Harry O'Connor
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Harry O'Connor

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

Services

$890 / month

Weekly 45 min calls, hands-on help, priority booking + access to my Slack group for ongoing guidance

4 calls per month (45min/call)

Unlimited Q&A via chat

Expect responses in 24 hours or less

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About

I work with agency founders, freelancers, and digital professionals to win bigger clients, earn more, and reduce stress.

About

I’ve spent the last 25+ years building and running agencies, founding six businesses along the way. Like many in the digital world, I know what it’s like to juggle clients, deadlines, and growth while still trying to have a life outside of work.

That experience shapes how I mentor today. I don’t hand out theory; I share practical strategies I’ve used myself to win bigger clients, build stronger teams, and navigate the challenges that come with running a business or career in digital.

Over the last 8 years I’ve mentored more than 300 people — from freelancers starting out, to agency owners scaling up, to leaders at global companies. My focus is always the same: helping you grow in a way that feels sustainable, rewarding, and far less stressful.

I only work with a maximum of 10 mentees at a time and I’m usually at or near capacity. If I’m not available, please press the “Save to Wishlist” button to be notified when a spot opens.

Clients & Mentees
• Agency Clients: AliExpress, Engel & Völkers, City of London, Ministry of Defence, The Design Museum, plus over 1,000 clients worldwide — from global brands to local independents
• Mentees: Professionals from JP Morgan, Microsoft, Salesforce, McKinsey, Deloitte, Arsenal FC, alongside hundreds of independent agencies, freelancers, and marketing professionals

Achievements
• 25+ years running agencies
• Founded 6 businesses in the UK and Dubai
• Mentored 300+ founders, freelancers, and professionals worldwide
• Backed by Techstars and Seedstars

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 is a fabulous mentor who truly pushes you to grow. He listens carefully, gives thoughtful advice, and never hesitates to challenge you to go beyond your comfort zone. Harry has pushed my boundaries many times, giving me challenges that have been instrumental in helping me become a better professional and build my business. His support and guidance have been invaluable, and I’m grateful for his dedication to my success. Highly recommend him to anyone looking for a mentor who actively helps you reach your potential!

Heidi

Heidi

Standard Plan • 22 months

Heidi wrote 1 more review for the same mentorship

5 out of 5 stars

I can't say enough good things about Harry and his mentoring style. He has a natural talent for guiding and motivating people, and he truly cares about his mentees' success. When I first started working with Harry, I was feeling stuck and unsure of how to move forward with my (millions of) goals. But Harry was able to quickly understand my situation and provide me with the tools and resources I needed to take action. He helped me identify my strengths and weaknesses, set clear goals, and develop an actionable plan to achieve them. He pushed me to step outside of my comfort zone and take on new challenges, but he did so in a way that was encouraging and supportive. What I appreciated most about working with Harry was his ability to help me change my mindset. He showed me that success is possible if I am willing to put in the work and believe in myself. Thanks to Harry's guidance and support, I was able to make significant progress towards my goals in a short amount of time. I would highly recommend Harry to anyone who is looking for a knowledgeable and inspiring mentor. He is a great communicator, a good listener, and an all-around great guy. Thanks for everything, Harry!

Heidi

Heidi

Standard Plan • 2 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

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