What if the most useful thing your AI ever did was tell you no?
I went into this conversation expecting to talk about speed. Tara Reid took it somewhere better.
She builds her business with ADHD, without social media, and with AI doing a job most people never think to give it. Not writing faster. Holding the structure her brain doesn't want to hold on its own.
WHAT YOU'LL LEARN:
- Why AI's default behaviour works against an ADHD brain, and the one instruction that fixes it
- How Tara built a brain dump organizer that pushes back on her ideas instead of cheerleading them
- The hub question you have to answer before AI can be useful to you at all
- How she turned a transcript pile into tasks and content maps without touching it
- The internal fix that accidentally became her best selling product
- Her answer to the question every expert asks before building a tool on their own framework
CHAPTERS
02:00 Why hands-off AI is a hard no
03:15 What AI does to an ADHD brain
05:39 The brain dump organizer that pushes back
07:05 Building a hub AI can actually read
11:05 Turning meetings into tasks automatically
14:00 The data you collect and never use
17:15 Turning an internal fix into a product
22:15 Does this cannibalize your offer
24:30 Ask AI how it can help you
>MEET TARA<<
Tara Reid is a business and marketing strategist who helps introverted entrepreneurs build sustainable, hustle-free businesses using evergreen systems and organic marketing, without relying on social media. She's been an entrepreneur since 2007 and full-time since 2015, and she teaches a quiet marketing approach built on SEO, email, and smart systems rather than constant output. She's also open about running her business with ADHD, and much of her work now centers on using AI as a capacity multiplier that supports her thinking instead of replacing it. She lives in Ontario, Canada with her husband and two rescue dogs, and she believes quiet can still be powerful.
>CONNECT WITH TARA<<
Website: https://thetarareid.com
Threads: @introvertcoach
GRAB TARA'S RESOURCE
Tara's brain dump organizer is the system she built so AI stops piling new ideas on her and starts mapping them against her actual capacity. If your ideas live in fifteen places and none of them talk to each other, start here.
https://thetarareid.com/brain-dump
CANADIAN MADE: REAL TALK FROM REAL ENTREPRENEURS
Tara also hosts a collaborative guide featuring Canadian entrepreneurs, and I'm one of the contributors this year. It's available through November only, alongside a low-cost bundle of contributor resources.
https://4038046931--introvertmedia.thrivecart.com/canadian-made-bundle/
>Introducing wAIv
This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology.
wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before.
>Your Next Steps:
See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com
Build your first AI product live with us for $1 at the AI Product Build Lab: https://graviastudio.com/build/?code=podcast1
Get the Canadian Made guide and bundle, featuring Tara, me and a group of Canadian entrepreneurs. November only: https://4038046931--introvertmedia.thrivecart.com/canadian-made-bundle/
Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv
>Thanks for Listening!
If you enjoyed this episode, please help us share it by:
Following the show—this helps you stay updated and supports us!
Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast.
--------------------------
Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canadaceopodcasts/
If you're somebody with ADHD, is to sit down and do a kind of brain dump about how the AI tool that you're using could better suit you. So if it's like have those guardrails in place, specify what you need, what's going to help you best.
Kelly Sinclair: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.
Kelly Sinclair:Welcome, welcome to another episode of Entrepreneur School in the AI era. So excited to introduce you to Tara Reid today. She is a business and marketing strategist who helps introverted entrepreneurs build sustainable, hustle-free businesses using evergreen systems and organic marketing without relying on social media. I mean, immediately we're super aligned on that approach. Tara, I'm so glad to get into AI and how you approach this from an ADHD perspective and an introverted perspective. So let's start there. Everyone's talking about AI makes things faster, and you're not. So tell me more. Yeah, I think like I'm all for doing some things faster, but
Tara Reid:I think using AI kind of as a hands-off, fully automated. Like I, I'm a firm believer of keeping the human in the framework. So I know, like, there's a lot of people who are all obsessed with co work. I tried it. I don't, I don't really do much with co work. I'm, I don't know whether it's the perfectionism in me, but it's like I. I like having AI do things for me, but not actually like hit the send button or publish without me having any peace in that flow.
