Sunny Side is your weekly dose of real conversations, good vibes, and a little sunshine for the soul. Hosted by Ashley Layfield (@AshleyInFlorida), this laid-back yet meaningful podcast dives into the highs, lows, and in-betweens of life—from friendships and relationships to personal growth, family, and everything we learn along the way. Each episode features honest talks and inspiring guests who bring their stories, laughter, and heart. Whether you're sipping coffee on the porch or driving with the windows down, Sunny Side is here to remind you: life’s a little brighter when shared.
In this deeply personal, yet hopeful episode, Ashley shares her story of miscarriage, finding out at what was supposed to be a 9-week check-up back in February, after finding out they were pregnant in January.
She details the heartbreak, the questions, the grief, and the healing that follows. Talking about it so candidly may seem a little odd but with time to process it, Ashley's now ready to share, knowing so many women can relate, unfortunately. Pregnancy loss can feel incredibly isolating, but no one should have to walk through it alone. The hope in sharing this experience is to offer comfort, connection, and reassurance to anyone navigating a similar journey.
There's really no perfect way to describe or prep to talk about these types of life experiences. But, this is Ashley's personal journey of miscarriage, and what she's learning along the way about women's fertility in general, and really needing to be an advocate for yourself.
29 May 2026
Ep. 12 - Building Blacktop [Surf Shop] with Brooke
This episode is packed with energy, inspiration, and real talk as Ashley sits down with Brooke O’Hair, owner of Blacktop Surf Shop and Steel Magnolia Vintage, located in Largo, FL. Brooke brings an incredible mix of passion, drive, creativity, and unstoppable energy to everything she does — and it’s contagious.
From building a brand and community around beach & western wear to chasing big dreams with authenticity and heart, Brooke shares what fuels her mindset, how she stays motivated, and the lessons she’s learned along the way. Whether you’re an entrepreneur, creative, or someone looking for a little inspiration, this conversation will leave you fired up and ready to go after what you want just like Brooke did.
Get ready for laughs, motivation, and the kind of positive energy that sticks with you long after the episode ends, and be sure to visit Brooke's shops in Largo, FL! @blacktopsurfshop @steelmagnoliavintage
27 Mar 2026
Ep. 11 - More Than the Game: Brett Phillips on Baseball & Mindset
Growing up in Seminole, FL (Pinellas County) Brett Phillips quickly became a hometown hero in Tampa Bay in 2020 when he had a walkoff in the World Series playing for the Tampa Bay Rays - a story he vividly tells in this podcast as he remembers every detail and feeling that was going on, into that at bat.
But more than his big baseball moments and personality - Brett talks about creating his new role with the Tampa Bay Rays and really advocating for himself in what he could bring to the table - something we all could learn a thing or two about! This is Brett's first season as the Tampa Bay Rays Brand Management Executive - a role focused on bringing the fun and engagement to Rays fans at Tropicana Field.
Most importantly, it's Brett's outlook, positivity, and faith that make him one of those people in life you just want to be around - his good intentions, good heart and willingness to get the job done - no matter what it takes - even if it means creating your own role!
For the first time in 2025, the Tampa Bay Buccaneers hosted the very first She Is Football Weekend featuring the career summit - a networking event for women in which Ashley served as a mentor.
In this podcast you'll hear how Ashley's involvement had a lot to do with relationships - reaching out to the organization to see how she could be a bigger part of it, as she found the events' values and purpose really aligned with her personal and professional beliefs and goals. This is where Ashley and Kourtney's paths crossed. Kourtney Sanchez is the Chief Impact Officer for the Tampa Bay Buccaneers and key member of the Glazer Family Foundation.
Kourtney shares her career journey and the importance of how much relationships and networking truly matter in business, admitting "every single job I've ever gotten - especially this one - is because someone opened the door for me or they mentioned my name in a room."
Ashley joins the She Is Football Career Summit again this year, with an even bigger main stage speaking role.
The She Is Football Weekend is Friday March 6-7, 2026 in Tampa, FL with events like the career summit on Friday, March 6th, a 5K and market on March 7th, and a flag invitational tournament March 6-7, 2026.
30 Jan 2026
Ep. 9 - Ten Minutes with Tim McGraw
Ashley caught up with Tim McGraw about his upcoming visit to Tampa Bay for the NHL Stadium Series game Sunday 2/1/2026, plus - his connections to the Clearwater, FL area, his brand new release of the song "McArthur" with Hardy, Morgan Wallen and Eric Church, & so much more!
If only we could have ten minutes with Tim McGraw every day!
9 Dec 2025
Ep. 8 - The Road to Expanding Our Family & Life Update
If you’re a little squeamish about women’s bodies, cycles, or fertility… well, this might not be your episode! (Kidding — I don’t get that graphic.)
