Harry O'Connor
Play intro

Harry O'Connor

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

Services

$590 / month

Standard offering of 3 x 45 min calls per month + access to my Slack group for ongoing guidance

3 calls per month (45min/call)

Unlimited Q&A via chat

Expect responses in 24 hours or less

Hands-on support

Book an intro call
No credit card required
Book now
View all sessions
Lock in this price now!

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 15 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.

🔥 Recent Mentee Wins:

• Meta ads founder added an extra $5K MRR after just two sessions
• Web agency scaled from $1K projects to $18K builds in 3 months
• Leadgen client signed their first $10K/month deal after a single session with me

👥 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
• Top 1% mentor here on MentorCruise

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

Amazing mentor. 10/10 He will help you with everything you need and provide accurate and practical answers that will help you scale your revenue

Joseph

Joseph

Standard Plan • 1 month

Joseph wrote 1 more review for the same mentorship

5 out of 5 stars

Amazing mentor, really takes your concerns and questions seriously and provide a very practical and straightfoward solution, 100% recommended

Joseph

Joseph

Load more reviews