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/

In this solo episode, I’m taking a moment to pause, look back on Season 9, and share what’s coming as we head into a new year and our tenth season of the AND/BOTH podcast.

This season brought so many meaningful conversations on the mental load, the realities of modern motherhood, how we build community, what comfort and safety look like in hard seasons, and the ways we try (and often fail) to carry less than we’re used to. We also continued our roundtable series, with thoughtful, deeply resonant conversations about grief and holiday burnout that so many of you reached out about.

I talk through:

• The themes that kept surfacing across episodes
• What these conversations revealed about burnout, expectations, and the pace we’re all trying to keep
• The “colander list” moment with my friend Meg and why it hit me squarely in the chest
• What it’s been like to grow a tech company, run a podcast, and raise four kids during a very full season
• Why we’re taking a short break before Season 10
• What you can expect when we return in the new year

And I share an invitation: if you’ve listened to the show and haven’t yet heard your version of motherhood reflected, I would love to bring more voices and stories into the mix. You can submit a guest interest form at andbothpodcast.com.

We’ll be back in January with Season 10—rested, reset, and ready for the next chapter.

Wishing you a holiday season with at least one hot coffee, a moment of actual rest, and something small that fills your cup.

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 Lauryn Warnick, CEO and founder of Villain Branding. Lauryn shares how she went from film school to tech startups to leading a verbal-first brand consultancy—and how the business has grown and shifted alongside marriage, motherhood, and the many seasons real life brings.

We talk about:

• Building a business that doesn’t pretend life at home is paused
• Why B2B storytelling has more impact (and heart) than most people expect
• Working with a spouse and figuring out routines that actually work
• The pressure of being the primary income earner while raising young kids
• Moving away from “balance” and toward navigating what each season asks of you
• The Disney moment that unexpectedly reframed flexibility, boundaries, and perspective

This episode is full of the conversations that don’t always make it into the highlight reel—how we work, how we parent, and how we keep adjusting the picture as life keeps changing.

Connect with Lauryn:

Website: www.villainbranding.com

LinkedIn: Lauryn Warnick

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/

In this episode, I’m joined by Brea Starmer, founder of Lions & Tigers, a company she started after being laid off while seven months pregnant and serving as her family’s primary income. What began as survival quickly became a new way of thinking about work: flexible, skilled, sustainable, and built around real life.

We talk about the myth of stability in traditional employment, why so many women and caregivers are pushed to the margins, and how blended teams and fractional work are giving people more agency than ever before.

And of course, we talk about the real-life side of it all- parenting, logistics, exhaustion, boundaries, and the seasons where everything feels like “a lot”… and also deeply purposeful.

In this episode:

• The layoff that sparked Lions & Tigers
• How Brea built her own maternity leave through freelance work
• Why blended teams are becoming essential in enterprise companies
• How AI, caregiving, and shifting workplace norms are reshaping careers
• What it actually looks like to build a business while raising three kids
• The skill of knowing what’s worth your time (and what you can let fall through the colander)

Connect with Brea:

• Lions & Tigers: lionsandtigers.com
• Workforce Reimagined study
• Connect with Brea on LinkedIn

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/

November Roundtable: The Holiday Overwhelm Episode with Paige Connell & Allie McQuaid

The holidays are supposed to feel warm and joyful- but for most moms, they also come with nonstop logistics, emotional labor, and a running mental checklist that never really turns off. And for millennial moms especially, the expectations feel higher than ever.

In this month’s roundtable, Erin Holland (PG-ish Podcast) and I are joined by Paige Connell (@sheisapageturner) and Allie McQuaid (@millennialmomtherapist) for a conversation that goes right into the thick of it: the mental load, the pressure to make things magical, the generational friction that shows up the minute you walk into a family gathering, and the complicated mix of joy and burnout that this season brings.

In this episode we cover:

• Why the holidays hit so hard when your plate was already full in July
• The “fun mom” pressure and why it doesn't make sense, when you’re the one noticing, planning, packing, and remembering
• How early messaging around anger and emotions shows up again in motherhood
• The emotional gymnastics of blended families, divorced parenting, and juggling multiple households
• Why social media intensifies holiday expectations (and how to spot what’s actual life vs. content creation)
• What our kids really remember and why it’s almost never the expensive or elaborate stuff
• How to rethink traditions, drop the “shoulds,” and pay attention to what actually brings joy or ease
• The permission to let this year look different than last year (or any year)

It’s honest, relatable, a little funny, and full of the kind of “oh right, it’s not just me” moments that make the holidays feel a little more doable.

Listen in, especially if the season feels like a lot before it’s even started.

Connect with Paige and Allie:

Paige Connell — @sheisapageturner

Allie McQuaid — @millennialmomtherapist

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/

In this episode, I sit down with Kendra Koch, the founder of Divergently, a private community built for late-diagnosed neurodivergent women who want clarity, support, and a softer landing than the internet usually offers.

Kendra came to this work through her own late diagnosis, years spent in the Silicon Valley wellness world, and a growing sense that the tools available to neurodivergent women were either too shallow, too loud, or too overwhelming to actually use. What started as her personal search for answers eventually became Divergently- a curated, trauma-aware space built to help women understand themselves and make daily life feel less chaotic and more doable.

We cover a lot in this conversation, including:

• What it feels like to receive a diagnosis later in life
• Why so many women only start connecting the dots after their kids begin evaluations
• The emotional and logistical realities of navigating care, systems, stigma, and uncertainty
• How trauma keeps showing up in ways many of us don’t expect
• The difference between “having information” and actually being supported
• Why “just disclose at work” isn’t simple — or safe — advice for everyone
• How creating boundaries inside a community can be what makes it truly inclusive
• The small, practical shifts that make life less prickly: body doubling, environmental tweaks, lowering the bar in smart, supportive ways
• And how Kendra is building a company while raising a young child, healing, and moving at a pace that fits her real life — not the one hustle culture demands

This conversation is thoughtful, honest, and full of moments that made me rethink how we support ourselves and each other. If you’ve ever felt like something wasn’t quite adding up, or you’ve been searching for a place that feels safe and steady, you’ll feel seen here.

Where to find Kendra:

Website: joinedivergently.com

Social: @joinedivergently

LinkedIn: Kendra Koch

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/