ADHD entrepreneurs often face impulsivity, burnout, and co‑occurring conditions that impact business outcomes. In this episode, psychiatrist Michael Freeman shares research and coaching insights on ADHD business strategy, resilience, and executive function in business.

You’ll hear how ADHD business coaching helps founders balance creativity with structure, manage risk, and build sustainable growth. By understanding vulnerabilities and leveraging neurodivergent strengths, small business owners with ADHD can design systems that support leadership, decision‑making, and long‑term success.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - Introduction to Business Strategy and Operations

05:10 - Identifying Pitfalls in Delegation and Accountability

10:25 - Overcoming Decision Fatigue and Cognitive Load

15:40 - Preventing Burnout With Sustainable Workflows

21:00 - Building Effective Team Leadership and Communication

26:15 - Mastering Executive Function and Time Management

31:30 - Establishing Long-Term Self-Trust and Overcoming Doubt

36:45 - Stepping Into the Role of a CEO and Scaling Up

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

Why do so many entrepreneurs have ADHD tendencies

Dr. Freeman breaks down fascinating research on why we’re more likely to go solo in our careers—and why we struggle in traditional workplaces.

The double-edged sword of the ADHD entrepreneurial brain

We chat about superpowers and vulnerabilities, with a big emphasis on how to recognize your “zone of genius” (and when to call in backup!).

Building your own ADHD-friendly toolkit for sustainable success

From teams and routines, to handling sleep and “offloading the boring stuff,” we talk actionable strategies (yes, including coaching and medication).

The myth vs. reality of the entrepreneurial life

Spoiler: it isn’t all glamor and “get rich quick”—and Dr. Freeman shares why radical self-awareness and resilience are must-haves.

Why fun is non-negotiable for the entrepreneur with ADHD

Turns out, fun isn’t just a bonus—it’s the main event for the ADHD brain, and Dr. Freeman explains how to keep your business (and life) playfully sustainable.

Make it actionable:

• Take three minutes to reflect: what feels fun, energizing, or “flow-y” in your own work? What support do you need more of?
• Feeling inspired to start, pivot, or quit? Get a “personal board of directors” before you make big decisions or take big risks.

Get to know Michael Freeman, MD

Michael A. Freeman, MD, is a clinical professor at UCSF School of Medicine, a researcher and mentor at the UCSF Entrepreneurship Center, a psychiatrist and executive coach for entrepreneurs, and an integrated behavioral healthcare systems consultant. His current research focuses on the identification of emotional overwhelm with early intervention and support.

Dr. Freeman’s thought leadership on entrepreneurship and mental health has been featured in the New York Times, Washington Post, Wall St. Journal, Fortune Magazine, Inc., Entrepreneur, CNN Money, Financial Times, and Bloomberg News.

Mentioned in this episode:

UC San Francisco, UC Berkeley, Stanford University, the Gallup Organization

Connect with Michael A Freeman, MD

Website - LinkedIn

🎙️ Fun Fact From the Episode:

Did you know? For most of human history, people with ADHD traits were actually high-status in hunter-gatherer societies! We were the original “economic first responders.” (So if you’ve ever felt out of place, maybe you’re just in the wrong era!) To learn more: Thom Hartmann’s ADHD: A Hunter in a Farmer’s World or John Dini’s Hunting in a Farmer’s World: Celebrating the Mind of an Entrepreneur.

Every guest on ADHD is hand-picked and invited personally by you-know-who, so if you enjoyed this interview, let me know:

Leave a review

Share the episode

Thank you!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

ADHD entrepreneurs often chase new ideas, tools, and platforms, leaving proven offers unfinished. This episode explains why shiny object syndrome happens and how it sabotages ADHD business strategy.

You’ll hear practical solutions like dopamine scheduling, accountability structures, and reframing the messy middle. These ADHD business coaching insights help small business owners prevent burnout, improve executive function in business, and build sustainable systems. By channeling creativity without losing focus, entrepreneurs can scale a business with ADHD while staying aligned with their vision.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 – Spotting Shiny Object Syndrome in Entrepreneurship

07:10 – How to Stay Focused and Execute Business Strategy

13:25 – Building Systems to Prevent Constant Pivots

19:40 – Leadership Lessons for Small Business Owners

26:05 – Sustainable Growth without Distraction and Burnout

Loan me your ear holes for the next 25 minutes for:

🧠The Neuroscience-Based Truth

Why your ADHD brain is forever thirsty for dopamine—and why trying to force yourself to focus just doesn’t work for us.

