AND/BOTH Podcast

• 83. Making Room for the Messy Middle: Parenting, Business & Identity Shifts with Amy Leclerc from Sit Still Kids

  Support AND/BOTH: Help us offset production costs while we're growingIn today's episode, Ashley chats with Amy LeClaire, co-owner and president of franchising at Sit Still Kids, shares her journey from magazine publishing in NYC to scaling boutique fitness with Bar Method to revolutionizing the children's haircare industry. In this conversation, Amy discusses how she's built multiple franchise businesses while raising two kids, the importance of work-life integration over balance, and why she believes there's a huge untapped market in specialized services for children. She opens up about navigating the messy middle of parenting teens, the changing landscape of education and career paths, and how taking exceptional care of yourself isn't selfish—it's essential for showing up as your best self in all areas of life.What You'll Learn• How to identify and capitalize on underserved markets (like the 1:92,500 ratio of kids' salons to children under 12)• The difference between building a business versus building a brand, and why that distinction matters for scalability• How to navigate major career transitions while growing a family without sacrificing either• Why work-life integration beats work-life balance, and how companies like Bar Method pioneered flexible work cultures long before it was trendy• The reality of franchise development and what it takes to scale from one location to 150+ nationwide• How to maintain your entrepreneurial edge while co-parenting teens who are figuring out their own paths• Why the traditional college-to-career pipeline might not be the best option for every kid (and the alternatives worth considering)• The importance of modeling resilience and showing your children that adults are still learning and growing too• How to practice "exceptional self-care" as a busy parent and business owner without guilt• Why intuition is an underrated but essential business skill, and how to develop your ability to spot trends before they become mainstreamConnect with Amy LeClaireWebsite: sitstillkids.comInstagram: @sitstillkidsSit Still Kids is expanding to New England with locations opening in the Boston area and Providence!Connect with Ashley:Website: https://dovetaildesigns.coPodcast website: https://www.andbothpodcast.com/AND/BOTH Community: https://www.andbothpodcast.com/andboth-communityDovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/formSocial:Instagram: @dovetailappFacebook: https://www.facebook.com/dovetaildesigns.coLinkedIn: https://www.linkedin.com/in/ashleyblackington/

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• 81. From Basement to Brand: How Julie Cole, Mom of Six, Built Mabel’s Labels Without Losing Herself

  Support AND/BOTH: Help us offset production costs while we're growingAshley Blackington welcomes Julie Cole, co-founder of Mabel’s Labels, for a rich conversation on motherhood, entrepreneurship, and building a life and business that actually works. Julie shares her journey from lawyer to mom of six to label mogul, and all the messy, meaningful moments in between. She opens up about flexible work, raising independent kids, and the unfiltered truth of growing a business out of a basement into a beloved international brand. Expect inspiration, humor, and hard-won wisdom from someone who’s done it all, with a label for literally everything.What you’ll learn:What inspired Julie to leave law and launch Mabel’s Labels with her sistersHow entrepreneurship evolved alongside raising six kids (yes, six!)The mental load of motherhood and how to protect your identity through itReal talk on flexibility, burnout, and the myth of #BossMomThe role of community, visibility, and mentorship in building a sustainable businessQuestions answered in this episode:How do you balance entrepreneurship with parenting, especially in the early years?What conversations and sacrifices are required when leaving a traditional career?How did Julie and her co-founders grow Mabel’s Labels without social media?What lessons does she share with new founders and mompreneurs today?How can women show up as leaders and still prioritize their families?Connect with Julie Cole:Website: mabelslabels.com/juliecoleInstagram: @juliecoleLinkedIn: Julie ColeBook: Like a Mother: Birthing Businesses, Babies, and a Life Beyond LabelsConnect with Ashley:Website: https://dovetaildesigns.coPodcast website: https://www.andbothpodcast.com/AND/BOTH Community: https://www.andbothpodcast.com/andboth-communityDovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/formSocial:Instagram: @dovetailappFacebook: https://www.facebook.com/dovetaildesigns.coLinkedIn: https://www.linkedin.com/in/ashleyblackington/

