CardCast

I read an article the other day from a cafe owner who was six months in and still losing money. Their question was: What are we doing wrong?

I couldn't tell you from the outside, but I know that you'd better figure it out before you invest more and try to scale. Otherwise, you’ll end up losing money on every sale and hoping volume will make up for it.

This card started with a conversation with my friend Casey Jones of Essentialist CEO. People kept coming to her with what looked like a marketing problem or a customer acquisition problem, then she would discover the model itself was not working. Her advice? Prove and improve the model first.

It sounds obvious, but it’s surprisingly hard, because ideas are emotional.

When you have found a problem you care about, passion can override logic, and pulling yourself back to ask whether it stacks up takes real discipline. 

Even a strong sales engine can hide the problem. I once worked with a client who was probably the best salesman I have ever met. He closed the contracts and won the customers, and it looked like growth. But too much was missing behind the model. Investor money can do the same thing. Someone giving you money is not validation of your idea.

Then there is the part nobody enjoys: a model that works can stop working. Sometimes it is a tariff, a rising cost, a new law, or a shift in what your customer's customer wants, and you might never quite learn why.

Ask the uncomfortable question while you are still winning: how could this fail, and what would need to be true for it to keep working?

The work is not finished once the model is proven. Prove it, improve it, and keep re-proving it. 

Key-Card points:

• Prove the model before you scale it 

• Customer discovery comes before the build 

• Loving an idea is not a good enough reason to start 

• Strong sales, big contracts, and investor money can hide a model that does not work 

• Keep re-proving the model, and set tripwires before a crisis 

Links & Resources

• Prove and Improve Your Model

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

"Given where the company is, we don't really have the luxury of a full hiring process."

A CEO said that to me while hiring a CTO. His company was already in a difficult spot, and this was the person meant to pull them out of it.

It stopped me cold.

You cannot afford not to do it. Get this hire wrong, and it might be the end of the company.

The point of the process isn't finding great people. It's avoiding the wrong ones. An empty chair beats the wrong person in the chair, and it sounds controversial until you've watched a mishire play out.

The objection is always time, and it's a misunderstanding. The process is a funnel: very little time with most candidates, a lot with one at the end, after you've already chosen them.

A mishire is the most expensive thing that happens to a company. The salary is the small part. It's the months before you realize, the team disruption, the confidence lost when another leader turns out to be the wrong fit, and everything you weren't doing while you were fixing it.

So, no excuses. The hiring process is not a luxury.

Key-Card points:

• The purpose of a good hiring process is to avoid mis-hires 

• An avoided mis-hire is as valuable as a successful hire 

• The final-stage interview exists to defeat confirmation bias 

• AI makes reference checks and structured final interviews more important, not less 

• If the process drives candidates away, that's a feature 

Links & Resources

• Topgrading as a luxury?

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

Strategy is probably the most misused term in my industry.

Everything is "strategy." Yet ask a CEO "what is your strategy?" and you’ll rarely get a good answer. 

Ged has a story that captures the problem perfectly. He'd just kicked off with a new leadership team, and the CEO kept telling him the same thing: don't spend time on strategy, we're already aligned. 

So Ged handed out Sharpies and sticky notes and asked each person to write down the strategy. Would it surprise you to know that no one wrote the same thing? 

The problem starts with what "strategy" actually means: the creation of a unique and valuable position, involving a different set of activities.

Unique: compete to be different, not best. Choose what you'll be great at and what you don't care about. 

Valuable: to whom? Just because what you make is cool doesn't mean it will sell. A white space in the market might be empty because nobody has claimed it, or because there's no customer standing in it.

Set of activities: strategy is not a single action. It's the framework that decides which actions deserve your time and what gets left in the dust.

Strategy is not what you want to do next. It's the framework that tells you what deserves your time. If yours can't do that, you don't have a strategy, you have a to-do list with ambition. 

Key-Card points:

• Strategy may be the most misused word in business 

• A strategy is NOT a plan

• "Strategic" as an adjective has become a marketing word like "organic" 

• Strategies don’t work without a core customer

• A strategy is complicated to get to but easy to play

Links & Resources

• On Strategy

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

Today, myself, Ged, and our very special guest, Louis Retief, attempted to define what trust really is.

Aaaaaand I'm not sure we managed it. However, Louis was the right person to attempt it with. I've known him since 2020, from his years as founder and CEO of Hubly, a company he took from founding all the way to exit. For Louis, trust is a topic he's been living, not theorizing.

He opened with a question I'm still thinking about: how does a dog know who to trust? No language. No framework. Almost instant, and almost always right. Babies do the same thing. Whatever trust is, it lives somewhere underneath the rational definitions we keep trying to give it.

