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Every founder hits a moment where the thing that got them here stops working. Usually it shows up as burnout, a stall, or the creeping sense that the whole operation is riding on your back. Debbie Simmons knows that moment better than most, because hers nearly took her out.

Debbie is the CEO of AnchorPoint and the mind behind a framework she calls the architecture of trust. She built a multimillion-dollar organization from nothing, running on control, hustle, and urgency. It worked—right up until her body shut down and handed her a lesson she couldn't outwork.

Turns out the thing she thought was her greatest strength was quietly capping everything she built.

What she had to face about her own role in the company is where this conversation gets uncomfortable—and honest. She ended up rebuilding the whole thing from the inside out, starting with herself.

If you've ever felt like the whole operation rides on your back, you already know the pull she's describing. The hard part is what she learned to do about it.

The company that only runs on you can only grow as far as you can carry it. Debbie found a way past that ceiling, and it's worth hearing how she did it.

🎧 Listen now and discover how to build a company that grows beyond you.

If you’d like to be a guest on our Hello Chaos Podcast, ​click here​ for more information and to sign up. We look forward to connecting with you soon!

If you know another founder or creative who would benefit from being part of the OrangeWIP community, invite them to subscribe and explore more inspiring founder stories and resources built for entrepreneurs. OrangeWIP shares real, raw, and honest stories—the unvarnished truth of what it means to build something from the ground up. It’s why our mantra is Where A-ha! Meets Oh, sh*t.TM It’s 100% free and gives founders access to a one-stop content hub designed to inform, inspire, and connect.

How Jennifer Aniston’s LolaVie brand grew sales 40% with CTV ads

For its first CTV campaign, Jennifer Aniston’s DTC haircare brand LolaVie had a few non-negotiables. The campaign had to be simple. It had to demonstrate measurable impact. And it had to be full-funnel.

LolaVie used Roku Ads Manager to test and optimize creatives — reaching millions of potential customers at all stages of their purchase journeys. Roku Ads Manager helped the brand convey LolaVie’s playful voice while helping drive omnichannel sales across both ecommerce and retail touchpoints.

The campaign included an Action Ad overlay that let viewers shop directly from their TVs by clicking OK on their Roku remote. This guided them to the website to buy LolaVie products.

Discover how Roku Ads Manager helped LolaVie drive big sales and customer growth with self-serve TV ads.

The DTC beauty category is crowded. To break through, Jennifer Aniston’s brand LolaVie, worked with Roku Ads Manager to easily set up, test, and optimize CTV ad creatives. The campaign helped drive a big lift in sales and customer growth, helping LolaVie break through in the crowded beauty category.