Support AND/BOTH: Help us offset production costs while we're growing

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/

Support AND/BOTH: Help us offset production costs while we're growing

In this episode of the AND/BOTH podcast, Ashley sits down with Mary D’Agostino, mother of five, grandmother of seven, intuitive healer, and author—to explore the evolving identity of motherhood across decades. As the show’s first grandmother guest, Mary brings a grounded, wisdom-filled perspective to the conversation, touching on everything from teen pregnancy and single motherhood to building a life that reflects your truest self. With warmth, candor, and a touch of humor, Mary invites listeners to pause, reflect, and trust their inner voice through every season of life.

What we discuss:

• What it means to create a life that truly belongs to you
• How motherhood evolves across generations—and what stays the same
• The importance of listening to your intuition, especially when the world gets loud
• Why the stories and support of those ahead of us matter so deeply
• How generational healing, grief, and caregiving shape identity
• The power of saying a firm “no” when something doesn’t resonate
• Ways to center yourself during life transitions—without “burning it all down”
• Why showing up for yourself is showing up for your family
• How Mary ended up sharing her story on Oprah (!)
• How modern motherhood can reclaim agency without the pressure to perform

Connect with Mary D’Agostino:

Website: www.marydagostino.com

Be a guest on the podcast!:

• Visit andbothpodcast.com to apply to be a guest

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/

Support AND/BOTH: Help us offset production costs while we're growing

In this behind-the-scenes solo episode, Ashley offers a much-needed update and peek into what’s happening on and off the mic. From wrapping up Season 7 and kicking off Season 8 with a brand-new roundtable series, to pressing pause on summer recording and launching a care logistics platform years in the making—this episode is full of transitions, clarity, and new beginnings. Ashley also shares the personal “why” behind Dovetail, her care coordination tool built from years of experience as an OT and caregiver advocate.

What you’ll learn:

• Why Season 8 is already shaping up to be the biggest yet
• The story behind the new Roundtable Series (and how it came to be)
• What summer looks like when you’re running a business and parenting
• Why the podcast recording calendar is going dark until September
• A peek into Ashley’s changing season of life—with all kids headed to school
• The origin story of Dovetail, a care logistics platform built for family caregivers
• How Ashley’s work as an occupational therapist shaped the platform’s mission
• Why care planning needs to start before crisis mode hits
• The demographic time bomb facing the caregiving system
• How Dovetail aims to make caregiving more collaborative, connected, and sustainable

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/