Most people define trust as, “I trust him to do what he says he'll do”. Useful, but it's not the thing. The trust a leadership team actually runs on is vulnerability-based: I can be vulnerable in your presence, and you will not take advantage of it. 

Without it, nothing above it works. No vulnerability means no healthy conflict. No healthy conflict means no real commitment. You can watch that chain break in real time if you know the signals.

We also went somewhere harder: whether trust, once lost, can be re-earned. I'll be honest, I'm a one-shot guy. Louis put it more generously by being open to people changing, but you don't have to be part of the process.

Both of us agree on the uncomfortable part, which is that sometimes the team in the room cannot get there, and the job is not another trust exercise. The job is building the room where trust is possible. Sometimes that means changing who's in it.

Louis's parting advice was the right place to end, and it's where I'd point you too: before you diagnose your team, ask whether you trust yourself.

Not a casual yes. A deep one. Everything else starts there.

Key-Card points:

• Trust is nearly impossible to measure or define 

• Vulnerability-based trust enables healthy conflict 

• Meeting-after-the-meeting behavior is a trust alarm 

• Trust is given first, then earned back 

• It's not the CEO's responsibility to create trust between people 

Links & Resources

• In Trust We Trust

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

You bring in a coach because you want different results, but you won't get those results with the same behavior. Something needs to change, and that starts with learning something new.

It's why I look at whether a CEO is a learner before anything else. If they're not learning, they're probably not coachable, and there is no helping them. Simple as that.

The shuffle gave us something new this episode: our first joker. The card about the cards. 

Here's the uncomfortable truth about how most leaders "learn." There's a stack of books by the desk or the bed, and it only ever gets taller. Unless something in that book changes what you actually do, you've just bought expensive paper.

And let's be honest about business books. Very often, you finish one and think: this could have been three pages. Sometimes the thing worth keeping is one sentence.

That's the problem the cards were built to solve, though I didn't know it at the time. They started as my second brain. I can only pay attention or take notes, not both, so I started writing concepts on cards as triggers. Eventually, other coaches and clients saw the deck and said, that's pretty, but it doesn't help me. They didn't have the context in the back of my mind. So I wrote the article behind each card.

Ged gave the whole thing a name in this episode that I'm going to keep: microlearning in the wild. One topic. Three to five minutes. One tool you can use the same day. Whether the card comes to you by random draw over morning coffee, around a table with your leadership team, or from the daily draw on theceogame.com, the job is the same.

Because the real question was never whether to learn. It's what to learn next, and what will have the biggest lift on where you are right now.

Key-Card points:

• A CEO who isn't learning isn't coachable 

• One book a quarter is the absolute minimum 

• An unread book stack is money invested in paper 

• If one idea from a book can be applied or taught to someone else, the book was worth reading 

Links & Resources

• On Learning

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

I suggest hiring an assistant quite often. And almost every time, I get the same collection of excuses back.

We're too small. I can't afford it. Cash flow is tight. And my favourite: I'm not that kind of CEO. As if only assholes have assistants.

But there's one excuse that tells me more than all the others combined: I don't have time to teach them what I do.

Let that sink in for a moment. What that person is actually saying is: I am prepared to do this task ten more times, a hundred more times, and absorb all of that cost, rather than teach someone once.

Here's the reframe that matters. This is not about hiring somebody. It's about buying back your time so you can repurpose it for something of higher value. One more sales call. Better preparation for the board meeting. Even an extra hour of sleep pays back.

And you don't earn this hire by reaching a certain size. That's the mindset we're trying to flip. An assistant is one of the first hires you can make, because those tasks are the easiest to hand off and the lift is immense.

There's a modern twist to this conversation, too. The same CEO who claims they have no time to train an assistant will happily spend four extra hours a day playing with AI to automate something.

Which is fine. It's the same principle: you spend some time to save a lot of time. But you cannot delegate or automate something that isn't defined. The difference with a human is that you get a new problem solver. You say "I need this outcome," and they figure out the details.

As someone once told Ged: "If you don't have an assistant, you are an assistant."

Key-Card points:

• The assistant is one of the first hires a CEO can make

• Every excuse has the same hidden cost

• Hiring an assistant is buying back your time

• A CEO doing an assistant's job is robbing their own company

Links & Resources

• On Hiring Assistants

• The CEO Game

Connect with Milan

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

Most people who say they want a coach don't actually want a coach.

They want someone who has been where they are, who knows the industry, who has solved the specific problem in front of them right now, and can just tell them what to do. That's an advisor. A consultant, maybe. Not a coach.

A coach doesn't show up knowing the answers. A coach shows up knowing the questions. The ones that get you to the next decision faster than you'd have reached it alone.

