Featured Founder: CEO Caitie Bradley Shea

In this series of posts, we’re diving into our Open Book to allow you a chance to become better acquainted with our co-founders through the eyes of each other. Each has written a post about one of the three founders of Outspoken so you may better understand who we are and why we think working together is SO FETCH. (Whatever, I’m getting cheese fries.)

Written by Tori

When I first met Caitie at our former agency, I thought there was no way I was becoming “buddy buddy” with her. I was one foot out the door when she was hired. We won’t get into specifics. Needless to say, I had work trust issues. But she persisted until I caved. Something about Caitie that I admire is that she’s naturally good at sliding into a situation and just fitting in. She doesn’t have to force it. She doesn’t overwork the room. She just has a way of becoming fast friends without imposing herself on others. And she’s patient when it takes time. Once she smoothly coerced me into a working relationship, it easily transitioned into a friendship and I knew she was going to be a part of my life for years to come. 

She has this same way with our clients. She makes them feel comfortable—will talk for hours about everything other than business. But she’s always persistent. She will come back time and time again until she wins your business because she knows we can provide a unique, transparent and reliable experience working with us. And she knows how special our speakers are and how important it is to share their messages.

When we decided to start the company over five years ago, I really leaned on her in particular to get me to take the leap. I never in my life thought I’d own a business. Both Caitie and Tara had. But we knew Caitie would ultimately be our leader and I think we all arguably needed her guidance and her persistence in the incredibly bumpy road that lay ahead of us in the process of becoming Outspoken. She took all of those bumps in stride, providing us with an amazing support system of professionals and her incredibly even-keeled thinking that got us through the most trying circumstances. Always welcoming us into her home to brainstorm (and let off some heavy steam), always providing us with sustenance (mostly wine and cheese), she gave us a space to create what we’re now so proud of. A lot of those long nights may be blurry from the wine, but we have the photo evidence to prove we had a lot of fun (and several good cries) in the process. Maybe we’ll share those for year 10? :)

It’s been a real pleasure to see Caitie’s whole life transform personally right at the same time as our company’s growth. True to form, she and her husband threw the most epic party—I mean, wedding—imaginable, catering to everyone’s wants and needs and ensuring it was a weekend we’d never forget. Only Caitie’s husband would DJ at their own wedding! And now that she’s a mom, I’ve loved to watch that part of her caring personality and pure admiration and love for her son shine through. I’ve never seen her face light up that same way for anything or anyone else. Okay, maybe her husband, but mom vibes are real strong over here these days. And she’s not like a regular mom. She’s a cool mom. Still hitting the workouts hard and always ready for her next adventure, there’s no doubt she’ll be back to those marathons in no time. Or at least running hard after a baby or two. For now, the three of us are running a marathon of building Outspoken and I wouldn’t have it any other way.

Founder 411: Q&A with Caitie

1) What is so fetch about being CEO/our fearless leader?

Oh that’s an easy one… It’s the daily affirmation I receive through working alongside my two incredible Co-Founders, that the vision I had five years ago about how and why this partnership could and would work, was indeed accurate. Outspoken would not and could not exist without the very specific chemistry of us three Co-Founders, and I pinch myself every day when I realize that that foundation, which (like every other start up) has been rattled many a times, has never budged or come close to cracking.

2) Most valuable business lesson you’ve ever learned? 

Just. Keep. Going. There will always be adversity and set-backs, and there will always be the temptation to succumb to this fear or that drama, but if you keep your head down and stay the course, you WILL get to where you are supposed to be, which sometimes winds up being a different (and better!) destination than you originally set out for.

3) If you could hear someone give a speech alive or dead, who would it be and why? 

Ohhh that’s a tough one because it changes depending on my mood or something I’m reading or watching at any given moment. BUT one person I have LONG been both intrigued and terrified by is Cleopatra. This goes all the way back to 4th or 5th grade when we first learned about Egyptian culture and I immediately had to be her for Halloween. Girlfriend was just such a FORCE. She was an exceedingly charismatic, savvy and unapologetic ruler who famously did mental gymnastics around her adversaries to achieve her goals. Despite what the Roman’s sexist version of history would like to suggest, it was her captivating intellect that landed her in the throne, NOT her temptress ways and spellbinding beauty. Sure, she may have made some questionable decisions regarding mixing business with pleasure while leveraging her irresistible charm and prowess to get what she wanted, but any woman whose equally controversial and awe-inspiring life story transcends millennia and the history of humanity itself — is a woman I’d put at the TOP of my list of people I’d like to see deliver a BANGIN’ keynote speech.

4) What class superlative would you most likely be now and why? 

Most likely to quit her job and start a company with two badass women. Because… Happy Birthday OUTSPOKEN!

5) If the limit does not exist as they say in “Mean Girls”, where do you see your company in year 10?

I see us chartering private jets to Mykonos where we will have launched a Goop meets “WeGrow” school for budding young speakers and future thought leaders of enlightenment who only deliver speeches via hologram and VR. 

Either that, OR we’ll be doing the same exact thing we’re doing today, but with a few more inspiring folks in the stable to help spread the good word about equality and progress… and maybe we’ll be back in an office with an office pet added to the mix? WHO KNOWS!?

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Outspoken Agency is a women-owned speaking agency representing leaders, founders, public intellectuals, authors and entertainers for paid keynotes, workshops and panels at in-person and virtual events. Learn more about our female founders here.