If dreams were lightning, thunder was desire, this old house would have burnt down a long time ago.”

– John Prine (1946 – 2020)



Win. Joy. Repeat is a family creation. It’s birth – from the personal struggles that gave rise to our call to create the system to the underlying motivations and priorities that guided our efforts to do so – is detailed in “The Origins of Win. Joy. Repeat”. In this piece we focus on connecting our personal and professional journeys to the work we do at Win. Joy. Repeat – work that is purposed to overcome change, challenge, and resistance across all areas of the Life enterprise.

As a venture that faces the whole of individual Life, our personal experiences as the proprietors rise to the forefront and are every bit as relevant – if not more relevant – than our professional experiences. And perhaps even more important is our exposure to both progress and regress, to both Joy and Pain, to both success and failure.

The systems, processes, training, and tools that we’ve created at Win. Joy. Repeat are designed to protect and optimize external and internal well-being – to Secure Life-Wide Freedom by defending against regress and Pain and Maximize Meaning by manifesting high value progress and Joy. 

  • Securing ourselves from regress and Pain demands that we understand how regress and Pain behave. In other words, to defend against regress and Pain, we must know regress and Pain. With respect to our efforts at Win. Joy. Repeat, the wisdom afforded us through our failures has been at least as valuable as the intelligence we’ve gathered through our successes.
  • Maximizing Meaning demands that we understand how progress and Joy behave. In other words, to ascend and transcend we must know progress and Joy. With respect to our efforts at Win. Joy. Repeat, the value of knowing how to create external and internal value (to Win & Joy) is vital to our offensive efforts to create high value meaning, Maximize Potential and become all that we’re capable of uniquely becoming in honor of the opportunity we’ve been afforded.

The Life Enterprise System & Value Creation Process we’ve built has been forged by our experiences with both success and failure – both personally and professionally. We touch on the extremes of these experiences in both domains below:



“We” are Bill & Karie-Ann Bradley. We’ve been married now for over 20 years and have been blessed with three amazing boys – now teenagers. We came from far and wide to unite – Bill is a multi-generation American (Colorado) and Karie-Ann is a first generation Canadian (Toronto) – Karie-Ann’s mom immigrated to Canada from Jamaica and her dad from Italy.   

From a personal standpoint, we’ve had our share of lows and highs:

  • We both come from families of divorce and have experienced all of the struggles, insecurities, and scars that children and families of divorce have to deal with and we’ve also experienced the fortunes of creating and sustaining our own family culture that has thrived now for over 20 years.
  • To create our family we persevered through 10 pregnancies and overcame seven difficult miscarriages along the way to do so. The deep physical and emotional trials we experienced individually and together were Life changing for us in so many ways and the fruits of our collective resilience made our shared struggles more than worthwhile.  
  • Through the years, we’ve been exposed to any number of personal changes, challenges, and resistances – some more severe than others, all additive to our Character tread:
    • From the normal course self struggles and trough points that we all go through as individuals to peak periods and stretches of high vitality that mark the plus side of health and self-development.
    • From dysfunctional, dishonorable, debilitating, and highly disappointing relationships to deep and meaningful connections – most successfully with one another and with our children.
    • From financial strains and mismanagement to material successes.
    • From disorganized chaos to discipline and order. From discipline and order back to disorganized chaos and then back again and again.

From a professional standpoint, both of us come from entrepreneurial families going back multiple generations. For most of our married Life, Karie-Ann has played the lead role in running the day-to-day of our home and our family – “stay-at-home mom” style. To a great extent, Bill has had point on the financial pursuits and resource generation efforts of our family enterprise. And in sync with the diversity of our personal experiences, he has created and been at the center of both material failure and success in the professional realm:

  • A self-made entrepreneur and CEO by trade for over 25 years, Bill has built businesses up and shut them down – birthed them and buried them – time and again.
  • From a one-person operation in a home office to over 2,000 employees in hundreds of offices across the country, he has nurtured ventures from seed and start-up through early and late stages with a full spread of financial partners from the millionaire and billionaire classes to private equity and hedge funds to money center banks.
  • He has grown them with amazing teams of people from vision and ground floor concepts to hundreds of millions of dollars of annual revenue and awarded achievements.
  • He has navigated professionally from the highs of acquisitions, expansions, and industry leading growth to the lows of bankruptcy, closure, and dissolution.
  • From wind up to wind down, Bill has led, managed, and governed ventures he founded, co-founded, majority owned and operated, and minority owned and run with both high success and marked failure.



The diversity of our exposure both personally and professionally is, if nothing else, distinctly human. Our experiences have afforded us perspectives and insights that have been justly earned through the trials of Life, through our successes and our failures. What has remained constant along our way has been the depth and loyalty of our love and connection and our impenetrable passion to make the most of our Life individually and together.

Where failure and adversity have shown up, resilience and perseverance have responded. Setbacks have been met with vulnerability and accountability – sometimes slowly, sometimes reluctantly, but always eventually. We’ve worked hard to sustain an attitude of continuous learning and improvement, an approach focused on overcoming, adapting and transcending all that restrains our potential as human beings.

The creation of Win. Joy. Repeat is our joint creation, our joint response to our own struggles, our joint effort to do all that we can to become all that we’re capable of becoming in honor of the opportunity that we’ve afforded.

Ultimately, Win. Joy. Repeat is the learned product of success and failure, a product designed to embolden our own personal efforts to Maximize Our Potential, a product designed to empower our boys with the foundational capacity to self-create and self-sustain their own well-being as they journey through their own Life, and a product designed to enable other individuals and families with similar ambitions.