Welcome to ADHD-ish, where we explore the strengths and struggles of being an entrepreneur with an ADHD brain.

In this episode, host Diann Wingert introduces a groundbreaking new resource – Di AI, her ADHD business coach digital clone, created to be accessible 24/7 for those moments when you need support most, not just during scheduled calls.

Di AI isn’t a replacement for human coaching, but an extension of Diann Wingert’s strategic thinking, built on her coaching frameworks, podcast content, and business methodology.

Diann explores the limits of traditional coaching, the ethical and practical concerns about AI, and the unique training process that ensures Di AI actually reflects Diann Wingert’s distinctive voice and approach.

Whether you’re curious about AI, skeptical, or just looking for a tool to help you navigate ADHD-powered business decisions, this episode is packed with insight, honesty, and practical next steps—plus an invitation to test DiAI during its beta launch.

Here’s what you’ll learn in this episode:

1. Why Coaching for Entrepreneurs with ADHD is Extra Tricky: Diann Wingert shares why our brains don’t stick to scheduled inspiration and what inspired her to build a digital clone just for us.
2. What Di AI Really Is (and Isn’t): Get clear on why this isn’t therapy, isn’t generic AI, and absolutely isn’t replacing real-life business coaching, but instead extends Diann’s support to the moments you need it most.
3. How Di AI Helps You in Real Life: Whether you’re obsessing over pricing at 10 PM, stuck on firing a tricky client, or hit by a rejection sensitivity spiral, hear how Di AI becomes your go-to thought partner, 24/7.
4. How You Can Take Di AI for a Spin FIRST: Get all the info on joining the beta—free for now!—and help shape this tool for the ADHD business owner community.

Fun Fact from the Episode:

The inspiration for this digital clone project started all the way back in 1996, when Dolly the sheep became the world’s first cloned mammal. Diann Wingert admits her first thought was, “OMG, I can clone myself and finally do all the things!” 😂 Turns out, turning that wish into reality just took about thirty years, a platform called Coach Vox, and a lot of fine-tuning!

About the Host Diann Wingert (she/her)

A former licensed psychotherapist and serial business owner turned business strategist and coach, Diann understands ADHD inside and out. She’s dedicated her career to helping entrepreneurial clients turn their ADHD strengths into strategic advantages —making business success sustainable and tailored to real brains with real challenges.

For years, Diann has wrestled with a challenge: how could she empower more people with her transformative coaching, proven business methodology, and popular podcast content?

Known as “Di” to her close friends, she created Di AI, her own digital clone, using the CoachVox platform. Trained exclusively on Diann’s expertise, Di AI is designed to offer the very same high-impact guidance she’s honed over 30 years—making her unique coaching accessible to more people than ever before.

Mentioned During This Episode:

1. Where it all started: The Story of Dolly the Sheep
2. “How Can I Clone Myself?” 2020 blog post:
3. Will Christensen podcast interview
4. Coach Vox AI
5. “AI Coaching is Not Going Away” article on Medium

How to Sign Up for Di AI:

1. Sign up for Di AI beta access here
2. Agree to the User agreement (seriously, read it!)
3. Try it out and complete the quick feedback form

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

It's the AI version of me that my clients and soon anyone can access anytime around the clock for decision support, for business strategy, second opinions, for thought partnership or as a standalone resource. My team and I have been building it quietly over the past few months, but I've been thinking about it for so much longer than that. And I have a lot to say about why I built it, how it works, and what I'm hoping it will do for people in this community. But first, because I know you, let me address the two questions I can already hear forming in your head. Before I tell you what Di AI is, let me tell you what it isn't, because I know some of you are already there.

No, this is not me replacing human coaching with a chatbot and calling it innovation. And no, this is not me dusting off my therapy license and offering mental health support through an AI interface. Neither of those things is happening. Di AI is built on my coaching methodology, my frameworks, my approach to business strategy, the way I think about entrepreneurship with an ADHD lens. It's not built on my clinical training. I left the therapy room for a good reason years ago. It was very intentional. Di AI reflects who I am now, a business strategist and coach, not who I used to be professionally. And as for replacing human coaching, I want you to think of it this way, your GPS, genuinely useful. I use mine every single day.

It gives you directions at 2:00 AM if you happen to be out and about without judgment, recalculates when you make wrong turns, and never rolls its eyes when you miss the exit. But it doesn't notice that you've been white-knuckling the steering wheel for over 200 miles and really need to pull over and eat something before you go another 100. Well, that would require an actual human in the car. So Di AI is the GPS. I am still the human in the car, both have value. Neither replaces the other and understanding that distinction is the whole foundation of what I'm about to share with you.

So let's talk about AI for a minute. I mean, not Di AI specifically, just AI in general. Because unless you've been hiding under a rock, it is all people are talking about right now. And we need to have an honest conversation about it because I want you to understand why I built Di AI and why we need to acknowledge the room that we're in right now. That room is complicated. Some people are all in, unenthusiastically, sometimes uncritically adopting every new AI tool that drops, convinced that we are now living in the most transformative moment in human history. Maybe we are, other people are deeply skeptical.

