In this episode of the Weekly Wrap-Up, Olivia and Jenny reflect on their week, sharing personal updates, business insights, and reflections on growth and resilience. They kick off the episode by talking about the importance of having an agenda and how the weather can shape their productivity and mood. Jenny shares the experience of buying their first coffee table for their apartment, navigating the quirks of furnished UK apartments, and the satisfaction of finding sustainable, used furniture. This sparks a broader conversation about the joys of home furnishings and the unexpected challenges of home maintenance, especially when dealing with landlords and inherited items from previous tenants.

Olivia discusses her newfound love for her walking pad, highlighting how walking has become a lifestyle change that significantly improves her productivity and mental health. They both reflect on how walking has become a key part of their daily routines, boosting not only their physical health but also their creative energy during long workdays. They touch on the idea of small wins, like finding the perfect pair of jeans after years of searching, and how these moments signify personal growth and confidence.

The conversation takes a serious turn as they address the issue of content theft and plagiarism, highlighting Olivia's recent experience with a man stealing her words on social media. They emphasize the importance of protecting one's work and the unsettling responses Olivia received when addressing the issue. This sparks a discussion on kindness in digital spaces, the importance of empathy, and how being mean online accomplishes nothing positive.

They also discuss the significance of healthcare proxies, especially for young adults and college students, sparked by their recent conversation with Shawnee Baker about her daughter Baylie Grogan. This leads to plans for Fresh Starts to host a series of workshops focused on organizing crucial documents like healthcare proxies, wills, and financial plans.

Olivia and Jenny celebrate the launch of the Divorce Education Library on Fresh Starts Registry, a comprehensive, searchable resource filled with 50+ commonly asked questions about divorce. They express their commitment to providing free, accessible divorce education and outline plans for its continued expansion.

They wrap up with reflections on growth, the importance of community support, and the joy of finding just the right things—whether it’s a piece of furniture or a comfortable pair of jeans. They also tease the launch of How Does She Do It All?, their new podcast celebrating single and solo motherhood, which will drop its first four episodes this weekend.

It began with a mother’s intuition, an uneasy text from her daughter, and a phone call that would shatter the world as she knew it. In this unforgettable episode of A Fresh Story, Shawnee Baker walks us through the life-altering days that followed a tragic accident involving her daughter Baylie Grogan, a brilliant pre-med student with her entire future ahead of her. As Shawnee and her husband raced to Miami from a remote sailboat off the coast of Maine, they were plunged into a nightmare of trauma, legal barriers, and helplessness—held back not just by grief, but by a medical system that refused to acknowledge her as her daughter’s legal advocate due to the lack of a healthcare proxy.

What followed was a month-long battle for truth, agency, and peace. Shawnee shares how she navigated the heartbreak of watching her daughter remain unresponsive in a hospital bed, denied access to toxicology results, second opinions, and even basic updates on her daughter’s condition. With fierce love and resilience, she fought for Baylie’s right to be released from a life she had once said she never wanted—one without consciousness or freedom. This story is not just about a mother’s worst fear come true—it’s about the laws that failed her, the signs Baylie left behind, and the sacred, painful work of letting go.

But this is also a story of new life. Amid unimaginable loss, Shawnee gave birth to two daughters—both conceived through IVF and wrapped in the spiritual echoes of Baylie’s presence. With a renewed mission, Shawnee now leads the Baylie’s Wish Foundation, advocating for college safety, digital healthcare proxy access, and systemic transparency. This episode is a reckoning with maternal love, legal injustice, and the powerful belief that healing can begin—even when it starts with heartbreak.

Learn more about Baylie’s life at: https://www.baylie.com/

In this week’s jam-packed episode of The Weekly Wrap-Up, Olivia and Jenny catch you up on all the behind-the-scenes wins, woes, and wisdom. From award nominations to media features to the eternal struggle of finding a summer camp that actually has spots left, this episode is equal parts celebration and commiseration.

Jenny shares the thrill of a long-awaited breakthrough—years in the making—and Olivia spills the tea on what really makes a great media pitch (hint: it’s not just vibes, it’s good email copy). The sisters celebrate their friends’ publishing milestones, reflect on the mess and magic of parenting, and remind us that growth doesn’t follow a timeline—or a Pinterest-worthy blueprint. They also reveal their weekly “rose and thorn,” and end with a reminder that it’s okay to do things your own way. Because, truly, there are no rules—just fresh starts.

