ADHD-ish

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

How to Sign Up for Di AI:
Sign up for Di AI beta access here
Agree to the User agreement (seriously, read it!)
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.

If you’ve ever felt weighed down by burnout or the urge to abandon it all and start fresh, you’re not alone.
In this lively conversation, serial entrepreneur Megan Eckman shares her delightfully candid journey of starting, scaling, hibernating, and moving on from multiple businesses, offering honest lessons you won’t find in most business books.
We talk about Megan’s recent ADHD diagnosis, the three distinct ways she’s learned to transition in business, the emotional toll and freedom of letting go, and how curiosity and self-awareness have kept her evolving as both a creator and entrepreneur.
Why You’ll Love It:
Megan walks us through the three ways she’s learned to pivot and the circumstances that led to each one, allowing her to follow her curiosity and pursue her creative impulses, without risking her well-being or financial stability:
Test & Build - Learning to listen to your customers, running small experiments, and transitioning into new opportunities
Jump Without a Parachute: The Hard Stop Pivot - When a dramatic, not-so-planned exit from a thriving business is the way to save your sanity —and what it really takes to walk away.
The Hibernate & Resuscitate Pivot - Sometimes the best move isn’t quitting cold turkey, but putting a project “in the freezer” while you work on your next big idea.
Three key takeaways:
Pivoting isn’t failure—it’s evolution. Whether you’re testing and building, taking a bold leap, or putting a project into hibernation, each pivot can be a strategic step toward growth and alignment. (Diann said it perfectly: “You can burn out on your own success just as easily. Maybe even easier.”)
Curiosity is your greatest asset. Megan Eckman reveals how following her curiosity—not just passion or profit—helped her create unique offers and build true superfans, even when the work didn’t “look” like her dream on paper.
Burnout prevention requires boundaries and self-awareness. Recognize when you’ve hit your scale ceiling—or when you’re simply not excited anymore. It’s okay to say “enough,” recalibrate, and design your next chapter intentionally, not reactively.

Mic Drop Moment:
“It was basically a ‘hold my beer, I’ll go build that business for you.’ To be fair, they did wait a month.” Megan Eckman
About today’s guest, Megan Eckman
Megan Eckman is a serial entrepreneur who constantly finds new ways to delight her audiences, from fantastical pen-and-ink illustrations to bold embroidery kits to fantasy rom-coms.
For 14 years, she ran an embroidery kit business, managing revenue streams from wholesale, retail, and subscriptions. She's a published author and now also a podcast co-host for a show all about networking.
When she’s not working, she’s likely out on one of her bicycles exploring new routes in the woods. She lives in Vancouver, WA, with her husband and tri-color cat. Megan was diagnosed with ADHD in her 30s.
Connect with Megan:
Fat Cap Design
PDX Spellbound
The Awkward Handshake podcast
LinkedIn
Email
Your ADHD-ish host, Diann Wingert
Diann Wingert brings decades of experience as a psychotherapist and serial business owner and is now a sought-after coach to entrepreneurs with ADHD traits. Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the neurodivergent experience.
Known for her candor and her refusal to compromise on what matters, Diann Wingert is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship.
Mentioned during this interview:
Etsy
Colonial Patterns
Lisa Congdon

Simple suggestions for preparing for your next potential pivot:
1) Assess emotional, financial, and market conditions regularly.
2) Define your personal “red flags” for burnout and your criteria for build and grow, hard stop and hibernate, and resuscitate pivots
3) Inventory current and planned activities, noting which are energizing versus draining.
4) Keep communication open with your clients/community during hibernation phases. You never know who might want to be a part of whatever you do next.

If this episode saved you from burnout (or burning your business down…), now would be a perfect time for that 5-star rating and review you keep meaning to leave. Here’s the link to make it happen. Be sure to mention what you loved about the episode or the show in general.

