From banking manager to bottleneck buster

Boxers & Briefs Podcast #49: Business bottlenecks: How to unblock your growth with Jon Randles

When growth flatlines in your business, the culprit might be closer than you think. Sometimes it’s external circumstances. Sometimes it’s you.

Jon Randles knows this reality intimately. His career journey reads like a business experiment gone right—telemarketer, language school GM in Japan, business banking manager at ANZ, co-owner of a marketing agency, and now business coach. Each role taught him something different about what makes businesses tick and what makes them stall.

His coaching philosophy centres on a simple premise: business owners don’t need more information. They need clarity, accountability, and the right framework to execute what they already know needs doing.

The six-figure turnaround

In 2008, Jon and a friend spotted the social media wave building. Neither had marketing backgrounds, but they were early enough to matter. They created a social media marketing company and landed Hell Pizza as their first client—a connection from Jon’s university days working at their second-ever store.

From the outside, the business looked brilliant. Fletcher Building and other blue-chip clients filled their roster. Inside, it was chaos. Money flowed out faster than it flowed in. The deficit grew to six figures. They juggled credit cards to pay wages. Jon developed anxiety from the stress.

“We couldn’t afford a mentor, but we couldn’t afford not to have one,” Jon recalls.

That mentor didn’t know their industry. He didn’t need to. His tools were a mirror and a spotlight—shining light on neglected areas and holding Jon accountable for the work that mattered.

The solution wasn’t complex. They identified the right projects, worked on them systematically, and completed them before moving to the next. In 12 months, they went from six figures in debt to six figures in the bank.

Three years ago, Jon was mapping out an organisational (org) chart with his business partner. He looked at one of the circles and realised they didn’t need it. That circle was him. Twelve years after starting, the business no longer required his daily involvement.

Their mentor suggested business coaching. Jon’s background—marketing agency experience, business banking knowledge, and Cambridge training in teaching methodology—made it a natural fit. He’s been helping business owners escape their own bottlenecks ever since.

The warning signs you’re blocking your own growth

Two signals indicate you’ve become the bottleneck.

Internal signal: You can’t take two weeks away without leads slowing, quality dropping, or operations faltering. You need to be there.

External signal: Growth has stalled. You’re working as hard as possible, but the ceiling won’t budge. The business can’t scale beyond your personal capacity and available time.

“I just finished a session with a couple who took last Friday off for their daughter’s birthday,” Jon shares. “Everything ran smoothly. That’s the transformation—from being unable to step away to taking time off without a second thought.”

The challenge is knowing when normal startup hustle crosses into bottleneck territory. Early on, doing everything yourself is expected. You’re building the foundation. But there’s a point where flatlining signals you’ve created a job for yourself rather than a business.

If your goal is a job that pays enough and gives you enough time, stay there. If you want to scale—whether that means more revenue, another business, or simply having Fridays free—you need to start delegating.

One client’s journey from overwhelmed to overseas

Jon started working with one client in November last year. Everything ran through him. The business wasn’t performing well.

First, they sorted foundational issues. You need a functioning business before you can step away from it. After three months, the client found traction. He’s been profitable every month since—nine consecutive profitable months.

Profitability breeds confidence and creates capacity to bring in help and outsource tasks.

The client brought in someone to systemise his admin processes. They worked through implementation one project at a time. They ran a DISC workshop with the team.

“He said it was like a shortcut to understanding his team,” Jon explains.

The client is a high D—fast-moving, direct. Some team members are slower-paced and need detail. He used to shout instructions and wonder why tasks weren’t completed properly. After the workshop, he asked his team what they needed to feel confident taking on delegated work.

Some wanted detail. Others wanted visual aids. He adapted his communication style to match their needs.

Recently, he spent three and a half weeks travelling Southeast Asia. The only work he did was a couple of hours of payroll each fortnight—the last task he hadn’t delegated. He didn’t check emails. A VA sorted those according to systems they’d built. He came back refreshed.

That’s the transformation. From everything flowing through him to nearly complete operational independence.