Kelly Sinclair:Yeah, I totally agree. It's absolutely kind of terrifying to think about just handing over decision making and things like that to AI. I'm a big proponent for human centered AI adoption and human in the loop. And there's little pieces that it can help close gaps for you, but it doesn't have to do the whole task. So, what do you primarily like? How do you approach AI in a different way that you want to share with our listeners about, particularly from that ADHD perspective?
Tara Reid:Yeah, I think my biggest thing when I started going deep into AI was I did get lost a little bit initially because with AI, you know, it's always like it never wants to end a conversation. It always wants to do more or do the next step and do more. And as somebody with ADHD, that can be overwhelming because it feels like like my husband asks me every night when he comes home from work, like, oh, are you all caught up? And I'm like, that doesn't exist as an entrepreneur. Like, I'm never caught up. Like, did I do what I wanted to get done today? Yes. Do I have like 10 more things that came up today that I'm gonna have to do now? Yes. So I feel like AI is kind of the same. It's like it always prompts you to do more or create more when you're communicating with it, and that can get very overwhelming, especially if you're already somebody who has a bazillion ideas, is multi-passionate, has ADHD. So you're constantly like, "Ooh, shiny object." That can be a lot. So I think understanding that that's kind of how AI is designed to work, unless you tell it differently. And I think it's realizing what your strengths are and how you need it to work best for you. So for me with ADHD, I was like, we can't keep going on these tangents of like, oh, now we're gonna do this and this and this, and I'm like, I just ask like one thing. We're just doing one project, and now I have this massive 20 task list that I have to get done, and that is very overwhelming and not at all what I wanted to use AI for, which is to help me actually get things done, be more. Organized, save time.
Kelly Sinclair:Yeah, such a good point. It is like, like the like the opener of all of the rabbit holes. Like, let's try this. Let's do that. And yeah, like you say, it's very. It is predictive. That's literally what it is. I was having this conversation with an engineer recently, and she's like, "It's predicting what it should say next always, so you do have to put those boundaries on. So what do you do there? Do you have a particular like way that you open a conversation or some setting that you've changed that helps to like keep that from going off the rails, so it doesn't suck you into those rabbit holes?
Tara Reid:Yeah, I think the best thing I ever did was I created a skill that's basically like, here's when I ask something, here is what I want you to do. I want you to summarize things. I don't want you to give me like a whole spiel. I want you to put it in bullet points. Like, I had to train it kind of like what I want, what's going to help me best as somebody with ADHD. So I, I called it my brain dump organizer. Is basically the main skill of like when I spit out all of these ideas to you. I don't want you to then just start wanting to run and like create all these things for them, like I want you to actually map out what it's going to mean in terms of my capacity. Like, are some of the like I want you to push back on some ideas. Like, Tara, this you do you do not have time for this in September. Like, you have way too many things already. Like, let's park this for later. So now it's more of a tool that not only understands how I work, but it also understands a little bit better about what I need when I'm asking for something. Oh, that's really good. That's like a it's like a scope filter, and you also so I imagine you also have a good hub built around what it can reference, so that it knows what your capacity is. What like what does that look like for you? Yeah, so it definitely it always looks at my current promo calendar, which is in ClickUp, sort of the ClickUp connector. It looks at my Google Calendar. I love like I keep everything in ClickUp, and I love that Claude connects to ClickUp so that it can actually go in and see. I'm also been really utilizing ClickUp AI super agents a lot to have trained agents that have access to everything that I already have in ClickUp, so they can go back and look. Like, oh, these are you know recurring projects that Tara does every month. This is like they could also look at my Google Calendar. Like, I love that it's connected to be able to see the important pieces to actually have more context instead of me
Tara Reid:saying like, oh, in September, here's a recap. But like, I don't need to repeat that. It has access to go and look.