✨ This episode includes:

• A breakthrough Jenny thought might never happen
• Olivia’s media moment + the underrated power of a good email
• Summer camp planning = chaos + spreadsheets + tears
• Why tiny progress is still progress
• A rose, a thorn, and a reminder that success doesn’t follow a script

Tune in for laughs, insight, and sisterly chaos—and don’t forget to vote for us in the podcast awards! VOTE HERE: https://www.quillpodcasting.com/qpa/quill-podcast-awards

🎧 Listen wherever you get your podcasts

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Welcome to Weekly Wrap-Up with Olivia and Jenny!

This week, Olivia and Jenny are pulling back the curtain and letting you all the way in! 🎤✨

Listen in as they chat about the real story behind launching this podcast idea (spoiler alert: it started with a casual convo and a big dream), the highs and lows of running a bootstrapped startup, and why community feedback literally shapes everything they do.

They’re spilling all the juicy details on:

• How running a business together sometimes feels like emotional Jenga (but with more coffee and memes).
• Why affirmations aren’t just “cute quotes” in their newsletter — they’re a major vibe.
• The panic moments behind the scenes and how they manage to stay (mostly) calm.
• Their love/hate relationship with reels and how they leaned hard into them to grow their online world.
• The honest, hilarious story involving Elvis (the cat) that had them (and us) cracking up.
• Open office hours, audience connection, and what happens when you actually listen to your community.
• Manifestation tricks, creative chaos, and what’s next
• The latest scoop on their books and updates on their literary agent.
• What they accomplished this week at Fresh Starts (hint: it’s giving growth and gratitude).
• The real highs and lows of their week — because business (and life) isn’t just highlight reels.
• And of course, they wrap it all up with their Weekly Wisdom — a little something to inspire you to keep moving forward, no matter what.

✨ Questions for you!

Olivia and Jenny want to know:

• Have you ever had a lymphatic massage? (They have thoughts.) 💆‍♀️
• What should we do with A Fresh Start to the Day newsletter? (Help us shape the future!) 💌

🔥 Gossip you don't want to miss: Listen to this episode as they spill the details on who’s always on, why Olivia feels organized in a very specific way, the most honest conversation Jenny’s ever had, why making things fun is basically their secret weapon, and the behind-the-scenes drama (and excitement!) of their writing journey.

Tune in, laugh with them, and leave feeling like you just had a late-night catch-up call with your besties. 💬💖

🔗 Check out Fresh Starts Registry:

The first & only divorce registry + support platform ➡ https://www.freshstartsregistry.com/

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When Trystan Reese received a call from a social worker about two toddlers in need of a home, he and his partner made a decision that would change everything—they said yes. What followed was a beautifully complex journey into parenthood as a transgender man, one shaped by love, learning, and the fierce desire to build a family rooted in connection. In this moving episode, Trystan shares the raw truth of what it means to step into fatherhood unexpectedly, the realities of parenting in a world that doesn’t always recognize your family, and the emotional weight—and joy—of keeping siblings together through adoption.

From navigating societal perceptions to advocating for his children's needs in educational systems, Trystan opens up about the challenges that come with being a trans parent in a non-normative family structure. He speaks to the incremental nature of change within the trans community, and the power of community support in weathering both personal and political storms. Through tender reflections on blended family dynamics, teenhood, and partnership under pressure, Trystan brings a deeply human voice to the layered experience of LGBTQ+ parenting.

This episode isn’t just about one family—it’s a reflection of many. It’s about redefining what parenthood looks like, reshaping narratives around trans identity and family creation, and recognizing that support, advocacy, and love are the cornerstones of every kind of family. Whether you’re parenting through challenge, creating a family that looks different, or simply seeking stories that honor both the struggle and the triumph, Trystan’s journey will leave you deeply moved and powerfully seen.

Check out Trystan Reese’s book, How We Do Family: From Adoption to Trans Pregnancy, What We Learned about Love and LGBTQ Parenthood.

Check out Trystan’s website: https://collaborate.consulting/trystan-reese

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The first & only divorce registry + support platform ➡ https://www.freshstartsregistry.com/

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Olivia Howell:

Welcome back to A Fresh Story! This season, we’re diving into what makes a family—blended, chosen, unexpected—and we’re thrilled to be joined today by someone incredibly special. Trystan Reese is a transgender man, a father of three, and an advocate who’s been shaping the cultural conversation around LGBTQ+ family life for years. I first connected with Trystan when I was doing marketing for a gender-neutral children’s clothing company and instantly thought, this is the perfect family to work with. We’ve been internet friends ever since, and when we started planning this season, Trystan was the first name on our list.

