A “Novel” Way of Losing to Win

I believe that the true gift of connecting with someone online is the opportunity to meet them in person. Seeing someone in the flesh, face-to-face, voice-to-voice, can impact our lives in unforeseen ways

A few months ago, I had the good pleasure of meeting author Will Simpson at Mozart's Coffee Roasters while in Austin, Texas for the Texas Book Festival. The conversation was easy going and light, akin to two brothers having reconnected after years of being out of contact. 

For me the coolest moment was Will autographing his book “You’ve Got To Lose to Win” prior to dropping me off at the festival. 

Isn’t life a beautiful thing?

In "You’ve Got To Lose To Win," the inaugural novel by Will Simpson, we are introduced to Slade, a protagonist whose journey encapsulates the tumultuous transition from the naivety of youth to the complex realities of adulthood. 

Set against the backdrop of the 1980s, Slade's story unfolds, marked by his upbringing in a home where religious dogma reigns supreme, shaping his world into a narrow corridor of beliefs and practices. 

The narrative traces Slade's life from the confines of this strict religious household, where any deviation from the prescribed path was met with stringent reprisals. The rigid upbringing he experiences created in Slade a yearning, a deep-seated curiosity for the world beyond the walls of his sheltered existence. 

His journey begins at the conclusion of his high school years, where he stands at the precipice of a world teeming with mysteries and possibilities, a stark contrast to the sheltered life his parents had meticulously curated for him.

As Slade steps into this new realm, he finds himself in the throes of a reality starkly different from anything he has known. The narrative vividly captures his sense of bewilderment and awe as he navigates through this strange, exhilarating world. 

He immerses himself in learning new concepts and jargon like '9-ball' and 'Texas Hold ‘em,' a far cry from the simple poker and pool of his former life. This knowledge becomes his arsenal as he delves deeper into the underbelly of gambling and hustling, a brutal subculture populated by small-time con artists and shady figures. 

Slade's metamorphosis is profound as he distances himself from his past, forging a new identity in this uncharted territory.

A pivotal character in Slade's journey is Wild Phil, a bookie who becomes a mentor and a surrogate father figure to him. Phil's influence is profound, potentially holding the keys to Slade's future. It is through this relationship that Slade confronts the moral ambiguities of his new life, grappling with the ethical dilemmas that come with his chosen path. 

This introspection leads him to question his actions, pondering whether his pursuit of success is justified or merely a path littered with the casualties of his ambition.

Slade's story is a compelling exploration of self-discovery and redemption, underscored by the poignant lesson that victory often comes at a cost. His journey from a repressed upbringing to the high-stakes world of gambling is not just a mere transition; it is a transformative odyssey that challenges his beliefs, values, and his very identity. 

"You’ve Got To Lose To Win" is thus not just a story of growth and change; it is an illuminating exploration of the complex tapestry of human experience, where loss and triumph are inextricably linked.

How does Slade's upbringing in a strict religious household in the 1970s shape his character and worldview at the beginning of the book?

WS: Every bit of his world is set and controlled by the extreme conservative views of his parents and their church. He is taught that straight white men are THE authority and all others, including women and people of color, are “less than.” All criminal influences come from people of color, and women are there to tempt men, causing them to do evil things. The only path of good is through the church; the rules are set first by God and next by the family's eldest male.

Slade is a thinker who never really understands why things should be accepted without question. This is his internal conflict, and as he comes of age, this will be his driving force.

In what ways does Slade's childhood environment enforce the idea that thinking beyond his immediate surroundings is forbidden, and what are the consequences for him of breaking these unspoken rules?

WS: His father and mother rule with extreme and immediate consequences. Things are black and white as defined by the church and interpreted and enforced by his parents. Merely questioning his father is considered a “sin” and is met with immediate consequences, which always include some form of physical abuse.

The emotional abuse is also there from a very young age, whare Slade is forced to “parrot with a smile” that “spankings make a good boy.”

Describe the transition Slade experiences as he moves from a life of oppression to the unknown yet captivating world of gambling and hustling. What challenges does he face in adapting to this new environment?

WS: Slade has all but zero point of reference to anything outside of his church indoctrination. He is naive in every way. Fear has kept him from asking or learning anything else.

There is an underlying anxiety of being free to do whatever he wants to do. He knows there needs to be limits, but self-imposed limits are not something he has ever learned. His big loss at the arch of the book is fully due to this lack of self-imposed limits. His ego and hubris took over without difficulty. Having the universe dictate what is a win or a loss is totally foreign to Slade until this point.