Kelly Sinclair:Yes, totally. I was trying to break down the other day for someone who was kind of new to using AI and trying to think through what does that overall structure look like to get it to work well for you, and in a framework that can be applied and customized to the actual user because the reality is AI can do everything and anything, and so that's overwhelming. Like we're not going to start with that, but what it really needs, in my view, is it needs context. So it needs whatever instruction that you want to give it, whatever reference material that you want to provide it with, it needs a hub. That hub needs to be the place that it can keep going and adding to, and like letting that ongoing memory not just within like a Claude or a ChatGPT itself, but within like your work ecosystem in a place that you actually own that you're feeding its memory and improving its skill set based on that, and then and then it does a process, whatever that is, like the tasks, the obstacles, and whatnot. So, like, I love that too. The having a place where it goes, it learns, it sees everything, and you know that, so you can be like, "Hey, you don't have to keep it all in your head, right?" Like, and I think that one of the things that in your in your like podcast application you mentioned having like a scaffolding for your brain, so you're not holding all of the things there, and you're really controlling and structuring and leaning on AI to do that. What does what does that look like for you in practice?
Tara Reid:Yeah, because I feel like that's very exhausting for most entrepreneurs. Is like we keep so many pieces of or ideas, things that have to get done. Like we keep everything. In our head, or we have it in so many different places, and I think that's the biggest thing is like putting everything into one system that then AI can access. And luckily for me, it's always been ClickUp. So there is like like I've been using ClickUp for literally everything. Like I always say, if it's not in ClickUp, it's probably not going to get done because that's where that's my go-to. Like I work off of ClickUp, ClickUp every single day. Everything is in there. Every project, every launch I've ever done is in there in some way. So there's a lot of context and history in there, and I think that's the hardest part. Is like if you don't currently have a place that has a lot of the context and a lot of the info, like putting that together. So maybe it's just Google Drive, maybe it's just organizing your Google Drive folders so it's more understandable to AI because that's something simple that most AI tools can connect to and have access to and read. But whatever is going to make that easier for you to get things out of your head and into like I even have it. The most recent one I've connected to is Otter, so I've created like a transcript, a content system where anytime there's like it checks a couple times a week if there's a new Otter transcript, and Otter follows me around everywhere in any Zoom meeting that I do. Then it will take that transcript. It will see if there's any tasks that I need to do from that call or that meeting. It'll add them as ClickUp tasks for me automatically with due dates, and it will then create like a content map from that transcript automatically. So, yeah, like little things like that that I can. So I don't have to remember, like, oh, what did I say I was going to do on that last coaching call? Like, what do I need to send that
Tara Reid:person? Like, it's already mapped out and in ClickUp for me as a task, so I don't have to remember. Do you have any team members? Are you solopreneur? Do you have team, or have you ever? I used to have a massive team at one time, and it was very overwhelming for me. I didn't like being the bottleneck at that time. I was definitely the bottleneck, and so now I just have one VA who's been with me for like six years, and she just she does about 10 hours a month. Wow, yeah. So, because I'm just thinking about this and
Kelly Sinclair:going, this is a shift for me in knowing that AI is something I can outsource things to. It requires you to think differently about what what am I out there? Like, what am I asking it to do? What could it collect now that really was just totally falling through the cracks before? And I joke, I did not have a system like a ClickUp. I just got Airtable in like April. How did I even do anything before having like an organizational central place, truly. Because I was like, well, it's just me. I'll just keep it all in my head and remember everything. Yeah. Actually, I probably wasn't at all doing that, but there
Tara Reid:were probably some balls dropped somewhere. Million balls were dropped.
Kelly Sinclair:All the balls were dropped, and I was just going on my way. Whatever. So now it just it all of a sudden like things that I never even I was just never doing like you know data analysis of things like how are my emails performing how was that what were those sales page stats like things that I just never even bothered to do because I just couldn't we now have the ability to be like, okay, this project has actually got 25 more pieces to it than if you were just executing it by yourself as one human. So now, what's AI going to do in that project for you, right? Yeah, you kind of made
Tara Reid:me think of I have I I love Airtable. I've always loved Airtable too. But I have a Airtable base where basically on the first of the month I go in and I like record metrics and stats and put in notes of like what I did that month, any collabs or promos, and so I had a lot of data in there, but I wasn't using it. Like I was just putting it in on the first of the month, and then it just lived there. And I was like, "Yeah, like I need I AI can do this." Like anytime I so I actually created a a Claude artifact that once I add the data on the first of the month, I can then go into the artifact and be like, "Okay, I've added another new month." Like, go into that Airtable base. Let's like review it and analyze the last 30 days, the last 90 days. Like, compare it to last year, the same month. What did I do? Like. How was revenue compared there? Like actually using even data that we already have available that we never actually took that further step to actually use.
