Articles

What I'm thinking about

Frameworks, lessons, and perspectives on digital agencies, acquisitions, and online growth.

6 min read

What Reduces the Value of a Business? 9 Hidden Discounts

Asking for a retrade post-LOI can sour a relationship. Here are some of the surprises that come up when selling an agency.

4 min read

You Decide Your Level of Involvement: How to Take Initiative at Work

Six words from my manager changed how I saw my career. Here's the timeless lesson behind them, and how to take initiative at work before anyone asks.

6 min read

Can You Sell an Owner-Dependent Business?

When I see "fractional CMO" in an agency listing, I skip it. Here's what sellers should know about founder dependency.

9 min read

Do You Need a Business Broker? What They Charge and When They're Worth It

I've sold four companies without a broker, and now buy agencies from the other side of the table. Here's what brokers charge and when they earn it.

5 min read

What Happens to Your Team When You Sell Your Business

When I sold Sapling, the team was what kept me up at night. Here's what really happens to staff after a sale, from both sides.

8 min read

What Is an Earn-out? A Guide for Agency Owners

What an earn-out is, how the maths works when you sell your agency, and how to tell a fair structure from one that ties your hands.

9 min read

Asset Sale vs Share Sale: How to Structure the Sale of Your Agency

Asset sale or share sale? What buyers worry about, what founders gain, and why recurring revenue changes the answer.

4 min read

The Most Helpful 6 Words Anyone's Said to Me

In year 7, a mate told me I'd never be good at basketball. Twenty years later, at our reunion, he said something I didn't expect.

5 min read

Types of Business Buyers: A Guide for Agency Owners

Private equity, holding companies and consulting firms all want something different from your agency. Here's how to tell who you're really talking to.

5 min read

How Long Does It Take to Sell an Agency?

How long does it take to sell an agency? About 6 weeks to sell and up to 6 months to transition. Here's what drives both, from the buyer's side.

4 min read

The Lion King Hits Different as a Dad

I took our girls to see The Lion King, the film I loved at 5. Three scenes landed in ways I didn't expect.

5 min read

What Happens to Your Customers When You Sell Your Agency

Worried about your customers if you sell? What I've learnt from both sides of the table about protecting relationships through a handover.

5 min read

Working Capital Adjustments: The Second Negotiation

You've agreed the price. Then comes the second negotiation. How prepaid revenue and expenses move what you actually walk away with.

6 min read

Why Recurring Revenue Changes Your Valuation

Not all recurring revenue is equal. The five types buyers see, how margin and churn set the multiple for each, and why it has to transfer.

5 min read

What It Feels Like to Sell Your Business

Selling a business runs through five feelings: anxiety, commitment, fear, relief and letting go. Here's what each feels like.

5 min read

The First 100 Days of an Acquisition

The first 100 days of any acquisition are critical. They set the tone, determine whether the team stays or leaves, and decide whether customers panic or stay loyal. Here is the exact playbook we use.

4 min read

The Death of the SEO Production Line

Generic SEO content is failing. It's time to focus on unique, expert insights.

4 min read

10 Lessons Learned from Buying Agencies

Ten hard-earned lessons from buying and integrating agencies.

8 min read

How Much Is Your Web or Digital Agency Worth?

Market data from four marketplaces, what moves your multiple, and the mistakes that cost agency owners when they sell.

2 min read

How to Sell Your WordPress Agency

A five-step guide to the agency sales and closing process.

4 min read

3 Lessons from 2025: Uninvited, Unannounced, Unexpected

What I learned from a bad taco, a third baby and a forgotten conversation.

4 min read

Why Custom Software Is Suddenly Affordable

AI has dramatically lowered the cost and time to build custom software.

5 min read

3 Rules Before Hiring a Freelancer

3 non-negotiables for safely hiring and working with website freelancers.

4 min read

Competing on Price Vs Certainty...

A strong online presence builds trust and lets you charge a premium.

4 min read

The Most Powerful Realisation You'll Ever Have

My girlfriend moved across the world for me. It turned out I was someone else.

5 min read

3 Simple Rules to Multiply Your Money

Most people think the best path to financial freedom is to earn more. But that's not enough.

3 min read

The Hardest Move You Can Make

In a world where most things are a commodity, standing out is everything.

4 min read

3 Career Traps Nobody Warns You About

Lessons from delivering pizzas for $5 an hour

5 min read

How to Think Better…

If we want to win in life, we need the ability to solve problems.

4 min read

How to Get Investors to Give You More Money

One of the most important things a founder can do is keep investors in the loop.

4 min read

4 Lessons from 2024

2024 was a year that brought massive change.

6 min read

How to Start a Side Hustle (While Doing Your 9 to 5)

I've done side hustles myself and learned some valuable lessons. My view on them has completely changed.

2 min read

The Worst Advice for Founders Launching a New Product

There’s no shortage of advice out there. Some of it's misguided.

4 min read

How to Double Conversions on Your Demo Page

Your website is your #1 marketing asset. Here are 4 steps to get your demo page right.

5 min read

Hard Work Won't Make You Rich: 4 Money Myths That Held Me Back

The four biggest myths about making more money: hard work alone, owning a business, focusing on income, and expecting fair pay.

4 min read

Equity for Early Employees: 7 Mistakes Founders Make

Sharing equity can transform a startup, but it is fraught with risk.

5 min read

How to Manage Your Boss: 4 Managing Up Tactics That Work

Managing your boss is about making their job easier. 4 uncommon tactics to accelerate your career.

6 min read

6 Lessons from 30 Startup Investments

I’m no expert, but I have picked up some lessons along the way.

8 min read

How to Get Your First 10 Customers for Your Software Product

Landing your first 10 customers is tough. This is a repeatable process to make it happen.

3 min read

Sleep, Creep, Then Leap: Why Startup Growth Isn't Linear

How the "sleep, creep, then leap" pattern shapes the success of startups.

7 min read

How to Make Your Stories Work

How a botched anniversary speech led me to discover a storytelling framework that changed everything.

5 min read

The Day When Everything Changes…

In 2017, my wife and I faced a $10k vet bill for our rescue Chihuahua. This experience sparked my pursuit to "escape velocity."

7 min read

The 4 Regrets of My Twenties

My 20s were chaotic, filled with mistakes and regrets. Here are the four things I wish I had done differently.

9 min read

4 Big Lessons from a Decade Away

In 2014, I left Australia for a decade in the US and Canada. Here is what I learned.

8 min read

How to Deal with Failure

Telling my dad I had failed really hurt my ego. I wish I had found these tools earlier.

11 min read

How to Negotiate the Sale of Your Company

BATNA, ZOPA, price vs terms and your team. Six negotiation lessons from selling four companies, including the mistakes I'd avoid.

12 min read

12 Books That Changed My Life

Recommendations are hard, but these 12 had a major impact on me.

7 min read

I Should’ve Been Fired

How a team emergency at my work pushed me into the valley of despair.

5 min read

How to Change Careers

A chicken bus ride in Guatemala helped show me the way.

6 min read

Feeling Behind in Life? Read This.

Ever felt down after doomscrolling social media? Me too.

8 min read

How to Become Luckier

How an unexpected encounter in a Portugal dorm room changed my life.

10 min read

I Met a Billionaire - Here Are 5 Things I Learned

In 2017, I was raising money for my startup. Here is what happened.