ADHD-ish

Diagnosed recently with both ADHD and autism,  Cat Orsini’s candid storytelling takes us on a journey from feeling like an outsider to building a thriving business based on authentic relationships, automation with heart, and radical self-acceptance. 

In this interview, Cat reveals her unique approach to business—one that centers curiosity, genuine connection, and meeting people where they are (with a little tech magic to make life easier and more fun). 

You’ll hear not just the triumphs, but also the complex, sometimes messy moments of “unmasking” and designing a business that fits your actual brain and values, not someone else’s idea of success.

Episode Highlights:

Strategic Relationship Marketing vs. Automation

Cat breaks down why automation and relationship-building aren’t mutually exclusive—and how smart systems can let neurodivergent business owners focus on authentic, meaningful connections.

Attract, Don’t Chase

Move over “hustle culture.” Cat and Diann discuss how building genuine relationships and letting people self-select nurtures business without the creepiness or pressure of hard selling.

Neurodivergent Thriving in Business

How Cat’s ADHD and autism traits fuel her ability to notice patterns, create unique solutions, and support her clients in efficiently reaching their goals.

Automating the Human Touch

Learn how emails, follow-ups, and event workflows can be automated, freeing up energy for one-on-one connections with those who are ready for deeper engagement.

Ethical Reciprocity & Non-Bro Marketing

Cat outlines how heart-centered reciprocity builds lasting relationships and why neurotypical tactics often miss the mark for neurodivergent individuals.

Meet our Guest: Cat Orsini

Cat Orsini has an MBA, is a master-certified coach, an entrepreneur, and co-author of the book "Experts Never Chase." 

She specializes in relationship marketing, strategic conversations, and building automated systems that allow her—and her clients—to focus on human connection over busywork. 

Through radical acceptance of her neurodivergence and trauma history, Cat has crafted a career and life that honors her strengths and refuses to squeeze herself into a neurotypical mold.

Links & Resources:

Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with her client Steph Cotrell for a candid and relatable discussion about what it really means to build—and rebuild—a business when you have ADHD traits and life throws you curveballs. 

Originally hired to help Steph Cotrell grow and scale her successful business, Diann quickly uncovered some uncomfortable truths about her business model, specifically how her notion of collaboration revealed a lack of boundaries, which led to burnout. 

Their coaching journey took an unexpected turn as Steph was faced with redefining her work, grappling with exhaustion, and eventually reshaping her business to prioritize authenticity, personal connection, and family in the wake of a heartbreaking loss.

Together, they explore the challenges of managing emotional labor, the reality of ADHD-driven blind spots, and the courage it takes to rethink your path when everything changes. 

If you've ever felt caught between ambition and overwhelm or questioned how your neurodivergence shapes your entrepreneurial journey, this episode is for you. 

Here are 3 key takeaways from this conversation:

Scaling “as-is” can scale your problems, not just your profits: Before trying to grow, pause to check if your foundation—relationships, workload, boundaries—truly supports the life you want.

• Give yourself permission to redefine success: It’s not all-or-nothing. You can reshape business relationships and paths to fit changing needs, values, and energy levels.
• Clarity fuels action: The sooner you move from overthinking to taking action (even messy, uncertain steps), the faster you learn, adapt, and build the business—and life—that truly work for you.

Mic Drop Moment: 

"You don't have to be the glue holding all of this together.  If you enjoy working with them, work with them, and if you don't, don't."

Connect with Steph Cottrell: 

In this episode, I’m sitting down with my good friend, business strategist, consultant and author, Jessica Lackey, for a candid conversation about what it really takes to build a sustainable business—especially when you have an ADHD-ish brain. 

Jessica shares her journey from Harvard, McKinsey, and Nike to the wild world of entrepreneurship, revealing how even with such impressive credentials, she found herself trapped in the endless loop of online business tactics, quick fixes, and shiny promises.

Drawing on her upcoming book, Leaving the Casino: Stop Betting on Tactics, and Start Building a Business That Works, Jessica explains why so many of us end up gambling away our sanity (and savings) on the latest tactics, instead of building actual strategies that work for our lives and brains. 

Get ready for frameworks, real talk about defining your own version of success, and practical advice on bringing more intentionality and enoughness into your business (and life). It’s time to leave the casino behind—and reclaim your agency.

Top Takeaways from this Episode:

Start with Strategy, Not Tactics: 

The endless cycle of purchasing the latest digital course or marketing hack often leads to overwhelm, wasted resources, and lost confidence. Sustainable businesses are built on strategy and thoughtful decision-making, not reactive, one-size-fits-all tactics.

Ask Yourself the Big Questions: 

Before chasing the next big thing, get clarity on key fundamentals:

• What type of business do you really want to run?
• What stage are you in?
• What is the right pace and amount for your life and brain?
• What level of responsibility and commitment matches your reality?
• What does “enough” look like for you? These questions ground your business in reality instead of fantasy.

