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From Starting Blocks to Summiting Success: Charting My Business Voyage
A Chronicle of the Defining Detours, Decisions, and Destinations on My Path to Pinnacle
Once Upon a time...
My wife and I were living in College Park MD. I was engaged in very meaninful work leading a college ministry we started. Like many other people, we were on one income just trying to be the best parents, friends and human beings we could be.
Life was mostly good, considering that we had just moved to College Park with only about $7,000 in our back pockets. The sum total of everything we had.
We lived in an ordinary little house that my wife made into an extraordinary refuge for so many.
We had debt like most people; debt that seemed to move a little further into the red each month, but hey-ho.
I guess we represented a snapshot of an average middle-class family in the ant colony of this extraordinary world
I was 31, Jenni 30.
In the winter of that year I flew to Louisville Kentucky for a conference. The short version of this conference story is that I caught a vision at that conference that would have a shaping influence on my life thereafter. It was a vision for my life's work - building businesses and helping others do the same.
Sounds cool, maybe normal for many, but...
I was a pastor, not a business man. I knew how to start non-profits, lead, speak, counsel, write and more but build a business? No freakin idea. This was a game I had no idea to play.
The important part of the story though was that it put into motion a goal, a dream, a hunger that would later guide other moves on the game board of life and business.
I had a picture of where I wanted to be albeit a vague one.
We didn’t know how or even when this vision would be fulfilled (but this didn’t matter; the “how” would come later), and we had no money (we had negative money).
So we hatched a plan that we would explore one action step at a time and test and figure it out as we went. It seemed so inspiring at the time; we love adventure.
It was an adventure that slowly evolved over the next ten years and would eventually culminate with me entering the real game of Monopoly.

Custom Monopoly print that hangs in my office as a daily reminder to play the game wisely
Stepping onto "the board" as a player was scary as hell & we gave ourselves a two-year time frame to play before we made the decision to stay and play or exit the game entirely.
That was the extent of our crazy idea. Play the game for 2 years and figure it out along the way.
It was time to make moves and improve our position on the board. So we did.
We moved from VA to MD buoyed by the stability of family here and we began rolling the dice and making advancements on the board.
Then an inciting incident happened.
Fast forward to Dec 2022, just under 3 years into the game and I've been able to help people with more than 62M in real estate transactions, lead and coach agents across the country, and help lead our team as a C-level executive. We bought a dream home that we just renovated, own a multi-family investment property, and other assets that produce monthly cash flow that covers 1/3+ of my total living expenses and I'm on pace to have 2/3 of my expenses covered with passive income by the end of 2023.
If someone had told me that this would be my story 3 years ago I would have struggled to believe them.
How will we get there? How will we become the kind of people that are able to play the game at that level especially given who we were when we stepped onto the board to play?
How did this happen?
I've wrestled with this question for almost a year now. Can I really answer this question with one meta idea? I believe so and I believe this one lesson was perhaps the greatest shift I made and will continue making for the rest of my time playing the game of business.
It’s the meta idea of becoming a Professional vs an Amateur. By that I mean a strategic entrepreneur vs a shiny object chaser and opportunity addict that was important, not the details (the tactics).
Between 2020 and 2022, I had gradually transformed from a type of character I'll call Ken to Dave, and it had made all the difference.
This transformation was the key.
Let’s take a closer look at Ken, at Dave, and what’s required to make the transformation. But before I do:
The first step to becoming a different person is choosing the “call to adventure” in fulfilling your assignment.

Hero’s Journey Pathway
It’s a decision.
Do it or don’t do it.
Not everyone is cut out to be an entrepreneur nor should everyone be.
The risk profile is not something most people want or choose to take on.
It’s too risky and difficult for many.
You might fail, and actually will over and over again.
Neither decision is right or wrong.
If your choice is to receive a weekly or monthly salary like I did for 20+ years, great! It’s right for you and a game that you can play and still win big. The game needs people like you and the world needs what you do. I'm not throwing shade on this position at all. Quite the contrary, I commend it. Truth be told, in my dark nights of the soul I sometimes wish for that life again. The simpler life of a W2 and being a cog in the machine but that's not my assignment so I forge on, roll the dice again and seek to put my self in a position to wisely make my next move whether that's the next green house or I'm able to level up for a red hotel.
