Ina Coveney: The person we're interviewing today... you've probably heard of the global phenomenon of the online coaching world, and I can't wait to introduce you to Jen Casey

Ina Coveney: Hi, Jen, how are you today?

Jen Casey: I'm good. So happy to be here.

Ina Coveney: I am so happy that you're here. Why don't we start really simply? What is it that you do right now, and who do you do it for?

Jen Casey: Hmm, so it is interesting to ask that because we are in transition right now. For many years, I was working with online coaches who wanted to build and sell online coaching programs, helping them niche down, really work on their program design, launch, and sell.

Jen Casey: And in the last year, things have really been shifting. I still have those offers, but things are transitioning into much more spiritually aligned offers, really helping people with more of the inside job of entrepreneurship.

Ina Coveney: I can't wait to dive into this. By the way, one thing that I'd like to start with— you’ve made an amazing business on your own. You've had an incredible amount of success. And anybody that I say the name Jen Casey to knows who I'm talking about. They’ve been following you for so long. You have an incredibly loyal and supportive fanbase.

Ina Coveney: And I like to start with, how did you become a global phenomenon? Take me back. I'm going to start in college. Okay, take me back. You’re a college student. You're studying psychology, correct?

Ina Coveney: I want to know, first of all, was psychology something that you were always drawn to? Is that something that you knew you wanted to study? Tell us how you arrived at that major, first of all.

Jen Casey: Yeah, so I was sort of wanting to pursue musical theater but also wanted to do psychology and ended up transferring schools a bunch. I couldn’t really find my footing. Now I know—I don’t know if you are into human design—but as a 3/5 projector, it is my aligned energy to be in trial and error and experimentation. So it all makes so much sense now. But at the time, it just looked like, “What the heck is Jen doing?”

Jen Casey: And so, yeah, I really loved psychology. Since I was a little kid, I was always that friend that was the listening ear and giving people support. My mom and aunt are both therapists. So I was the three-year-old that was using words like "ambivalent" to express how I felt. Instead of saying my brother was annoying, I would say, “Mommy, Peter’s being passive-aggressive.”

Jen Casey: And I really understood those words. That was my lexicon for life. Most people had no idea what I was talking about, but my mom thought it was funny to teach us psychology-based words. So it's always been a part of who I am, just because that was what I was raised on—talking out your feelings and all of that stuff.

Jen Casey: After college, I went to really pursue my acting career. And what I found very interesting about the parallels of the psychology world and the acting world is that in psychology, you’re looking at a fully formed human. They have this challenge or struggle, and you’re peeling back the onion layers to try to get to the essence and root of what is causing them to be stuck.

Jen Casey: But in the acting world, you’re looking at a piece of paper with some lines that an imaginary person said. And you have to take those words, bring them to life, and build this three-dimensional, truthful, authentic human with all of the quirks and nuances that people have. I see acting as the reverse of psychology.

Jen Casey: And so it was really interesting for me to explore that world from both angles, and I feel like that really gave me a different insight and perspective on the human condition.

Ina Coveney: Let me ask you, there are two people in your life that I can't wait to talk to you a little bit more about. One of them is Angie Lee. Can you tell us who Angie is? And right now, remember, contextually, we’re thinking about the time when you really decided to go all in on your online business. Who is Angie Lee, and what part did she play at that time?

Jen Casey: So she and I decided to partner in business together in 2016, and we had a program that we launched together. We did that for a year and a half.

Ina Coveney: And that was the Worldpreneur Academy, right?

Jen Casey: Yes! Funny things happen with partnerships, right? It’s like, how do you know when it’s going to be a good one, that it’s going to serve you for that time, and when it’s time to part? I see this usually as a marriage, you know, because you’re really aligning both of your visions together and saying, “We’re all in together.” I’d love to know, what was that partnership like? And how did it finally evolve into you two going into business on your own?

Jen Casey: Yeah, so it definitely evolved. Like you said, partnerships are like a marriage. The lessons I’ve learned are to make sure you have the same vision but also recognize that everybody’s vision evolves. Being able to come to each other, have open conversations, check in, and figure out if the vision you have still aligns with where you’re going is crucial.

Jen Casey: Things grew very quickly for us. I think a big lesson I learned is to have a conversation about values in business. It’s not that we didn’t have the same values, but it was more about the order of priorities. Like, what are your top three values? Those are the things that primarily drive your behavior.

Jen Casey: For me, customer service and quality experience were above all. So I was willing to go the extra mile if someone felt their expectations weren’t met. Because we grew so fast—we had over 100 people in our programs overnight—there were growth challenges. Coaching calls had to be run differently. Not everyone could ask questions, so we had to navigate that.

Jen Casey: Ultimately, we saw the business evolving in very different ways, so we decided to end the partnership.

Ina Coveney: What was going on with you at the time of that first big launch? Did you expect such an amazing success? And in hindsight, why do you think it worked?

Jen Casey: That first big one was in 2016, and it was when live video had first come out on Facebook. Most people weren’t getting on live. It’s funny to think about now because everyone does live videos and stories, but at the time, people were terrified of it.

Jen Casey: I had a performance background, so by my third or fourth live video, I felt like I had the hang of it. The first couple were definitely full-blown sweaty moments. Angie and I met through a community. She saw some of my live videos and suggested we connect and mastermind together. That was the beginning.

Jen Casey: We both had fast visibility through Facebook Live and active Facebook groups. When we combined forces, I think we cornered the market on health coaches. She had a certification background, and I had network marketing and group fitness experience. Our past experiences aligned perfectly to serve that niche.

