Kaitlynn is joined by Nichole Holmes & Sarah Miller, Hosts of Netflix’s: Marriage or Mortgage to discuss their journey to television, some of their most memorable episodes, the importance of being a support system to their clients and their advice for those planning a wedding or purchasing a house.

Kaitlynn is joined by her mom, Michelle Carter, for a special episode to share their bright spots of the week, memories from Kaitlynn's childhood, and answer listener's questions.

Kaitlynn talks with Lauren Paul and Molly Thompson, Co-Founders of Kind Campaign, about launching The Kind Campaign which started as an idea for a documentary about girl-against-girl bullying after having both been affected throughout their youth, their free of charge school programs, how they’ve adjusted their business during a pandemic, and some of their most memorable experiences on tour.

Amanda Batula, Summer House castmate and head of Creative, Branding and Marketing for Loverboy, joins Kaitlynn to discuss leaving the corporate world and pivoting full time into Loverboy with her fiancé, Kyle, navigating her relationship, work and filming during quarantine and the importance of communicating your feelings, and how she celebrates a success.

Kaitlynn is joined by Crystal Hefner, to discuss relationships, feeling connected and associated with one person and discovering yourself again, finding your own identity, her experience living in the Playboy Mansion and her journey with Lyme disease.

Chrissy Rutherford, Fashion & Social Media Expert and Co-Founder of 2 Black Girls, joins Kaitlynn to discuss launching Harper's Bazaar Instagram in 2012, utilizing Instagram as an editor, creating boundaries for yourself, launching 2 Black Girls Consulting, and astrology.

Kaitlynn and Janne Robinson, Societal Visionary, Poet, Film Director and Retreat Leader, discuss the importance of raw conversations with complete vulnerability and transparency, Janne’s book “This is for the women who don’t give a fuck”, their commitment to self-discovery and connecting with your body.

Paige DeSorbo, Summer House castmate, creator of Front Paige News and co-host of Giggly Squad, joins Kaitlynn to talk about her dream of being a news reporter, launching Front Paige News, her journey to Summer House and using Giggly Squad to make a difference.

Alli Webb & Adrian Koehler, Hosts of the podcast, "Raising the Bar", join Kaitlynn to chat about the inspiration behind their podcast, coaching entrepreneurs and helping people get connected with the future they want, launching a new business during a pandemic and the biggest lessons they've learned from each other.

Kaitlynn is joined by Zak Williams, Co-founder and CEO of PYM and Mental Health Advocate, to discuss his journey with mental wellness after the loss of his father, his efforts to remove the stigma around mental health, and developing PYM, a safe, natural and supportive anxiety and stress relief product.

Kaitlynn talks to Shelley Sanders, Jewelry Designer and Founder of The Last Line, about how the brand started and some of the challenges as a jewelry designer and business owner, what goes in to the branding and promotion, the history of the tennis bracelet, and what she learned working alongside successful and influential women like Rachel Zoe, Nicole Richie and Andrea Lieberman.