200 Episodes Later: The Business I Never Saw Coming

Maybe the biggest thing that I've learned over 200 episodes is that you don't have to know exactly where you're going when you start. You just have to be willing to start and stay curious and let yourself evolve along the way.

Welcome to the next evolution of the podcast Entrepreneur School in the AI era, we are here to figure out how to integrate AI into the business you've worked so hard to build in a way that still feels like you. I'm your host Kelly Sinclair, award-winning marketer turned AI platform co-founder. AI has fundamentally changed how I thought about work, systems, and what's actually possible. This show is about navigating that new reality together. It's going to be a wild ride, my friend, but I truly believe there's a way to leverage AI in a way that's intentional, human-centered, and aligned. It's an ongoing evolution, so let's explore because AI may just be the unlock you need to achieve the life first business you truly desire.

I can't even believe that I just hit record for the 200th time for this podcast, 200 Episodes, and like most things in entrepreneurship, I feel like this is a milestone. I was just gonna skip right past. I wasn't even gonna specially record an episode 200 until I got to thinking that no, this is an opportunity. I should take a moment to reflect, to thank you for listening to me. Whether you are coming here for the first time or the 200th time, I am so grateful for the opportunity to be able to turn on this microphone and speak about things that I care about, and have amazing conversations with some incredibly smart humans from all around the world who have been on this show. So as I reflect on 200 episodes, the thing I automatically wanted to look at were the numbers, right? Like how many people have I reached? How many guests have I had? How many downloads? All those things. It's also easy to feel like those numbers aren't good enough. I have had just about 22,000 downloads of this show, and I'm reminding myself that that's 22,000 opportunities to impact people with the words that I choose to say, and there's a lot of power and a lot of pride for me in having that opportunity. I've spoken to over 100 guests on this show from literally all around the world: the UK, Australia, India, all through North America. Amazingly smart people that I have relationships with now that I would never have had the opportunity to talk to. Probably a lot of them, if it wasn't for this podcast, this podcast has taken me traveling around the world to speak. It has just been an amazing creative outlet for me to have a space to come and try and kind of pull my thoughts together on everything that's happening in the space that we talk about when it comes to business and entrepreneurship, and that's what I'm truly grateful for. So, if this podcast has made a difference for you in any way at all, I am just truly honored to have been able to join you on your morning

walks, your workouts, your carpool pickups, your doing the dishes, folding the laundry, whatever it is that you're doing while you're listening to me. I am truly grateful to you. What's crazy to me is how much has changed in my life and my business since I first recorded my very first episode, which was almost four years ago. I remember, actually, here's a little story. I remember making the decision, like I want to start a podcast. And I went from making that decision to getting the whole thing up and running and four episodes recorded within 30 days over the Christmas break before I had a trip to Hawaii planned with my family, and so nothing like a deadline for me. Big fan of having some something to celebrate as well. So having that trip to Hawaii was like perfect. I'll just record and be a podcaster by the time I go to Hawaii. That sounds amazing. And I want to give a big shout out to my podcast production company, Amplify you, Niaz and Troy and Michelle and Brayden and everybody over there who has helped bring this show together. Honestly, for almost four years, one thing I know about myself is that I am committed.

I I will keep showing up. I think I missed one episode, one week ever in the entirety of producing this show, and that was because we were switching from the original version of Entrepreneur School to what we are now, which is Entrepreneur school in the AI era, so I want to share a little bit about like the evolution of this show, and also the fact that my business is absolutely nothing like it used to be, or it's nothing like I expected it to be either. In all of those years, when I found the need originally to create a podcast, I was thinking about how starting a business is so multifaceted. There's so many challenges and layers that are so much farther beyond business strategy and like how to set up a corporation and how to market yourself and how to find clients and all those things, which are important. But the other side of being an entrepreneur, especially as a parent, is how do you figure out how to run your day when you have to go pick your kids up at kindergarten? Like, like kindergarten was like 11:50am. pickup, and are you going to be working from home, or do you send your kids to childcare? How do you deal with the guilt of doing that sometimes, and all of those things that I I was navigating for myself, and I wanted to share and go through with my listeners when I was first starting this show, because I just thought there's no entrepreneur school. There's no place where you go to learn how to be an entrepreneur. This is not about how to start a business. There is business school. There is this is the the fact that it's now infused in your life, and oh my God, is it ever like entrepreneurship is an addiction? It's, it's. I think once you catch it, you never, you never stop. You your brain doesn't stop when you go to bed. Your brain doesn't stop when you are taking your kids to activities, when you are watching your kids play sports. Your brain doesn't stop when you try to go to bed for yourself. It just keeps going

