AND/BOTH Podcast - Real Conversations, Shared Experiences, and the Community You've Been Missing

In this episode, host Ashley sits down with Nikki Weiss- digital thanatologist, project manager, and founder of Endevo, for a candid, eye-opening conversation about the intersection of caregiving, death planning, and our increasingly digital lives. Nikki brings not just professional expertise, but hard-won personal experience: she lost her father at 11, became her mother's primary caregiver at 21, later cared for her grandmother through dementia, and is now supporting her daughter as she navigates a caregiving role for her fiancé, diagnosed with stage four brain cancer.
Together, they tackle the questions most families avoid and make the case for why starting the conversation early isn't morbid; it's one of the most loving things you can do.
In This Episode
What thanatology is and why the "digital" specialization matters more than ever
Nikki's personal caregiving journey: losing both parents young and what that shaped in her
The "panini generation" why today's sandwich generation feels more squeezed than ever
Why most caregivers wait until crisis to plan and the real cost of that delay
The project management approach to end-of-life planning: de-emotionalizing the process so families can actually do it
How to build a caregiving community instead of letting one person absorb everything
The "silver wave" of late-life divorce and what it means for adult children
Digital legacy: what happens to your phone, social media, subscriptions, and photos after you're gone
Grief bots, digital avatars, and QR codes on headstones the emerging world of digital memorialization
Why you need a Digital Legacy Advance Directive alongside your will and medical POA
The Final Playbook: Nikki's framework for building a comprehensive end-of-life plan

Key Quotes
"Live fully, die ready. Carrying an end-of-life plan is like carrying an umbrella on a rainy day — if you carry it, you won't need it. If you need it, you know where it is."
— Nikki Weiss
"Death is indiscriminate. It doesn't care how old you are. We'll all die one of three ways: sudden and unexpected, a terminal diagnosis, or a long decline. You better have a plan for all three."
— Nikki Weiss
"The most humanistic experience we will all go through is death, dying, and incapacitation. What keeps me focused is this concept of human equity."
— Niki Weiss
Action Steps for Listeners
Have the conversation before a diagnosis forces it. Pick a low-stakes moment (Nikki suggests the day after Thanksgiving).
Know the three core legal documents: will/estate plan, power of attorney, and medical advance directive.
Add a Digital Legacy Advance Directive — designate someone to manage your digital accounts and assets.
Take inventory of your digital life: phone passcodes, social media accounts, recurring subscriptions, online financial accounts, and stored photos.
Build a caregiving team — no single person should carry the full load. Identify who handles what before it becomes urgent.
Visit finalplaybook.com to start building your own end-of-life plan.

Connect with Niki
https://official.endevo.life
https://www.youtube.com/@DigitalLegacyPodcast
https://www.endevo.life/

What does it look like to make a huge life pivot in the middle of raising small kids—and during a global pandemic?
In this episode, Ashley talks with Danielle Alvarez, a mom of three who walked away from the business she’d spent years building and went to law school with a six-, five-, and one-year-old at home. Now a corporate attorney with her own small business-focused firm, Danielle shares what it really looked like to start over, and how she made room for ambition without sacrificing everything else.
This is a conversation about redefining success, letting go of timelines, and figuring out what actually feels right—instead of chasing what’s expected.
Whether you’re in the middle of a pivot, thinking about one, or just trying to hold your own dreams alongside your real life, this one’s for you.
We talk about:
– Making a big life change when the timing isn’t ideal
– Doing things differently than the “traditional” path
– Ambition, burnout, and the pressure to do it all
– Parenting while building something new
– Starting a business that reflects your values
– Letting go of old expectations (and other people’s opinions)
Connect with DanielleLinks + Resources:
Website: sblslaw.com
LinkedIn: Danielle Alvarez, Esq., MBA
Email: [email protected]

Connect with Ashley:
Website: https://www.ashleyblackington.com
Podcast website: https://www.andbothpodcast.com/
Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822
Instagram: @mydovetail.app
LinkedIn: https://www.linkedin.com/in/ashleyblackington/

Burnout doesn’t always show up as falling apart.
Sometimes it looks like holding everything together for too long.
In this episode of AND/BOTH, Ashley sits down with Sarah Smith — founder of Iconoclast Innovations, mom of two, and self-described iconoclast — for a deeply honest conversation about motherhood, mental health, and rebuilding yourself after burnout.