But if life-long employment in the 9-5 system isn’t your bag, then the only path you can take is your call to adventure in the game of biz development.
It’s risky, but you accept this risk and choose to play with it.
Embrace it.
Lean into it.
If this is you, it's time to meet our first character, Ken.

Ken
Meet Ken (Character #1)
Ken is likely to represent a part of you or all of you right now. He could possibly be a close enough match to make you very uncomfortable as you read this. Not to worry. He's not who you are just where you are so read on.
Ken
Opportunity Seeker (Fear of missing out)
Solopreneur with no leverage (Tries to do everything himself)
Needs constant inspiration and "novelty" (Doesn't do the consistent boring work that the pros do)
Seeks magic bullets and hacks
Operates in his comfort zone. Chooses easy over hard, fast over slow
Avoids commitment and breaks promises he made to himself and others constantly
Product-centric approach
Short-term money makers (based on hacks and loopholes)
Is apart of free groups and forums with others like him (all with egos, opinions, and lots of ideas but very little results to show)
Always overwhelmed (Has no rightly sequenced and proven game plan rooted in models and principles)
Focus is on "always be closing"
Consumes endless webinars, VSL's, YouTube videos and books allthewhile his behavior fails to align with the new information. He effectively learns nothing but can tell you all about the stuff he's "learned" but not done
Is satisfied with knowing tactics and scripts but not principles and patterns that support the tactics.
Has to know the "how" before he does anything
Owns a "job"
Represents the 99%
Ken has big dreams of making it in business. BTW, I was Ken. Remember, I was birthed into the real-estate world as a Ken just a short time ago.
I didn’t know what the heck to do in the beginning but I knew other people did. I knew the only reason that I hadn't sold 60M in real estate was because I had no freaken idea how to play the game at that level but I could learn.
So...
I hired coaches before I could afford them to provide the path and compress my time frames to success but I was still like every Ken and simultaneously subscribed to what seemed like endless “make money in real estate” email lists I would find in the little internet real estate ecosystem. I purchased products and watched replays of webinars on this lead list or that marketing strategy.
What happened next didn’t take long.
Today this dynamic is even worse, as more and more people flock to entrepreneurship to “make it big.”
Before I knew it, I was the recipient of every “shiny-object” squirrel offer under the sun. I would receive multiple offers every day, without fail.
I was getting buried in ignorance debt and was deceived by people who knew better than I did.
And with the little bit of money I had in the bank, I went on a buying spree for every little "hack" I could find.
It started slowly because I was broke. But soon I was sucked in like an alcoholic seeking the next fix.
I was helpless.
I would flip-flop from opportunity to opportunity, with little regard for opportunity cost. I was an “opportunity seeker.” I was seeking the new over the old, proven path that few take because it's hard, boring and slow.
One morning I journaled my "flawed" and suicidal protocol below:

Loop of Death
There is a lot wrong with operating this way. I had become stuck in this “loop of death”.
Roughly speaking, the “loop of death” is the process of cycling through points 2 to 6:
....and just in case you can't read my chicken scratch
2: Buy Magic Bullet Product
3: Take action and implement (90% of people don't do)
4: Make (some) $
5: Road block (problem). Too much competition and too hard
The realization came as I was listening to a guy named Lars Hedenborg. It was in this moment when I realized that I wasn't thinking like a strategic business owner but a non-strategic opportunity seeker...like an amateur, not a pro.
SEO, yup, had done it. Writing blog articles, yeah, had done that too. Podcasting in the way the gurus were teaching, yup yup, did that. Buying adds. Creating YouTube videos. Yeah, I did it all. Direct mail? Yup. Facebook ads? Yup. The list could go on and on
Some things I did, worked. But it was never as advertised.
The results I earned as I cycled from “thing” to “thing” were only ever "singles" at best.
Never any “home runs” or even doubles.