Kelly Sinclair:Yeah. Well, now AI can actually collect and and do that push for you. I have that happen every like every Friday. I have a task that runs that this skill that goes through my email stats and then pushes them all into my Airtable for me. So I'm like, I'm building the things now. We'll eventually use them, and that's kind of the shift for me and how I've had to look at the way that I'm working. That's different. It's how do you feel about that? Like, give us a little bit of your journey into AI, if you will. Like, when did you start, and how how has it shifted for you the way that you approach work overall? So I was very early on. Like, I was so excited
Tara Reid:when AI first came out, I was I was creating images. They were horrible back then. They were like, oh my gosh! Like I just pulled one up on my phone and was like comparing it to what you can create now. And I'm like, this is just terrible. Like the advancements in just a few years is really mind blowing, and I'm excited for AI, and it's totally changed how I work. Like, I was keeping a lot of stuff in my head. Balls were definitely being dropped, even though I was like, "If everything's in ClickUp, I'll remember it." It was like I was context switching all the time. I was making so many micro decisions that I really didn't need to be making, and putting all of that on myself. And now AI has a has alleviated so much of that that I feel like I'm able to be a lot more creative, and I'm able to experiment more, and I'm able to play more in my business and with marketing and the things that I'm doing, and I'm able to show up better because a lot of my energy isn't going to admin work or the little micro decisions of like, oh, what should I pitch for this podcast interview or what should I contribute to this bundle. It's like AI can kind of give me like here's top three ideas for you, and then I pick one. Like it's so much easier. Yes, that barrier to entry and the friction just goes down so much. How are you using it for monetization? So I've definitely dove into creating AI tools. My most popular one I actually created for myself first because I am I'm not on social media really at all. So my most of my marketing is long term evergreen strategies, but then I also do a lot of collabs, which I call like my quick win to get an influx of new people, get in front of new audiences, and I found that I was doing a lot of collabs, and I'm also doing a lot of launches. I love sharing affiliate promotions that I think my audience will love, and I found that I was just there was some months where I would just have so many things at once that I needed to
Tara Reid:share with my audience that I felt like I was overloading my audience, or again balls would be dropped and I'd forget to promote something when I said I would. So I created a. It started as a Claude artifact that basically was a calendar where you put all of the collab information. So if you're participating in a bundle, if you're doing a live panel, if you're a guest on a podcast, like you can add all of that to the calendar. Then it generates an email plan for you, including like roundup emails if there's a week that's really heavy, and then it would write the emails for you in your brand voice. And I loved like it helped me so much because I do email my list a lot, and I do a lot of collabs and a lot of promotions, and it helped me so much. And I shared it, and my audience loved it, so I turned it into an app that I built in Lovable, with a little bit more bells and whistles and customization too. For anyone who does a lot of stuff that they want to tell their audience about, it's amazing for keeping you organized and having a email strategy that you don't have to keep all of these dates and things in your head again. Going back to getting it out of your head and getting it somewhere else.
Kelly Sinclair:Oh yeah, and then the accountability of actually following through on the thing that you committed to do. Yes. Oh, that sounds that sounds like a great tool.
Tara Reid:Yeah, it's probably the best one that I've created. I've also created. It's kind. On pause right now, but I created a entire like one to one networking app for entrepreneurs. I've created a ton of. Initially, it was custom GPTs. Like, I just love what can I create with the help of AI that's going to help a student or a client get results quicker versus having to like get on a call with me and me going through it or doing it for them. Like, what is going to give them that shortcut in a quicker way?
