The Entrepreneurial Quest

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In hindsight, I wish we’d been filming it…

We weren’t considering sharing the work with the world, not back then.

After all, marketing agencies aren’t known for giving insights and “trade” secrets” away for free.

We do things differently now.

If you were to ask me to show you the most important work in business growth, I would want to rewind to the moment we made what I’m about to share, and give you a peek at an absolute bedrock practice in our industry:

Avatars and Personas.

I would show you everything about the process…

  • How we create them
  • Why we create them
  • How they assemble to form an archetype representing the people in our audience.

But, I have no footage… so, I’ll explain it instead.

Once you see what’s happening under the surface here, it can change how you approach your business, and its marketing, forever.

The context of the story is simple:

We had two segments of people to represent.

I named one archetype, Jerry (the larger segment). The other, Jasper (the much smaller segment).

The gap between Jerry and Jasper represents The Hero’s Journey for our pocket of people, our tribe.

If you’re unfamiliar, this short video summarizes the Hero’s Journey concept well. Watch it, then read on:

As the team and I did the work of creating Jerry and Jasper, I couldn’t help but notice parallels between them, and the tale of my own journey.

  • Successful commercial photographer, dominating my niche for 10+ years
  • Burn out in 2015 (more on this in a moment…)
  • Started Wabbit — with $200 — in 2018
  • Built it into a thriving web agency earning tens of millions for its clients by the end of 2020.

(If you want to know more, the story, up to present day 2022, is on the about page.)

All this sounds kinda scammy, I know — like the beginning of some guru’s big pitch, doesn’t it?

But, you should understand, these are the endpoints of the story as they stand today. 

They say nothing of the grind it took.

That it still takes.

It’s the shit and the pain, the drama and the trauma, and the never ending onslaught of obstacles we will encounter in “the messy middle” which are the important (yet tragically disregarded) details.

Messy Middle

Those details are the parts we need to hear about!

How do we make the journey?

How do we make it from one side to the other?

You already know it won’t be easy do reach your dream. Nobody has to tell you that. But, what truly needs to be said to you — or any other aspiring entrepreneur — can’t be summed up in some vapid 1,000 word listicle.

So nobody says it.

They leave you lost.

Don’t you feel like you’re missing something?

That feeling is why Wabbit stopped accepting new clients in 2020, shifted focus away from ourselves, and began investing in you instead — it is why we started working with our “garage door” wide open.

Find a comfortable seat, let’s talk a while.

First and foremost, we built this place for you.

If you’re feeling, or have ever felt lost about your side-hustle or small business, I hope you learn from the story I’m about to share.

Most importantly, I hope it reframes your worldview of what’s really required to finally reach the top of the mountain you’re climbing, and…

Transform from Jerry to Jasper.

Why it matters...

Working our asses off only to feel we are getting nowhere, sucks. It is the definition of being stuck in “the grind,” and it is not the best path to a fulfilling life.

You’ll see as we go, like many of us, there’s an underlying issue sabotaging one of our avatars, and he can’t see it — it lurks in his blind spots.

The other views the world through a different lens.

The two avatars I’m about to introduce (Jerry and Jasper) are the driving the focus of the asset you’re reading right now, several others on the site, and multiple lessons in our curriculum.

These conceptual tools usually stay invisible to the public, but, not here… not anymore.

Today, we lay it all out on the table.

Among an avatar’s many uses, we marketers will often engage with them like a conversation partner when writing copy.

For Wabbit, the characters Jerry and Jasper are avatars who represent the majority of our larger tribe. 

Broadly speaking, they are the small business owners and would-be entrepreneurs who are setting out on (or in the middle of) their quest for success and freedom.

In addition to driving the voice and focus of our marketing efforts, these avatars point a path forward.

Within the gap between Jerry and Jasper we can glimpse the benefits of shedding our broken mental models, and adopting those which serve us better.


While discussing the Hero’s Journey within the context of business building, the team discovered we could easily map our personal entrepreneurial experiences to each phase.

In a moment, you will learn about the two avatars we built, and the mental shift that separates them, but, before we get to the meat of this content…

I want you to know that if you feel uneasy along the way, as if I’m talking about you… it’s only because I’ve been there too, I know the terrain.