🏃‍➡️The Cost of Chasing Novelty

The sneaky ways shiny object syndrome drains your revenue and energy (and how to recognize it hiding in your business).

📋5 Practical Strategies

Including: dopamine scheduling and reframing the “messy middle” to creating shiny object parking lots and setting up accountability that actually works.

🎨How to Enlist (Not Resist) Your Curiosity

Specific ways to channel your creative bursts into profitable execution, instead of abandoned projects.

📇Systems That Make Space for New Ideas (Without Derailing Your Progress)

Learn how a “shiny object fund” can keep your creativity alive while protecting your core business

Fun Fact from the Episode:

ADHD expert William Dodson, MD, coined the expression “interest-based brain” to explain how we operate differently. Here is an article from ADDitude magazine that explains it ( including a one-minute YouTube video with a “House of Cards” style soundtrack).

🏆Ready to start creating more consistent business success—and work with your interest-based brain?

To make it extra easy to go from innovation to implementation, I created a free companion handout with all the go-to strategies mentioned in this episode. Grab your copy right here.

🎙️And be sure you're following/ are subscribed to ADHD-ish on your favorite podcast app, because next week, I’m chatting with Dr. Michael Freeman, a leading psychiatrist, entrepreneur, researcher, and consultant. Trust me, you’re not going to want to miss it.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Many ADHD entrepreneurs feel pressured to scale or build teams, but solo business models can be more sustainable. This episode explores ADHD business strategy for small business owners who want simplicity and flexibility.

Through ADHD business coaching insights, we discuss executive function challenges, burnout prevention, and authentic leadership. By focusing on sustainable growth and systems that fit neurodivergent brains, entrepreneurs can design businesses that align with their strengths and thrive without unnecessary complexity.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - ADHD Business Strategy for Neurodivergent Entrepreneurs

05:50 - Common Pitfalls in Delegation and Accountability

11:40 - Solutions for Decision Fatigue and Cognitive Load

17:30 - Sustainable Systems and Workflows to Prevent Burnout

23:20 - Effective Team Leadership and Communication Habits

29:10 - Executive Function and Time Management for Founders

35:00 - Long-Term Self-Trust and Overcoming Founder Doubt

40:50 - Strategic Growth and Scaling Your Venture

Episode Insights:

• The Solo Advantage: Maggie explains why being an intentionally small business owner can be the best option for neurodivergent individuals, offering greater flexibility and reducing stress.
• Cultural Conditioning and Entrepreneurship: Maggie & I unravel how the cultural celebration of hyper-successful entrepreneurship models can be misaligned with many neurodivergent experiences.
• Recognizing Personal Capacity: Our conversation explores the importance of understanding one's own sensory and emotional capacities and why it's crucial for sustainable business operations.
• Reality of Business Growth: We discuss the myths around scaling businesses and the reality of what it means for the entrepreneur's role to shift from creator to manager and marketer.
• Dismissing Magical Thinking: Maggie emphasizes the importance of discerning which ideas to pursue and recognizing that not every new venture has what it takes to succeed.
• Navigating Neurodivergence and Business: With personal anecdotes, the episode highlights the importance of understanding one's unique neurodivergent traits and leveraging them for business success.
• Challenging Toxic Advice: You’ll find yourself nodding along to our critiques of the flawed business advice often targeted at women and neurodivergent individuals, encouraging you to trust your own judgment.

Maggie Who?

Maggie Patterson is a seasoned entrepreneur, consultant, and small service business owner who is passionate about demystifying societal conditioning around business success and encouraging entrepreneurs to prioritize their well-being.

She is also a blogger, podcaster, and author of the long-awaited new book, “Staying Solo: Your Guide to Building a Simple, Sustainable Service Business.”

🎙️ Mic Drop Moment:

”So often we think about getting support in the context of our business, but what about our friendships, the communities we're in, and the personal supports we're getting?"

Maggie Patterson

Mentioned in this episode:

• Ideation StrengthsFinder theme
• Our mutual friend Michelle
• Duped, Maggie’s Podcast with Michelle Mazur

Connect with Maggie Patterson:

Website - Podcast - Instagram - LinkedIn

Buy the book “Staying Solo: Your Guide to Building a Simple, Sustainable Service Business.”

Does Maggie sound familiar?

That’s because she’s a returning guest. Check out our first conversation on ADHD-ish, Episode # 196 “Why Opting to Stay Small Doesn’t Mean Limited Success.”

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

ADHD entrepreneurs often default to saying yes, leading to burnout and blurred boundaries. This episode explores why unexpected requests overwhelm ADHD brains and how rejection sensitivity fuels people pleasing.

