How to Clone Yourself as an ADHD Entrepreneur with Automation, AI & Apprentices

ADHD-ish Blog, ADHD-ish Podcast, How to Clone Yourself as an ADHD Entrepreneur with Automation, AI  & Apprentices, business automation, small business ownership, scaling a business, Diann Wingert, Diann Wingert Coaching, Will Christensen

In July 2020, I wrote a blog post titled “I Want to Clone Myself” and I’ve fantasized about cloning as the solution to growing my business many times since then. I bet you have too.  Being an entrepreneur means wearing many hats, especially in the early years, and most of those hats are unflattering and don’t fit well. 

Enter serial entrepreneur and fellow ADHD-er, Will Christiansen, who has been called “The Tony Stark of Software” in the field of automation.  In this fast-paced episode, Will and I unpack the challenges of scaling a business and how AI, automation, and what Will calls “top-tier human talent” are the elegant solution you may be looking for.  

If you’ve struggled with overcomplicated, clunky systems that slow you down and failed to find team members who match your drive, creativity, and commitment, this candid conversation is packed with practical strategies that move the needle and boost your bottom line.  

Guest Bio

Will Christiansen (he/him) is a systems thinker and automation expert who helps entrepreneurs take back their time and scale their business.  Will is the founder of The Entrepreneur’s Apprentice and host of Automation Hunter. He specializes in building teams and tech stacks that let visionary minds focus on what they do best.

Will is also a champion of the “Automate, Delegate, Eliminate” approach and has a brilliant strategy for hiring “entrepreneurial apprentices” who help founders scale without burning out.  Will’s revolutionary“15-1-1-5” framework, which he developed to manage his own executive functioning challenges, is an ADHD-friendly alternative to traditional time management strategies. 

Episode Highlights

  • You Don’t Need a Clone—You Need Your Opposite: Will reveals that hiring someone just like you might double your chaos, not your output. The real solution? Find an apprentice or two who complements your weaknesses and excels where you struggle. Sometimes, your best partner is someone with a different brain!

  • Automate, Delegate, Eliminate—In That Order: Learning to let go is harder than it looks, so start with identifying what can be automated (especially now that AI makes it easier than ever). Save your executive functioning and cognitive energy for the big, creative stuff rather than routine busywork.

  • Equity and Ownership Breed Commitment: Want your team to “own” their work? Will recommends offering phantom equity to empower top-tier talent to act as “mini-CEOs.” This transforms their sense of responsibility and buy-in, leading to loyalty and drive you can’t just hire for.

Mentioned by our guest 

Want to Find Out More?

Will is offering a FREE 15-minute call for ADHD-ish listeners to jumpstart your “Automate, Delegate, Eliminate” journey. And if he doesn’t blow your mind, he’ll give you a $50 Amazon gift card. (Spoiler: it never happens!)

Book your call now, for listeners of ADHD-ish only: EntrepreneursApprentice.com/adhd-ish/


Don’t forget to subscribe/follow the podcast, and leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.


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

Diann Wingert

Former psychotherapist and serial business owner turned business coach for ADHD-ish creatives, entrepreneurs and small business owners.

https://www.diannwingertcoaching.com
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