Founder & CEO CoachingFor founders making the big calls without a peer to test them on.
Format
90-minute sessions, fortnightly
Length
Ongoing
Where
By video, wherever you are
Fees
From USD 1,500 a month

Coaching for
founders
& CEOs

Fortnightly one-to-one coaching with an operator who has built, scaled and exited his own business. I focus on the whole person running the business, not just the performance metrics.

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Jonathan O'Byrne in conversation at a café table
Image 01 Ninety minutes, every two weeks: long enough to go deep, with room to act in between.

Why Founders Call

Founders are rarely short of ambition or ideas. By the time they reach out, what they're short of is time and perspective.

Usually one of two things has happened. Either the business has grown faster than the systems underneath it, and the founder is carrying the difference. Or the business has stalled, and fixing it has fallen to the founder alone.

Either way, the founder feels isolated. The business they built is now running their life, and taking up more headspace than they can spare.

“I needed some guidance from someone who had been there and done that.”
IsaacCoworking space and creative agency founder. Working together since January 2026.

Where he started

Isaac, a serial entrepreneur, started with me in January. He had just launched a new marketing business alongside his coworking and property businesses.

“When we started in January, I was very new to marketing and working with clients whilst managing a growing team. I barely had any clear systems in place and mentally it could also be quite overwhelming. […] We were simultaneously in talks with multiple investors and determining whether to expand to a 2nd location or focus on growing our operations in Chiang Mai.”

Isaac smiling during a studio interview, in black and whiteImage 02 Isaac in the studio.

What he needed

What he was missing was not more information. It was a thinking partner and advice from someone who had made those calls before.

“I was struggling to envisage how the business could scale without overstretching myself.”

Isaac behind the camera on a video shoot, with his crew, in black and whiteImage 03 Behind the camera on a client shoot.

What we work on

  • Pricing, margin and cash: what the numbers are telling you, and what to change
  • The staffing and systems plan for the business
  • Where your time goes, and what only you should be doing
  • Growth decisions: new sites, new markets, investors and partners
  • Bringing AI into how the business runs
  • Your patterns: how you lead, where you get stuck, and how to stop being the bottleneck

How the coaching works

We meet fortnightly for 90 minutes. That gives us time to go deep, and gives you space to implement between sessions. You're welcome to email or message between sessions if you need advice or support, or just want to share a win.

  1. 01

    Start with you

    An intake session and a profile of how you operate, particularly under pressure, alongside what you want from the business and from your life outside it.

  2. 02

    Resolve what's live

    We catch and work through the urgent live issues, be those pricing, hires, client mix, expansion or investors, making room for bigger picture work.

  3. 03

    Start setting your agenda

    Creating capacity teaches both of us how the business really works. We put in long-term fixes that align with your goals, whether that is scale or winning back more time.

  4. 04

    Measure what matters

    Most founders know their numbers. We put them in a form you will actually use to make decisions, and to motivate and empower your team.

  5. 05

    Between sessions

    When a decision can't wait a fortnight, you message me.

Direct, never harsh

Most founders get two kinds of feedback: encouragement that tells them nothing, or criticism with no reasoning behind it. My job is to tell you which parts of the business are working, which aren't, and why, so you can act on it.

He pinpoints key areas where we are working well or poorly,
and outlines the exact reasons behind it.

One thing I love about working with Jonathan is he rarely sugarcoats anything. He's never harsh or unfair, but contrary to much of the advice/comments I receive, it's not vague and needlessly complimentary, but instead far more decisive. It's refreshing and doesn't feel like more sycophancy or unfounded criticism without basis.

Isaac · Serial entrepreneur, coworking and creative agency founder

Isaac: coworking space and creative agency

Isaac was spoilt for choice: his business was delivering great work that his clients loved and that gave him lots of options to expand, partner or take investment.

We worked through those scenarios while refining pricing and positioning, the client mix, the shape of the team and the systems underneath it. Isaac didn't need investment: he had the makings of a highly successful business with a little help. As the business strengthened, Isaac started to feel that too:

“Since working with Jonathan, I gained a lot of confidence in many crucial areas. I increased my prices by about triple and attracted much higher ticket clients, with lengthier retainers. My team has grown from 3 to 7 in under a year and I use AI tools far more effectively to manage communications between both the team and the clients. The quality of our content, as well as our systems have improved hugely.”
ISAAC · SERIAL ENTREPRENEUR, COWORKING & CREATIVE AGENCY FOUNDER

METRICS IN THE FIRST 9 MONTHS

3× Price Increase

With high ticket clients on longer retainers

3 → 7 Team

Rapid growth in under a year

High Value Retainers

From one-off fees of a few hundred dollars to monthly retainers worth thousands

AI Deployment

Moved from ad-hoc to highly systemised

The founder is part of the system

Founders are exceptional people. The traits that help them build businesses are usually the same ones that start to limit them when they hit a certain scale. So the work goes past the numbers into how you make decisions, where you overreach, and the early adaptations that once served you well and now get in the way. I'm a coach, not a therapist, and that allows me to be more direct. But the work goes deeper than most founders expect.

“Founders that want to dig deeper than just the numbers and get to the root of the issues that hinder them. This can mean delving into your psychological strengths, weaknesses and coping mechanisms which can of course be scary. However it's so worth it. People's superpowers can also become their Achilles heel as they start to scale; aiding founders to recognise that is one of Jonathan's key strong points.”
ISAAC
The eight patterns →

Questions

Is this coaching or consulting?
Isaac asked the same question in his testimonial: "coaching (consultancy?)". The honest answer is both. Sessions are coaching: they start with you and how you are making decisions. But I've built, scaled and exited several businesses, so when you need an operator's view on pricing, a hire or a deal, you get one.
How is this different from business coaching?
Most business coaches teach a framework. I've built, scaled and sold several businesses and led a turnaround, so the conversation is operator to operator.
Is this therapy?
No. I'm a coach, not a therapist, by choice. That leaves me free to be direct and give a straight opinion. Where personal history gets in the way, we work on how it shows up at work, alongside your therapist where that helps.
Why fortnightly?
It suits most founders: time to act between sessions. Some engagements start weekly while there's a lot in motion.

See whether it fits

A free 20-minute call.

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