Entrepreneur School

I started 2025 with one rule: “Only if it’s a hell yes.” I ended it as the co-founder of an AI company. I didn’t see it coming!

This episode is a little nerve-wracking to share, but it’s the real, unfiltered story of my wild ride through 2025. I ditched the 12-month goals, the rigid launch calendars, and all the “shoulds” I’d been forcing for years. As an Enneagram 8 who loves control, this was… uncomfortable.

Instead, I followed alignment, curiosity and relationships. The result? A year that was messy, non-linear and more transformative than any I could have meticulously planned. I went from feeling fed up and stuck to building something entirely new that feels more aligned than anything I’ve ever done.

In this episode, I’m breaking down the five biggest themes that shaped my year—from micro-experiments that actually worked to the scary-as-hell identity shift I’m still navigating. This isn’t a highlight reel; it’s a roadmap for your own reflection.

What’s in this episode for you:

  • The “Hell Yes” Compass: How I ditched control and used alignment to guide every decision, even when it led to some big, scary “no’s.”
  • Micro-Experiments > Master Plans: The power of small, curious tests—including the $1 workshop that sold 135 spots and taking the entire summer off social media.
  • Relationship-Led Visibility: Why deepening connections and collaborating in shared rooms will always beat chasing followers or sending cold pitches.
  • When the Universe Screams, Listen: How I recognized the repeating patterns that pointed toward partnership and finally stopped trying to do everything alone.
  • Becoming Before You Declare: The vulnerable truth about the lag between your growth and your identity, and why it’s so damn hard to publicly claim the next version of yourself (I’m right there with you!).

Ready for your own reflection?

If your year felt non-linear, you’re not behind. Ask yourself this: **What did this year teach me about how I want to move forward?**

To help you get started, here are the 5 journaling prompts from the episode. Grab your journal (or your favorite AI tool) and give yourself the space to explore what your year taught you.

1.  Where did I choose alignment over expectation this year?

2.  What did I try this year that gave me clarity (even if it wasn’t a huge win)?

3.  Which relationships quietly opened doors for me this year?

4.  What keeps showing up in my business that I might be meant to approach differently (and not abandon)?

5.  What version of myself am I already living, but not fully claiming yet?

Here’s to a 2026 that’s led by you, not your to-do list. Happy New Year

>>Your Next Steps:

🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™  

🔹 Done for you visibility plan by Valerie the Visibility Auditor

🔹 Let’s work together: https://ksco.ca/

🔹 Get visible without social media

🔹 Connect on Instagram

>>Thanks for Listening!

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Transcript
Kelly Sinclair:am going to be reflecting on:Kelly Sinclair:

themes that shaped my year. And this is definitely not a highlight reel kind of episode. I want to share mine with you, and I want you to think about yours as well. And I have to share also that I used AI to help me create this outline, because I wanted to do some of the thinking in advance, but I also wanted to be able to come here and just openly share that was another thing that I learned last year in my human design. I'm a generator, and so responding is the best way for me to feel an alignment and feel really connected. So I just kind of brain dumped all of the big things that I could think about that happened that kind of played a role in the way that this year ended up for me. And then I asked AI, the new platform that we're developing that I'll share a little bit more about again, at the end, I asked it to turn that into questions for me to reflect on as I'm walking you through this. So when I said I was a little bit nervous, I don't know entirely what's going to come out in this experience, but this is kind of an important thing to do, and if you're currently kind of sitting in some extra white space and feeling reflective about your year. Something I love to do at the very end of the year or early into the next year, is just take some prompts from this. I'm going to give you a question around each of the themes that I have to share with you, and take those and sit with those and do your own version of this. It'll be super powerful. So let's get into the first one. The first theme is the hell yes compass, which was all about letting alignment lead instead of control. Oh, but it feels so much better. I have to say that, like, it's it's funny. And again, if you know me, this is like, it's crazy to think I could just walk into a year and be like, I don't know what's gonna happen and end that year being like, well, I'm starting an AI company now. So that's what happened. But here we are. So this was all about choosing responsiveness over