Through ADHD business coaching strategies, you’ll hear practical scripts, boundary‑setting techniques, and mindset shifts that help small business owners protect their energy. By reframing boundaries as strengths, entrepreneurs can prevent burnout, improve executive function in business, and scale authentically without sacrificing well‑being.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - Breaking Free From People-Pleasing as an Entrepreneur

05:15 - Boundaries and Protecting Your Energy in Business

10:30 - Overcoming the Fear of Disappointing Clients

16:00 - Reclaiming Self-Trust and Prioritizing Your Needs

21:30 - Sustainable Workflows That Honor Your Capacity

🔑 Key Takeaways:

• The Default Yes: Why impulsively saying yes is more than just people pleasing and how it ties to ADHD brain wiring.
• Deer in the Headlights Effect: Unexpected requests often leave individuals with ADHD feeling frozen and overwhelmed.
• The Reciprocity Myth: The misconception that saying yes will always lead to reciprocal benefits in a professional setting.
• Setting Boundaries as a Muscle: Strengthen your ability to say no with practice, patience, and a bit of training.
• Practical Techniques: The buffer phrase technique, physical resets, and guilt-free language patterns to help you say no and not feel bad about it.
• Handling Emotional Aftermath: Insight into managing the guilt and anxiety that can follow after setting boundaries.
• Forgiveness and Progress: Shifting away from the default yes with self-compassion and patience.

Mic drop moment:

"People who consistently get what they want are often those who clearly communicate boundaries, not those who say yes to everything."

Start here:

Physical Reset Technique: Practice taking a deep breath, pressing your feet into the ground, and rolling your shoulders back when under social pressure to help redirect your focus (and buy a little time before answering.)

Climb the No Ladder: Start by saying no to small, low-stakes requests, gradually moving to more significant ones as you gain confidence.

What’s next?

In order to rewire your brain from the default yes to more intentional answers takes practice, so be sure to grab my free worksheet that combines all the strategies shared in this episode, including practice scripts with guilt-free responses.

Good intentions will not change the situation, but a handy guide that reminds you exactly what to do will. Click here to get your copy.

© 2024 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

When long projects drag on, focus fades and overwhelm takes over. This episode explores creative sprint days as an ADHD-friendly strategy to channel energy into fast, collaborative execution.

Discover how sprint models support executive function, reduce burnout, and build sustainable systems. By aligning creativity with structure, you'll learn how to scale authentically and design a business that finally fits your brain.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 – Creative Sprint days to Unlock Entrepreneur Strengths

04:15 – Coaching Insights for Business Owners with ADHD

09:40 – Building Strategy for Sustainable Growth

15:05 – Small Business Owners Navigating Unique Challenges

20:30 – Shifting from Solo Entrepreneur to Business Owner

26:10 – Essentials of Team Leadership and Collaboration

32:45 – Scaling a Business Sustainably with Neurodivergent Strengths

38:20 – Preventing Burnout and Building Resilience

Fun fact about today’s guest:

Evan Sargent co-authored a book for young people called “We the People: the US Constitution Explored and Explained.” How timely is THAT?

Connect with Evan Sargent:

LinkedIn - Website - Contact

Want to be part of the movement to help girls get identified with ADHD in childhood, instead of struggling for years before getting a “late diagnosis?” Join me in a mission to #FindTheADHDGirls by clicking on this link.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Missed deadlines, lost paperwork, and impulsive purchases exact a heavy financial and emotional toll on neurodivergent founders. In this episode of ADHD-ish, host Diann Wingert breaks down the hidden mechanics of the ADHD tax across daily operations.

Establish simple automation, supportive administrative routines, and cognitive safeguards that protect hard-earned revenue. For entrepreneurs seeking specialized ADHD business coaching to build an efficient, friction-free business structure, these strategic insights offer a sustainable path forward.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Understanding the Real Cost of ADHD Tax

06:40 - Identifying Friction Points in Daily Business Operations

12:20 - Automating Financial Workflows and Recurring Payments

18:00 - Reducing Cognitive Load to Prevent Costly Mistakes

23:45 - Building Practical Systems to Stop Task Slippage

29:15 - Mitigating Impulse Decisions and Late Fees

35:00 - Restructuring Delegated Support to Guard Energy

41:10 - Creating Sustainable Systems for Long-Term Savings

Mic drop moment:

“Now, for entrepreneurs and small business owners with ADHD, this invisible tax doesn't just drain your bank account. It taxes your well-being, your relationships, and your ability to show up as the business owner you so want to be."