And that’s when it hit me. I'm a freaking moron. I need to think and see differently. It almost felt like I needed to download a new and different program to run in my brain.
Enter my ongoing transformation to become Dave (stress ongoing since some Ken-like qualities are still present and don't like to die easily).

Dave
Meet Dave (Archetype #2)
Relentlessly executes on one core biz model
Strategic Entrepreneur with leverage (invests in teams and systems and peer groups)
Driven by desire to create preeminent value for people
Seeks skill and value "stacking" relentlessly
Seeks being uncomfortable (chooses hard over easy, slow over fast)
Values commitment and promises kept especially to oneself
Customer-obsessive approach
Builds a long-term, sustainable business (based on strategic fundamentals)
Is in private paid peer groups (seeks to never be the smartest person in the room)
Has an execution plan of what to do now (and what to do next)
Focus is on "always be contributing"
Learns by executing a wise ratio of learning to action and believes nothing is learned until behavior changes to align with new information
Understands tactics, strategies and the essence of things. This from first principles
Is attached to the vision and possesses unwavering faith that he can figure it out along the way
Owns a high leverage system and avoids the perils of leverage poverty
Represents the 1%
Dave operates entirely differently from Ken.
Dave isn't distracted by shiny objects. He knows what really moves the needle and what doesn't. He can control what he invests in and what he chooses to ignore.
His attention is selective and focused on the few inputs that produce disproportionate outputs.
Dave is driven by the need to matter and guided by strategic business wisdom that has consistently proven true throughout the history of entrepreneurship
To create work he’s proud of, and work that matters to the people he seeks to serve and work that has appropriate leverage
Dave builds a durable business that serves him and has staying power.
A business that earns him his freedom to do the things he cares about.
And this was one of my aha moments in my entrepreneur journey...when I opened my eyes and saw things for what they were.
It was my very own Neo/Morpheus moment:

“This is your last chance. After this, there is no turning back. You take the blue pill—the story ends, you wake up in your bed and believe whatever you want to believe. You take the red pill—you stay in Wonderland, and I show you how deep the rabbit hole goes. Remember, all I’m offering is the truth, nothing more.”
— Morpheus (The Matrix)
I was so focused on the EVENT of acquiring Park Place——that I had missed the “truth” of the situation. That this allocation was the culmination of wise decisions and actions taken time and time again, behind the scenes process and wisdom acquisition. Hard freaken grinding-it-out work done with wisdom
When zoomed out this is obvious.
But it’s easily forgotten when in the weeds of the daily battle. Ken can’t see this obvious truth. Dave can.
Dave builds leveraged assets for the long term
One such asset is trust, which takes time and commitment to earn. Ken doesn’t see the value of going slow, so he seeks shortcuts and hacks.
When looking at the real estate world through this lens, it allowed me to see everything very differently. Like I was watching a different movie
Dave is successful because he focuses on the PROCESS; the journey (which doesn’t end; an EVENT does).
The process of showing up each day and doing the hard work.
Not checking email for the next opportunity, but prioritizing on what’s really important. The disciplined pursuit of less, not more.
Dave makes a choice to not be all things to all people.
He understands that his job is not to find the BIGGEST possible market, but rather, to find (create) a viable market— the weird few— then serving and delighting them by making them feel like badass hero’s.
Dave knows that great leaders have empathy; empathy for what’s going through the other person’s head, so his ledership is lead with empathy.
Dave knows that the Holy Grail of business is to build a happy client factory, delivering happiness, and earning repeat business and an automatic client system
Unlike Ken who sees people as transactions, Dave believes it’s his fiduciary responsibility to not wait for money to change hands before starting to add value, contribute, guide, advise, and protect the people he seeks to serve.
When I had made these shifts from thinking and behaving as Ken, to Dave, everything changed.
Conclusion
Ken sees opportunities as events — where results are, at best, a flash in the pan.
Ken is a jack of all trades and master of none. He chases tactics and loopholes and hacks, never going deep. He tries this and that, gets bored, then moves onto the next shiny-object thingamajig.
Each “shiny-object” is the big answer — the reset button — for a new life. But, of course, that’s just an illusion set up by the gurus, and Ken falls for the lie every time.
