What It Means to Go All In

You don’t have to drop everything.

You don’t have to quit your job, or leap without a net, or take on a bunch of debt, or start a new life.

Going all in is figuring out what matters to you and claiming it. It’s putting a stake in the ground and showing up for the future you’re building. It’s starting where you are with what you have.

Going all in looks different for everyone. It’s easy to hear someone else’s story and tell yourself, “If I do that I’ll get those results”. Much harder to get quiet and listen to what’s right for you, to honour and forge your own path.

Going all in isn’t glamourous. It’s a quiet commitment you make to yourself.

And you don’t have to do it all today, you simply have to start.

Four Marketing Skills to Develop

1. Curiosity

Curiosity is meeting the unknown with humility. It’s about asking questions others aren’t willing to, allowing you to do things others aren’t able to. This is how you get attention.

2. Curation

Curation is connecting people with what matters to them. It’s about discernment, taste, and timing. This is how you provide value.

3. Empathy

Empathy is the desire to understand and advocate for an experience that’s not your own. It’s about making people feel seen by helping them make sense of themselves. This is how you earn trust.

4. Ownership

Ownership is taking responsibility for a group of people and leading them to where they want to go. It’s about being in it for the long haul, owning the cause over the product. This is how you create change.

Frustration vs Disorientation

“A video game must frustrate a user, but it must never disorient them.”

That’s Howard Scott Warshaw discussing why E.T. the Extra-Terrestrial, a game he developed for Atari, is the worst video game ever.

Frustration in a video game is essential. It’s a motivator to get better, faster, and stronger, which ultimately leads to satisfaction.

Disorientation, on the other hand, is terrible. If you don’t know what’s going on, where you are, or what you’re working towards, there’s no motivation to play the game.

Consider how this applies to whatever it is you sell. Frustration is the tension that exists between where we are and where we want to go. People pay to get rid of that tension.

Disorientation is a result of inconsistent messaging. Confused people don’t become customers.

You Have A Trust Problem

Most brands don’t have an awareness problem—if only we could get in front of more people then we’d get more business!—they have a trust problem.

People know you exist, they just don’t believe you’re right for them.

This is hard to hear and even less fun to talk about in meetings. Trust problems aren’t sexy. They can’t be solved with money and funnels and ad campaigns.

When you’re solving a trust problem, there’s no clear roadmap to follow or metrics to measure. This is about strategy, not tactics, and more than anything it demands empathy. Good ole’ emotional labour.

That said, how do you work on a trust problem?

Be consistent.

Your brand isn’t your logo, it’s the story I tell myself every time I see it. Strong brands are consistent brands—everything they do and every touchpoint they have with their audience reflects everything they’re about.

Consistency means we know exactly who you are, what you stand for, and what we can expect when we buy from you. It makes you a strong yes to the right people and a strong no to the wrong ones. This polarizing reaction is what you want.

Before you layer on new tactics (see the aforementioned funnels and ad campaigns), start with where you are and who you’re already serving. Look for the gaps. Address those first.

It’s tempting to try, but you can’t buy trust. You have to earn it.


Caution! Do not pass go, do not collect $200, do not launch another Facebook ad campaign until you’ve addressed this first.

The Iceberg Theory of Marketing

Behold! The iceberg theory of marketing.

There’s what we see: product, tactics, messaging, etc.

And what we feel: values, strategy, brand, etc.

The tangible versus the intangible. The explicit versus the implicit.

You with me?

The things we can see, we’ll refer to that as “above water”, are what people think they want: a budgeting software, a new mug, etc.

The things we can feel, we’ll refer to that as “below water”, are what people actually want: empowerment, sustainability, etc.

Everything above water requires hard skills, like coding or throwing clay on a wheel, to develop.

Everything below water requires soft skills, like empathy and creativity, to develop.

The tangible stuff scales with money.

The intangible stuff scales with emotional labour.

When you work at the tangible, above water stuff your customer experience will improve. You will see short-term gains.

When you work at the intangible, below water stuff the trust between you and your customer will strengthen. You will lay the foundation for long-term growth.

You can, and must, develop both.

The tip of the iceberg does not a business make. That’s how you get fragile companies and hollow brands that crumble unexpectedly (think of all the VC-backed companies we’ve watched fail in the last year…).

