A Fresh Story

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. 💬💖

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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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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 massive adjustment. I was raised in a home that always had kids coming and going—friends, foster kids, chosen family—so for me, it was a yes right away. My partner took a little longer to process what this would mean. They said, “If we’re doing this, it has to be stable. You have to stick with me as long as they’re with us.” That was the deal, and 13 years later, we’re still all together.

Olivia Howell:

That’s a beautiful evolution of family. And eventually, you decided to carry and give birth to your third child—Leo?

Trystan:

Yes. I was about five years into parenting when the idea of a biological child became a real possibility. In the trans community, this wasn’t shocking—trans men have been giving birth for decades. But outside that space, it felt radical. I was really clear with every journalist I worked with: I am not the first trans man to have a baby, and I don’t want to be labeled as such. What I wanted was to add nuance to the public story of what it means to be a trans parent—to show the love, the commitment, and yes, the very real challenges.

Jenny:

And your older kids—how did they react to the news?

Trystan:

Mixed reactions! Our daughter was excited. She wanted someone to teach, dress up, and boss around—which she still does. Our oldest son was more uncertain. He was worried the baby would get more love because they’d be biologically related. That’s something we worked through together, and honestly, we still do. Blended families have so many layers.

Olivia Howell:

You’re navigating all of that while doing advocacy work, raising a neurodivergent teen, and living in a world that’s increasingly hostile toward trans people. How do you keep going?

Trystan:

I remind myself that we can do hard things—and that my community has done them before. We’re still here. I lean into my ancestors’ resilience, my kids’ joy, and the belief that sharing these stories creates real change.

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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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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In the kickoff episode of A Fresh Story’s new Family Season, sisters and co-hosts Jenny Dreizen and Olivia Howell sit down to reflect on the evolution of their podcast and their ever-deepening curiosity about what truly defines a family. With over 200 episodes under their belt, the duo shares how their fascination with storytelling—and particularly stories rooted in family dynamics—has shaped both their show and their own understanding of identity.

Pulling from their own lives, Jenny and Olivia open up about their rich and complex family history. From their grandparents’ love stories and heartbreaks to the multi-generational impact of divorce, the sisters explore how the past threads its way into the present. They talk candidly about growing up in a blended family, the roles community and chosen family play, and why connection is at the heart of everything they do—on the podcast and beyond.

This season sets the stage for a series of episodes exploring all the ways families are formed, challenged, and celebrated. With their signature warmth and curiosity, Jenny and Olivia invite listeners to join them on a journey through the messy, beautiful, and deeply human stories that make up the modern family experience. Whether your family is biological, blended, or built from scratch, this season is for you.

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Olivia and Jenny sit down with Ashley Spivey and Alexa Spivey to discuss their relationships as sisters and the support they provide to each other. They talk about their childhood nicknames, their close bond, and how they supported each other through their father's passing. They also discuss their ambitious nature and where it comes from, as well as their upbringing in a small town in North Carolina.

The conversation highlights the importance of family and the resilience they have shown in difficult times. In this conversation, Alexa and Ashley Spivey discuss their experiences with loss and grief, including the death of their father and the loss of Ashley's son, CJ (listen to Ashley’s episode about CJ here).

They share how these experiences have shaped their lives and relationships, and how they have found support and healing through their sisterhood. They also discuss the importance of mental health and self-care, and how they use their platforms to raise awareness and support others who are going through similar experiences.

We chatted with our aunt and uncle about the family dynamics after divorce in our own family system. Jon Dreizen and Leslie Dreizen Kilgour are our father's younger siblings, who walk us through their own parents' divorce in the 1980s. In this heartfelt conversation, we explore the impact of divorce on sibling relationships, caregiving roles, and childhood memories in a large family. Jon and Leslie reflect on their unique experiences growing up in a divided household, sharing stories of contrasting parental environments, nostalgic moments, and the ways family members navigated post-divorce relationships. Through their perspectives, we gain insight into the lasting effects of generational trauma and the importance of sibling bonds during life’s transitions.

Our discussion delves into the complexities of growing up in a family system shaped by divorce and changing dynamics. Jon and Leslie share how custody arrangements and household differences impacted their lives, as well as the crucial role caregivers and siblings played in providing support. They reflect on the emotional challenges of their formative years, including the lack of fully articulated care and encouragement, and how these experiences influenced their own parenting styles. This candid exploration highlights the significance of being heard and supported as children, the healing of the inner child, and the enduring importance of family connections.

Throughout the conversation, we celebrate the humor, love, and resilience within our family. Jon and Leslie’s memories of shared experiences and the bonds of siblinghood illustrate the strength and laughter that have carried them through life’s ups and downs. We touch on the importance of conscious parenting, honesty in communication, and fostering a nurturing environment for future generations. Ultimately, this episode serves as a reminder of the value of family culture, the ongoing journey of healing, and the powerful legacy of sibling relationships.