Jen Casey: Even other people teaching business were doing it broadly, while we narrowed in and provided depth, like bringing in an expert on the legalities of food plans based on state laws. We added a deeper layer that made our program uniquely valuable, and people got amazing results.

Ina Coveney: What you just mentioned about live streaming reminds me of how groundbreaking it was—a brand-new way to deliver a message. What do you think is the 2022 version of live streaming, not necessarily live streaming itself, but the thing that’s catching fire right now?

Jen Casey: I think for a second, it was Reels, like early last year. But I’d say TikTok is where the attention is right now. I love Gary Vee, and he talked about how people were hopping off Facebook a few years ago and growing their businesses on Instagram as it introduced new features. Now, TikTok has taken over and dominated the market.

Jen Casey: People are asking, “Where’s all my Instagram engagement?” because the attention has shifted. Back in 2016, we hit the Facebook Live market when everyone was eager to watch live videos. TikTok feels like the closest equivalent today. YouTube also remains massive—friends of mine who consistently generate automated revenue have built audiences there. Even if they don’t post regularly, their older content continues to perform.

Ina Coveney: There’s someone else I mentioned earlier—Lauren Elizabeth. She’s a very successful spiritual healer. Everyone can listen to her episode with me; it’s episode 37 of this podcast. I know you just had her on your podcast. Can you plug that in quickly?

Jen Casey: Sure! My podcast is CEO Psyche. I don’t remember the exact episode number, but it was around May. Go check it out.

Ina Coveney: Lauren is love. She was the first global phenomenon I saw as a global phenomenon. She showed me what an online business could be. I followed everything she did. She talks about feelings of comparison while building her business—especially in relation to you—and how she wondered, “Why isn’t my business working?” What’s your perspective on that? Did you know she felt that way?

Jen Casey: Lauren and I have had so many conversations behind the scenes. We’re best friends and mastermind partners since the early days of her business. She was the first person who could hold space for me and match my hunger and tenacity to build something. We’d go to Tony Robbins events together, and she was my roommate at every one.

Jen Casey: Over the years, we’ve had different challenges, but we’ve always come back to knowing that we’re not going anywhere. Even if one of us is making 10 times more money or going through a tough season, we hold space for each other. We’ve learned to navigate our triggers and support each other deeply. It’s been beautiful to grow together in that way.

Ina Coveney: Have you ever struggled with comparison yourself, especially with people you admire?

Jen Casey: Oh, absolutely. I’ve told the story of walking into a high-level mastermind in 2017 with some of the top names in the online space—people making millions. At the time, I had just ended a partnership and was starting over. I walked in and saw a table of people I admired most. I thought, “Please, let there be another seat. Don’t make me sit there.” But there wasn’t.

Jen Casey: It was an amazing experience of challenging my fears and upper limits. I questioned how I could possibly add value to people with so much more experience than me. But sitting there, I realized everyone had their struggles. They’re human too. It quieted a lot of my comparison because I got to see their humanness.

Ina Coveney: From your podcast episodes and the research I’ve done, I noticed that your business started with a lot of strategy-focused, Type A energy. Now you’re pivoting toward a more spiritual approach. For many listeners, those two things feel like opposites. Can you teach us why they seem that way and how they can coexist?

Jen Casey: People often distort feminine and masculine energy into female and male, which creates a binary that isn’t helpful. For me, it’s been about embodying both. My clients often say they sought a mentor who could do both—dive into webinar slides one moment and clear energetic blocks the next.

Jen Casey: It’s about integrating both energies authentically. You don’t need to fit into branded archetypes or pigeonhole yourself. Your self-expression can be whatever you want it to be. If you embody both, you can create something unique that resonates deeply with others.

Ina Coveney: What would you say to someone who feels trapped by the belief that they have to do things a certain way, even if they don’t want to?

Jen Casey: I’d tell them they get to choose their own narrative. Be the author of your life. That doesn’t mean changes have to happen tomorrow, but you can give yourself permission to envision a different future. Start small, but keep giving yourself permission to dream and build the life you truly want.

Ina Coveney: As we wind down, let me ask you this: You hit seven figures in your business. What’s the biggest difference between being a six-figure entrepreneur and a seven-figure one?

Jen Casey: The biggest difference isn’t about the problems you face—it’s about how quickly you resolve them. Successful entrepreneurs have done the inner work to regulate their nervous systems and stay clear-headed when solving problems. They understand their decision-making style and have learned to navigate challenges without burning out. That clarity and alignment make all the difference.

Ina Coveney: What’s the biggest misconception people have about you as a successful businesswoman?

Jen Casey: That everything comes easily. People see the polished result but not the hours of work, grit, and even tears behind the scenes. I’ve had moments of wanting to burn my business to the ground. Those feelings don’t necessarily go away, but you learn to navigate them.

Ina Coveney: If everyone listening had to do one thing in the next 24 hours, what would it be?

Jen Casey: Take off the mask and stand in your authentic truth. If everyone did that, it’s mind-blowing to think of what could be possible—conflicts gone, everyone living their truth.

Ina Coveney: Thank you so much for being so generous with your answers. Where can people go to follow you and learn more?

Jen Casey: You can find me everywhere at @heyjencasey, or visit my website at heyjencasey.com. And of course, check out my podcast, CEO Psyche.

Ina Coveney: Thank you so much, Jen. This has been wonderful. And thank you, everyone, for listening. Don’t forget to check out CEO Psyche.