78. Sustainable Growth, AI Conversations with Kids, and Reinventing Your Career—with Joselyne Walter

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In this episode, Ashley is joined by Joselyne Walter, a first-generation Latina business owner, marketing expert, and founder of The DIGG Agency. With a background in dispatching 36,000 truckloads a month and leading marketing efforts for some of the top companies on the Fortune 500 list, Joselyne shares her powerful journey from supply chain to C-suite to self-employment.

Their conversation dives into how she built a scalable agency rooted in sustainable growth, why she walked away from corporate leadership, and how AI is reshaping not just her work—but her parenting. From career pivots to teaching kids about tech to redefining success on your own terms, Joselyne’s story will resonate with anyone navigating ambition and real life at the same time.

What You’ll Learn:

• How Joselyne transitioned from dispatch supervisor to marketing director to agency founder
• The meaning of sustainable growth—and how to actually build a business around it
• How she’s using AI to increase efficiency and reduce overwhelm
• Ways to introduce AI tools to your kids (and have fun doing it!)
• Why giving yourself permission to grow slowly might be your smartest move
• The impact of being raised by immigrant parents on her entrepreneurial mindset
• How to work smarter (not harder) using tools and delegation

Questions Answered in This Episode:

• How do you pivot from a nontraditional career path into entrepreneurship?
• What does building a sustainable business as a mom really look like?
• How is AI changing the way marketers and entrepreneurs operate daily?
• Can AI actually support creativity, parenting, and project planning?
• What mindset shifts are needed when leaving a high-level corporate job?
• How can we teach our kids to be responsible and creative with AI?
• What does prioritization look like when you have limited time and big goals?
• What are the risks and opportunities AI brings to future generations?
• How does someone with limited formal education raise a child who leads at the highest level?

Connect with Joselyne Walter:

• Website: www.thediggagency.com

Connect with Ashley:

Website: https://dovetaildesigns.co

Podcast website: https://www.andbothpodcast.com/

AND/BOTH Community: https://www.andbothpodcast.com/andboth-community

Dovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/form

Social:

Instagram: @dovetailapp

Facebook: https://www.facebook.com/dovetaildesigns.co

LinkedIn: https://www.linkedin.com/in/ashleyblackington/