Dana Bahr started her Pinterest marketing business in 2020 with her laptop on an Amazon box, a baby in a carrier, and an office manager job she hadn’t quit yet. She went full time two years later. She now has five kids, a twelve-year-old who schedules client content, and a very clear philosophy: build slow, build sustainable, and build something that lets you wander.

In this conversation, Ashley and Dana talk about why Pinterest is a search engine and not a social media platform, what the “I did it in three minutes” crowd leaves out, why visibility doesn’t have to mean being on camera, and what it looks like to build a business that funds a life rather than consuming one.

In This Episode

• Starting a business on a lunch break with a baby in a carrier and a laptop on an Amazon box
• Two years side-by-side before going full time — and losing two clients within a month of quitting anyway
• Why the “launch in six weeks and quit your job” narrative leaves out the iceberg underneath
• What financial freedom actually means when you’re a single mom of three — stability, a savings cushion, and the ability to wander
• Pinterest as a visual search engine — why it’s closer to Google than Instagram and what that means for business owners
• Why being omnipresent on every platform is a strategy for people with a team, not solopreneurs
• Content that compounds vs. content that spikes — and why you need both
• Wedding professionals and the opportunity hiding in pre-Pinterest galleries (vintage sheet cake, anyone?)
• Why visibility doesn’t have to mean being on camera — and how Dana got confident enough to show up anyway
• The twelve-year-old who now schedules Pinterest content for three clients and earns money from the business
• The Style Pin Collection membership — thirty pin graphics a month, plug-and-play, forty-seven dollars
• The Pinterest strategy intensive — ninety-day content calendar built from your existing assets
• Building slow and sustainable on purpose — automations, systems, and not sitting at the desk after 4pm
• Not everything is Pinterest perfect — and what actually goes into the before

Quotes From This Episode

“I wanted a lot of different variations of freedom. Time freedom being the majority of it because I’m very wander-filled.”

— Dana Bahr

“Visibility doesn’t have to mean being on camera. It is possible to grow a business and not keep your face.”

— Dana Bahr

“It’s the tip of the iceberg that everyone sees — do it in three minutes. But underneath that iceberg is a lot of work that got you to that place.”

— Dana Bahr

“Not everything is Pinterest perfect. And if it is Pinterest perfect, there is a whole lot that went into getting it perfect.”

— Dana Bahr

“The idea that you quit your job and just walk outside with a sign and someone hands you a hundred thousand dollars is Looney Tunes.”

— Ashley Blackington

Find Dana

• Instagram: @danas.desk.nc
• Podcast: The Unapologetic Pinner
• Style Pin Collection membership: $47/month — find via Instagram or The Unapologetic Pinner

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/

Lana Pummill started her business in 2019 charging twelve dollars an hour. In 2021, her marriage ended when the twins were three months old, and that business — scrappy and underpaid as it was — became the thing that made leaving possible. She said it directly: without it, she wouldn’t have had the financial means to get out.

She’s been building ever since. From her mom’s house. From the food bank line at six in the morning. Through a hail mary cold email that changed the direction of everything. In this conversation, Ashley and Lana talk about what it looks like to build a business when you’re starting from zero, why financial independence isn’t a luxury for women in hard situations, and what the pivot from survival mode to actual freedom looks like in real time.

In This Episode

• Single mom of four — a twelve-year-old, a ten-year-old, and boy-girl twins — and how that shapes everything
• Starting a business in 2019 for twelve dollars an hour — and the awkward conversation that follows when you undercharge for a year
• The marriage ending when the twins were three months old — and why having a business made leaving possible
• Living with her mom, going to the food bank at six in the morning — what the early years actually looked like
• The hail mary cold email — how responding to a newsletter got her in front of the right person at exactly the right time
• Why brutally honest networking lands with the right people — and why that’s the whole point
• The pivot from social media scheduling to cold pitching to consulting — and why the business keeps finding its own shape
• AI — the good, the cold, and why treating it like a rough draft is smarter than treating it like a shortcut
• Why you can’t outsource the human voice and what happens when you try
• The Water Llama hydration app and what it says about who’s actually designing these things
• The McDonald’s parking lot breakdown — an hour and fifteen minutes from home with four kids, a hundred degrees, and a car that wouldn’t start
• What the freedom she built the business for actually looks like now — and why consulting is getting her closer
• Her long-term goal: building something for moms who are financially stuck and need a way out
• Why you have to figure out you first before the tools and platforms can help

Quotes From This Episode

“If I wouldn’t have had my business, I wouldn’t have had the financial means to get out of the marriage that I was in.”