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

In collaboration with other independent podcasters during the global Podcasthon charity event, ADHD-ish host Diann Wingert is opening up about the real costs women face when their ADHD goes undiagnosed for far too long—especially those running their own businesses.
From emotional tolls and damage to self-worth, to identity crises and financial setbacks, Diann unpacks how the ADHD diagnostic criteria based on the behavior of young boys has resulted in several generations of females going undiagnosed, forcing them to struggle and overcompensate just to get by.
This episode is a heartfelt exploration of what it means to finally get answers after decades of struggle, and the reckoning that follows. Diann shares her own journey from therapist to entrepreneur, the lessons she learned raising kids with ADHD, and the impact a late diagnosis had on her life and work.
She also introduces listeners to the nonprofit “Find the ADHD Girls,” an organization dedicated to closing the diagnostic gap for girls everywhere, and invites you to make a difference. You can make a donation or simply share this episode to raise awareness.
So grab your favorite drink and settle in, because this week’s episode is about honesty, hope, and shifting the narrative for women and girls who’ve always felt just a little out of step with the world.
3 key takeaways:
Masking isn’t thriving. Many women spend years camouflaging their struggles, only to later realize they were “passing for normal” rather than actually okay.
Delayed diagnosis has real professional costs. Every ounce of energy spent managing ourselves is bandwidth that’s not going into growth, strategy, or creativity in our businesses—and it adds up.
Early awareness changes lives. The sooner ADHD is identified—especially in girls—the fewer years are lost to self-blame and missed opportunities.

About the host
Diann Wingert is a passionate advocate and expert on ADHD, rooted in her own delayed diagnosis, as well as two decades of experience as a licensed psychotherapist, serial business owner, and parent of several children with ADHD.
For years, Diann—and many women like her—carried a persistent sense that “something’s wrong with me,” a quiet conviction fed by a lack of answers and the feeling that everyone else had life figured out. This experience led her to see the reality: women with ADHD were hiding in plain sight, while the world slowly learned to recognize their struggles.
Now, as the host of the podcast ADHD-ish and an internationally recognized ADHD business coach, Diann welcomes a community of listeners searching for understanding and authenticity, promising strategic guidance and an honest exploration into what it means to live and run a business with ADHD
Suggested Listener Action Steps:
Donate to Find the ADHD Girls: help close the ADHD diagnostic gap for girls.
Share the Episode: If a donation isn’t possible, share this episode with someone who might benefit from it, raising awareness about ADHD in women and girls.
Visit the Podcasthon site and support other independent podcasters and non-profit organizations.
Visit the Find The ADHD Girls site for additional resources

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

Welcome to another episode of ADHD-ish! In today’s conversation, Diann Wingert, host and therapist-turned-business strategist, sits down with longtime ADHD coach and thought leader Jeff Copper to explore his groundbreaking new approach: “Cognitive Ergonomics from the Inside Out.”
Together, they dive into the roots of executive function challenges, drawing on insights from Dr. Russell Barkley, and discuss why traditional ADHD advice doesn’t always translate to real-world results.
Jeff Copper explains the concept of “cognitive illiteracy” and shares how his attention scope experiences can help make the invisible struggles of ADHD tangible. You’ll hear practical strategies—like the power of direct, oral conversations in problem-solving—and fresh perspectives on mindfulness for busy brains.
Why You’ll Love It
Whether you’re newly diagnosed, deep in your ADHD self-awareness journey, or have “tried all the things,” this episode invites you to see your challenges—and strengths—through a radically new, pragmatic lens. If you geek out on intellectual curiosity and want to see what’s “under the hood,” check out Jeff Cooper’s Cognitive Ergonomics resources (link below).
What you’ll learn:
Cognitive Ergonomics, Explained: No engineering degree required—Jeff Copper breaks down this powerful new way to understand how your brain REALLY operates.
The Concept of “Cognitive Illiteracy”: What does it mean to be cognitively illiterate? Why is it not as negative as it sounds? Spoiler: it’s about discovering things you couldn’t see before!
Experiencing Attention Scope: Learn how using your non-dominant hand during everyday tasks can help you feel executive function challenges—and practice self-awareness.
Mindfulness, Reimagined: Forget trying to get your mind to go blank—get practical tips for being present in the now (and why that matters for your productivity and focus).

