

ADHD-ish
Diann Wingert
ADHD-ish is THE podcast for business owners who are driven and distracted, whether you have an “official” ADHD diagnosis or not. If you identify as an entrepreneur, small business owner, independent professional, or creative, and you color outside the lines and think outside the box, this podcast is for you.
People with ADHD traits are far more likely to start a business because we love novelty and autonomy. But running a business can be lonely and exhausting. Having so many brilliant ideas means dozens of projects you’ve started and offers you’ve brainstormed, but few you’ve actually launched. Choosing what to say "yes" to and what to "catch and release" is even harder. This is exactly why I created ADHD-ish.
Each episode offers practical strategies, personal stories, and expert insights to help you harness your active mind and turn potential distractions into business success. From productivity tools to mindset shifts, you’ll learn how to do business your way by
embracing your neurodivergent edge and turning your passion and purpose into profit.
If we haven't met, I'm your host, Diann Wingert, a psychotherapist-turned-business coach and serial business owner, who struggled for years with cookie-cutter advice meant for “normies” and superficial ADHD hacks that didn’t go the distance. In ADHD-ish, I’m sharing the best of what I’ve learned from running my businesses and working with coaching clients who are like-minded and like-brained.
Note: ADHD-ish does have an explicit rating, not because of an abundance of “F-bombs” but because I embrace creative self-expression for my guests and myself. So, grab those headphones if you have littles around, and don’t forget to hit Follow/Subscribe so you don’t miss a single episode.
People with ADHD traits are far more likely to start a business because we love novelty and autonomy. But running a business can be lonely and exhausting. Having so many brilliant ideas means dozens of projects you’ve started and offers you’ve brainstormed, but few you’ve actually launched. Choosing what to say "yes" to and what to "catch and release" is even harder. This is exactly why I created ADHD-ish.
Each episode offers practical strategies, personal stories, and expert insights to help you harness your active mind and turn potential distractions into business success. From productivity tools to mindset shifts, you’ll learn how to do business your way by
embracing your neurodivergent edge and turning your passion and purpose into profit.
If we haven't met, I'm your host, Diann Wingert, a psychotherapist-turned-business coach and serial business owner, who struggled for years with cookie-cutter advice meant for “normies” and superficial ADHD hacks that didn’t go the distance. In ADHD-ish, I’m sharing the best of what I’ve learned from running my businesses and working with coaching clients who are like-minded and like-brained.
Note: ADHD-ish does have an explicit rating, not because of an abundance of “F-bombs” but because I embrace creative self-expression for my guests and myself. So, grab those headphones if you have littles around, and don’t forget to hit Follow/Subscribe so you don’t miss a single episode.
Episodes
Mentioned books

Jan 27, 2026 • 28min
ADHD and Working Memory Challenges: The Business Problem Nobody's Talking About
They spotlight working memory as the hidden bottleneck for entrepreneurs with ADHD. They explain how limited mental RAM derails client calls, onboarding, and follow-up. They debunk brain games as a cure-all. They suggest practical fixes like voice memos, checklists, templates, batching, automation, and systemizing to reduce cognitive load.

Jan 20, 2026 • 46min
Adding Novelty in Your Business with Pop-Up Offers
In a lively discussion, content strategist and conversion copywriter Erin Ollila shares her insights on pop-up offers, stemming from her ADHD-driven creativity. She explains how these limited-time offers can transform businesses with quick wins that meet client needs. Erin dives into the mechanics of her own mini-offers, emphasizing their strategic design and low overwhelm for clients. Learn why pop-up offers are particularly beneficial for ADHD entrepreneurs, and how they can create momentum and satisfaction, proving that novelty can lead to unexpected success.

10 snips
Jan 13, 2026 • 20min
"Enough Already": Breaking the ADHD Habit of Overcompensating in Your Business
Discover why those with ADHD often struggle to gauge their 'enoughness.' Explore the difference between overachievers and compensators and learn how these traits impact entrepreneurial habits. Dive into the five-part Enough Already Framework to recalibrate your sense of enough for sustainable success. Gain actionable tools like the Enough Algorithm to help discern when work is enhancing value versus simply easing anxiety. Embrace a path to sustainability in business without burnout.

Jan 6, 2026 • 34min
The Neurodivergent Edge: Redefining Strength in Relationships & Business
Dante Assad Williams, aka Dr. Dante, is a psychologist and entrepreneur known for advocating for neurodivergent women as 'neuro baddies.' In this engaging discussion, he shares the empowering origins of the term, emphasizing honesty and hyperfocus as attractive traits. They delve into the complexities of relationships, including why neurodivergent individuals often enter toxic bonds and how to reclaim self-trust. Dante also discusses the unique entrepreneurial advantages of ADHD, showcasing resilience and creativity as superpowers for success.

