Motherhood, Speaking and Much More with Shark Tank Alumni Megan Reilly

June 12, 2024
Jess and Megan discuss the intricacies of being a speaker and balancing motherhood.
Motherhood, Speaking and Much More with Shark Tank Alumni Megan Reilly
June 12, 2024
Jess and Megan discuss the intricacies of being a speaker and balancing motherhood.



In this podcast episode, Jess and Megan O’Reilly discuss the nuances and challenges of public speaking, especially for women. They share personal anecdotes about the importance of choosing the right outfit to avoid distractions, like visible sweat or uncomfortable microphones, which can undermine confidence on stage. Megan emphasizes the need to “clear the mechanism” to fully engage with the audience.

The conversation also delves into the unique challenges women face in a speaking environment designed primarily for men. Megan highlights the logistical issues women encounter, like where to clip a microphone pack when wearing a dress, and shares how she improvises solutions to stay comfortable and focused.


Megan Reilly – Shark Tank Alumni

Megan O’Reilly is a keynote speaker, podcaster, entrepreneur, and the owner and COO of Tippi Toes, a children’s dance company. She co-founded Tippi Toes with her sister, initially teaching dance classes locally before expanding the business into an international franchise. Megan is known for appearing on the reality TV show Shark Tank, where she pitched Tippi Toes and gained valuable business insights.

Beyond her work with Tippi Toes, Megan is passionate about empowering women, mainly working moms, to succeed in their careers. She shares her experiences and lessons learned through her speaking engagements, emphasizing the importance of authenticity, preparation, and focus.

Megan also hosts a podcast called “Who’s Your Mama?” where she interviews the mothers of successful individuals, exploring the parenting styles and life lessons that contributed to their children’s achievements. Megan’s engaging storytelling and relatable approach have made her a sought-after speaker and thought leader in business and parenting communities.


How do you juggle being an entrepreneur, mom, and keynote speaker? Meet Megan Reilly, the founder behind Tippi Toes’s children’s dance company, who was featured on a little-known show called Shark Tank. (You may have heard of it.)
She and Jess discuss balancing motherhood with career aspirations and embracing both simultaneously.

Rate Amplify on Spotify and Apple Podcasts and leave a review for Jess Ekstrom.

Amplify with Jess is produced by Earfluence, and brought to you by Mic Drop Workshop.


[00:00:00] Jess: Good morning. Oh, it went off. Your AC just went off.

[00:00:30] Megan: It just went off right when I started. It’s new. It’s waiting for the moment.

[00:00:38] Jess: Well, you’re not even sweating yet, so it’s perfect. And I was telling you, I’m like, I sweat even when it’s like 60 degrees. And it has been, I mean, I know we’re talking about speaking. Like, I will say just woman to woman. Learning what to wear on stage that doesn’t show sweat was a big part of my growth as a speaker.

[00:01:02] Megan: Hey, that’s a big deal because the last thing you’re going to be thinking about when you’re on stage is, do I have sweat dripping between my eyes?

[00:01:11] Jess: Yes. Between anything. It’s the worst. To feel self-conscious in any way, like when you’re on stage, anything visually, like even if you’re wearing shoes that you don’t feel good walking in. You just don’t want any reason to doubt yourself.

[00:01:33] Megan: 100%. And you don’t know. Sometimes, like I was all set working on my outfit the other day, making sure I felt comfortable just cause I wanted it to not be a thought in my mind. And then I got the microphone put on and I was like, “Oh,” and it was rubbing. And I was like, I don’t want to be thinking about my microphone during this. So I taped it to myself. I don’t want to be thinking about it. Now having said that, I also wonder, like, when I’m on stage, I get so in the zone. I feel like I kind of lose some of the things like that. Like I might not, I don’t know that I would even have noticed it, but I just like to clear the mechanism as much as I can so that I am fully there for the people and for the audience. You know, I feel like that’s important.

[00:02:19] Jess: But even talking about microphones shows how this was built for men. Like, you know, a lot of women might wear a dress or a skirt. And then you go to soundcheck and the tech asks, where do we clip the mic pack? They usually end up clipping it on my bra, and I have an antenna poking in the back of my head the whole time.

[00:02:57] Megan: Right.

[00:02:58] Jess: Where do you go?

[00:02:59] Megan: Yeah, it’s funny. I don’t know that I’d want to be that technician because I one time wore an outfit I thought was really cute. It was more like a lounge outfit though, but it was a look. But my waistband was really soft. So they put the mic on and my waistband was like, “Oh, shoot.” Now, before I get dressed, I’m like, where would the mic go? It’s just one of those things. Usually, the audience isn’t thinking about it, but as a speaker, you want to do as much as you can and be ready to rock and roll.