Fun Fact from the Episode:
If you’ve ever solved a problem just by voicing it to someone (or even sending a voice note!), you’re already practicing cognitive ergonomics. In fact, Jeff Copper says some folks can process and solve their own issues simply by “downloading” a problem out loud—even if nobody responds!
About today’s guest, Jeff Copper
Jeff Copper is a cognitive engineer, thought leader, and ADHD coach. He is the founder of DIG Coaching, Attention Talk Radio, and Attention Talk Video, and holds professional designations from ICF and PAAC and certifications from ADD Coach Academy and Coaches Training Institute. Jeff developed Cognitive Ergonomics From the Inside Out®, a radical departure from the current ADHD intervention paradigm. In recognition of his contributions, he received the ACO's 2022 Professional Excellence Award. Jeff continues to innovate in attention coaching, helping individuals understand and manage their ADHD challenges.
Connect with Jeff:
DIG Coaching Practice - Attention Talk Radio Podcast - LinkedIn - Email
Cognitive Ergonomics From the Inside Out

Your ADHD-ish host, Diann Wingert
Diann Wingert brings decades of experience as a psychotherapist and is now a sought-after coach to entrepreneurs with ADHD traits. Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the neurodivergent experience.
Known for her candor and her refusal to compromise on what matters, Diann Wingert is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship.
Mentioned during this interview:
Russell A Barkley, PhD - Dr. Charles Parker - The Four Tendencies - John Maxwell
Now what?
If this episode got you thinking in a new way about your ADHD, now would be a perfect time to leave that 5-star rating and review you keep meaning to leave. Here’s the link to make it happen. Thank you!
And, if you are connected with Jeff Copper, or are going to start now, be sure to reach out and let him know your thoughts on cognitive ergonomics: [email protected]

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

If you’re an entrepreneur or founder who feels like you have to work twice as hard just to keep your business from spiraling, you’re not alone—and your company’s chaos might not just be “part of the job.”
Most founders don’t realize their business “vibe” is a mirror of their brain. ADHD traits like chasing dopamine, avoiding conflict, or struggling with structure aren’t just personality quirks– they ripple through your team, processes, and business operations.
Whether you’re a founder, team lead, or anyone building something from scratch, this episode will deliver a clear framework to assess your current culture, recognize what’s working (and what’s not), and take the first practical steps toward building a company that truly fits and supports the neurodivergent way you do business.
Organizational Psychologists Quinn & Cameron identified that 90% of companies worldwide fall into one of these four types of company cultures in their Competing Values Culture Model:
Clan (Family): Collaborative, relationship-focused, but slow to make tough calls.
Adhocracy (Innovators): Fast-paced, risk-taking, constant brainstorming – but often unstable and unfinished.
Market (Competitors): Results-driven, clear metrics, high stakes – can burn people out.
Hierarchy (Machine): Structured, predictable, rule-heavy – can stifle creativity.

Most founders with ADHD unintentionally create either:
“Accidental Adhocracy”: Innovative (read: scattered), chasing novelty for dopamine, team struggles with chaos and change, projects rarely get finished.
“Accidental Clan”: Warm, fuzzy, avoiding confrontation, underperformers stick around, roles are blurry, you feel more like a therapist than a CEO.

3-Step Plan to Build Your Business Culture on Purpose
1. Honestly Assess Your Current Culture
Ask tough questions—from “Who really solves problems here?” to “How many projects did we actually finish this quarter?”
2. Get Real About What’s Working… and What’s Not
List out where your accidental culture is winning—and where it’s burning you or your team out.
3. Pick ONE High-Leverage Change
Don’t try to overhaul it all. Make one intentional hire (like a project manager or COO) or put a single new process between your ideas and your team. Act, observe, and iterate.
You get to choose your culture.
The question isn’t if your ADHD is shaping your business, but how.
About the Host, Diann Wingert:
Drawing from her experience as a psychotherapist and serial business owner and her understanding of ADHD, Diann empowers founders to understand the default culture their ADHD brain creates, and shows them how to transform it into a purpose-driven environment that supports both their goals and the well-being of their team.

Sharing is Caring
Know a fellow ADHD founder who’s quietly fighting fires (or fighting themselves) every day? They might need this wake-up call, too, so be a pal and share the episode.
Want one-on-one support?
If you’re ready to intentionally design a company culture that works with your ADHD, click here to book a free consultation. It’s the first step to transforming what you’re building intentionally through expert ADHD entrepreneur coaching.

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