Master Project Revenue Estimation in One Detailed Guide
I’ve been working on a doozy of a newsletter issue to answer a question I get a lot: 👉 How do you estimate the revenue a project will create? I finally wrote a detailed guide on it. It’s going out in tomorrow’s newsletter to 67,241 readers.
Win Rate Alone Misleads; Pair It With Profit
Is a 34% win rate good? In 2019, my agency’s win rate was 12%. That means 9 out of 10 prospects said no to us (or we said no to them). That was our best overall year: $2M in revenue, $1M in...
Leaders Win by Acting Like the Least Useful Person
I told an agency owner to act like the least useful person in the room. He’s a super smart, experienced practitioner, running a team of 20. Every sales call he joins, they close. Every call he skips, they don’t. He thought the...
Sell Solutions, Not Services: Pitch What They Need
One of my students sent 33 pitches one week and got 0 replies. Why? I asked to see some examples and spotted the problem immediately. All of them were offering the same thing: a $1,000 marketing audit. I asked him if he...
Authentic Design Wins: Embrace Your Unique Style
May the 4th be with you, from someone who almost wasn’t ready for it. 15 years ago, I art directed the redesign of the Star Wars website. What I’ve never said publicly: I almost didn’t deserve the shot. Just before that project...
Agency Success Now Hinges on Strategy, Not Tools
Too many AI conversations for agency owners right now are about tools. I’ve spent the last few weeks in conversations with agency owners over private roundtables, group sessions, and one-on-ones. I talked to dozens of owners running agencies of all different...

Physical Mapping Turns Jungle Retreat Ideas Into Action
The best coaching I’ve done recently was at a long table in the middle of the jungle. I ran a small retreat this February: five days with three agency owners at a private lodge in the Belizean jungle. It took a...

Proactive Service Agreements Prevent $20k Disputes
I’m bringing my friend Matt Sherlock into the Make More Money program this Friday. And I mean friend for real. We’ve known each other since middle school. We take photography trips together every year. He’s also been my lawyer for the...

My Unfiltered Take on AI Before Agency Roundtable
I’ve been quiet about my take on AI. Here it is. Later today, I’m moderating a private roundtable for agency owners to discuss how AI is affecting their businesses. My job will be to facilitate, not to share my own opinions. So...
Thoughtful Strategy Docs Spark Excitement and Deeper Collaboration
I just reviewed a 41-page strategy document from a team I hired to help me with a few things. I LOVE working with professionals. Every line in this doc is thoughtful and attentive, reflecting all the conversations and working sessions we’ve...

Salary Value Is All About Personal Context
Is $50K a good salary? For a seasoned executive? Probably not. For a first job out of college? Probably. For a seasoned executive who just got laid off and has no other offers right now? Maybe. For a first job out of college but...

AI Design Tools Force Agencies to Sell Expertise, Not Output
Every agency founder’s quiet fear is that AI will make their business obsolete in six months. That’s not true. It's much worse than that. Six months was last week’s timeline. This morning, Anthropic released Claude Design, a tool that turns a sentence into...

Believe in Untapped Potential: Coaching Unlocks Hidden Ability
One of my favorite passages from one of my favorite books, Coaching for Performance by Sir John Whitmore: “Unless you believe that people possess more ability than they are currently expressing, you will not be able to help them express it.” This...
When Fixes Fail, Agencies Must Own Solutions
In August 2024, I paid $24,724 for a completely new heating and cooling system in my house. Since the day it was installed, it hasn’t worked the way we agreed upon. They acknowledge that it’s not working the way it should. They’ve...
My AI Chief of Staff Boosts Productivity, Yet Still Falters
Like a lot of folks, I’ve been slowly building my own Chief of Staff agent. It works really well for some things, like: → Evaluating my upcoming week on Sundays so Monday morning is clean → Facilitating the start and end...