Dec 30, 2025 • 17min
The ADHD Brain's Year-End Inventory (That Has Nothing to Do With Goals)
As the year wraps up, traditional goal-setting can feel overwhelming, especially for those with ADHD. Instead of the usual methods, a refreshing inventory approach is introduced, focusing on three core areas: energy, money, and time. Listeners are prompted to explore what lifts their spirits versus what drains them, revealing valuable patterns. The discussion also highlights honest assessments of revenue sources versus expectations, and identifying optimal work times. The emphasis is on subtraction and refining practices that truly energize, setting up for a more aligned year ahead.

Dec 23, 2025 • 43min
Chasing Butterflies: Managing ADHD Idea Overwhelm as a Serial Entrepreneur
Sarah Dowd, a cultural strategist and creative entrepreneur, shares her insights on managing idea overwhelm as a serial entrepreneur. She discusses the 'burden of creativity' and why ADHD-driven individuals often thrive as polymaths. Sarah introduces her six-stage process for organizing ideas and emphasizes the importance of using AI tools for capturing and structuring thoughts. She also explores designing audience-specific messaging and the interconnectedness of multiple projects, providing practical strategies to harness creativity without burning out.

Dec 16, 2025 • 26min
Why Entrepreneurial ADHD Traits Don’t Always Mean You Should Start a Business
Is it possible to have a brain wired for entrepreneurship, but actually thrive best within traditional employment? This insightful episode flips the script on the common narrative in both the ADHD and business worlds: that entrepreneurial traits automatically mean you should start your own business. Instead, host Diann Wingert explores the concept of intrapreneurship—bringing creativity, innovation, and entrepreneurial spirit into an existing organization—and how this path might be the most strategic decision for many ADHDers.If you’re wrestling with the decision to go solo or stay employed, give this episode a listen. It just might give you permission to build a life—and career—that truly works for your brain.Three key takeaways:Entrepreneurial traits ≠ Entrepreneurial career: You can be creative, visionary, and disruptive without having to start your own business. Don’t fall for the myth that employment is “settling.”Intrapreneurship unlocks impact & stability: Express your entrepreneurial strengths inside an organization. Lead without authority, innovate processes, and treat your role like you own it—while benefiting from structure, resources, and a steady paycheck.Signs that traditional employment isn’t right for you:Not everyone is meant to shine as an intrapreneur. If every manager is a nightmare, structure feels suffocating, or your best ideas die in committee, maybe going solo is your move. But it’s all about matching your brain and real life with the right path—not shame, not hustle-culture FOMO.Workplace roles & cultures where ADHD-ish traits thrive:Look for product development, business strategy, internal consulting, startups, project-based work, or innovation labs. Go where experimenters are rewarded, hierarchies are flatter, and outcomes matter more than bureaucracy.Mic Drop Moment:“Infrastructure isn't the enemy of innovation. Structure, when it's the right structure, is what lets your brain do what it does best without getting derailed by all the shit you hate doing."Action Step:Take 10 mins for honest self-reflection. Where do you really do your best work? What structure supports you? Then, make the choice that serves your life—not LinkedIn optics or anyone else’s expectations.About the Host:Diann Wingert is a seasoned business coach, consultant and speaker. Drawing from her many years of experience as a former psychotherapist, serial business owner, and someone who thinks "outside the box," ADHD-ish host, Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and the world of work. Enjoyed the Episode?Share your thoughts! Leave a review and let Diann know what resonated, challenged, or inspired you. Your feedback helps ADHD-ish reach more listeners who need to hear these honest conversations. © 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Dec 9, 2025 • 38min
Attract, Don't Chase: Relationship Marketing & ADHD
Cat Orsini, an MBA and master-certified coach, shares her inspiring journey as a neurodivergent entrepreneur. Diagnosed with ADHD and autism, she discusses how these traits fuel her unique approach to relationship marketing. Cat highlights the harmony between automation and genuine connections, advocating for a shift away from hustle culture to building authentic relationships. She emphasizes the importance of unmasking to attract clients who align with her values and the strength found in embracing one’s limitations while focusing on personal strengths.

Dec 2, 2025 • 37min
Redefining Success After Loss: An ADHD-Informed Approach to Grief & Burnout
In this conversation, Steph Cottrell, a web and marketing consultant and founder of Blue Elephant Creative, shares her journey of rebuilding her business after experiencing profound personal loss. She discusses the toll of boundary-less collaborations that led to burnout and her realization of handling 90% of the workload. The two explore redefining success, prioritizing authenticity, and integrating family needs into business. Steph's father's illness became a catalyst for urgent change, urging her to refocus on solo projects and a clear niche.

Nov 25, 2025 • 41min
The Big Questions Every Business Owner Needs to Ask
Join business strategist Jessica Lackey, an author and former consultant at Harvard and Nike, as she explores how to build sustainable businesses without falling for shiny tactics. She reveals the gambling-like nature of chasing quick fixes, emphasizing the need for a solid strategy. Discover her framework of crucial questions every entrepreneur should ask, how overstimulation affects decision-making, and the importance of separating passion from profit. Jessica's insights provide practical advice for reclaiming agency and building a business that truly works.