Kelly Sinclair:really needed this going into:Kelly Sinclair:

of the other themes. But not having this long term plan can be very scary. It can kind of feel like on a daily basis, I wake up and go, What do I need to do today? And now, of course, I'm really good at getting shit done. That's another part of being a generator. Is like, once I've got a project or a goal, I am going to make that happen, no doubt about it, I'll reverse engineer. I'll work back plan. I'll get all the dates, I'll have it all written out, but I'm just, I was like, doing these in little micro bursts, instead of having a big look out ahead of the whole entire year. And so that's not for everybody, that's for sure, but that is what ended up working for me. I

Kelly Sinclair:pursuing, like I rolled into:Kelly Sinclair:crazy outcomes of:Kelly Sinclair:

use it in for my clients and building AI tools I was building, I built brand calibrator this year, which was huge in helping to create that really core brand DNA that's necessary for training AI to actually function like you. It's kind of useless if it's generic, but it's really useful when it understands you, your business, your target audience, your personality, the way you say things, and is able to replicate that for you. It also. One of the experiments I did this year was hosting my first bundle. So I've participated in so many lead generation bundles over the last several years, and I've always found them really an effective way to gather leads for my email list. So growing my email list, and then I decided I'm going to now step into taking on a leadership role here. This was putting myself at the forefront and being the host of something related to AI. So that was kind of like, this is like September timeframe. Now I'm going, Okay, we are getting to a place where I'm going to have to start forward, facing, publicly, declaring what my role is and how AI is involved, and how I'm involved with AI. And so the ease in alignment with AI bundle was one of those opportunities, and I was just testing different marketing strategies all year. So that led to accept, like doing a speaking. Opportunity in the middle of the fall, and I also decided to host a $1 workshop. So that was actually super effective. Rather than making it free, I made it $1 I gave it away for free, for people who purchased an upgraded package within a different event. But otherwise, people from my podcast, people from my email list, were invited for $1 and we sold 135 ish spots to that workshop. And you guys, I have never sold 135 of one thing ever in my whole business. Like free things, sure, but actually paid. And so this was an interesting experiment, and I'm excited to see, because it's still kind of mid way, how that translates over to people joining and participating in

Kelly Sinclair:l consider again, moving into:Kelly Sinclair:at to propel you forward into:Kelly Sinclair:have heard on the podcast in:Kelly Sinclair:some kind of online event in:Kelly Sinclair:

been in business partnerships, trying to figure out, what does that look like? There's a lot of things. Games to figure out behind the scenes, from a structure perspective, what, how do you build your company? Who gets what is equity? And now I'm in a place where it's like, what does the IP licensing look like? How? What are all these things? And there's a lot. So I definitely know that's where the universe was sending me this year, was into into a partnership, and it's interesting how one actually led to the other, because I was the first one was similarly technology related, even me stepping into the tech space was new for this year, like it kind of just all made sense, right? I was doing AI stuff, but still marketing and the other business that I was originally working with had an app and was technology based, so I was able to access a few kind of training programs through that which put me in rooms with people in accelerator programs, incubators, things like that. We have an incubator here in Cochrane, where I live, that is

Kelly Sinclair:,:Kelly Sinclair:

place, shared values, open, good communication, willingness to be flexible, these are kind of the core pillars of building a partnership. And here we are now. We're starting this AI platform, I really hope to be able to share name of it and access to it like in the coming weeks, like we are just only weeks away at this point, for being able to turn, turn the key and open the door and let people in and let you see what we're really up to, because it's kind of crazy, and this will kind of flow into my next theme. It's so crazy to be doing things behind the scenes and not not fully out in the open yet, because there's building in public is definitely good, but also there's, like, some pieces that just need to be in place before I can be super public about certain things, right? So anyways, that sounded a little coy, but here's your reflection question, what keeps showing up in my business that I might be meant to approach differently and not abandon so if it was like for me, it was like partner, partner. No, not this one, but maybe this one. And even the year before that, I was, I was pursuing getting a job, so like I'm looking at being involved with other people. I was ready to move out of solopreneurship, for sure. So I wonder what that might be for you, if you sat and thought, thought about it. Okay, let's get into the last one. And this is. Yes, this is a big one. The theme number five for me, is about identity shift and becoming before you declare doing the work, before you claim the title. And what is this really about? There is a lag between growth and self identification. So like I was just saying this concept of building in public, there's like layers, right? I'm certainly sharing with people that I interact with on a regular basis, people in my mixer mind, collaboration partners, people like that. They know a little bit more about what's up in terms of how I'm stepping into this role as a tech co founder, as an AI platform creator and owner. It's

Kelly Sinclair:

just been such a big shift for me, like it doesn't seem like a natural evolution of what you would think somebody was a PR degree goes into communications, goes into being an entrepreneur who helps people with marketing and communications and just different flavors of what that has looked like in terms of visibility, branding, all those things to me, though, are related, technology, not related. I can trace the I can trace the path, but it doesn't seem as natural to me. And so I feel like it might be jarring to others to to see that. And so there's this like battle that I'm kind of having where it feels really scary to say out loud what I'm doing. The other day, I had a moment I was talking to a friend who has been a collaboration partner, who is somebody who is willing to make an introduction to me, to somebody who is hosting a big event and has a podcast and community that I'd really like to get in front of. And she said, Okay, just send me what you'd like me to share with him. And I was like, Ha, I don't know. I don't know how to say. I don't. Moving forward, I am not just a visibility coach who uses AI like that. Enough was a shift that I made earlier on in this year to just bring AI into the description of what I do into my bio. But moving forward, I am an AI founder who is teaching business owners how to use AI in a human first way. Who is who cares about the way that this technology, more broadly, actually gets adopted into our world? I know that it is so important, it's going to make it's a huge shift, like I was a teenager when the internet came out, and that was monumental, this is also monumental, and we don't know yet if it's more monumental in terms of the shift in how the world operates than when the internet was introduced, right? And I just know that there's such an important role to play, because there can definitely be negative impacts and how this all comes into fruition. And I want to, and Andrew, my business partner, we want to make

Kelly Sinclair:

sure that we are taking on a role of supporting how it can be done that allows humans to do more, humaning, not just do more, not just increase the volume and productivity and reduce the workforce and all those things that might happen. We want to stake our role in how this can be shaped in a human first way, my new bio is going to be entirely different, but I am just having a hard time putting it out there. For some reason I cannot make myself update my LinkedIn. So you know when you see it, if you follow me on LinkedIn, when you see me shift that you'll know that it's been a big moment for me. I'd love, love for you to reach out if you see that happen, when you see that happen, because it won't be too long, but it's truly like it's truly challenging to step into this expansion publicly, to think about what that actually means, and I can really understand now, because a lot of my clients that I've worked with In the past have had a hard time talking about what they do. And I don't think it's just about being at whether or not you can articulate the words about what you do. It's actually owning it. It's actually believing that this is what you're doing and staking your claim in a leadership role in what you're doing. That's the truth. Challenging part. It's not like, what are the words that will describe how I do what I do? That doesn't matter. That's easy. It's actually believing those things. And that's where I am at right now. Is like, behind the scenes. I know this is what's happening. We know this is what we're doing. Some people know about it, but as soon as I put it out there to like the world, it feels a lot more challenging to do that. So I mean, we are, we have an alpha test group. There's real people using our platform right now, giving us feedback, trying it out, seeing what we're doing. They know, but that's seven people, and I have to let the rest of the world know very soon.

Kelly Sinclair:d oh my gosh, what a year has:Kelly Sinclair:ish you an amazing kickoff to: