With Whit

It's Date Night! We're back in our home and Sonny is back to school tomorrow!! We’re talking back-to-school August chaos, upcoming travel, our latest house projects, my hernia surgery, ideas for Timmy’s 45th birthday, and Timmy being the new assistant football coach. Plus all the Date Night usuals, airing of grievances, and a little lesson in trusting yourself. Love you guys!

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello darling people I adore! How are we? I have a chill evening solo for you with a lot of thoughts. I've made some big decisions for myself. I'm making my world smaller and my dreams bigger and it feels good. I feel ready. I dive deeper into my decision to try to carry our baby myself, why I finally feel ready to move forward with our two remaining embryos, and how I'm trying to prepare myself without letting fear or pressure take over. I also get into where I'm at with social media and my career, and why creating content just for the sake of creating content doesn't feel fulfilling to me anymore. I'm trying to figure out what I actually want to wake up and do, not what I think I'm supposed to be doing. And I think I finally have an answer: I want to open a store!!! I share where this dream comes from, how connected it feels to my mom and my childhood, and why creating a space for fashion, connection, and community feels so exciting to me right now. 

Lots of life updates, some tears, some rambling, and a lot of figuring things out in real time. Love you all! 

This epIsode is brought to you by Monarch. 

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it really mean to be part of The Sandwich Generation? This is a really personal one for me and I'm honored to welcome back Jill McNamara, LICSW, Vice President of Senior Care at Care.com and a senior care and aging expert, to talk about the emotional realities of caring for aging parents while raising a family. Following the release of Care.com's first-ever Sandwich Generation Report, Jill shares insights from a survey of 1,000 caregivers, revealing just how common and often invisible this experience has become. Together, we get into why so many caregivers don't recognize themselves as caregivers until they're already overwhelmed, the emotional weight of decision fatigue and anticipatory grief, why asking for help can feel so difficult, and the surprising personal growth that can emerge through caregiving. I open up about what's currently going on as my siblings and I continue to navigate our mom's Alzheimer's diagnosis and all the difficult decisions that comes with it as we figure out the best way forward. 

Whether you're currently caring for aging parents or simply want to be better prepared for the future, this conversation offers practical guidance, reassurance, and a powerful reminder that you don't have to navigate caregiving alone.  

To learn more, explore Care.com's 2026 Sandwich Generation Report and caregiver resources at care.com/sandwich, and follow @WeAreTheSandwichGen for ongoing support and practical tips. And if you're looking for care for your own family, whether that's childcare, senior care, or anything in between, you can use code WHITNEY35 for 35% off a Care.com membership.

This episode is brought to you by Starbucks:

• At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at Starbucks.com/partners

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello hello it's Date Night with Whit with Tim! We are catching up after our Summer in Vermont and might need a little time to process the whole month, but we are sharing some of our biggest takeaways. We get into what it was like living in close quarters with family, how we didn't have a single fight, parenting through the moments when you're about to lose your sh*t, and what we're learning about patience, self-improvement, and letting go of the need to have everything figured out. Plus, Sonny's 9th birthday, our Vermont food faves, Love Island thoughts, and why the journey really is the destination. How wise are we? Happy dating to you and you. 

This episode is brought to you by Monarch & Starbucks. 

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50
• At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at Starbucks.com/partners

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it actually take to build a wildly successful business? And is following your passion really the best advice?

I am so excited to share this conversation with you! I sat down with entrepreneur David Royce to unpack the mindset, habits, and lessons that shaped his journey. From growing up with financial instability and nearly going bankrupt in his first year as a business owner to becoming one of the top salespeople in his entire industry, David shares the biggest lessons he's learned about spotting opportunity, building scalable businesses, hiring great people, and creating systems that last. We dive into why some of the least glamorous industries can be the most profitable, what makes someone truly persuasive, how to stop confusing busyness with progress, and why "luck" might have a lot less to do with success than we think. David is a true wealth of knowledge and this episode is full of practical advice and mindset shifts that you can apply right away. 

Connect with David Royce on LinkedIn https://www.linkedin.com/in/david-royce-22539425/

This episode is sponsored in part by the YAP Media Network, the #1 self improvement podcast network. Visit: https://yapmedia.com/

This episode is sponsored by Staples. Back To School Season is almost here. To shop the most wonderful deals for school, check out staples.com/WithWhit

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hi everybody, I'm coming to you from Vermont, where life feels slower on the outside, but my mind has been Busy. In this solo episode, I'm sharing an honest catch-up on everything that's been rattling around my head lately: why I've been feeling so exhausted, the anxiety of always thinking about what's next instead of where I am, the guilt and heartbreak of navigating my mom's illness, and a major shift in how I'm thinking about our fertility journey. If you feel similarly pulled between gratitude and grief, struggle to stay present during good moments, or wonder why one difficult thing can suddenly consume your whole mind, I hope my swirling thoughts help you feel a little less alone. Xx Whit

This episode is brought to you by Monarch and Staples. 

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50.
• Back To School Season is almost here. To shop the most wonderful deals for school, check out staples.com/WithWhit

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Helloo from beautiful Vermont! We are obsessed with being here and are having such a wonderful time, but also...Why does everyone here seem so mad at us?? We kick things off by venting about some less than friendly encounters before talking about everything we love about being here. Then, we dive into listening to your voicemails! We get into friendship fallouts, taking big leaps in your 20s, wedding budget stress, and the importance of keeping things fun in your relationship. We love you, keep the voicemails coming! 

Leave us a message here: https://www.speakpipe.com/WithWhitHotline

This episode is brought to you by Staples. 

• If there’s ever a time parents deserve an Easy Button, it’s back to school season. To shop the most wonderful deals for school, check out staples.com/WITHWHIT

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey hey! It's the first pod from Vermont Summer 2026 and I'm coming to you slightly jet lagged from a beautiful porch. First, a little life update now that we have landed in Vermont and have the next 3 weeks here. Then, Rapid Fire Questions. I decided to turn this into a rapid fire episode and I get into all my little obsessions, current thoughts, ideas, and alllll the things I've been loving. 

Hope everyone had an amazing 4th of July weekend! 

This episode is brought to you by Staples. 

• If there’s ever a time parents deserve an Easy Button, it’s back to school season. To shop the most wonderful deals for school, check out staples.com/WITHWHIT

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Oh hey! We recorded a little Sunday morning Date Night sode and got into everything from preparing to leave for Vermont to Love Island hot takes, bad grocery store fruit, cuticle struggles, our growing list of grievances, and all of the random conversations in between. We are off to Vermont for a month! Please don't rob our house. 

If you’re starting a business, or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down. Right now, you can get up to $200 off Square hardware at square.com/go/withwhit

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello Hellooo, time for a solo catch up! Sharing a bit of everything this week: the joy of watching the Knicks' playoff run, mom stuff and the uncertainty that comes with caregiving, the pressures of staying culturally relevant and do I even care about that??? Plus all the sweet things I'm looking forward to, namely Summer in Vermont that is coming up so soon and all the reasons I absolutely can't wait for it! This is a classic mixed bag With Whit solo for your ears, hope you are having a wonderful summer so far! 

This episode is brought to you by Square and Monarch. 

• If you’re starting a business, or running one that deserves better tools, Square helps you sell, manage, and grow without slowing down. Right now, you can get up to $200 off Square hardware at square.com/go/withwhit
• Monarch helps you plan ahead, set goals, and make sure you're actually on track before it's too late to adjust. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.