You cannot, no matter how tempting it will be, ignore what’s going on below water. The work is less sexy down here and progress is harder to measure (it’s easy to know when ads are working but how will you measure empathy? Creativity?), however, this is where change lives.

Resilient brands are rooted brands. All the above-water stuff we see as customers (social media profiles, products, advertisements, web copy) is an expression of what’s going on below (strategy and values). Products reflect values. Tactics reflect strategy. Messaging reflects brand. You can mess up the tangibles if you’ve got a strong foundation. If your audience trusts you and is enrolled in the change you represent, they’re going to be a lot more forgiving when your app breaks or you send out the wrong link in your newsletter. It’s not that it makes mistakes okay! It simply means that your audience trusts you to figure it out. They’re not going to seek out alternatives at the first sign of inefficiency or discomfort.

You cannot build a business by writing code or making mugs, by only working above water. That’s how you end up with a commodity.

What we truly want, what we’re actually buying, and the change you seek to make lives below. This is how you build something remarkable.

Start there.

When is doubt, look there.

And remember: marketing is a privilege.

It’s a privilege to be able to show up and advocate for a group of people that trust you to lead the way.

Use that responsibility wisely.


My expert graphic skills at work AGAIN, aren’t you lucky. There are about a zillion ways you can slice and expand on this theory but this feels like a good place to start. And it’s certainly not original to think of it in terms of an “iceberg”, this is simply a take on this theory that makes sense for my brain. See here for iceberg theory and applying the iceberg theory to content marketing.

Your Competitive Advantage

Empathy, your competitive advantage is empathy.

It’s an advantage because few people are willing to put in the hard work to develop it. It requires humility to admit that you don’t know anything about the person sitting across from you. It takes curiosity, compassion, and courage to hold space and advocate for an experience that’s not your own.

Empathy is the only shot you have at getting to know your audience and building something that serves them.

You can’t outsource it. You can’t buy it. And you can’t make the change you’re seeking to make without it.

The best thing about empathy?

It’s a skill all of us can learn.


Taken at Golden Gate Park in San Francisco. It’s a journey, a climb, or some such reference?

Are You Willing To Look Dumb?

We all talk about the importance of taking risks. It’s a common regret (not taking bigger ones) and a common piece of advice (to take more of them).

When it comes to taking risks in our work, we usually think of it in terms of risking time or risking money.

But what about risking your reputation?

Are you willing to look dumb? To have people not understand you or your idea? Are you willing to walk away from something that’s “working” and towards something unproven?

Being widely understood shouldn’t be the metric you hold your idea against because by definition if everyone got it it wouldn’t be new.

Don’t risk your integrity. But do risk being misunderstood.

You’ll often find that the people who matter respect the weird stuff, anyways.


H/t to Erik Torenberg for sharing this idea on this episode of the Click Here To Apply podcast. Don’t ask me what a picture of my boots has to do with this post it just feels right, okay? Path less traveled or some such?

Early Adopters vs Everyone Else

If you want to appeal to early adopters, you need to sell them on how innovative you are.

If you want to appeal to just about anyone else, you need to sell them on why they can trust you.

Early adopters seek innovation. They want the newest, shiniest thing. They like risk. They’ll put up with things breaking because it’s worth it to be ahead of the curve. They’re buying the cause the product represents.

Everyone else seeks trust. They want the thing that will work, every time. They like certainty. They’ll choose the thing that’s proven to work for people like them. They’re buying the security the product gives them.

All of us seek to be understood. We pick the thing that helps us tell the world who we are and what we believe.

Whatever you’re selling, innovation or trust, your marketing needs to be focused on proving it.


Taken on yesterday’s coffee break. Do you get your coffee from a chain because you like knowing exactly what you can expect… or do you seek out new places?

Grit is the New Gatekeeper

“Curiosity, courage, and persistence are the new gatekeepers.”

James Clear shared this in his newsletter recently and ain’t it the truth. He was (in my interpretation, at least) explaining how it’s never been a better time to build something. If you can access the internet you have the education resources of a university and the distribution power of a media company.

However, the easier it is to get in front of people the harder it is to be noticed. The harder it is to get, and keep, people’s attention.

That’s where curiosity, courage, and persistence comes in. This isn’t a game of skill or talent. It’s one of grit.

Lots of people start things. Far fewer have the grit to continue through the dip, to show up when no one’s watching.


Taken in New York last fall. H/t to Stephanie Pellett for sharing this gem.