We had the good fortune of connecting with Craig Cassey and we’ve shared our conversation below.

Hi Craig, is there something that you feel is most responsible for your success?
I’d say the most important factors behind my success are my audacity to be authentic everywhere and my willingness to put my logical brain down and trust my gut instead of needing to “know” everything. Both of which run counter to my inner perfectionist who prefers to only take leaps if he knows i’ll stick the landing and used to shy away from actions that could spark criticism. But in business, there’s no success that comes without a side of criticism, hell – sometimes it’s even our own! And if needing more knowledge is the thing holding you back from leaping, what better way to get it than to go out and start jumping.

When I first launched my coaching practice I had an ideal for what professional looked like which I thankfully quickly dropped. It felt suffocating and that was the real reason I got into business anyway, to get away from that feeling and enjoy more freedom and help others do the same be it in their relationships, at their jobs, or in life.

So I dropped the bull-shit and started sharing myself on loudspeaker and my full authenticity. Expanding from executive coaching into including sex coaching in my practice allowed for a lot more levity and play when it came to spilling some t and it’s that willingness to speak to what we all want but sometimes feel shame around that has people lean in again and again to support themselves with me by their side,

Similarly i’ll add, the more I let go of trying to “game” my way into growing my business and just trust my intuition – the more it grows! And sometimes through means as humorous as an IG real which got next to no response and was most definitely categorized by my perfectionist as a “flop” also being the exact *thing* 2 people needed to hire me on the spot the next day. It’s important to remember that we don’t always know who we’re serving, or who our next client is. We’d like to – sure. That certainty builds comfort and a safety our psyche prefers. But when I allow myself not to know and share the inspiration that hits me without filtering myself, the best outcomes happen. Every time. It’s this “not knowing” which has spurred on the best choices I’ve made and it’s that same skill of trusting your intuition that i support my clients around building every day.

What should our readers know about your business?
Today I call myself an executive life, business, and sex coach whose true commitment is for everyone to live a delicious life including everything from passionate relationships to abundant and outlandishly fun businesses! I say we’re all spiritual beings having an earthly experience so – why not f*cking enjoy it! And that’s what truly sets me apart. The clients who hire me – they want it all, and my coaching is a safe space to get playful and explore creating it all. They’re c-suite execs who want to experience the same success they have in the boardroom in their bedroom, they’re mothers who own businesses but are done living a life of martyrdom and are ready for some pleasure – EVERYWHERE. The truth is, whether or not we see it, the way we do one thing is the way we do everything. So why not stop compartmentalization our lives and learn to transform it all? We all deserve a pleasurable existence. So why not get support in making sure you get yours?

As far as what makes me most proud, it’s easily seeing my clients enjoy their life like never before when they’ve achieved the unimaginable. Many times a client hires me because they’re experiencing a problem. Business isn’t growing as quickly as the intimacy with their partner has dwindled and they don’t know how to get it back. 6 months later, when there’s more sex than there has been in years and business has never been better all while they’ve taken more time off – those are the moments that fill me with pride. All because of my client’s willingness to lean into the work and take the uncomfortable leaps needed to reach life’s pleasures.

Similarly I’ve built my business to be the embodiment of that ethos, where I work only 3-4 days a week, for only 3 weeks each month, and fill the rest of my time with sweet spaciousness, a lot of time with friends and dancing, and admittedly a ton of delicious food.

The journey to get here wasn’t easy, though for some of us entrepreneurs I think true hell would be doing anything besides running our own business. My experience as a beginner entrepreneur was plagued by perfectionism, financial scarcity, and a thousand small starts and stops. This coming after already launching other businesses and running small organizations for years. You’d think after doing it before that confidence would carry me over, and it did to an extent, but the real difference came when I learned to love my work relentlessly but to put down my attachment to the outcome. From care and love it can be easy for me to want the “ultimate” or the “best” for my business, which becomes a mental trap that holds me back from sharing pieces or my process that might not be perfectly packaged yet. It was essential for me to care deeply for my work but also to let it breathe, to know that it is an expression of myself and as someone inherently lovable, it needn’t be perfect to share. (I’ve yet to meet a perfect lover yet I enjoy so many things about my relationships so who says my business needs to be perfect to get clients. It can still be delightfully fun even if not the ultimate expression of my vision on the daily).

Other lessons I’ve learned are to own what you do and have f*cking fun with it. There’s not a single person in my world who doesn’t know I’m a coach, but its not because I go around giving everyone and their brother’s dog a business card. I let my business inspire me and because I’m so lit up by it, people naturally want to know more. I’m out loud on the daily about my client’s wins and my personal journey and that enrolls people in my work. They get to live it before they even work with me and that makes for an easier time attracting new clients. (Who doesn’t want to work with someone helping their friends live juicer lives?!)

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Easily we’d begin with a coffee shop tour of DC. People not from here might not know that our city is filled with street art and along the path to see it all are some of the best coffee shops and restaurants like Maketto (go for the coffee, stay for the baked goods and the aesthetic.) Then we’d do some yoga at a park or take the dogs hiking in the nearby mountains. A quick drive gets you out from the city and up in the clouds which I’ve found we all need more of these days. Lastly, knowing my friends, we’d likely end up at Echostage or a circuit party for a night of revelry followed by a homemade brunch because nothing quite makes a late night of dancing feel equally great the morning after like fresh muffins and bacon.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I’ll happily shoutout my family whose groundedness allowed me to fly as well as my accomplishment coaching family for whom their tutelage, humor, and love for my whole humanity, including my spicy bits, know no bounds.

Website: Www.CraigCassey.com

Instagram: @craigcasseyjr

Youtube: Craig Cassey Coaching

Image Credits
Lee Whitman

Nominate Someone: ShoutoutSocal is built on recommendations and shoutouts from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.