Meet Craig Cassey Jr, MA

Executive Life, Business, and Sex Coach, Relationship Researcher, Speaker & Trainer.

Your co-pilot in creating A life, business, and relationship dripping in pleasure and Purpose.

Meet Craig Cassey

Executive leadership coach, relationship researcher, and your personal champion as you build the business, life, and relationship of your dreams.

Like most cinematic personal growth stories, mine began on a rural mountaintop in Tennessee, camping with hundreds of queers and asking myself: What the fuck am I doing?

I had just experienced my most successful year as both an entrepreneur and a realtor for a luxury sales firm, yet I felt surprisingly empty. A lifelong wellness geek, my first foray into coaching began like many of my clients’ journeys—with a profoundly cutting ache that wouldn’t go away. I was successful, yet terribly unfulfilled.

Working more hours wasn’t going to change that. Nor did my professional “successes” improve my romantic relationships. Faced with a void I could no longer ignore, I began asking myself: What do I truly want? And what’s standing in my way?

What changed everything was tending to my inner world and nurturing myself—not just re-reading the stack of self-development books I’d acquired over 10 years of “doing the work,” but cultivating a new way of being. The old me couldn’t consistently generate a life that turned me on and got me off. I realized I needed to become a more authentic, audacious version of myself—one who listened to his gut and acted on it in service of being truly alive, no longer a suffering “success” in my comfort zone.

I began doing the deeper work, becoming softer with my partners while healing my attachment wounds and stopped avoiding sticky conversations, which led to profoundly deeper connections (and, frankly, much hotter sex). The more honest I was about my fears, doubts, and self-sabotage, the less they ruled my life. I made honest progress in my business and personal well-being, opening the doors to bold conversations about my dreams and taking action toward the life I yearned to live repeatedly. And when I found myself getting stuck or trapped in an old pattern, I stopped being so damn hard on myself and instead leaned in with curiosity to see what I needed to move forward and love myself even more.

Suddenly, my lack of joy transformed into deep and rich fulfilment. Leaps that once felt seismic now seemed inevitable. With newfound self-trust, I knew that no matter what leap I took, it would work out.

And from that place? Life got juicy.

Now I help clients do the same, whether it’s cultivating secure and steamy relationships with their longterm partners or learning to cultivate authentic and audacious self-leadership sufficiently

Professional Background

What do a Masters in Applied Positive Psychology, 8 years as a Leadership Trainer, and 5 years as a yoga and somatic practitioner have in common?

Me ;) And this experience is what you’ll receive a taste of when we work together to support your personal development.

After 6 years of coaching and supporting over 17,000 with my work, what I’m most present to is the impact of who I am being and the following experiences have profoundly shaped the man I am today.

For those curious of my academic background, I’m a very proud HOYA (Georgetown University), part Quaker (University of Pennsylvania), and most recently a Masters recipient from The University of Melbourne (Oz will always have a part of my heart!)

While my professional background spans from launching wellness non-profits, luxury sales, and startups prior to my time as a coach, I now spend my days supporting clients and the field of coaching and positive psychology grow as a relationship and wellness researcher.

But not included above are the transformative experiences I’ve had with my queer family, plant medicine, and personal healing journeys in my romantic relationships alongside my own coaches and therapists. It truly takes a village and I am blessed to be a part of that village for my clients ready to say yes to a life and love that truly fulfils them.

Keen to explore what changes coaching can bring to your life? Click the link below and we’ll set up a 30 minute intro call to explore where some more audacious authenticity and healing can shift you into your next pleasure filled and powerful era!

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Where could your life use more pleasure, power, and support?