The gurus know Ken's modus operandi better than he does.
They’re pros; he’s an amateur.
They’re always one step ahead.
They write copy specifically for Ken. Copy that acts as a Ken “Venus flytrap.”
The outcome is always inevitable and predictable.
Dave is different.
Dave knows that building a business that matters, that he’s proud of, is a process and not an event.
Dave understands that to build a business for the long-term, he needs to show up every day and do the hard work.
Continuously.
The work may get easier, but the deep work never stops.
Ken seeks the home runs. Dave seeks to just consistency get on base.
Dave knows that the road ahead is not easy. It’s not for most people. It requires pigheaded discipline and determination.
Ken sees the word as opportunities to be exploited.
Dave is focused on being the linchpin for a weird audience worth serving and leading. Solving interesting problems for them.
Ken sometimes gets lucky and earns a fortune.
But because it was built on a foundation of luck (right place at the right time; it happens), it’s not repeatable, and eventually that “business” crashes and burns.
Dave knows that luck isn’t a scalable and repeatable business model, so he chooses to take the time to lay deep foundations early on, then builds his castle.
Over time his moat becomes deeper and wider; a result of earned trust and attention and work that’s impossible to ignore. Work that some people can’t imagine being without.
Ken seeks money-makers. He’ll take whatever he can get in the shortest amount of time.
Ken is influenced by his ego.
Dave knows that ego is the enemy. Dave doesn’t value scaling a business bigger and bigger for bragging rights and basking in the “spoils of war.”
Dave values and prioritizes a richer and more fulfilling life; a life where he gets to do deep meaningful work he’s proud of.
Dave seeks strategic leverage so he can scale truth, wisdom, kindness and value to the appropriate amount of people Not too many or too few. But his driving force is to add as much value as he can too as many people as he can.
To prioritize making people's lives better over making his business bigger.
Ken trawls the inter-webs seeking more and more information. He thinks buying more marketing products is the solution, because at some point, he’ll learn the “big secret.”
“If more information were the answer, we’d all be billionaires with 6 pack abs.” — Derek Sivers
Dave knows that execution trumps theory.
He rarely buys new marketing products, but also values his time. So when he has a specific need to quickly “level up” his a knowledge gap, he invests in the best training on the market.
Ken hates reading.
He doesn’t have the time.
He doesn’t see the point.
Dave practices a learner’s lifestyle.
He sees books as an investment. A gift to everyone.
He devours them. He’s never not reading a book. He views books as a necessity:
As Erasmus, the 16th century scholar once put it, “When I get a little money I buy books; and if any is left I buy food and clothes.”
Ken chooses not to think for himself. He offloads that responsibility on others. So he seeks copy-and-paste templates, step-by-step systems, and clear instructions to follow (so long as they’re videos which he can binge on without much intention).
Dave chooses an unscripted path.
He chooses to not give a f*ck about how the status quo, who cram up the noisy middle of the bell curve, behave.
Dave knows an exact map, a perfect fit for him, doesn’t exist.
Instead has a strategic flexibility, makes little bets along the way, and focuses on creating his best work.
Finally:
Paul Zane Pilzer once said that millionaires are made as a result of “choice & attitude.”
The good news is that you get to choose to operate and think and behave as Ken or Dave.
It’s just a decision. And it’s 100% up to you.
As Steven Pressfield says in The War of Art, “You have a choice. Do it or don’t do it.”
There is no easy way tho.
It doesn’t exist. If you think there is, you’re wrong.
There’s only a hard way, fraught with trauma and obstacles.
Lean into it, because it’s the only way to breach the membrane shielding Ken from Dave.
If you’re a Ken and want to transform to a Dave, we can help with that. Or if you’re already a Dave, but wanna level-the-f-up, we can help with that, too.
Maybe you just need a nudge in the right direction. We’re great at nudging.
If we can’t help, we’ll tell you, and point you in the best direction. We don’t have all the answers. And what we have definitely here isn’t for everyone, or even for many.
What we have here is for the weird few, who choose to enroll in the journey and do hard work.