But truly, consider this one a bit of “word vomit,” because I open up about our current journey to grow our family — from trying fertility acupuncture, to bonus-parenting updates, to working with a mental health coach and reconnecting with my inner child.
I’m sure so many women who have walked the path of trying to conceive naturally will relate to more than a few moments in this episode.
And don’t forget to follow @SunnySideWithAshley on Instagram! I’d love to hear your thoughts, your stories, and anything you connect with from Episode 8.
10 Oct 2025
Ep. 7 -Catching Up with Cole Swindell
Ashley catches up with Cole Swindell - country artist/songwriter, husband to Courtney, and new dad to baby girl Rainey! Ashley shares how her career introduced them both when it was each of their very first ACM Awards in Vegas back in 2014. Ashley had just joined a morning show as a host at the time and part of the gig was interviewing 60+ artists for what they call "radio row."
Cole gives us such a beaming life update - good luck not smiling ear-to-ear as he gushes about dad life - how he feels like he's the most content he's ever been - and even shares a little secret he says he hadn't shared with anyone yet - the reason why he finally feels like he's in a place in life where he has purpose and a song he's written about it but hasn't released yet.
Cole is on tour and visits Clearwater, FL on October 25th at the BayCare Sound.
19 Sept 2025
Ep. 6 - Fitness, Food & Fertility
In Episode 6 of Sunny Side, Ashley talks about how it seems so many people nowadays (in a good way) are taking better care of themselves, drinking less, paying more attention to what we're eating. While certainly no expert, she discusses how getting workouts in helps with her mental health - how many options there are these days to find a workout that works for you - compared to 25 years ago.
Ashley wraps up this episode discussing a recent diagnosis of endometriosis, next steps, and where she and husband TJ are on their journey to have kids together.
12 Sept 2025
Ep. 5 - My Hubby & Marriage on the Mic
Ashley and TJ were set up by best friends after they each experienced divorces: Ashley, was 35, without children, and TJ, was just about to be 40, with a son. Now almost two years later at 37 and 41 - Ashley and TJ chat about their marriage milestones, the tough conversations revolving dating after divorce, divorce involving children, while feeling like they're able to offer other couples hope and light for the future - and proving that true love after all - is still possible. As Ashley and TJ share in this episode - it takes putting in the work, and being completely open, honest, and communicative with each other - no matter how uncomfortable the topic of conversation may be. It's what has strengthened their relationship and what Ashley believes is one of the most important, if not the most important, building block in a successful relationship: successful communication.
22 Aug 2025
Ep. 4 - Working for a Nashville Record Label with Guest Sarah Headley
Ashley's career in radio has evolved over the last 17 years when it comes to the positions she's held - with her most recent position as of almost three years ago - running the most listened to country radio station in Florida as the Director of Programming and Brand Strategy for US103.5 & iHeartTampa.
In this position, Ashley works with all of the record labels out of Nashville when it comes to learning about new artists, new songs, new projects & introducing them to the Tampa market. That's where Sarah Headley comes in. Sarah's "street title" amongst the industry is a "record rep" for Big Loud - but the official title is "Director of Promotion" - promoting, what, you may ask? Music. Artists. Sarah travels her region sharing the latest music from Morgan Wallen, Miranda Lambert, HARDY, ERNEST, Lauren Alaina, Ashley Cooke - and SO many more incredibly talented artists who are signed to the Big Loud record label based in Nashville.
15 Aug 2025
Ep. 3 -Being a Bonus Parent - Acknowledging the Elephants in the Room
Being a bonus parent looks different for everyone who's ever found themselves in this role - no two stories are alike. The stories are hardly told publicly, and most times, it's because bonus parents feel pressure that can sometimes cause walking on egg shells, not crossing boundaries, or ruffling feathers. The peacekeepers. Ashley describes this new role in her life as the one she's had more of a challenging time navigating - not for a lack of love or trying - but simply because of the unknowns of a role you've never experienced before.
8 Aug 2025
Ep. 2 - I Thought I'd Have Kids By Now
Spoiler alert: Ashley thought she'd be a stay-at-home-mom. Hear how her path changed, and how she's shifted to owning where life is right now. She shares important career bulilding blocks she's gained from personal experience to help you navigate and build your own professional confidence.
31 Jul 2025
Ep. 1- Where Did She Come From, Where Did She Go?
Ashley shares the full story in why she left Orlando and the morning show almost three years ago, clears up relationship questions, and sets the stage for what you can expect from Sunny Side.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
4.5 / 5
2 ratings
Contact Sunny Side with Ashley in Florida
Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Host of Sunny Side with Ashley in Florida?
Claim your podcast to manage its listing and keep your show details accurate.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