— Lana Pummill

“I was at a food bank at six in the morning because I couldn’t get groceries.”

— Lana Pummill

“It all comes down to whether you still believe in it or not. If you enjoy what you’re doing, ’cause I really do love what I’m doing.”

— Lana Pummill

“Treat it like your rough draft.”

— Lana Pummill (on AI)

“You have to figure out you first. And then you can go apply the tools and platforms and all that stuff.”

— Ashley Blackington

Find Lana

• LinkedIn: Lana Pummill
• Website: lanapummill.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/

Lisa Avila spent fifteen years in the wine industry, left to do migrant Head Start and advocacy work with families the system was failing, quit when COVID made the impossible impossible, and built a business strategy and nonprofit strategy practice on the other side of all of it. She works mostly with women. The question they all arrive with is the same one she had to answer for herself: now what?

In this conversation, Ashley and Lisa talk about the nonprofit trap — the idea that wanting to make an impact means you have to be a martyr about it — why women who help people deserve to make real money doing it, what it’s like to be sandwiched between kids and aging parents at the same time, and what the next right step looks like when you’ve spent decades outpouring and finally have some space to ask what you actually want.

In This Episode

• Mom of three boys, fifteen years in the wine industry, migrant Head Start director — how Lisa got here
• The COVID moment that made her quit — and why her boss didn’t understand until she had kids of her own
• The nonprofit trap — why women who want to make an impact keep being told it has to be unprofitable
• Why you can make a lot of money and still help people — and why we need to stop acting like those are opposites
• The golden handcuff — when the organizations saying “we support women” require them to be nonprofits to qualify
• What migrant Head Start actually looks like — and what happens to student records when families move across the country
• The political reality of advocacy in a conservative agricultural town in California
• Red cards, rights, and what’s changed for immigrant families since COVID
• The Panini generation — being sandwiched between kids and an eighty-one year old mother, in perimenopause
• Three boys 17, 19, and 20 — what it’s like when two come home from college for the summer
• The client going global with her nonprofit — four years from a Facebook group to international impact
• The client who sat on her cancer journey poems for seven years and finally published them
• What the “now what” looks like — the question every woman Lisa works with is asking
• Non-negotiables: a bath every night, coffee, a walk, girlfriends who keep it real
• The airstream barbecue and dive bar tour — her plan for empty nest life

Quotes From This Episode

“Why can’t we make a lot of money and still help people? There’s nothing wrong with that. Why do we have to wear our heart on our sleeve and be martyrs?”

— Lisa Avila

“I’m not putting it out there that I only work with mothers, but it’s just this energy we’re drawn to — this now what.”

— Lisa Avila

“I was checking boxes for decades. Just outpour, outpour, outpour. And what did it get me?”

— Lisa Avila

“Your impact can’t just be outpouring. It has to be self-sustaining. Otherwise that’s how everyone flames out.”

— Ashley Blackington

“I am physically hot and I am pressed for time and patience and all of the things.”

— Ashley Blackington (on the Panini generation)

Find Lisa

• LinkedIn: Lisa Avila
• TikTok: @LisaAvilaCo

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/

Lindsey Elliott spent seventeen years at a leading outdoor footwear brand — starting junior, ending as Global VP — and two months ago she left to build Product & Presence, her own company focused on brand visibility and public speaking coaching, with a particular soft spot for helping women show up in big rooms without the weight of everything they were never supposed to be carrying in the first place.

In this conversation, Ashley and Lindsey, who have been friends since University in Halifax, talk about what it looks like to leave a twenty-year career, why the safety net you build yourself is the only one that’s real, how partnership and parenting look different when there are no predetermined roles, and why making your kid breakfast every morning might be the best metric for success nobody talks about.