Trystan Reese:

Thanks so much for having me. I live in Portland, Oregon, I’m a dad to three incredible kids, and I’m also a small business owner. My journey into parenting started when my partner and I—just a year into our relationship—got a call from a social worker about his sister’s kids. They were being removed from their home, and if we didn’t step up, the kids would likely be separated and adopted into different families. We were 24 and 26 at the time, living in a one-bedroom apartment, and suddenly we were parenting a one- and three-year-old.

Jenny:

That’s such a huge shift—from new relationship to full-on parenting, overnight.

Trystan:

Absolutely. It was a...

When Lorraine Connell stepped into the classroom, she didn’t expect her most profound lessons on leadership to come from the very students she was there to guide. But over the years, it became clear: the traditional model of leadership—titles, hierarchy, perfection—wasn’t serving the teens she worked with. In this episode of A Fresh Story, Lorraine, a seasoned educator and Teen Leadership Coach, shares the powerful stories that led her to reimagine what leadership really looks like—and how one small act can change everything.

Through deeply personal reflections and moments that shaped her book, A Teacher’s Story: How One Act of Leadership Inspired Many, Lorraine invites us into the lives of teens who often felt invisible or uncertain, yet blossomed into leaders once someone believed in them. From a student who didn’t think she was “the leadership type” to another who quietly shaped her entire school culture, Lorraine recounts the subtle but seismic shifts that occurred when kids were empowered to lead on their own terms.

This is more than a conversation about education—it’s a wake-up call for parents, teachers, and anyone invested in today’s youth. Lorraine reminds us that leadership isn’t reserved for the loudest voice or the front row seat. It’s in the quiet confidence, the brave decisions, and the space we create for others to step into their power. If you've ever wondered how to truly support your teen or unlock their hidden potential, this episode will change the way you see the next generation.

Buy the book: A Teacher's Story: How One Act of Leadership Inspired Many by Lorraine Connell

When Olivia Howell’s life took an unexpected turn, she found herself standing at the edge of everything she thought family was supposed to be. In the aftermath of her divorce, she wasn’t just rebuilding a household—she was rebuilding an identity, a rhythm, and a new kind of love for her children and herself. In this episode of A Fresh Story, Olivia shares how she not only survived one of the most challenging chapters of her life, but slowly, intentionally, began to thrive in it.

With honesty and heart, Olivia invites us into the world she created with her two sons—a modern nuclear family grounded in laughter, rituals, and unconditional support. She opens up about the early days of motherhood marked by gestational diabetes and postpartum depression, the transition from teacher to entrepreneur, and the everyday magic found in sibling bonds and grandparent hugs. Through the cracks of what was lost, she built something beautifully untraditional and deeply rooted in authenticity.

This is more than a story about parenting—it’s a story about choosing joy in the middle of grief, about holding space for the mess and the miracles. Olivia shows us how traditions can anchor a family, how support systems carry us through, and how the definition of family expands when we allow ourselves to live without judgment. If you've ever wondered whether you could make it through your own fresh start, Olivia's story is proof that not only can you survive—you can bloom.

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The first & only divorce registry + support platform ➡ https://www.freshstartsregistry.com/

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What happens when love finds you across an ocean? In this episode of A Fresh Story, Olivia Howell sits down with her sister, Genevieve Dreisen, to talk about the beautifully complex journey of building a life—and a family—across continents. From a chance meeting in Scotland to the quiet triumphs of long-distance love, this is a story that blends vulnerability, resilience, and deep-rooted connection.

Genevieve opens up about the raw, emotional truth behind maintaining a relationship with her now-partner, Thomas, through the chaos of time zones, cultural differences, and immigration logistics. It's not just about plane tickets and paperwork—it's about staying grounded in love, trusting your instincts, and finding ways to grow as a team, even when miles apart.

As the conversation unfolds, we’re reminded that building a family isn’t always linear. It’s layered with intention, communication, and courage. Genevieve's story is not only about romance, but about choosing your people, over and over again—even when the world makes it complicated.

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🔗 Check out Fresh Starts Registry:

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