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/

This week on AND/BOTH, I’m joined by Nomiki Petrolla, founder of Theanna and a mother of four who is reshaping what early-stage entrepreneurship can look like for women in tech.

Nomiki has spent 15 years in the tech world, sitting beside founders, engineers, and venture-backed teams, often as the only woman in the room. That experience eventually led her to build Theanna: a platform designed to support women tech founders from idea to launch.

In this episode, we talk about:

• Why women are turning to entrepreneurship not out of ambition alone, but out of a desire for agency
• The realities of building a startup with four young kids
• How AI is completely changing what’s possible for early-stage founders
• Why venture capital isn’t the only — or even the most aligned — path for most entrepreneurs
• The difference between building your first business for money and your later ones for meaning
• How motherhood sharpens clarity, decision-making, and boundaries
• What Nomiki is noticing about the next wave of women building tech
• Sustainable entrepreneurship vs. the unicorn mythology we’ve all absorbed

It’s a conversation about choosing your own path, understanding your season, and building something that fits your actual life, not a version of life you’re supposed to pretend you have.

Connect with Nomiki:

Instagram, TikTok, LinkedIn: @nomikipetrolla

Theanna: @theannaio

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/