Why delegation feels impossible (and how to do it anyway)

Business owners resist delegation for predictable reasons:

• It’s quicker to do it myself
• Nobody will do it as well as I do
• I’ll lose control
• This task needs to be done right

The first step is establishing clear vision. What do you want? Why does it matter? Is it worth the short-term pain?

Delegation is difficult. People make mistakes initially. Doing it yourself often is easier. But if your goal is a month in Southeast Asia, a second business, or simply creating something that runs without you, you need to start somewhere.

Jon tells the story of Hell Pizza’s owner in the early days. A mentor asked him: “Could you find two people who could do 80% of what you’re doing?”

Yes, probably.

“If we put 80% and 80% together, and your 100% becomes 80% because you’re managing instead of doing, that’s 240% of what you were doing before.”

It reframes the question. Short-term pain for long-term multiplication.

The key is not handing over the keys to the Lamborghini on day one. You start with small tasks. Then bigger ones. Or components of larger tasks. Or have them complete work and show you before it reaches the client.

The bottleneck might worsen temporarily, but there’s a plan now. You’re moving toward something.

The $25 versus $250 question

Jon uses a simple framework to help clients identify which tasks to keep and which to delegate.

1. List out your week’s tasks. Separate them into low-payoff and high-payoff activities. Ask yourself: which tasks are worth $25 an hour and which are worth $250?
   1. Apply a hard lens. Be honest about which activities deliver $250 of value and which deliver $25.

Another tool is the Eisenhower Matrix—important versus not important, urgent versus not urgent.

Most business owners spend time in Quadrant 1 (urgent and important—usually client work) and Quadrant 3 (urgent but not important—emails, interruptions, phone calls).

The goal is moving into Quadrant 2: not urgent but important. Strategic work. Projects that build the business rather than just keeping it running.

“A lot of my clients already know what they need to do,” Jon says. “They need someone to hold them accountable and remove the noise and distractions. When we clear that away, they see the priority immediately.”

Hard work, guesswork, or framework

You can build a business three ways: rely on hard work, rely on guesswork, or rely on a framework.

Only one delivers consistent results.

Jon’s developing a framework for 2025 specifically for business owners stuck in bottleneck mode—those who want to stop being the constraint and start working on the business instead of in it.

The ratio of time spent on the business versus in the business depends on where you start. The goal is simply to shift it—more on the business than before. When you’re starting out, you’re on the tools, doing the work. Ideally, you reach a point where you’re not.

Jon’s client who travelled Southeast Asia now hyper focuses on strategic, on-the-business work. He doesn’t do client work anymore. If there’s a client error, he doesn’t lose sleep over it. It’s one of a hundred. Before, it was everything.

“It’s like Ray Kroc and McDonald’s,” Jon explains. “If someone drops a hamburger in an LA restaurant, how much does he care? Not much. Once you have systems in place, errors happen, but they happened when you were involved too.”

Creating the job you actually want

Every business owner has a zone of genius—work they love, excel at, and could do indefinitely. That’s where you should spend your time.

For some, it’s public speaking. For others, it’s podcasts and conversations. For others still, it’s building spreadsheets and working behind the scenes.

Jon’s business card at his marketing agency read ‘Head of Talking.’ He knew his strength.

“Whatever your zone is, that’s where you should spend your time,” he says. “Actually have the job you want.”

Your role changes as the business grows. Instead of being the doer, you become the business owner—the leader of the enterprise. You need different skills now: managing, delegating, reducing errors. It’s a different challenge, but it can be enjoyable to work out how to build systems that deliver quality without your constant involvement.

The business owner who travelled Southeast Asia understands this now. So does the couple who took their daughter’s birthday off without worry. They’ve replaced themselves in the day-to-day operations and created space to lead, plan, and enjoy the business they built.

That’s the point of breaking free from the bottleneck. Not just growth for growth’s sake, but creating a business that serves your life rather than consuming it.

This article and podcast is proudly brought to you by Gilligan Sheppard, the problem solvers in business who believe in thinking differently.