[00:03:39] Jess: Yeah. For anyone listening, women, wear what you’re comfortable with, but avoid things that show sweat because no matter what the temperature is, you’re going to glisten and glow. And avoid sheer material; it might look good in the mirror at home, but under stage lights, it looks different. Loose tops can fall when they clip the mic. You never know until you get there.

[00:04:19] Megan: You’re not practicing with lapels at home. Maybe you should do that.

[00:04:25] Jess: I don’t know. But I’m so glad you’re here. Everyone, welcome Megan. She is a speaker, a podcaster, entrepreneur, founder of Tippi Toes. You’ve been quite the franchise queen that I am in awe of because not only did you start a business for yourself, you’ve shown other people how to do it. First, I’d love to get the background on your business. I know you were on Shark Tank, which also plays a part in what you speak on. So let’s start with your business story and how speaking has played a role in that.

[00:04:57] Megan: Yeah, I would love to. Thanks for having me. I love what you do so much. I think it’s really important and these conversations are really powerful. Before I get started, I’m just pumped to be here. So my company is called Tippi Toes. It’s a children’s dance company. Actually, my sister started it as a sophomore in college. She lost her job and needed to make a car payment. She decided to go into a daycare and offer dance classes because she was really good at that. It was using her talents and skills to do something to make ends meet. Here we are 23 years later with an international franchise brand. Certainly, it was never our plan. She’s a few years older than I am. I came to school after her. We were both just teaching dance classes around Norman, Oklahoma. It was fun and easy, kind of effortless for us. Then life would change, we’d move, and we’d bring Tippi Toes with us, hire some managers. Over the first probably eight years, we just kept doing that. We had a lot of locations, but still weren’t really thinking anything about it. In 2009, the idea of franchising popped in front of us. I bought “Franchise Management for Dummies” because I had no idea what they were talking about. I didn’t understand it.

[00:06:00] Jess: Ok, let me tell you about Megan L. Reilly. She’s a keynote speaker, podcaster, and owner and COO of Tippi Toes, a children’s dance company that her sister founded in college. In 1999, Megan came on board, and together they started slowly expanding. By 2008, they had several locations, but they thought, maybe we should start franchising…

Megan: I got a book, started reading “Franchise Management for Dummies,” and thought we could do this. We sold our first franchise in 2009. We did it our way. We didn’t do the typical brokerage. There’s a very robust franchise industry, which we are now a part of, but we weren’t for many years. We did it our way because we were young women wanting to have a life and be at drop-off and pick-up with our kids. We wanted to organically grow. That’s what we did. We brought in a lot of other working moms who became working moms through Tippi Toes. They started their businesses in various cities around the country. It has been positive and wonderful. Our dance classes are recreational, bringing joy to kids. It’s about building kids up and giving them an opportunity to be on stage, like dance recitals. We want to build confidence and joy through dance. We’ve done that for many years now. We almost have 40 franchises in the United States. We have a master franchise in China. That is what I spend most of my time doing, and I love it. It’s a joy. During that experience, we found ourselves on Shark Tank. My brother-in-law submitted an application without telling my sister or me. We got a call saying, we’d like you to be on Shark Tank. We thought, “Oh my God, they found us.” It was incredible. Turns out my brother-in-law submitted an application. That experience is one of my keynotes. I talk about the lessons from Shark Tank and how they allowed me to find success in different ways. I keep relying on those tools from that experience. They’ve helped me in my business, as a speaker, in developing a podcast, and as a parent. The lessons from Shark Tank were valuable. It took me time to reflect on them and realize there was a lot I could pass on to others. It’s a rare experience to go on Shark Tank, but the lessons are robust. That’s what I like to share when I speak. Everything weaves together—podcast, business, speaking. I keep leaning into things I like and am into.

[00:08:38] Jess: The idea that we have to niche down and do one thing is so dated. We are all multifaceted human beings. Especially in the entrepreneurship world, once an entrepreneur, always an entrepreneur. Do things you like. Over time, you realize there’s probably a through line you didn’t even notice.

[00:09:08] Megan: A lot of times people see a story on the back end and think, how did they know to strategize all those things together? They didn’t. They started to do stuff. Then they look back and think, “Look at that.” I used to think, how’d they figure that out? They just tried the next thing and pieced it together.

