I had an incredible conversation with Jess DeRose recently, and it really got me thinking about the deeper strategies behind her story in our conversation about AI, tech and building businesses.
Strategies that any entrepreneur can use to grow, and even pivot to when they need it the most. Jess’ path honestly is a masterclass in rebranding, building systems, and leveraging technology like AI to amplify impact.
But it’s not just about what she’s done, it’s about why these elements matter and how they can be applied to anyone’s business.
That’s why this week, her story is one worth going into detail on because I know you might just find yourself in this.
Jess and I met in 2017, at a private dinner held by some of our joint friends when we were in Columbus, Ohio at Lewis Howes’ Summit of Greatness event.
Val and I ended up sitting next to Jess and her husband, Mike, and we of course got to talking about the whole “why are you here, what do you do” thing.
One thing that struck me about Jess that night was she had answers way deeper than the surface-level stuff you’d expect to hear. Not knowing who I was yet she got right into what she was working on, telling me she really wanted to make a huge impact with her business-building program and was looking for a connection to Pencils of Promise (a 501c3 based out of New York).
I replied with “well that’s easy, I know the founder and I’m their fractional CTO”.
Needless to say we became friends right away.
From there we found more ways to support each-other over the years. We hired each-other, we’ve worked with each-other and we’ve both evolved when we’ve needed it the most.
I wanted to catch up with Jess on The Prompt 🔗 because I knew with the new abilities of AI and automations, there has to be more she’s doing that I could learn from as well.
When we got into our chat we talked about some seriously big perspective shifts.
Her decision to rebrand from “Jess Glazer” to “Jess DeRose” wasn’t just a surface-level change. It was a deliberate move to align her identity with her evolving vision. What struck me most was her willingness to start fresh, even creating a new Instagram account from scratch.
That’s not easy.
But it gave her the chance to rebuild with intention, focusing on authenticity and attracting the right audience. It’s a reminder that sometimes, growth means letting go of what’s familiar to create something that truly fits where you’re headed.
This got me thinking about the power of systems and automation in scaling a business.
Jess shared how she breaks down overwhelming tasks into smaller, repeatable steps, using tools like Monday to create workflows that can be duplicated and adapted. This isn’t just about saving time, it’s about creating clarity and consistency, which are essential for growth.
And when you add automation into the mix, like using Zapier to eliminate repetitive tasks, you free up time to focus on the work that really moves the needle.
Then there’s AI.
Jess is using tools like ChatGPT to brainstorm, create content, and streamline her processes.
She’s not just using AI to save time, she’s using it to amplify her creativity and open up new possibilities. This is where the real power of AI lies.
It’s not about replacing human input, but enhancing it.
The better your inputs, the better your outputs, and that’s huge for entrepreneurs looking to stay ahead.
What ties all of this together is Jessica’s approach to growth.
She’s not chasing every shiny new trend. Instead, she’s focused on iterating and improving what works, while staying deeply connected to her audience.
Her free virtual event for example, Digital Business Evolution Live Experience 🔗, is a perfect example of how she’s building authentic relationships in a world that’s increasingly automated.
It’s a reminder that even as we lean-in to technology, the human touch still matters.
This conversation left me reflecting on how these elements: rebranding, systems, automation, and AI are all connected.
They’re not just tools or strategies. They’re a mindset.
They’re about being willing to evolve, to build with intention, and to use every resource available to create something meaningful and sustainable.
I mentioned her free event, and it’s one of those opportunities that feels like a no-brainer if you’re serious about growing your business, your efforts or your impact.
This isn’t just another webinar or a quick masterclass. It’s a hands-on, interactive experience designed to help you actually make progress, not just take notes.
What I love about this event is how intentional it is.
It’s broken into three live sessions spread over two weeks, so you’re not overwhelmed with information all at once.
You’ll have time to absorb what you learn, try it out, and come back with questions. There’s also a follow-along workbook to help you apply the strategies in real time, bonus trainings, and even hot seat coaching where you can get personalized advice for your specific challenges.
The focus here is on giving you tools and strategies that work. You’ll learn how to clean up inefficiencies in your business, build systems that save you time, and tackle marketing challenges without relying on paid ads. It’s like a reset button for your work, helping you realign with what matters and create a foundation for long-term success.
And the best part?
You’ll be surrounded by a community of like-minded entrepreneurs who are all in it with you. Whether you’re just starting out or scaling something big, this is a space where you’ll feel supported and inspired.
I’m sharing this because I genuinely believe in the value of what Jess is offering. It’s free, it’s packed with insights, and it’s designed to help you take real steps forward. If you’ve been feeling stuck or unsure of your next move, this could be exactly what you need.
The first session kicks off on March 20th and we’re talking about me doing a special session in the near future.
I’ll be attending, will I see you there?