Don’t Compare Your Solo Journey to the Big Players: 

The polished marketers often have large teams and structures flattening out the chaos. If you’re a team of one (especially with an ADHD-ish brain), your output and path will—and should—look different.

There’s power in slowing down, cutting through the noise, and building a business that fits you—not a casino of empty promises.

About Jessica Lackey 

Jessica Lackey is the founder of Deeper Foundations, a consulting and training firm that helps expertise-based business owners grow and scale sustainable companies rooted in stronger business foundations.

She brings a unique blend of corporate expertise and soulful business building, drawing on an MBA from Harvard Business School, a coaching certification from iPEC, and experience at McKinsey & Company and Nike, Inc.

Jessica has supported over 200 entrepreneurs through her programs, blending systems thinking, operational rigor, and deep values alignment. She lives in Charlotte, North Carolina, with her husband.

Ever launched a program, course, or membership that once set your heart on fire, only to find yourself completely over it just as it starts running like a well-oiled machine? If you’re an entrepreneur with ADHD, this scenario is all too familiar. 

In this straight-talking solo episode, Diann Wingert unpacks why boredom hits hardest when your business finally starts working—and what to do about it. 

7 Things You’ll Learn From This Episode:

The Real Reason You Get Bored: Learn the neuroscience of ADHD boredom and why your brain craves novelty (hint: it’s about dopamine, not discipline).

The “PROOF” Framework:

A practical tool to help you decide if it’s time to renew or release your business offers.

How To Build Boredom-Proof Systems: Discover strategies to rotate, redesign, and reinvent your business model so you stay engaged long term.

Strategic Delegation & Role Redesign: Find out how letting go of the dull stuff (or handing it off!) can reignite your passion—and even grow your business.

Permission to Evolve: Why shifting your focus is not failure, but good business and good self-care.

Want your entrepreneurial journey to last? Build boredom-proofing in from day one.

• Alternate focus areas each quarter.
• Design offers so they evolve or rotate naturally.
• Proactively plan breaks, new challenges, or learning cycles.

And, most importantly, give yourself grace when you need to pivot, change, or retire offers. Evolution isn’t failure; it’s strategic adaptation.

Fun Fact from This Episode:

Did you know that constraints—NOT unlimited freedom—are actually better for the ADHD brain? Giving yourself playful “rules” can boost creative energy and bring the spark back to your work.

Next Steps: 

If you’ve ever felt overwhelmed by advice to “hack your dopamine,” or wondered why traditional approaches feel incomplete, this interview with Dr. Miguel Toribio-Mateas, “The Creative Scientist,” delivers refreshing insights and compassionate tools for thriving as a neurodivergent human. 

ADHDers often spend years trying to “fix” themselves from the outside in—through medication, planners, routines, and hacks—only to discover that true thriving might come from learning to listen to and trust their bodies. 

Dr Miguel introduces the concept of embodied neuroscience and explains why ADHD is far more than a brain-based disorder, unraveling the complex interplay between our nervous system, gut health, hormones, and emotional regulation.

Get ready to rethink what it means to support ADHD—from the inside out.

Episode Highlights:

• It’s Not Just Dopamine: Sure, dopamine’s part of the story. But Dr Miguel reminds us it’s just one instrument in a much bigger orchestra of brain and body chemistry. ADHD isn’t just a “brain disorder”—it’s an embodied experience, affected by everything from our gut health to our hormones and daily rhythms.
• Stop Trying to “Hack” Yourself: Instead of endless hacks, planners, and productivity tools, what if we tuned into our internal signals? Think: listening to hunger cues, taking movement breaks, honoring our need for rest—a holistic approach that begins on the inside.
• Self-Trust Is Everything: If you’ve ever struggled to trust your thoughts, feelings, or impulses, you’re not alone. The conversation offered hope: as we learn to regulate (and accept!) our unique internal ecosystem, intuition and awareness can flourish.
• Bringing it Back Home: Instead of survival mode, Dr. Miguel encourages us to “come back home” to ourselves—filling our cups with connection, nourishment, movement, and acceptance, rather than burning out on outside fixes.
• ADHD as an Advantage: Messy, complex, and beautifully curious—these traits can be assets in business and life. Don’t let anyone oversimplify you! 

Meet Our Guest 

Dr Miguel Toribio-Mateas is a clinical neuroscientist, applied microbiologist, and nutritionist whose work bridges brain, body, and lived experience. For over 2 decades, he has explored how the gut, nervous system, and microbiome shape mood, focus, and emotional balance.

Dr. Miguel is an Honorary Research Fellow at Cardiff University’s School of Psychology and lectures in nutrition at the University of West London. His forthcoming book, “ADHD Body and Mind” (Jessica Kingsley Publishers) will be published in 2026.