We Just Hope Nobody Gets Hurt: A Conversation with Cuban & Sooner

What happens when two entrepreneurs, friends and sometimes colleagues put their proverbial money where their mouths are? A podcast is born.

Deseri Garcia (the “Cuban), founder and owner of Vida Aventura, and Michelle Freed (the “Sooner”), founder and owner of Woodfish Group, are still celebrating the recent launch of their Cuban & Sooner: Work-Life Teetering podcast, which explores the blurred lines of work, life, relationships, and the issues that intersect them all. They found the time to sit down and talk about the journey, which has included plenty of laughs, technical difficulties, formidable learning curves, and priceless moments of being human.

Michelle Freed: We did it! After months of conversations, research, planning and fumbling around to learn what we’re doing, we have episodes out there in the universe!

Deseri Garcia: It’s so exciting to see and hear something tangible. It’s one thing to be working hard to make something big happen, but before the launch, it was just us working together. Now, our work is in the public, and that’s a powerful feeling. It’s been a wild ride so far – we’ve definitely stretched ourselves.

MF: It’s funny, because for years we tossed the idea of a podcast around, but it was always over cocktails and during casual we-should-do-that conversations. Over time, we started getting more serious about it, but it still took a while. We each moved at different paces, but we got there in the end. Hey, that’s how we are in most things, aren’t we?

DG: Well, that’s one of the things that I think really makes us work as podcasters. We have different perspectives and approaches to things, but we usually get to the same place in the end. And in terms of all those conversations we had over the years, yes, lots and lots of adult beverages were consumed before the birth of Cuban & Sooner. But then there was a point when we looked at each other and basically said, “No, really. We’re going to seriously do this.” And here we are.

MF: Let’s talk about learning curves. As in, there are so many.

DG: Where do we begin? First, technology. Or should we go there?

MF: What you’re referring to is the fact that after we finally recorded our first episode – and we both felt very proud of it – it was discovered that I accidentally, sort of and without intention erased my track. Over 30 minutes’ worth. And you were not happy.

DG: Yeah, that was a tough one to handle. Plus, we were short on time, and of course we didn’t really know what we were doing at all in terms of a good recording set-up.

MF: After that, I knew I had to just let you, my Cuban friend, simmer while I stayed out of the way for a few days. But then, and I do have to point this out, you ended up doing the same thing during a later recording session, so I felt a little vindicated.

DG: So true. I think that was just one of many good lessons we’ve learned in friendship, partnership and teamwork. It was actually a real-life example of what we’re all dealing with in the world … trying to learn new things and venturing out there to take risks all the while knowing there will be failures and set-backs.

MF: I see what you did there. That’s one of the reasons why we’re doing this podcast, isn’t it? We want to share our “well-earned wisdom” and ongoing stumbles and challenges with others because hey, we’re all in this together.

DG: That’s right! You and I have both had countless experiences either with clients, friends or after speaking engagements when people have said, “I’m so glad you talked about that topic, or shared that personal experience, because I’m going through the very same thing right now and I’ve been feeling so alone in this. It’s comforting to know I’m not.”

MF: Yes! I don’t mind throwing myself under the bus or sharing truthful personal experiences because we’ve all experienced the same things and so it creates valuable moments of shared humanity. What have been some other big learning curves for you?

DG: It’s challenging to take on a big new project when you’ve already got a packed schedule – so figuring out how to prioritize everything is an ongoing difficulty. We knew it’d take commitment, and it certainly has. We’ve had to consider both of our work loads and carve out time to make podcast-related decisions, record episodes, accomplish specific goals and forge ahead while also maintaining our separate business and personal lives.

MF: Another thing we’ve learned is to help balance each other out – it’s never a 50/50 thing, right? Meaning, we both ebb and flow when it comes to our work load. But we’ve managed to pick up the slack when the other is swimming in the deep end, so to speak. We’ve had to learn to communicate better and speak up when we need to.

DG: That was a big part of our discussion on the “We Need to Talk” episode 8  – we went deep on that one.

MF: You surprised me with a candid question about a point in time when we were a little, let’s say, imbalanced in our contributions. I appreciated that, and it was a very real, honest and open conversation. Damn, we’re good! I’m really proud of us, and I’m looking forward to more challenges, and getting through them with lots of laughter. And probably more wine.

DG: And even though we’ve been friends for 11 years, we continue to learn more about each other, often while we’re in the middle of recording! I love it. And we know more about recording and other technical things than I ever thought possible.

MF: Speaking of tech, we wouldn’t have gotten this far without Jen Edds of Brassy Broadcasting Company. I know we’re both so thankful for her and everyone else who has offered so much support as we plunged into this new venture.  

DG: It takes a village! As you know I am a big proponent of “celebrating often,” and we both need to take time and recognize accomplishments, determination, grit and creativity in getting this podcast launched and off the ground. We’re still baby podcasters, but we’re getting there. And as we’re fond of saying, “We just hope nobody gets hurt.”

Access the podcast here.