A coach asks what would need to be true for you to figure that out yourself. That's not a lesser version of help. It's a fundamentally different one.

The accountability piece tends to surprise people who haven't worked with a coach before. I have a running joke with my personal trainer: 20% of what I pay them is for knowing what to do. 80% is so that I show up. 

The coach is the mirror. The person who isn't inside the building. Who sees what you can't see while you're running the place.

That's also why even coaches have coaches.

If you have the desire and the willingness, the help is out there. And if you already know everything? You probably don't need a coach. You need a better PR agent.

Key-Card points:

• Most people who say they want a coach actually want an advisor 

• The coach's job is not to fix the business but to develop the leader who will 

• Accountability is underrated as a coaching benefit 

• Behavioral change on your own is hard 

• Not everyone can be coached 

Links & Resources

• Why a Coach?

• Veverka.ca

Connect with Milan

• Veverka.ca

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

You do not need to know every step before you begin.

That sounds obvious, but it is one of the places leaders get stuck most often.

We want the full picture before we make the first move. We want every priority mapped, every risk solved, every decision validated, and every possible outcome accounted for. Then we call it being strategic.

Often, it is just analysis paralysis.

This card is called The Trip from LA to New York. The idea is simple: if you know where you are going, you do not need every detail planned out in advance. You only need to know enough to start in the right direction.

Where are we trying to go? What is the next useful step? What do we need to know before we take it? And what can wait until we have more information?

That is not an argument against planning. Planning is essential. But the finished plan is never the point. The goal is to set a direction, make the best next decision with what you know now, and keep revisiting the route as the landscape changes.

Sometimes, good enough is not settling.

It is the decision that gets you moving.

Key-Card points:

• You do not need every step mapped out before you start.

• A clear destination matters more than a perfect route.

• Strategic planning is different from trying to predict everything.

• Planning is essential. Plans are always provisional.

• Good enough can be enough to unblock the next decision.

• Plan to the level of risk and criticality involved.

Links & Resources

• Trip from LA to NY

• Veverka.ca

Connect with Milan

• Veverka.ca

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

Language is one of the most powerful tools a leader has. Not because it makes you sound polished, but because it shapes what happens next.

A small shift can change the whole conversation.

“I disagree” creates defensiveness. “Help me understand” creates discovery.

“We can’t do that,” shuts the door. “What would need to be true?” opens it.

“I have to” carries reluctance. “I get to” carries possibility.

And then there is “but.” The three small letters that can erase everything that came before them.

That is why The Power of Language matters. Leadership communication is not just about what you say; it’s about what people receive, what they feel invited into, and whether the conversation stays open long enough to find the truth.

Better language creates better conversations.

And sometimes, changing one word can change the entire outcome.

Key-Card points:

• Leadership communication is a skill, not an assumption 

• Inquiry creates better conversations than advocacy 

• Language can open a conversation or close it 

• Good communication is not just what is said. It is what is received 

• Every disagreement can become a learning opportunity 

Links & Resources

• The Power of Language

• Veverka.ca

Connect with Milan

• Veverka.ca

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.

People love to hate meetings. 

Most meetings start late. The purpose is unclear. People arrive unprepared. Decisions do not get made. Actions do not get followed up on, and everyone leaves wondering why they were there in the first place.

But meetings are not the problem; bad meetings are the problem.

This is why the Meeting Cadence card matters.

A good meeting rhythm gives every kind of conversation a proper place.

The daily huddle is not for problem-solving. It’s where the team synchronizes and decides “What needs attention today”?

The weekly meeting is not a reporting session. It’s where the leadership team removes barriers to the quarter’s priorities.

The one-on-one is not just a status update. It’s dedicated coaching time where a leader can help someone grow and make sure they have what they need.

The monthly meeting creates room for bigger operational questions. What are we hearing from the market? What are customers telling us? What needs a deeper conversation before it becomes a bigger problem?

Quarterly and annual meetings pull the organization back up into strategy.

Each meeting has a different job.

That is where many businesses go wrong. They try to solve every problem in every meeting, so everything becomes reactive and urgent.

Sometimes you need more structured meetings before you can have fewer unnecessary ones.

And with better leadership meetings, the business has a rhythm it can actually move to.

Key-Card points:

• Better leadership meetings need a clear purpose

• A strong meeting rhythm protects the rest of the calendar 

• Daily huddles synchronize the team 

• Good meetings reduce random interruptions

Links & Resources

• Meeting Cadence

• Veverka.ca

Connect with Milan

• Veverka.ca

• LinkedIn

Connect with Ged

• Crystalyzer.com

• LinkedIn

CardCast is produced by Lovemore Media.