In fact, I would argue that living through the transformation is the only way to fully realize how essential this mental shift is to success.

I used to be like Jerry

When I had to start my hero’s journey, I was the Jerry archetype, no doubt about it.

At the height of the story, I had long list of successes, and even acclaim in my field, but I was still struggling. 

Always on the cusp of scaling, but never quite there.

I worked constantly — never able to stop hunting for clients — to the detriment of relationships in every vein of my life. There was no time to focus on anything other than the work.

Yes, it was profoundly lucrative, so long as I was actively working, but if I stopped, it fell apart.

I could never take a vacation.

From the outside, I was at the top of my game, known planet-wide in my niche — yet, I had worked myself into a dead end, and I wanted out.

Yet, if I had anyone around me offering sound advice, I couldn’t hear them. I was too busy finishing a project, or signing the next client.

I was a runaway train, running out of track.

All of this was apparently predictable.

In an interview on ImpactTheory, Tai Lopez shares an interesting quote about how we evolve as adults.

“Adults learn through massive trauma.”
— David Buss (professor of psychology)

I’m aware that he can be divisive but, regardless of any opinion on Tai himself, I agree with him on the point he’s making. 

My life experience shows the truth of it.

Note: the entire interview is worth listening to.

There’s no sugar-coating this… it has been a truly arduous road. Every step of the way.

Through my journey, I’ve come to understand that Jerry was never capable of making the climb to the mountaintop. He was always doing the best he could, but he’s sabotaged from the start by operating from broken mental models.

Whatever dreams, successes, or goals he chased — they would always elude him…

Unless he could embrace change.

What I've learned

No matter who we are today, we can evolve. If you only take one thing, and really let it affect you, I hope it is that. We can answer the call to adventure, and set out on our quest, any time.

Along the way, during our evolution, we will be shown blind spots we never knew we had — and we will have to endure whatever it means to accept them, if we want to move forward. 

We will have to admit that there is a problem with our current state, and that we need to upgrade the mental models we are currently working with.

But only if you’re sure you want to head down this road. Because you need to be sure.

The truth is, not everyone is cut out for that fabled entrepreneur lifestyle.

We trade a 9-to-5 for a 24/7, with no way to guarantee that it will work.

This path is too risky for a lot of people.

We might fail. We probably will fail.

There’s a ton of stress, even when things go well.

If your choice is to receive a weekly or monthly salary, I don’t blame you! It is fine. It is right for you. You’ll get no judgment from us, we love you.

Yet, if life-long employment in the 9-5 system isn’t your bag, you have to heed the call to adventure.

We haven’t found a middle path yet.

Now, if you’re done with the 9-to-5, and you’re thinking about entrepreneurship, I’d like you to meet a friend of mine. There’s a better-than-zero chance that you two have something in common, maybe enough to make you uncomfortable…

Meet Jerry

The first thing to understand about Jerry, is that his demographics (outward-facing characteristics like, sex, age, income, ethnicity) are essentially irrelevant for what we are doing here.

When Wabbits do this kind of work, we focus on what matters most, the psychographics of our avatar. The characteristics of what is on the inside — their dreams, fears, aspirations, desires, etc.


If I want to live in Bali for 3 months out of the year, that is  is based far more on psychographic characteristics than any other factor. 

Psychographics are what determines which of us wants to leave our day jobs, and which are perfectly content with staying.

Jerry has big dreams. 

He’s isn’t interested in the grind of the status quo. He wants to build a fulfilling life, on his terms.

I’ve shared trait with Jerry since childhood.

Yet, Jerry doesn’t know what to do.

He’s tried learning online, but the internet is a wasteland of shallow information. A seething terrain of ignorant gurus and get-rich-quick systems. Anyone entering this hell-scape is guaranteed an endless assault of “secrets to success” until they give up, or go broke.

Jerry gets these offers daily.

He’s spent more than he would like to admit on charlatans with alluring false promises.

It was the same for me, and I’ve spent my entire working life in some aspect of the marketing industry! One would think I’d know better, but…

Back then, I didn’t have a clue.

I was too caught up.

I went on a buying bender of epic proportions.

It started slowly at first, but before I knew it I’d spent thousands on hacks, classes, and “solutions” that ultimately did nothing for me. I got swept up, forgot my fundamentals (for a long time), and before I knew it… kaboom.