[00:09:33] Jess: I used to think every successful person was walking around with a secret they weren’t telling me. Like they had a password on a card in their wallet they weren’t sharing. But no, you’re just doing the next thing. We don’t see the things that don’t work out. Talk about the speech of a lifetime—doing your pitch on Shark Tank. Was that your introduction to speaking? Were you speaking before that? It feels like going down the black diamond before the bunny hill.

[00:10:09] Megan: I never thought about that, but 100%, that was exactly what it was. I wasn’t speaking at that point. I started speaking later on, partly because I’m a mom. I’ve got kids who are 6, 8, and 10. I was building my business. I didn’t have time to start speaking before. Tippy Toes was getting all my time, and I had babies. That was it. I knew I always wanted to. I was reading, listening to podcasts, a lot of Gary Vee, personal brand stuff. I was being primed for the next season where I would be speaking. But when I went on Shark Tank, no, I didn’t have any experience. It was just, here’s how you pitch. We worked with producers, and that was quite a first speech to give.

[00:11:13] Jess: What were some of the tips or rules they gave you on Shark Tank that you still use today?

[00:11:22] Megan: It was more about putting together a show, entertainment. Making sure the percentages and money made sense for what we wanted to pitch. But in terms of how to pitch, there wasn’t direction. They were there with us, and I’m sure there was some coaching along the way. But I don’t remember anything specific like, this is important to do, or this is how it will land. They probably like to let people go rogue, flounder—it makes good TV. We just prepared. We were season two, and I remember watching season one, thinking you better know your stuff, or they will eat you alive on national television. Focus was important. Leading into a big goal, there’s nothing more important than focus. We were so focused on that pitch so nothing would throw me off in the moment. I use that in my speaking to this day. I have a typical speech I like to give and still work on it regularly, leading up to any presentation. I want to know it so if someone breaks a glass in the back of the room, I can make a comment, make it entertaining, and switch back to my topic. But I can’t do that if I’m in my head, worried about the cadence.

[00:13:17] Jess: Yes, exactly. I want to talk about how you can use speaking to grow your business, not in the form of a pitch. A lot of entrepreneurs want speaking opportunities, get them, and then it’s a profile about their business, like pitching on Shark Tank or to investors. They wonder why they’re not getting paid. I want to get paid to talk about my story, but it’s about extracting the universal experience from my business and laying it out in a way the audience can learn. Most people you speak to might not be on Shark Tank, but they can learn from the lessons you learned. While you share those experiences and lessons, they also learn about Tippi Toes and potential franchise opportunities. How has speaking helped you grow your business, and was it something you knew to do from the start?

[00:14:48] Megan: I’ve dreamed about speaking forever, but I didn’t start until the middle of COVID. Everything changed, and I found myself at home with my kids. I started my podcast and wanted to do more. There was only so much I could do with Tippi Toes once we were up and running, but things were still shut down. So, I started reaching out to speak. It’s interesting because, in business, when I go to sell to a school, I don’t think I’m pitching my business. I think I’m sharing stories of what we can bring to the school. I genuinely feel that because I know the value of Tippi Toes. That’s exactly how I think of a pitch or speech. I’m not thinking about someone buying a franchise after. I think about sharing experiences from business and entrepreneurship. Nobody wants to hear a pitch; they want to hear a story. Even if it ends up with the same outcome, going in with a heart of sharing stories has more power and impact. It was natural for me. Nobody wants to be pitched to, even the sharks. The way to get to that point is to not go in with the mindset of pitching but sharing lessons from experiences.

[00:17:08] Jess: 100%. That also goes into how you present yourself as a thought leader. It’s not like, “Hey, come on in, let me tell you how to franchise.” Or “Buy Mic Drop Workshop or headbands.” It’s, “Here’s what I have to offer, and this is the value I bring as a speaker.” If this is something you need, come on in. If you present yourself as asking for a favor, that’s not the mindset. Instead, you’re doing them a favor because you have something to offer. Get clear on what that is. Most of the time it’s not, “Hi, my name is Megan. I started a company, and I want to tell you about it.” It’s, “Hi, my name is Megan. I started a company, learned all these things, and want to tell your women’s conference about it.” Show up with a giver’s mindset, and things will happen. The best connection with an audience is when they connect with your founder story.

[00:18:36] Megan: It’s so much more engaging. It drops people’s guard. They’re not trying to avoid a pitch. A story opens everyone up. As soon as you say, “This is what happened to me,” people want to hear more. Then you’ll have more opportunities for details that might lead to business. If you start with the desire to pitch, people can feel it. People hear stories.