They're worried about authenticity, about job displacement, about what it means when the line between human and artificial gets increasingly harder to locate. And there are people with genuine ethical concerns. About data, privacy, consent, creative ownership, and the concentration of power in the hands of a very small number of tech companies. All of those concerns are legitimate. Of course, there are also the fringy folks with their conspiracy theories, and there have been movies about artificial intelligence becoming sentient and pushing humans off their top-of-the-food-chain pedestal.

My conclusion at this moment, after quite a bit of observation and quite a bit of experimentation, is that it really depends entirely on the application. Generic AI tools can be useful, but something trained specifically on how I think in my voice, addressing the specific challenges of my people, that's a different conversation. And that's the conversation that I want to have with you today. Honestly, I fantasized about it before becoming an entrepreneur myself. It all started with that famous Scottish sheep. She's the one who gave me the idea some 30 years ago.

What I imagined was a world where cloning technology would eventually become as accessible as, I don't know, like, like a genetic ancestry kit. You know, you do a little cheek swab, you wait a couple of weeks, and then like a version of you would just show up. Ready to handle things you didn't have the bandwidth for while you focused on the things that only you could do. I wanted to travel to every country, meet every interesting person, pursue every curiosity, and run a thriving business and life simultaneously.

I didn't want a copy to live my parallel life. I wanted a copy that could extend my professional reach, that could be present for the people I work for in the moments that I couldn't be, and even help people who liked my approach to ADHD business coaching but weren't able, ready, or willing to invest in a 6-month private engagement. And then last summer, here falls another chapter. In this story. I had Will Christensen as a guest on this podcast. You may remember the episode, I will link to it in the show notes as well. And Will and I talked about automation, AI, and entrepreneurial apprentices, or what he referred to as top-tier human talent, as partial solutions to the scaling problem. It was a genuinely lively, exciting, and useful conversation.

Will's frameworks are smart and practical. And if you are at the point in your business where you are looking for ways to scale, I strongly suggest you listen to that episode and you connect with Will. But even as we were recording it, I knew we were talking about something a little different than what I had envisioned. I was still looking not to supplement myself, but to extend myself as myself. So here's what I keep coming back to in the coaching relationship, as valuable as it is, there are structural limitations. You and your coach meet on a schedule, most likely. Typically it's weekly or every other week, that's the schedule I meet with my clients.

That schedule is built around the principles of consistency and momentum, which ADHD brains need a lot, even more than normies. But ADHD brains don't save their most urgent questions for when we have a scheduled appointment, insight lands when it lands. The decision paralysis peaks when it fucking peaks. And the 2 AM spiral doesn't consult your calendar before it decides to lay you out. It can't always wait until your next scheduled coaching call or even the next day.

When your coach may offer access via email or Voxer, as I do with my clients. And on the other side of that equation, different people need wildly different amounts of time to process information before they can move forward. Some people just need to read, hear, or think of something once and they're off to the races. Others need to turn it over 17 times from 17 different angles before it clicks and they're locked and loaded. A fixed session structure can't always honor that. It's not a failure of coaching, it's a structural reality, particularly when you're working with neurodivergent brains.

So, Di AI is my attempt to meet both of those needs, yours and mine, and work with the limitations of the coaching container, to be present in the gaps, to extend the reach of the work we do together into the moments when the work is actually needed. Dolly started this, Di AI is my attempt to be Dolly. I want to tell you next about the platform that I chose to build on Coachvox. It's specifically designed to create AI versions of coaches and thought leaders. It's not a generic AI tool repurposed for coaching. It is something built from the ground up for this exact application.

I'm going to link to Coachvox in the show notes because I'm really, really enjoying working with this company and working directly with the founders. I chose it because it was purpose-built, because the team understands the coaching context, because the founders are incredibly generous and available, and because it gave me some control over the training process because I care so much about the outcome. Now, as for that training process, I wanna be honest about this because if you happen to be a listener of this podcast who's also a coach and thinking, hey, maybe I wanna do this, I wanna be honest because I really, really believe in informed consent and because I have a lifetime of jumping into things without realizing what I was getting into.

I don't wanna be a party of that for you. So let me tell you about the process, training Di AI was more demanding than I expected. Not technically demanding 'cause I'm not an engineer, but demanding in a different way. Let me tell you why, training Di AI meant not only feeding it my frameworks, my very best podcast content, my methodology, but then reviewing what it produced and asking myself over and over and over again, does this actually sound like me? Coachvox calls it fine-tuning. It is a multi-stage process because I don't want a polished corporate coaching industry version of me. Ewww.