Mentioned in this episode:

• Goblin.tools Magic To Do - free app to break things down into smaller tasks
• ChatGPT - free thinking partner
• Claude - my favorite thinking partner
• Ned Hallowell, MD - why connection is essential for adults with ADHD
• Jessica McHabe water bottles - hydration prevents ADHD brain jerky
• Neurodiversion 2025 Conference - My first conference in 2025
• Time Timer - available in digital and analog format
• Voxer - my favorite app for leaving myself reminders

Now What?

Does paying less ADHD tax sound appealing? Be sure to grab my free worksheet that combines all the strategies shared in this episode. Good intentions won’t move the needle, but a PDF you can save on your desktop or print out and pin to your corkboard means you actually benefit from these strategies. Click here to get your copy.

© 2024 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Traditional organization tools rarely account for executive dysfunction. In this episode of the ADHD-ish podcast, host Diann Wingert meets with tech founder Mina Raver to examine how executive functioning challenges impact task management, focus, and daily workflows for every business owner with ADHD.

Together, they discuss adaptive technology, tailored ADHD business operations, and brain-based systems designed for neurodivergent leadership. Implementing systems built around your natural cognitive strengths allows your enterprise to scale sustainably without burnout or overwhelm.

EPISODE HIGHLIGHTS & TIMESTAMPS:

02:18 - Questioning Traditional Education and Systems

05:10 - Early Insights on ADHD Executive Function in Business

10:20 - Occupational Typecasting vs. Job Crafting for ADHD Strengths

15:30 - Misinterpreted Symptoms and ADHD Burnout Prevention

20:40 - Delayed Diagnosis and Impact of Internalized Feedback

25:50 - Nuances of ADHD CEO and Leader Experiences

31:00 - Critiquing the "ADHD Superpower" Narrative

36:10 - Aligning Career Paths for Sustainable Growth with ADHD

Episode Highlights:

1. Disruptive AF: With no technical background, Mina taught herself to code and is building tools to revolutionize productivity for neurodivergent brains.
2. Redefining Productivity: Dive into Mina's holistic approach to understanding brains and hear why she believes current productivity standards just aren't cut out for neurodivergent folk.
3. Passion Over Profit: Discover why Mina opted out of traditional funding pursuits and chose to pave her distinctive path, focusing on genuine impact rather than investor expectations.
4. Own Your Narrative: Mina liberated herself from people-pleasing and permission-seeking, setting an example for other neurodivergent visionaries ready to claim their space and impact the world on their terms.

Mic Drop Moment:

🎙️"I learned early that no submission is ever enough for reprieve." Mina Raver

Mentioned in this episode: Anastasia Simon - Techstars

Connect with Mina Raver:

Website

Email

LinkedIn

Try the Better CEO mobile app (desktop version in development)

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Transitioning from a hands-on solopreneur to an effective executive requires a fundamental evolution in how you direct your energy and team. In this episode of ADHD-ish, host Diann Wingert breaks down the essential cognitive adaptations necessary for neurodivergent founders to step confidently into authority.

Cultivate clear delegation frameworks, establish grounded decision-making habits, and build an infrastructure that supports your vision. For founders seeking targeted ADHD business coaching to step into empowered, sustainable leadership, this discussion delivers clear strategic guidance.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Transitioning from Solo Founder to ADHD CEO

06:40 - Overcoming Rejection Sensitivity in Team Leadership

12:15 - Building Systems to Support Delegated Authority

18:10 - Decision-Making Frameworks for Neurodivergent Leaders

24:35 - Aligning Company Vision with Sustainable Business Growth

Here are three key takeaways from this episode:

Leadership Mindset Shift: Transitioning from a practice owner to a business owner mindset allowed Kirsten to differentiate her personal identity from the needs of the business. This distinction has been crucial in making decisions that benefit long-term success, not just immediate needs.

Using Owner Days to Create Boundaries & Perspective: By designating one day a week away from the practice for strategic planning and decision-making, Kirsten was able to focus on bigger-picture issues, and reclaim her time. This shift allowed for better work-life integration and also empowered her team to step up and grow.

The Power of Self-Acceptance: Recognizing and accepting how her giftedness and ADHD were affecting her business has been a game-changer. This self-awareness has made Kirsten a more effective leader and manager.

Fun Fact from the Episode: Due to her change in perspective and shift in priorities, Kirsten recently adopted a puppy named Lemon. Not only is Lemon an adorable new addition to her life, but she’s also training to be a therapy dog for her practice! 🐾❤️

Want to connect with Kirsten?

Website - LinkedIn

Are you ready to become one of my Client Success Stories? Let’s connect and see if now is the time. Click here to schedule a free consultation.