I would flip-flop from shiny-object to shiny-object, with little regard for the cost or efficacy of what I was doing. I wanted to stay in my comfort zone and get quick, easy wins, not the slow (but sure) grind.

I was an opportunity seeker.

Even worse, I was getting just enough positive reinforcement from “the entourage” that I couldn’t see the problems hiding in plain sight.

One of my mentors laid the problem out like this:


There was a lot wrong with this cycle, but I was blind to it. Stuck in the same pattern for years. I couldn’t see the entropy happening right in front of me.

If we were to map the experience back to the hero’s journey, the hero would be stuck looping through steps 5-9, the perpetual cycle below:

We hit that moment of crisis and, rather than persevere, we look for a new “shiny object” instead.

The moment my blind spot was revealed to me hit me like a double-decker bus — utterly shattering my worldview when it came to business. 

Like Jerry, I had become fabulously skilled at a lot of things, but none of them really seemed to matter when it came to making consistent money.

Make no mistake, that’s a heavy blow when you’ve dedicated your life to something.

On paper, I’d done everything the common advice suggested. Some things worked better than others, but nothing worked as advertised.

  • Strong presence on social media? Did it.
  • SEO focused website? Yep, first page rankings.
  • Build a hyper-engaged audience? Yes indeed… tens of thousands of them.
  • Guest articles in popular media outlets? Mmhmm, weekly online, and monthly in print media.
  • Targeted Ad campaigns? Of course, print, television, and digital.
  • Affiliate relationships? Several
  • List building (like the gurus taught)? Check
  • Outsourcing my time-sucking tasks? You bet!

And yet, my earnings ebbed and flowed like a tide whose waves are never more than mediocre.

To my clients, I was a star… but, to me, the business never blasted a single “home run” out of the park.

That’s when it hit me…

Let me introduce you to our second avatar…


Jasper operates from completely different mental models than Jerry.

Where Jerry constantly chases money-makers, Jasper builds leveraged assets, engineered for success over the long-term.

He manages his addiction to the alluring “shiny-object” — and he controls what he invests his time and attention in, with wisdom.

Jasper values his time above all else.

He knows it is the only real currency he has.

He sees money as a tool, so he isn’t driven by the pursuit of it, instead, he’s driven by the need to matter.

Jasper wants to make a difference in the lives of the market he seeks to serve — by making something that cures a pain point in the lives of those people.

Something he can be proud of.

Something that matters.

He knows he’s playing an infinite game, so Jasper uses his resources to build a business (an asset).

That business becomes the engine allowing him to live with the freedom he so desperately craves.

When I finally saw the truth, and realized the reasons behind my struggles, it felt as if reality shifted underneath me. Suddenly, I could see new and immediate possibilities.

There was no going back.

Sadly, unlike our friends in The Matrix, no one in the real world “suddenly” becomes a master….

The Myth of Sudden Success

Mike Tyson didn’t wake up one day, suddenly the most terrifying boxer on the planet. He became that, in increments, over time. Every KO is the combined force of countless hours of behind-the-scenes training and effort.

Mastery takes years of “just fuckin’ grinding it out.”

Showing up every day, and doing the work.

It is a compounding process.

We master what we spend the most time doing.

When zoomed out, this is obvious.

“An overnight success takes an average of 10 years.”
— Jeff Bezos (Founder of Amazon)

With all due respect to the Beez, that quote probably isn’t universally true, but, the sentiment is spot on. We work toward a critical mass over a long period of time, and then… one day…. boom… everything comes together.

The success only appears sudden to those on the outside.

Yet, it is easy to forget that simple, inevitable truth when we’re in the middle of our daily struggle.

Jerry can’t see the obvious yet — but Jasper can.

Jasper is successful because he focuses his attention on the journey, not the destination.

He knows the result itself means little, because the process which generates the result is the real treasure.

He doesn’t create isolated “money makers” for himself. Instead, Jasper builds leveraged long-term Assets, engineered for service in the infinite game.

One of these Assets is trust.

Jasper understands that building trust takes time and commitment. It isn’t a process that can be rushed or half-assed. It’s a whole-ass endeavor.