Kelly Sinclair:Yeah, and I probably ask every single one of my guests this version of this question because I obviously am invested in in a belief that the way that we deliver our programs and offers now that AI is so prevalent is shifting the online education space needs to adopt AI in a different way in a like client facing way so that we can elevate that client experience and it is all about creating results. So, what have you seen actually happening with your students and people who are using some of those tools that you've built for them? Like, how has that changed your offers?
Tara Reid:Yeah, I mean, students definitely getting results faster. I've gotten so many amazing feedback on a lot of the tools. Like I created a custom GPT that is trained on my. I used to do like I called it a business blueprint session. So it was like a strategy session with me, and then I would go off and I would create this massive document of like here are some gaps in your business. Here are some suggestions on ways to better market your business. Like, and it was a massive document every single time, and took me so much time to go through. And I was like, why don't I create a tool on this process of like what to look at, things to consider, and turn it into a tool that they can use themselves, and so many people have gone through that and are like, "This is amazing!" Like I have so many ideas now, and it's like, I know some people are like, "Well, that's cannibalizing your offer." I'm like, I've always been under the belief of like, I want to help and impact more people, and even though I'm giving them this tool that is basically trained on my framework, my system, it's still not me. So they could still generate an entire blueprint report and still have questions or still need to fine tune things, and that's where they could come to me or come into a program and get human support. So it doesn't totally eliminate it; it just opens that barrier so that more people can get access and see the results that they want. Yeah, totally. And so, is that particular
Kelly Sinclair:tool part of a program that has human touchpoints, or is a in a one off, or maybe it's either or.
Tara Reid:So it's a it's kind of both. So it's a one off custom GPT that I built that people can get access to as a standalone product. But then everything I create, I have a main offer called the Introvertpreneur Club that is really focused on lifetime coaching and lifetime support from me. But it also includes access to every offer or digital product I create. So I'm basically creating these things for people in that lifetime program, and then I'm just also offering them as a standalone, lower cost product for anyone else.
Kelly Sinclair:Yeah, I love that. That just it gives you more variety too, and in revenue opportunities and what you can have in your offer suite, right? Huh? Oh, I feel like we've covered like a whole sector of topics already, from like using a AI to help you like keep on track and avoid going down those rabbit holes that it always wants to do. To selling AI tools as part of your programs and some of the skills that you've built. Do you have any like final words of wisdom that you want to share with our audience, Tara.
Tara Reid:I feel like the biggest thing I would say is, especially if you're somebody with ADHD, is to sit down and do a kind of brain dump about how the AI tool that you're using could better suit you. So if it's like have those guardrails in place, specify what you need, what's going to help you best. Think of it like you're speaking to a client or a student. Like, what do you need them to give you in order for you to take that and then do your job? So not just like what do I, what can I give this. AI tool. I try to think of it as like, if this was another person, like how would I want them to communicate and give me what I'm asking for in a way that's going to better suit my personality? Like, I want bullet points. I want summaries. I don't want you to go off on a three page tangent on something. Like, just break it down for me, and that's how I'm going to take action quicker. So, whatever works for you, just having sitting down and doing a brain brain dump about how you work best and what kind of changes your tool could make for you.
Kelly Sinclair:Yeah, so it's like asking AI how it can help you work before going straight to asking it to do work for you.
Tara Reid:Yeah, that's a really important frame that I believe a lot of people would overlook and just go into. Can you write me an email? Can you do this tab? Can you? Yes, of course. But but how and why? And there's so many things behind that. So that's fantastic advice, Tara. And where can people find you? Connect with you? You're not on social media. Well, I do play on Threads sometimes. So if anyone wants to connect over on Threads, my username is Introvert Coach. But mostly, you can find me on my website, theterrareed.com. I have a ton of free resources. If you sign up for any one of them, you'll get on my email list, and that's really where I'm sharing all of the stuff and all of the good resources and help that I can give you is on my email list. So amazing! So all your links will be in our show notes below. Thank you so much for your time today, Tara. Yeah, thank you so much for having me.
Kelly Sinclair: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.

