$990 / month
Start free, decide later
Harry is a Founder and CEO of multiple digital marketing agencies. He has more than 25 years of business experience, has founded six businesses, and has mentored more than 300 people. He helps agency founders and freelancers win higher-value clients, improve pricing and sales, and grow their businesses with less stress.
Based on 76 verified mentee reviews
I help agency founders, freelancers and digital professionals win higher-value clients, increase income and reduce stress.
Why work with me?
✅ Founder of six businesses, including two successful digital agencies
✅ Advice from someone who still runs agencies, not someone who used to
✅ 25+ years in business; 300+ mentees and 1,000+ agency clients worldwide
✅ Practical mentoring only. No theory or generic motivation
✅ Agency clients include AliExpress, Engel & Völkers and the Ministry of Defence
✅ Top 1% mentor on MentorCruise with 100+ five-star reviews
I only work with a maximum of 15 mentees at any one time, so availability is limited.
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🚀 Which plan is right for you?
💬 Lite ($500/month)
Ideal if you want practical mentoring and accountability.
• Two 45-minute calls each month
• Unlimited chat support
⭐ Standard ($990/month)
• Four 60-minute calls each month
• Priority support
• Reserved mentoring slot
• Full access to my Agency Mastermind, worth $300/month
The Agency Mastermind gives agency founders monthly support to make sharper decisions.
It includes one 60-minute live call each month, private Slack accountability and, once per quarter, a paid guest expert session in place of the usual monthly call.
It is a small group focused on real agency challenges including sales, pricing, hiring, positioning, operations, AI and profitability. Guests are paid to share practical insight, not pitch.
This is the plan I recommend for most agency founders.
👑 Pro ($2,200/month)
You get everything in Standard, but I also become your Strategic Growth Advisor.
This is more than mentoring. I’m available when important decisions need to be made, helping with positioning, pricing, sales, hiring, leadership, commercial strategy and growth.
You’ll have a much more hands-on relationship with me. You can add me to your website as your Strategic Growth Advisor, introduce me as part of your leadership team and involve me in key commercial decisions, proposals and planning.
It’s designed for founders who want experienced strategic support without hiring a full-time senior director or consultant.
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Recent Mentee Wins
• Added $5K MRR after two sessions
• Moved from $1K web projects to $18K builds in three months
• Signed a first $10K/month client after one session
• Grew a micro-agency from $2K to $10K/month within a year
• Increased average project value by 50% at a 25-person agency
• Referred over six figures in paid client work directly to mentees
• Increased revenue from $6K to $24K/month in eight months
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Who I Work With
• Agency founders who want to grow faster and make better decisions
• Freelancers who want higher-value clients
• Senior digital professionals looking for clearer direction
If you want direct, practical advice from someone who has built and continues to run successful agencies, I would love to help.
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!
Standard Plan • 9 months
5 out of 5 stars
Wonderful, knowledgeable and grounded mentor. Really enjoyed working with him and has given me a clear path. Thank you Harry
Lite Plan • 2 months
5 out of 5 stars
Harry has been a great mentor, and our sessions were genuinely productive. His advice on sales and outreach was clear and practical. I really appreciated his perspective and support throughout the mentorship.
Lite Plan • 1 month
I discuss my personal journey from a freelancing professional to an agency owner, the advantages and the risks.
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I help agency founders, owners and senior leaders make better decisions around positioning, pricing, sales, team structure and growth.
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You tell Harry your goals. They see exactly what you want to work on before session one.
You meet within days. Harry reviews your application and books your first session, usually within a day or two.
You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.
Harry O'Connor
Founder, CEO at multiple digital marketing agencies
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Book a free intro call with Harry
Connect with Harry in a quick call (usually 15-20 minutes)
One-off sessions with Harry
One-off sessions are a great option if you're looking for specific advice on a certain topic.
This is a no-commitment intro call so we can work out if we are a good fit without you needing to sign up as my …
1 hour mentoring session. This is a one-off session and you can book as many as you like and discuss any topic you like. Typically …
I offer in-person mentoring in the Faro region (Algarve, Portugal). Availability is limited, and once booked, you’ll be asked to join a short 15-minute call …
I offer in-person mentoring occasionally in the UK, typically in London. Availability is very limited. Once booked, you’ll be asked to join a brief 15-minute …