In This Episode

• How Ashley and Lindsey met — Lyle House, Halifax, a hockey stick, and Grey’s Anatomy every Thursday
• Twenty years in the outdoor industry — from retail footwear buyer to Global VP
• Why Lindsey chose entrepreneurship over the next big corporate role, even when the big roles were available
• The career coach she dismissed for years who turned out to be right about everything
• What transition looks like when you have a twelve-year-old watching how you handle it
• Product & Presence — what it is, who it’s for, and why public speaking is at the center of it
• Why the only safety net that will ever exist is the one you build yourself
• Women and financial independence, why self-care needs to include financial acumen
• Being the primary financial provider in a same-sex partnership and what happens when that changes
• How the absence of predetermined gender roles changes what partnership and parenting actually look like
• The woman who couldn’t get out of her own head before a keynote and what Lindsey did about it
• The backpack of garbage nobody asked for and why it shouldn’t be in the room when you’re on stage
• The lacrosse kids running summer camps instead of stocking shelves and what that says about what’s coming
• Making breakfast before getting after it and why that’s the whole point

Quotes From This Episode

“The only safety net that will ever exist here is the one that I create for myself.”

— Lindsey Elliott

“Success is not linear. And that’s not bad — it’s just important to acknowledge.”

— Lindsey Elliott

“If I get to make my son breakfast and put him on the school bus, and then I get to put in a day that’s as long as it needs to be — I’m good with that.”

— Lindsey Elliott

“There are no predetermined gender roles. So you define whatever that relationship looks like in the capacity that makes sense for you both.”

— Lindsey Elliott

“You’re not building the airplane while you’re trying to figure out how to fly the thing. Plane’s done. Pass the peanuts.”

— Ashley Blackington

Find Lindsey

• Website: productandpresence.com
• LinkedIn: search Lindsey Elliott

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/

Becky Selbie is a London-based psychotherapist who specialises in motherhood and maternal mental health — and she has a gift for taking the frameworks she uses in her therapy room and translating them into language that actually lands in everyday life.

In this conversation, Ashley and Becky cover a lot of ground: matrescence and why the word matters so much, the rule book that high-achieving women carry into motherhood that starts working against them the moment they get there, the mums who look like they’re coping but feel like they’re failing, the difference between motherhood and mothering, and why the inner critic telling you you’re not good enough isn’t your voice — it’s the noise of a culture that has never held mothers in the regard they deserve.

It’s one of those conversations that leaves you seeing yourself differently.

In This Episode

• How Becky came to specialise in maternal mental health — giving birth and thinking “how has nobody prepared me for this?”
• Matrescence — why the word matters, where it came from, and why it took 50 years to reach mainstream language
• The moment Becky heard it for the first time and ran downstairs to tell her husband
• Sharing the concept with her mother — who had her first child in the 1960s and was prescribed tranquilizers for what was actually matrescence
• Why high-achieving women struggle in motherhood more than others — and the rule book that explains why
• Mums who look like they’re coping but feel like they’re failing — and what the swan metaphor gets exactly right
• The “tab open” metaphor — why you never feel fully disconnected from your children even when you’re away from them
• Not loving every chapter — and why that has nothing to do with how much you love your kids
• The problem with parenting content on social media — theory without context, and who pays the price
• Why Becky’s clinical supervisor said “well, she will” when a client was terrified of messing up her kids — and why that was the most freeing thing she’d ever heard
• Motherhood vs. mothering — the doing versus the being, and why we’re graded on the wrong one
• The inner critic is the patriarchy — and why turning down its volume is the whole point
• What fills Becky’s bucket: creativity, building community, and the retreat she’s planning for mums

Quotes From This Episode

“Not loving motherhood doesn’t mean that you don’t love mothering. Just because you don’t enjoy bits of motherhood, there is no connection to how you feel about your kids.”

— Becky Selbie

“The inner critic is wrong. The inner critic is the patriarchy — it’s society, it’s all those messages about what motherhood should look like. And it’s nonsense.”

— Becky Selbie

“Motherhood is the doing. Mothering is the being — the relationship, the love, the knowing them inside out. But we’re graded on the doing.”

— Becky Selbie

“Even when you’re away, there’s a tab open all the time in your head. It’s just that as they get older, the tab gets smaller.”

— Becky Selbie

“Don’t compare the back end of your business to the front end of somebody else’s.”

— Ashley Blackington

Connect with Becky:

• Instagram: @_motherway_
• Website: motherway.co.uk

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/