Sarah shares her experience navigating postpartum anxiety and depression during the pandemic, being laid off multiple times, starting a business while pregnant, and learning how to advocate for herself in a system that often loses sight of mothers after birth.

Together, Ashley and Sarah talk about identity shifts after becoming a parent, why burnout is information (not failure), how community and support can be lifesaving, and what it really means to choose yourself and your family — even when it’s messy.

This episode is for anyone who has ever wondered: Why does this feel so hard — and am I the only one struggling?
You’re not alone. And you’re not doing it wrong.

Connect with Sarah:
Website: https://iconoclastinnovationsllc.com/

Connect with Ashley:
Website: https://www.ashleyblackington.com
Podcast website: https://www.andbothpodcast.com/
Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822
Instagram: @mydovetail.app
LinkedIn: https://www.linkedin.com/in/ashleyblackington/

What do you get when you mix startup experience, mother-of-a-newborn energy, and a deeply broken system for working parents?
You get Recess.

Amy Kiska is the co-founder and CEO of Recess, a platform parents are calling “the Booking.com of kids’ activities.” In this episode, she joins Ashley to talk about building a tech company while parenting a newborn, the invisible mental load of managing care coverage, and the bold decision to solve a problem most people don't recognize until they’re drowning in it.

Amy shares what it took to launch Recess, including fundraising 10 days postpartum, and how she’s designing a business that helps families and providers thrive.

This conversation covers:
The truth about camp registration (and why it feels like the Hunger Games)
How Recess supports both parents and activity providers
The underestimated power of mom-founders
Building a company without pretending you’re doing it alone
And why some of the best ideas are born in the bath 🛁

Connect with Amy:
Website: hello-recess.com
Social media @hellorecess on Instagram and TikTok

Connect with Ashley:
Website: https://www.ashleyblackington.com
Podcast website: https://www.andbothpodcast.com/
Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822
Instagram: @mydovetail.app
LinkedIn: https://www.linkedin.com/in/ashleyblackington/

What if fertility and reproductive health were treated like skincare or mental health, something we talked about before it became a crisis?
In this episode of AND/BOTH, Ashley sits down with Sam Diamond, co‑founder of Bird & Be, to talk about building a clinically‑backed fertility company in the middle of a global pandemic, and why proactive, inclusive fertility care matters more than ever.

Sam shares the deeply personal experiences that shaped Bird & Be’s mission, including miscarriage, fertility treatment, and the gaps she saw in education, access, and support for both women and men. Together, Ashley and Sam explore why fertility conversations are still too reactive, how male fertility remains stigmatized, and what it looks like to build a company rooted in science, ethics, and care.

They also talk about:
Launching a startup during COVID — and why at‑home testing was harder than expected
Why male fertility must be part of every fertility conversation
The shift from “cute” branding to clarity as Bird & Be entered retail
What it took to land Bird & Be in Ulta — and why placement mattered
How early education and testing can shorten or even prevent long fertility journeys
Why women are not “small men” — and how research still fails women’s bodies
Blending motherhood and entrepreneurship without pretending it’s balanced

This is a conversation about health, agency, science, and building systems that actually support people, not just sell to them.

Connect with Sam:
Bird&Be site: https://birdandbe.com/

Connect with Ashley:
Website: https://www.ashleyblackington.com
Podcast website: https://www.andbothpodcast.com/
Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822
Instagram: @mydovetail.app
LinkedIn: https://www.linkedin.com/in/ashleyblackington/