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• 79. From Lost to Found: A Roundtable on How Moms are Redefining Identity & Belonging (Roundtable #2)

  Support AND/BOTH: Help us offset production costs while we're growingIn today's roundtable episode, Ashley and Erin chat with two women building deeply human solutions for working moms: Kate Tovsen, founder of The Society of Working Moms and Kate Tovsen Media, and Alli Kushner, founder of BeeKyn, a soon-to-launch playdate matching and scheduling platform for modern families.This honest, wide-ranging discussion explores why loneliness is a shared, but rarely talked about part of motherhood, especially for those balancing careers, businesses, and caregiving. Each guest offers a unique lens into how accessible community, supportive tools, and even digital innovation like asynchronous connection or curated online spaces can create more room for joy, help, and human connection in this messy middle of parenting.Whether you’re raising toddlers or teens, running a company or running late to pickup, this conversation will help you feel seen, and remind you that building meaningful community is possible, even in a world that feels increasingly noisy and disconnected.What you’ll learn:Why 70% of moms report feeling lonely—and what to do about itHow motherhood changes your ability to connect (and what community can look like now)Why the “right” community for you will change over timeThe difference between joining a community and staying in oneHow tech can support, not replace, real-life connectionTips for building your own support network, even in small, siloed waysHow parenting, business, and identity overlap in real-world community-buildingWhy perfection isn’t the point—starting messy is often the keyConnect with Erin: Website: https://www.pgishparenting.comInstagram: @pgishparentingPG ish podcastConnect with Kate:katetovsenmedia.comSociety of Working Moms Connect with Alli:allikushner.comBeeKynConnect with Ashley:Website: https://dovetaildesigns.coPodcast website: https://www.andbothpodcast.com/AND/BOTH Community: https://www.andbothpodcast.com/andboth-communityDovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/formSocial:Instagram: @dovetailappFacebook: https://www.facebook.com/dovetaildesigns.coLinkedIn:

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• 78. Sustainable Growth, AI Conversations with Kids, and Reinventing Your Career—with Joselyne Walter

  Support AND/BOTH: Help us offset production costs while we're growingIn 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 founderThe meaning of sustainable growth—and how to actually build a business around itHow she’s using AI to increase efficiency and reduce overwhelmWays to introduce AI tools to your kids (and have fun doing it!)Why giving yourself permission to grow slowly might be your smartest moveThe impact of being raised by immigrant parents on her entrepreneurial mindsetHow to work smarter (not harder) using tools and delegationQuestions 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.comConnect with Ashley:Website: https://dovetaildesigns.coPodcast website: https://www.andbothpodcast.com/AND/BOTH Community: https://www.andbothpodcast.com/andboth-communityDovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/formSocial:Instagram: @dovetailappFacebook: https://www.facebook.com/dovetaildesigns.coLinkedIn: https://www.linkedin.com/in/ashleyblackington/

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• 76. Behind the Mic: What’s Next for the Podcast, Parenthood, and Dovetail

  Support AND/BOTH: Help us offset production costs while we're growingIn 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 yetThe story behind the new Roundtable Series (and how it came to be)What summer looks like when you’re running a business and parentingWhy the podcast recording calendar is going dark until SeptemberA peek into Ashley’s changing season of life—with all kids headed to schoolThe origin story of Dovetail, a care logistics platform built for family caregiversHow Ashley’s work as an occupational therapist shaped the platform’s missionWhy care planning needs to start before crisis mode hitsThe demographic time bomb facing the caregiving systemHow Dovetail aims to make caregiving more collaborative, connected, and sustainableConnect with Ashley:Website: https://dovetaildesigns.coPodcast website: https://www.andbothpodcast.com/AND/BOTH Community: https://www.andbothpodcast.com/andboth-communityDovetail® App: https://airtable.com/appn6w6IWipJYIuA3/pagZys7UnECzM46iJ/formSocial:Instagram: @dovetailappFacebook: https://www.facebook.com/dovetaildesigns.coLinkedIn: https://www.linkedin.com/in/ashleyblackington/

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