With Whit Sponsors

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With Whit has produced 397 episodes. 262 of those episodes have been sponsored by 221 companies. We last recorded an episode on Aug 11, 2026.

Latest Episodes

  • Caregiving, Community, & The Sandwich Generation with Care.com

    Aug 11, 2026

    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...

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  • A Month Together & We Didn't Fight Once: Date Night!

    Aug 4, 2026

    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,...

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  • How to Make Your Own Luck: Lessons From a $500 Million Entrepreneur

    Jul 28, 2026

    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...

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  • Solo: I Have Something Embarassing To Admit...

    Jul 21, 2026

    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...

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  • Date Night From Vermont: The Hotline Is Open!

    Jul 14, 2026

    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,...

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  • Current Obsessions & Summer Thoughts: A Slightly Jet-Lagged Solo From Vermont!

    Jul 7, 2026

    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...

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  • Date Night: The State Of Everything + Love Island Hot Takes

    Jun 30, 2026

    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...

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  • The Beauty & Weight Of Ordinary Things: A Solo

    Jun 23, 2026

    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...

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  • I Am So Not Good With Money & We Need To Talk About It: Mrs. Dow Jones Is Here To Help Us All

    Jun 16, 2026

    Today’s conversation is one I’ve been really looking forward to having because we’re talking about something that impacts all of us, whether we love to think about it or not, and that’s our relationship with money. It was an absolute pleasure sitting down with Haley Sacks, aka Mrs. Dow Jones—Financial Expert, host of the Financial Tea podcast, and New York Times bestselling author of Future Rich Person—for a refreshingly honest conversation about money, wealth, spending, and the stories we...

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  • Redfin, The Tinder for Adults: It's Date Night!

    Jun 9, 2026

    Welcome back to Date Night! We have lots for you today: A failed house bid, a service dog airplane plan for Penny, Summer House hot takes, Love Island feelings, Knicks obsession, and a surprisingly deep conversation about trusting your own instincts. Plus, Bodega vs Deli, Whit's sweet + tart cravings, several airing of grievances, and a new family dream that may involve pulling Sonny out of school and traveling the world. Sweetness and chaos, as always. XOXO This episode is brought to you...

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