$990 / month
4 calls per month (60min/call)
Unlimited Q&A via chat
Expect responses in 24 hours or less
Hands-on support
Start with a free intro call to see if it's the right fit.
$990 / month
4 calls per month (60min/call)
Unlimited Q&A via chat
Expect responses in 24 hours or less
Hands-on support
$990 / month
4 calls per month (60min/call)
Unlimited Q&A via chat
Expect responses in 24 hours or less
Hands-on support
$990 / month
Start free, decide later
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
✅ 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
✅ Standard Plan mentees and above also get access to my Agency Mastermind
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 web 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 over six figures in paid client work directly to mentees
• Mentee jumped revenue from $6K to $24K per month in 8 months
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● Who This Is For
• Freelancers that want better-paying clients
• Agency founders stuck at a revenue, profit or confidence ceiling
• Senior digital leaders who want clearer direction and leverage
If you want straight, practical guidance from someone who has done it, I can help you.
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● Agency Mastermind Access
Mentees on the Standard Plan and higher also get access to my private Agency Mastermind.
This is a small, structured group for agency founders and senior freelancers who want to grow stronger businesses, improve sales, increase profit, make better decisions and stay accountable.
It includes group discussion, practical problem-solving, peer support and guest expert sessions. These are paid, high-quality guests, so they are there to share useful insight, not pitch at you.
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🔥🔥🔥 Strategic Growth Advisor - Pro Plan
My Pro Plan is for agency founders who want more than mentoring.
This is more like having a senior strategic member of your team, without the cost or commitment of a full-time senior hire.
As your Strategic Growth Advisor, I help you make clearer decisions across positioning, pricing, offers, sales, hiring, leadership, client quality and commercial direction. We look at the business as a whole and focus on decisions that create more growth, more margin and less founder dependency.
You get flexible access and calls when needed, not just a fixed call schedule. That means we can respond when important decisions come up, review opportunities, challenge assumptions and keep momentum between sessions.
You can start with the Pro Plan and downgrade later if standard mentoring is a better fit.
Please book the Pro Plan here on MentorCruise. More information about my advisory work is here:
5 out of 5 stars
In my first session with Harry, he pointed a huge issue with how I position my services and gave me tactical next steps for what I need to make happen TODAY. Looking forward to our next call!
Session: Intro Session
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
5 out of 5 stars
The calls I had with Harry were exceptional, he gave me tactical advice on how I can scale my agency. He went through similar situations I'm going through right now, so his advice was super valuable. Can't thank you enough!
Lite Plan • 2 months
I discuss my personal journey from a freelancing professional to an agency owner, the advantages and the risks.
Read more
I help agency founders, owners and senior leaders make better decisions around positioning, pricing, sales, team structure and growth.
Read more
Mentees who work with a mentor for 3+ months reach their goals 2x faster than those going it alone. Long-term mentorship means fewer false starts, more focused sessions, and support that builds week after week.
97% satisfaction across all mentors
Personalized feedback and growth plans
Trusted by thousands of mentees
Harry O'Connor
Founder, CEO at multiple digital marketing agencies
Enter your email and we'll let you know when Harry has open spots. You'll also get a link to manage your wishlist – no account needed.
Book a free intro call with Harry
Connect with Harry in a quick call (usually under 30 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 …