[00:19:11] Jess: Another important thing I love about you is that it would be easy for you to just speak to entrepreneurs or people wanting to start businesses because of your experience. But you speak to different industries worldwide because it’s not just about going on Shark Tank and starting a business. It’s about the lessons you learned that can apply to HR, sales, or construction. Extracting that universal experience is something you can do. What advice would you give to founders or anyone looking to apply their story to a wide range of people, not just their industry or market?

[00:19:59] Megan: Thank you for saying that. I appreciate it. When I crafted what I speak about, it was about what really was powerful and meant a lot to me. I spent time working on it, thinking about the lessons, and giving speeches. I’d hear feedback from people, which was incredibly helpful because everyone heard it differently. It was an unlock for me. I realized it applies to everything. Instead of Shark Tank lessons for business success, it’s Shark Tank lessons for success in whatever you want. Part of it was being open to what people were telling me. I’d love to act like I knew that, but I didn’t. I reflected on the speech, worked on crafting it, making it meaningful, and true to my experiences and stories. Over time, it evolved. It applies to everything—business, personal life. Part of that comes from my experience as an entrepreneur. The lessons in life we all hear and know are the same. Whether you’re listening to Megan Reilly, Jesse Itzler, Gary Vee, or your next-door neighbor, the true lessons in life are the same. No one says sleep in, talk trash, don’t work out, and throw shade. That doesn’t work. There are certain things that work. The true lines in many life lessons are the same, whether you’re a billionaire, trying to make ends meet, an executive, or not. Those lessons are constant.

[00:22:32] Jess: I love that because it shows we have something to learn from everyone. Don’t just look up, look around. And two, artificial intelligence in the creative space. There’s talk about writing and AI. But speaking and the heart of speaking come from lived experiences. That’s something only humans have. Our lessons, like failure, conflict, how we talk to ourselves, are unique. When thinking about what you want to speak on, don’t worry if someone like Brene Brown speaks about vulnerability. Your lived experience adds your fingerprints to it, contextualizing it. You don’t have to reinvent the wheel. Speaking of lived experiences, I want to end with being a mom and a speaker. That is something new to me. I’m six months in. You’re a little more seasoned in that. We’ve had talks around this.

[00:23:58] Megan: Seasoned or burnt? I don’t know which one it is.

[00:24:03] Jess: Yes. So, we’ve talked about balance. Speaking requires travel and time away, which can be tough for parents. How has being a mom influenced your speaking or career in general?

[00:24:27] Megan: It’s a real thing. It can be a challenge. It’s about being honest about where you are and what you want in life. I wanted to be all in as a parent, at pickup and drop-off, doing everything myself. That was my choice. I pushed my speaking career later because I couldn’t do both the way I wanted at that time. I already had a full-time job with Tippi Toes. If I was a full-time speaker and had kids, I would have done it during nap times. One important thing is being honest about what you want to be true about your life. If your career means so much to you and you want your kids in school, or have a staff, own it. That’s wonderful. Live that and figure it out. If you have a different plan, know there’s always something to give up. You can’t be a full-time everything to everybody. When my kids were babies, I thought I just wasn’t tough enough to do it all. But nobody can do all of it. You can’t be fully present raising kids and have three jobs. For young moms thinking they’re not doing it right, do what you want. Choose your path, whether at home a lot or not, and own it. Know this season changes. My kids are still young, 6, 8, and 10, but life is different now than when they were 1, 3, and 5. I can travel more now. It’s all different. Time goes by quickly. Decide where you want to spend your time and know we’re not superhuman. There is only so much we can do, and that’s okay. For years, I listened to Gary Vee, dreaming of speaking, having a podcast, thinking I’d never be able to. I had a full-time job and was a full-time mom. Then my youngest went to preschool full-time, and I had five hours a day. That’s when I started doing more. I thought I was not catching up with everybody. Now I know it’s okay. I’m here now. Being present in the moment and owning where you are is huge for moms. It gives you a break. The season will change in a few years. It will look totally different. I remember the struggle of feeling behind, thinking I’ll never do it. Then I realized I can, just a few years later than I thought. And it’s great.

[00:28:25] Jess: I’m glad I’m wearing my glasses because I feel emotional from your response. You can’t help but second-guess yourself and your identity when it shifts so drastically after becoming a mom. I’m in a season of choosing less, being selective about when I get on a plane. You can’t help but feel like things are falling through your fingertips. You feel the need to stay relevant and exposed. But it’s not my turn, not my season. It will change, and it’s going to be fine.