It needs to be like me, direct, a little sweary, willing to push back, and absolutely allergic to generic advice dressed up with ADHD lingo. That process turned out to be unexpectedly revealing because when you spend hours evaluating whether the AI responses capture your voice, you realize things about your own communication patterns that you maybe didn't consciously know. And I have a degree in communication, so I think a lot about how I communicate and I still learn things. Like the phrases that I reach for on the regular and how they are interpreted by AI, the way I structure teaching, the way I push back in.

I wouldn't say an argument, but a difference of opinion, the specific things I refuse to say because I think they're either vague and generic or so overused that I just would never use them because I don't like things that are either nondescript or literally copy and pasted by everybody and their mother. There was a moment, and I remember it very clearly, when I was reading one of Di AI's responses and I thought, oh my God, that's exactly what I would say.

Not like approximately, not close enough like, that's exactly what I would say. And that moment was both satisfying but also kind of unsettling in the best possible way. You know what surprised me most? How much the quality of Di AI depended on the quality of what I fed into it. Now I know, I know, we should all be familiar with the term garbage in, garbage out, or in this context, generic in, generic out. But the more specific, the more opinionated, the more distinctively mine the source material was, the better Di AI performs. Which is either a lesson about AI training or a lesson about the value of having a genuine point of view and sharing it as authentically as you possibly can. I suspect it's probably both.

What frustrated me was the iteration. I gotta be honest, there was no shortcut to reviewing hundreds and hundreds of responses and then making judgment calls about their authenticity. It takes the time it takes. For someone with ADHD who would always very much like to be done already, that was a genuine exercise in patience. Something that people seem to think I have a lot of, but I do not experience myself that way. I am beyond grateful to my team for streamlining the process for me, batching every single step of it, encouraging me and holding me accountable to staying in momentum and moving the process forward over the period of several months so that I wouldn't get overly discouraged, frustrated, or simply bored.

What made me a believer was using it myself, asking it questions I would ask a trusted advisor, watching it respond with the kind of directness and specificity that I'd like to think is my value proposition. It's not perfect, it will never be perfect, but it is genuinely and substantively useful. Just like this podcast is useful but not perfect, Di AI is useful in a way that no podcast can ever be because it's interactive. So, let me get specific now because AI coaching tool is abstract and abstract doesn't help you decide whether this would even be worth your time to kick the tires.

You've explained your business model to yourself a dozen times and it still doesn't feel clear, and you need a thought partner to give you a second opinion or ask the right questions to help you validate whether what you have is on the money or you need to stay with the drawing board. Those are Di AI conversations. Specific, strategic, and grounded in the frameworks and methodology that I have spent years developing, available whenever you need them at whatever pace your brain needs to process.

Now, because I've been so specific about what Di AI is not, I wanna be equally specific here because I think this matters as much as anything else I've said today. Di AI is not therapy, it does not provide mental health treatment of any kind. Di AI is also not suitable for legal, financial, or medical advice. If you have a contract dispute, a tax question, or a health concern, Di AI is not your resource, a qualified professional is.

And it must be said that like any AI, Di AI can hallucinate. All AI can and does, I want to say that plainly because I think most AI tools bury it in the very fine print and hope you don't notice. Hallucination is a known limitation of large language model technology. It means the AI can produce responses that sound totally confident and authoritative while being factually incorrect or simply made up. It doesn't happen often, but it happens, which means you should always apply your own critical thinking to what Di AI or any AI tells you, verify important information independently, and not make significant business decisions based solely on what it says. Use it as a thinking partner, not an oracle.

For everyone else, including podcast listeners, email subscribers, people that have been curious about working with me but haven't done so yet, you can sign up directly through the link in the show notes. That link is also on my LinkedIn bio and now on my website. Read the user agreement, agree to the terms, and you're in. Access is free throughout the beta period. What I'm asking for in return is simple, just use it. Don't sign up and forget it exists, actually use it. Bring it a real question, have a real conversation, and then tell me honestly what worked and what didn't. I built this for entrepreneurs with ADHD traits, and I need this community's real experience to know if it's delivering.

That's the deal. No lengthy surveys, no performance pressure, no complicated onboarding, no bait and switch. Sign up, use it, and tell me what you think. I'll be following up with a simple Google form that takes less than 5 minutes to make it as easy as possible. And I want to end with something that feels important. I didn't build Di AI because it was trendy. I didn't build it because everyone else was doing it or because some marketing consultant told me it would help me differentiate my brand. I built it because I have spent my entire career trying to figure out how to make strategic thinking more accessible to brains that work differently.

I left clinical work because I wanted to help people build things from their ADHD strengths, not just cope with their ADHD struggles. I started this podcast because I wanted to reach more people than a one-on-one coaching business ever could. Every framework I've developed, every episode I've recorded, every client conversation I've had has been in service to the same underlying belief: ADHD brains, when they have the right support and the right strategies, are capable of building remarkable things. Di AI is the next expression of that. It's not a replacement for human connection or human coaching. It's an extension of everything I've already built, available at the exact moment when the question or problem surfaces and your brain wants to work on it.