One-to-one mentoring for agency founders and freelancers

Build a successful agency and a better life.

Harry O'Connor

I’m Harry O’Connor. I’ve run digital agencies for 25 years and I still run two of them. I mentor founders and freelancers who want better clients, higher prices and more of their time back.

100+ five-star independent reviews

Sunset over the pool and the hills from Harry's villa in the Algarve

Mentor with

Techstars
Seedstars
IMPACT Accelerator
Association of Business Mentors
Harry O'Connor in his garden in the Algarve

I started at a kitchen table in a rented house.

I couldn’t get clients, I couldn’t manage the ones I had, and the money never added up. It took me years to work out what a successful agency actually runs on.

My first agency is 25 years old. I started my second in 2017, and I still run both. These days I do it from a villa in the Algarve, where I live with my family.

This wasn’t an overnight success, and you should be sceptical of anyone who tells you theirs was.

25 years
running agencies

500+
founders and business owners mentored

Six
businesses built

Two
agencies I still run today

Read how I got here

What mentees say

More than 100 five-star reviews, all independent. These are a few of them.

Monthly turnover has increased over 300% as a direct result of the changes we’ve discussed and actioned together! As well as his friendly, helpful approach it was encouraging to work with someone who had direct experience of the industry that I work in.

Tim Ryan
Founder, Echo Eighty

In a matter of weeks of speaking with Harry he’d devised a straightforward plan, one thing to focus on for that specific quarter. I got to work with what Harry had proposed. As a result of working with Harry and the referrals he sent our way, which were greatly received, our business went from a struggling agency of one to a growing agency of 3 including a graphic designer and a freelance web developer.

Robert Haylor
Web design agency founder

Harry is an amazing mentor! In just one meeting, he has removed most of my dilemmas and anxieties regarding my agency business. For me, he is very inspirational! Big recommendation!

Nikola Novakovic
Agency founder

Harry has great experience in launching, scaling, and running agencies and has a wealth of actionable insights to share. From business development, over pricing and proposals, legal or hiring. And practical advice on how to get from 0 to 1.

Petr Hejtmánek
B2B lead generation agency founder

Harry is an amazing mentor! Very knowledgeable & effective. He helped me solve every single problem I had + solve problems I DIDN’T KNOW I had. I wholeheartedly recommend him, you will be amazed.

Matija Djumic
Digital marketing strategist

Harry has been an absolute pleasure to work with and makes me feel very supported as a business owner. That’s because every time I talk to Harry about an issue I’m dealing with, he has relevant experience to draw upon and thoughtful advice to share.

Colin Van Ert
Agency owner and head of product

Harry is a great mentor and has a vast experience in setting up and running a web design and development agency. His insight and knowledge was really helpful when trying to handle difficult strategic business decisions.

Ash Hewins
Virtual reality agency founder

Read all the reviews

What we work on

Better clients

Where they are, how to reach them and what to say when you do.

Pricing

Charging what the work is worth, and saying the number out loud.

Proposals

Fewer of them, sent to the right people and written to be accepted.

A niche

Deciding what you’re known for, so the right work starts coming to you.

Your first hires

Who to bring in first, when to do it and how to afford them.

Your time

Getting out of the day-to-day until the business runs without you in every job.

See how I think before you book.

I share what I learn from running agencies and mentoring founders on YouTube.

Play video: My mission: why I help agencies grow
My mission: why I help agencies grow
Play video: The problem with low-ticket offers
The problem with low-ticket offers
Play video: Fear nearly cost me £120k
Fear nearly cost me £120k

Three ways to work with me

The monthly plans start with an intro call, so we both know it’s a fit before you commit to anything.

Power Hour

$250

one-off

  • One 60-minute call
  • Bring your most urgent problem and leave with a plan
  • Nothing to sign up to

Mentoring

$500

a month

  • Two 45-minute calls a month
  • Message me between calls
  • The private Slack group of 150+ mentees
  • Cancel whenever you like

Standard

$990

a month

  • Four 60-minute calls a month
  • Message me between calls, with replies inside 24 hours
  • A reserved slot in my week
  • The private Slack group of 150+ mentees
  • Cancel whenever you like

For established agencies

Founder Counsel

$2,200

a month and up

When mentoring calls aren’t enough. I get involved in the decisions themselves: the price, the proposal, the hire. It runs on my advisory site.

Prices are in US dollars. Plans are paid monthly and you can stop at any time.

The Perfect Proposals course shown on a monitor, laptop, tablet and phone

A course you can take on your own

Perfect Proposals

How I write proposals that win bigger projects. 24 short videos, a little over two hours in total.

Questions people ask first

Who do you work with?

Freelancers and agency founders, mostly in web, design and marketing, with businesses up to about a million dollars in revenue. Some are still working alone or only just starting out. I only take on people aged 21 or over.

My agency is already established. Is this still for me?

It can be. If you want me involved in your commercial decisions between calls, look at Founder Counsel on harryoconnor.co.uk, which is built for that.

How long before I see a difference?

It depends how quickly you act on what we discuss. Most people who commit see a real change in their business within six months, and many see it sooner.

Can I cancel?

Yes, at any time and without notice. Plans are paid monthly in advance, and a month that has started isn’t refunded.

If you’re so successful, why do you charge for mentoring?

I’ve never claimed to be the most successful person out there. The work I do as a mentor helps my mentees build their own bank balance, so I think it’s fair to charge a reasonable amount for my time. I’ve also noticed that the people I help for free tend to be less committed.

More questions and answers

Start with a call.

Tell me where the business is and where you want it to be. I’ll tell you how I’d get there, and whether I’m the right person to help.