and going and going. And you know, there's there's definitely pros and cons to that whole experience. But I just recognize that we're kind of a different breed. People who want to start their own business. There's all kinds of pressures around growth and hiring and social media and all of the things. And I just wanted a place to have those conversations. And I still, I still do. Before I hit record, I I went back and listened to the original intro clip from the show when it first started, and I'm going to play it for you now so that you can hear what the goal of the show was when it first got started. is the Entrepreneur School podcast, where we believe you can run a thriving business and still make your family a priority. This show is all about supporting you, the emerging or early stage entrepreneur, on your journey from solopreneur to CEO, while wearing all of the other hats in your life. My name is Kelly Sinclair, and I'm a brand and marketing strategist who started a business with two kids under three. I'm a corporate PR girl turned entrepreneur after I learned the hard way that life is too short to waste doing things that burn you out. On this show, you'll hear inspiring stories from. Other business owners on their journey and learn strategies to help you grow a profitable business while making it all fit into the life that you want. Welcome to Entrepreneur School. When I first started this show, it was really about building a life-first business, and this goal has not shifted at all. The way that I'm attempting to do that has absolutely changed, and I think it's important actually to acknowledge that the goal can be the same, and the method to achieving that goal is something that's going to adjust and switch over time, and especially just as you evolve, as things evolve around you.

And for me, it was going from working in brand and visibility, helping people to get seen for their expertise and find ways to build a business around doing the thing that they love, and then generative AI came onto the scene, and I had that plot twist that I was not expecting, where I started co-founding a technology company, and now all I talk about is AI and how it impacts the way that we do business, the opportunities that we have to truly have this life-first business have shifted as well. If we can deploy AI in ways that can help us to achieve those goals, to buy back our time, time that is always fleeting. This morning I walked my kids to school, and I realized that this is the last year that I'll be taking them both to the same school. My oldest daughter is going to fricking high school next year, and when I started my business, she was not even in kindergarten, and that's a lot of life that has happened in the meantime, and I'm just like really grateful. Like I'm not here just to be clear. I'm not here to say, "Oh, I've made it. Everything is so amazing, and I make so much money, and business is great. And no, it's freaking hard. It is hard to start up a new company in an era of a technology that nobody understands, including the people who are building it, shaping a new industry, shaping new rules, and how this actually works. It's so unknown, and I just live in that every single day. But the fact that I can do that and still walk my kids to school, which was my definition of success from day one, and that I can take them to gymnastics at 330 in the afternoon, and take them to orthodontist appointments in the middle of the day. And if somebody's sick, it doesn't cause somebody to have to take a sick day at work. Like I have that flexibility to start cooking dinner at 4o'clock or do a workout in the middle of the day, or things that I know that I actually need to make my life work the way that I want it to, and I don't know. It took a

long time to move away from that corporate mindset of you have this part of your life that is your job, and you show up at this job, and the only thing that matters is the job and being there. And there is no like there's like that check your personal life at the door kind of vibes that I used to be part of. Not that I even thought there was an option to not subscribe to that thought process. I just did that, and the unraveling of that training has is still hard. It's still hard, and I've been an entrepreneur now for nine years. This coming March will mark 10 years since I walked into my corporate job for the last time, and that is crazy. Wow, I hadn't thought about that yet. But that's all to say that there were so many things that have happened in this time that I could have not predicted when I hit record on episode one of this podcast, and I'm still learning and experimenting and getting things wrong and figuring out the next steps, just like I was at that at that point in time. But I want to say that I I don't see not podcasting in my. Like this is just something I really enjoy doing. I enjoy the relationships. I enjoy the opportunity to get on this microphone and feel like I'm talking to my people, the people who want to have these conversations, who get it? Who are going through similar things? Not always all the same thing, but there's always going to be like some crossover point. And while I wish it was a two way conversation, to be honest with you, I just love having it. And you know, I think when when people start podcasts, they go, "Okay, well, I'm gonna monetize my podcast. It's like, what the hell does that mean? What does that mean? Does that mean you're getting advertising paid for? You're getting brand partnerships. Maybe that's never been the goal of mine.

The goal of my podcast has always been to establish myself as the expert in whatever I'm talking about, so that I can sell the services of my business and or get more speaking opportunities on other stages because I just love public speaking. I know I'm a freak of nature in that way, but I've been public speaking since I was nine years old in 4-H, where I would write speeches about my papa, my line dancing. What else did I talk about? I talked about body image. I like dealt with all these topics, and and I was in competitive public speaking. Like I would go and compete at talking. That's what I did. I didn't play elite sports as a kid. I did talking competitively. My dad's like probably laughing so hard. Yes, and it's a skill that I had, and I needed a place to be able to put that. I needed an outlet for that, and I still need that outlet. And that's what this show is for me: being able to talk through my thoughts, share my ideas, share what I'm learning, and and share share other experts with you as well, and since we're here, being a little nostalgic and reflective, I thought I would share one story that I know was entirely driven by the fact that I had this podcast, and it was very much like a a dream come true for me in a very roundabout, completely backwards way. So, one little piece, one little tidbit for you, is that, like, I grew up in a rural community. I have always been a huge country music fan, and I just wanted to be a country music singer when I was a kid. I loved Reba McIntyre, Dolly Parton, R.I.P., Trisha Yearwood, like Faith Hill, Pam Taylor. Give me all the good country women, and I wanted to be that. Turns out, not a good singer at all. I cannot carry a tune, despite having gone to singing lessons for a couple years as a kid. But all that to say is that was not that was not my path. But when I started this podcast. It felt like you know the closest thing to being a singer is to be a speaker, and I was living proof of the strategies that I