Are you Going to Neurodiversion 2025 in Austin, TX March 27-29th?

I’ll be there too, and hosting a Meetup for Neurodivergent Entrepreneurs and Business Owners. DM me on LinkedIn or send me an email to let me know. I’d love to meet you there!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Putting yourself and your ideas in front of an audience often triggers vulnerability hangovers and rejection fears for neurodivergent founders. In this episode of ADHD-ish, host Diann Wingert examines why authentic self-promotion feels so daunting when navigating neurodivergent traits.

Build grounded confidence, align your message with core values, and connect with ideal clients without relying on high-pressure sales tactics. For entrepreneurs seeking targeted ADHD business coaching to build a courageous, highly visible brand, this conversation offers clear strategic perspective.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Marketing with Courage as a Neurodivergent Founder

06:20 - Overcoming Visibility Fears and Rejection Sensitivity

11:45 - Authentic Storytelling for ADHD Business Growth

17:10 - Simplifying Content Creation to Prevent Burnout

22:35 - Building Sustainable Audience Connection Systems

Here are three key takeaways from this episode:

👉 Systems Thinking as an ADHD Strength: Iris emphasized the importance of having team members who understand the interrelated pieces of the puzzle. This holistic approach ensures smoother operations and greater overall success.

👉 Empathy and Emotional Intelligence: Empathy is a crucial skill for understanding and addressing client needs effectively. Iris shared how truly listening enables you to envision solutions and build deeper, more meaningful client relationships.

👉 Authenticity Over People Pleasing: Being true to who you are not only attracts the right kind of clients but also allows you to bring your best, most creative self to your work.

Fun Fact from the Episode: Iris has a "fuck jar.” It's an oh-so-relatable way of managing those moments when you just run out of fucks to give. A must-have for any ADHD entrepreneur, if you ask me! Jar of F*cks

Recommended reading/listening:

“The Let Them Theory” by Mel Robbins - how to break free from letting other people’s opinions and judgments affect you. And, in case you didn’t know, Mel was diagnosed with ADHD at age 47.

Want more Iris in your life?

Website - Podcast - LinkedIn - Free website audit

Are you going to Neurodiversion 2025 in Austin, Tx March 27-29th?

I’ll be there too, and hosting a Meetup for Neurodivergent Entrepreneurs and Business Owners. DM me on LinkedIn or send me an email to let me know. I’d love to meet you there!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Is an overflowing inbox hijacking your daily productivity? In this episode of the ADHD-ish podcast, host Diann Wingert addresses how compulsive email checking triggers dopamine loops, fuels task avoidance, and drains valuable focus for every business owner with ADHD.

Streamline your digital workflow using practical ADHD business operations methods, including dedicated email blocks and a simple three-folder system. Implementing clear client communication boundaries protects focus and elevates neurodivergent leadership without sacrificing client satisfaction.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - ADHD Brains and the Email Dopamine Loop

04:30 - Why Compulsive Email Checking is a Coping Mechanism

08:45 - The Hidden Costs: Time Blindness and Task Switching

13:15 - Strategies for Managing ADHD Executive Function in Business

18:20 - Setting Professional Boundaries and Owning Your Worth

Shared in this Episode:

Dedicated Email Blocks

Start by setting two defined email blocks per day. This limits distractions and prevents email from dictating your schedule. Use autoresponders to set client expectations and provide alternative contact methods for emergencies.

The 3-Folders System

Simplify your inbox with three primary folders — “Action Required,” “Waiting For,” and “Archive.” This method streamlines email management, reducing the clutter and stress of a crowded inbox.

Leveraging Email Templates:

Create templates for routine responses. This reduces cognitive load and enhances efficiency. Customize these for common client questions, project updates, and scheduling queries.

Ultimately, email management is not merely about efficiency but about owning your worth as an entrepreneur. Running a business should offer freedom, not bind you to other people's priorities.

By fostering better boundaries, entrepreneurs can build better work habits, which in turn boosts confidence and productivity. It's essential to remember that you are not always at others' beck and call.

Your time and attention are invaluable, so it’s time to let your inbox serve you, not the other way around.

Mentioned in this episode:

TidyCal - the online calendar that prevents me from overscheduling & sends reminders to my clients so I don’t have to

Now What?

Ready to start dealing with your Inbox? Be sure to grab my free worksheet that combines all the strategies shared in this episode.

It’s a simple to implement, step by step approach that will begin to free up time and attention for what matters most, which is not going to be found in your Inbox. Click here to get your copy.

© 2024 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.