Jerry doesn’t see the value of going slow, so he’s constantly hunting for shortcuts and hacks.

Jasper understands how to validate his offers slowly and systematically, scaling them once they prove their worth.

He knows the infinite game will swing in his favor as the results of his process compound over time.

(The process of showing up each day and doing the right — and probably hard — work.)

He embraces that his is a journey of a thousand little steps, not giant and infrequent leaps.

Discipline is what carries him through.

His pace and method are powered by his relentless pursuit of his Most Important Question (MIQ).

Most days, he’s asking some version of:

What is the next, smallest step I can take toward my goal?

He doesn’t spend time hunting for the next opportunity. Instead, he focuses on value creation.

He’s made the conscious, intentional choice not to try to be all things to all people.

Jasper understands that his job is not to try to cater to the masses and their fickle desires — rather, he knows his job is to find (or create) the smallest viable market.

The tribe.

The pocket of people.

The weird few.

And then, to delight them, enriching their lives by serving them and making them feel like badasses.

What it means for you

When I first got into this business two decades ago, I knew all the jargon of my field (marketing), but I didn’t understand the heartbeat of it.

I didn’t understand how incredibly powerful it can be to relentlessly focus on a single business model.

Back then, in my early days, my downfall was: I didn’t know how to leverage my work into a long-term asset that could serve me, instead of enslaving me.

I had entirely forgotten the heartbeat of what really makes great marketing so effective.

That is… until I found someone capable of guiding me.

Marketing is the work of helping people get what they’ve wanted all along. Marketing is about establishing the conditions for a small group of people to eagerly spread the word and build connection. Modern marketing changes the culture by establishing what the new norms are, and does it in a way that makes things better for those it serves.”

Seth Godin

I’ve added the bold emphasis to draw attention to something important.

Sometimes it’s easy to make the mistake of thinking marketing is solely a way to help us sell our stuff; our tech, our widgets, our services, our shiny objects, etc.

It’s not.

The sale is a natural byproduct of helping people get what they’ve wanted all along.

When our focus is on helping and serving, the selling process takes care of itself organically.

That’s the big secret Jasper understands.

In fact, adopting that mindset is one of the key components which helped me make my eventual transformation from Jerry into Jasper.

It’s like looking through a lens that reveals new dimensions of reality to you.

Once you see it, you can’t un-see it.

And it isn’t just me experiencing this…

The results we’ve seen at Wabbit, when our students choose to think like Jasper, are astounding. Some of them are enjoying regular $100,000 weeks! You can find a few of those stories in our case studies section.

Relevant to our goals, the conclusion is clear…

Who we are is a choice

“Knowledge is only potential power. It becomes power if and when it is organized into definite plans of action and directed at a definite end.”
— Napoleon Hill

Jerry is stuck believing that opportunities are singular events — where results are, at best, a flash in the pan.

He sees all this website talk as a hassle because he doesn’t understand how the value works out for his unique situation.

He’s never considered his site to be an asset because he believes it exists only to tell the story of his business, and give people paths to purchasing.

He is a jack of all trades and master of none — chasing tactics and loopholes and hacks, seemingly allergic to going deep.

Jerry will try something for a while, get bored with the lack of instant result, and move onto the next shiny-object “solution” so fast you’ll get whiplash.

Each “solution” is the big answer (the reset button) in his never ending quest for a new life.

But this is an illusion built up entirely by the gurus charlatans, and Jerry falls for it every time.

They know Jerry better than he knows himself.

They’re constantly one step ahead, setting traps.

They write copy specifically for Jerry. Copy which acts like that little light on the head of an Angler.

The allure of that beacon in the lonely, intimidating darkness is utterly irresistible for Jerry.

What happens next is inevitable, and predictable.

When stuck in the shadows (ie. frustration & confusion), Jerry will gravitate toward any light (hope) he sees.

The trouble is, some lights are deadly…

Jerry would get eaten in that situation too.

Most people would.

Yet, Jasper is different.

He sees the game.

He knows building his business will take time — that it is an ongoing process, not a singular event.

He operates in nimble iterations and relentlessly fails forward into his success.

He builds evolution into the system from day one, because he understands how to leverage lean feedback loops to his benefit.

Jasper doesn’t rest, even if he thinks he has something working well. Once one flywheel runs effectively, he builds another.