How does Slade's interaction with the dangerous and thieving individuals in the gambling subculture differ from his experiences in his previous life?

WS: From Slade’s point of view, these kinds of people are very few and are confined to the “bad parts” of town. Again, always black and white, he was taught that these people are bad all the time, only doing bad things to good people as god allows to test the good people. People are good, or people are bad. It is binary. His family has “protected Slade” from interacting with anyone who is not “good.”

When Slade realizes that people can be good or bad, or in fact, that people are both, this starts an inner dialog that both excites and scares Slade. He is excited that there is more to life than simple toil and serving the church but scared that his father will somehow know what he is thinking.

Slade sees that he is, in fact, interacting with many people and has been his whole life, which does not fit the mold of the church’s definition of “good.” These are “just regular folks” that he goes to school with and include his teachers and parents of kids he has known and interacted with.

Slade does not fear this world or these people. He has lived in daily fear of being emotionally and physically abused to the point of sociopathic tendencies. He is “numb” to what might happen. From his point of view, it can not be as bad as the 18 years he has endured to this point.

Discuss the significance of Wild Phil in Slade's journey. In what ways does Phil act as a surrogate father figure, and how does he influence Slade's path?

WS: It is very significant, and Slade does not realize it at first. Phil is the first person in Slade's life who wants to help Slade become more and does not want anything in return. Phil pulls Slade from his darkest moments and teaches from a place of empathy, not authority. This is a love that Slade has never felt before.

Slade learns and pays attention to Phil. In many ways, Slade respects and loves Phil in ways that are also unfamiliar. Respect based on fear or ignorance is all that Slade has known to this point.

As we learn more of Phil’s story in subsequent books, we will also learn why this kind of relationship is important to Phil. It is a purposeful relationship, not just happenstance.

Throughout the story, Slade grapples with his own identity and the concept of winning and losing. How does his understanding of these concepts evolve, especially in the context of the gambling world he is immersed in?

WS: We are present as Slade makes this progressive journey.

As a child being abused, surviving without being punished is winning. This means that winning is really just avoiding a loss. While Slade may not see it, in the end, this lesson will serve him well.

As Slade starts to venture out, winning is still day-to-day. Another day where Slade is not forced back to his old life is a win. There is nothing long-term in his mind, just as there was not in his previous home life.

As Slade starts to understand the world he has landed in, he starts to master it quickly. He becomes bored. He wants more. It is not just about winning “big enough” to have security; it is about building something. 

We end with Slade starting this path to winning. We can see that his early life, “winning as a defense,” plays well at the poker table. This will be a theme that is built upon as we progress Slade’s Story in subsequent books.

Reflecting back on the book's central theme, as suggested by the title "You've Got to Lose To Win,” how does this theme manifest in Slade's life and decisions, and what lessons does he learn about winning and losing?

WS: Life is a series of losses and wins. A series of lessons that come from those losses.

As the title suggests, we, the human race, learn from losing, or at least we are supposed to.

In Slade's early life, there is no opportunity to learn from a loss. The loss WAS the oppression, and only after Slade found the courage to venture out on his own could he learn from it.

This first lesson teaches Slade that he is in control of what winning is, his decisions, his observations, and his actions. The win is the ability to have self-determination. The hypocrisy of his church is LOUD with this discovery. Self-determination in choosing to “turn to god and away from the devil” is supposed to be foundational. The fact is that in that world, there were NO choices.

The business sense meaning of the phrase comes into play as Slade learns “rounder marketing.” Giving the appearance that others have a realistic shot of winning is important. It is why Las Vegas plays loud bells and whistles when someone wins. No one wants to “gamble” with a person that wins 100% of the time. You have to let people see you lose to have a chance to win.

On the human side, the major loss of Slade in this book comes because Slade has no inner or self-imposed limits. The failure of his hubris is debilitating. The win from this loss (as with any real win) is not simply “set some limits” on how one does things and “don’t be so damned arrogant with a chip on one’s shoulder.” 

These are good lessons, and they were learned, but much larger and more important was the lesson of allowing love in and giving it back. Let people help when you need it. The story could have ended as with many in depression and possibly a return to the “safety” of the oppressive former life had Slade not learned to let Phil in, to let Phil help.

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