preach when it comes to visibilities. You've got to put yourself out there. You've got to take risks. You've got to try and make asks for things that you don't necessarily think are gonna work. And when this show started, I did a little bit of media outreach. I was just sharing about the podcast and telling. I told the local radio station, and they had me on, and I also got in the paper, the newspaper, which actually ended up, funny enough, with a shout out on the front page next to an article about George Fox, who is a country music singer who is from our town of Cochrane. And so, anyways, I got all this press for the podcast, and I was like, "Oh, that's pretty cool." I mean, I downplay everything when I when I achieve a goal. Like, oh yeah, well, you know, I know the local paper because I've been working with them for clients and such, so not a big deal. But all of a sudden, I get this. Podcast pitch, so I get guest pitches to my show from day one. Like surprisingly, a lot. I probably get I probably get 10 or more every single week of guests being pitched to the show. And I read this normally. I just go no because I want strategic relationships. Generally, the guests that I bring on here are people that I know and have met in other contexts and want to show them to you. But I took a cold pitch because the guy was pretty persistent, and it was like a publicity agency pitching this this person. And I look into this person, I'm like okay. Well, seems to have a big audience. Has like a million Instagram followers. Has just you know sold out a big in person event with six or 7000 people at it. You know is associated with people who I respect in personal development. Okay, I'll talk to him, and his name was Keaton Hoskins. And I will. I'll link the episode below because I did interview him on the show.

It was a great conversation. To be honest, he was very raw about his own journey to success and the things he sacrificed along the way, and I think those are the kinds of conversations that we need to hear more of, where we're learning about not just the end result of yeah, look at me, I own a helicopter, and you know I'm a millionaire now. But what did it take to get there, really? And what would you do differently about it, so it was a really good conversation. But the momentum that I felt from having that conversation is what was the most impactful to me, because after that, I saw a speaking opportunity in Nashville, Tennessee, Nashville, home of country music. I'm circling back here, and I saw that a friend of mine was speaking at this conference called the Podcasting Moms Conference, and so I reached out to her and said, "Hey, I would love to be introduced to the hosts of that conference, I would love to come and speak, and so because I made that request, I got the introduction. I was able to reach out to the event hosts, come up with a great topic for their podcasting moms conference, which was about pitching yourself to media, and truly, the conversation that I had with them when I did end up in Nashville speaking that year was about how it's not just about like the publicity itself, but it's about the momentum that you get when you take action around anything, and so I ended up in Nashville at the Grand Ole Opry on stage at the Ryman Theater, and standing in places where Reba McIntyre and Dolly Parton and Tricia Yearwood and all my favorite childhood heroes were, because of something that I did, and I don't think I ever would have expected like the fact that I'm sitting here with a microphone into my laptop webcam right now, leading to opportunities like that, and I just, I just feel like sometimes we try to over strategize everything that we do, and it's like, well, if it's not monetizing, and you're not getting this many downloads, and it's probably not

working. And I'm still just kind of going with my heart is in it, and I love it, and I intend on continuing for the foreseeable future, and since I'm kind of psychotic about not quitting things, I expect that you'll be hearing from me for a long time moving forward. So, what's next? Well, we'll continue talking about the topics of this show, which is navigating business in an AI world. However, that hits for you and what you're doing. Sharing my journey as a tech co-founder, the new challenges and opportunities and lessons that come from that. Definitely more conversations with interesting people, more behind the scenes experiments, more sharing what I'm learning in real time. And I have no predictions. I have no predictions about what episode 300 will look like or 400 because 200 episodes. Episodes in is truly been such a shift that I could not have seen coming. But I'm also so grateful for the entire journey. And maybe the biggest thing that I've learned over 200 episodes is that you don't have to know exactly where you're going when you start. You just have to be willing to start and stay curious, and let yourself evolve along the way. So I want to leave you with that little thought, and thank you again for being here for 200 episodes of Entrepreneur School Now in the AI era. And I will see you next week.

Thank you for listening. If this episode got you thinking about how AI is impacting your business and what it might look like to integrate it in a way that actually fits, I'd love to help you think that through. You can book an AI strategy chat using the link in the show notes. It's a space to talk about where you are, what's shifting, and how to move forward with intention. And if this episode was helpful, please share it with another business owner who's navigating this evolution too. And make sure you're subscribed so you don't miss what's coming next.