Unlike Jerry, who spends all his resources building his one Big Idea (before validating it), Jasper uses quick, small-scale, budget-friendly tests, to help the asset evolve in profitable directions.

Jasper is willing to invest his own time and money, he doesn’t want to rely on investors. He wants his business to pay for its own growth.

He’s frugal, not cheap. He doesn’t waste money chasing shiny objects like Jerry does.

Rather than try to hit a home run with every swing of the bat, Jasper approaches his web asset as a series of refining tests, because he’s spent the time learning about lean / agile concepts.

He understands that the only way to build success is with discipline, so he shows up, every day, and does the hard work.


Jerry sometimes gets lucky and earns a fortune.

Even a broken clock is right once a day.

But, because it was built on a foundation of luck (the right place at the right time; it happens), it’s not repeatable, and eventually that “business” crashes and burns.

Jasper knows that luck isn’t a business model, so he chooses to take the time to lay deep foundations early, then builds his little castle.

The value he provides to his pocket of people is like a moat surrounding and protecting that castle, keeping it safe from invaders (competitors).

The more time passes, the deeper and wider that moat becomes — the result of earned trust and attention and work that’s utterly impossible to ignore. Work which some people can’t imagine being without.

Jerry is an opportunity-seeker. A tactic-hopper. A “money-maker” hunter seeking magic bullets. 

He’ll take whatever he can get in the shortest amount of time.

His ego rules him.

Jasper knows his ego is the enemy. He isn’t trying to build and scale a business so he can feel important at parties. He isn’t after bragging rights or mountains of gold.

Jasper wants a deeper, richer, more fulfilling life. One where he gets to do meaningful work he is proud of (and take a vacation without checking his bank balance first).

He actively seeks to keep his company intentionally small — whether that means a team of fifty, or a team of one — because he believes staying intentionally small is key to serving and mattering in the noise, distraction, and sameness of the modern world.

He believes it is more valuable to make his business better, rather than bigger.

Jerry is perpetually trapped in thinking too big.

Always overwhelmed.

He cruises the internet, perpetually acquiring information, rarely putting any into practice — thinking he’ll eventually crack “the big secret.”

He buys marketing products and courses on tactics constantly, cobbling them into some horrific Franken-solution — which of course doesn’t produce results — because he doesn’t understand what he’s attempting.

He chooses not to think for himself, instead offloading that responsibility onto others. He seeks copy-and-paste templates, step-by-step systems, and clear, fool-proof instructions to follow.

Jasper takes the unscripted path.

He knows a perfect paint-by-number system doesn’t exist, so he doesn’t waste time looking.

Instead, he leverages strategic flexibility, focuses on creating his best work, and makes little, measured bets along the way.

“Every man builds his world in his own image. He has the power to choose, but no power to escape the necessity of choice.”

Ayn Rand

The great news is, you get to choose to operate and think and behave as either Jerry or Jasper.

It’s just a decision, and it is yours to make.

In his book, The War of Art, Steven Pressfield says “You have a choice. Do it or don’t do it.”

Yoda said “Do or do not, there is no try.”

I’m saying “who do you choose to be?”

I know, it sounds too simple to be true.

Our minds try to wiggle out of the spotlight of it.

Here’s the mental squeeze point…

If you choose to honestly chase this dream of yours, you will have to find a way.

And there is. no. easy. way.

It doesn’t exist.

If you think there is, you’re wrong.

There’s only a hard way, and it will challenge you in ways that neither of us can predict.

That’s the game.

We have to lean into it, because it’s the only way to cross the chasm separating Jerry from Jasper.

If you’re a Jerry today, and want to transform into a Jasper, we can help with that. 

If you’re already a Jasper, but want to level-the-fuck-up, we can help you with that, too.

Maybe you just need a hand with a project, or a nudge in the right direction.

We are olympic-level nudgers.

If we can’t help, we’ll tell you.

Not only will we tell you, we will do everything we can to point you in the best direction.

We don’t have all the answers. We don’t serve everyone. We don’t build everything. And what we have here isn’t for everyone, or even for many.

We are here for those “weirdos” who choose to enroll in the journey and do hard work.

For the outliers.

For the tribe.

Because we are stronger together.