and gives you ongoing, board-level strategic guidance, with calls as needed. In-person meetings are available if travel costs are covered, and I’m happy to be listed on your website or pitch material if appropriate.

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FAQs

● Is this 1 to 1?
Yes. All mentoring is 1 to 1. Group mentoring is available at an additional cost; please get in touch before booking.

● Are you one of those fake gurus?
No. I build businesses, make mistakes, learn from them, and help others do the same, faster.

● What’s your revenue, headcount, or agency size?
I don’t share internal figures. The focus is on what improves your business, not mine, as reflected in my feedback and reviews.

● Can you guarantee results?
No. I provide clarity, direction, and proven thinking. The work is still yours.

If this feels like the right fit, book a call. If I’m full, save the slot and I’ll notify you when space opens.

What mentees say

5 out of 5 stars

Harry has truly been a remarkable mentor in my life. From the moment we started working together, his passion for teaching and supporting others stood out. His deep knowledge and experience in the field were always complemented by his patience and understanding, making even complex concepts seem accessible. One of the most significant lessons I learned from Harry was the importance of resilience. He often shared stories of his own challenges and setbacks, emphasizing that failure is not the end but an opportunity for growth. This perspective has helped me embrace difficulties and view them as stepping stones on my journey. Additionally, Harry taught me the value of clear communication. He had a knack for breaking down intricate topics into simpler terms, ensuring everyone was on the same page. This has inspired me to focus on clarity in my own communication, both in writing and speaking. Not to mention how he was very understanding when I needed to separate paths from my co-founder. His advice meant a lot to me. Perhaps the most vital lesson came from his approach to leadership. Harry demonstrated that true leaders empower those around them rather than simply directing them. He encouraged collaboration, actively sought input, and celebrated the successes of his mentees, which fostered a positive and motivating environment. Overall, my time with Harry has been transformative, and I am incredibly grateful for his guidance. His mentorship has shaped not only my professional skills but also my approach to challenges and my interactions with others. I will be coming back seeking more mentorship from Harry!

Nebojsa

Nebojsa

Standard Plan • 9 months

5 out of 5 stars

Harry was able to provide some much needed perspective on the aspects of my work that were most important. I have had a change in direction professionally, but will happily reach out to Harry in the future when my circumstances can take advantage of his expertise.

Nuno

Nuno

Standard Plan • 19 months

5 out of 5 stars

I've been with Harry for nearly a year now. It's been one of the most productive years yet. Harry's calm knowledge and perspective on building agencies from scratch have been countlessly helpful. Highly recommend Harry!

Erica

Erica

Standard Plan • 12 months

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