[00:29:12] Megan: And it’s not like you’re sitting at home playing video games. You’re raising a human being, a sweet, precious kiddo you’ll do life with forever. What’s a better place to let things go through your fingertips? They’ll be there. I didn’t have a presence until literally 2020. All that time being a mom has helped me as a speaker. If I hadn’t been engaged, when a mom stands up and asks how I do it all, I’d have to fake an answer. But I can say I used to cry in the pantry, crush it at work, not be a very good mom sometimes, and be a great mom other times. I can relate because of that time I had. Your identity shifts as a mom. You live your whole life working on your career, and then it switches on a dime. You’re trying to learn this whole new thing, raising a person, which is kind of important. Everything in your season, Jess, will serve you in a bigger, better way when you share more. It’s not going away. It’s all serving you, just maybe not immediately. Those years of listening to Gary Vee, nursing a baby, feeling overwhelmed, sweating, and crying in the pantry, having happy days at the park—it all serves me now on stage, in my company, all the time.

[00:31:29] Jess: I was saying to someone the other day how I’ve changed. Before Ellie, I lived life between a 3 on the emotional scale. Now I find myself between 10. Even though I can feel really low lows, I also feel really high highs I never felt before. Speaking gems come from lived experiences. I feel the richness of my lived experiences. They’re still in the driver’s seat. I say, don’t speak unless your experiences are in your rearview mirror. I know I’m being shaped in a way that in a few years, I’ll share this on stage. It’s added more depth to my life. I have to understand I’m in a season of change. Hearing your story, how chapters kept turning, and all of a sudden you have five hours a day—it’s all evolving.

[00:32:48] Megan: Constantly. If I could tell myself one thing, it would be to embrace it, not fight it. I wasn’t outwardly fighting it, but mentally, I thought I’d missed the boat, was too late. But none of that was true. I told myself that for years and was wrong. For anyone in that phase, it doesn’t matter. It has nothing to do with you. I have an abundance mindset—there are plenty of stages, plenty of messages. Your lived experience is unique. The truths are the truths, but the beauty is in the stories. You’re writing chapters of your book now, and you’ll share that book with the world. It will make everything more dynamic, interesting, and relatable. People say I’m authentic. I share real stuff. You do that really well too. Your experiences now will strengthen that outcome, make it more exciting and engaging. When you add the experience of having a baby at home while building an empire, that’s a specific scenario to talk about. It will serve you. As soon as you know it’s serving you, you can embrace it more. It just looks different.

[00:35:09] Jess: Feeling like I should be here when I’m there. Man, we have to wrap before I need to call someone to get tissues.

[00:35:18] Megan: I love it. Well, I’m so happy for you.

[00:35:21] Jess: Thank you. Everyone who has been chiming in the comments on LinkedIn and sharing your experiences, especially in parenthood, it’s been great. Lived experiences are the best medicine. If you’re not following Megan already on LinkedIn, please do so. You are one of those people. Where else can people find you, your podcast, speaking, all of that?

[00:35:54] Megan: LinkedIn is my favorite place. Actually, I went rogue, and I know we have a time thing, but I said I was going to give a giveaway.

[00:36:00] Jess: Oh yay!

[00:36:00] Megan: It’s so random, but I was like, maybe people will come. I’m going to give Tariqa a gift card. It’s the first time I’ve seen her in the comments.

[00:36:16] Jess: Tariqa is a Mic Drop student as well.

[00:36:18] Megan: Okay. I’m going to send her a gift card. I’ll get with you afterwards. I posted it last night, thinking let’s have something happen. Tariqa, thank you for being here and commenting. I’m going to send you a gift card. Sorry, that was so random. I interview moms who’ve raised extraordinary people like Sarah Blakely, Jesse Itzler, Ramit Sethi. It’s available on all platforms, “Who’s Your Mama?” LinkedIn is the best place for me. Tippi Toes is growing, hopefully in a city near you soon. Tippi Toes Dance is a fun company. If you’ve got little ones, we can serve you with some fun dance classes. Hit me up on LinkedIn. I love seeing people in the comments. Comments are better for me than messages. Messages on LinkedIn can get overwhelming.

[00:37:18] Jess: Yes. I’m sorry for responding four years later, but here we go.

[00:37:18] Megan: True.

[00:37:18] Jess: Thank you so much. Thank you, everyone, for listening. We’ll talk to you soon. Have a great day. Bye, everyone.


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