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This week we welcome our first guest of the season: beauty creator, lifestyle blogger, mom, and digital OG It’s My Raye Raye. From her Tumblr beginnings to becoming one of YouTube’s early success stories, Raye breaks down how the creator landscape has evolved, how she protects her peace, and why authenticity still wins in 2026. We also get into the wild story of how we met and became friends, parenting in the public eye, creator burnout, and a MAJOR announcement she drops exclusively on the pod!
0:00–1:30 It's the Rasheed Wallace number episode!
1:30–2:05 “All Black Everything,” lotion jokes & Crown Skin shoutout
2:05–3:12 Introducing our lovely friend/guest: It’s My Raye Raye
3:12–5:13 The origin of the name “It’s My Raye Raye”
5:13–8:13 Becoming a YouTube OG: experimental Tumblr era → repost culture → early success
8:13–9:32 “There’s enough for everybody” creator wisdom
9:32–12:13 Charles’ viral R&B Nightfall party moment + the universe made the connection
12:13–14:14 Realizing we lived two doors down + instant friendship
14:14–15:54 The pressure of “What’s next?” and the shift in content culture
15:54–17:36 Boundaries, oversharing & protecting your peace online
17:36–19:47 YouTube → Instagram → TikTok: navigating platform shifts
19:47–21:37 Parenting, privacy & letting kids set their own boundaries
21:37–23:18 YouTube comments vs. Instagram comments: which is harsher?
23:18–26:02 Developing thick skin + the “Joe, you need help” troll story
26:02–27:46 Glam + goofy: embracing duality and staying true to yourself
27:46–28:21 Why authenticity always wins on social media
28:21–29:28 Raye’s top 3 creator tips: consistency, representation, be yourself
29:28–30:14 Competing with Gen Z + why representation matters now
30:14–30:53 Posting rhythm: Type Z scheduling & avoiding burnout
30:53–31:13 “Reduce, reuse, recycle”: repurposing content to stay sane
31:13–31:36 Major announcement: Raye’s launching a haircare line
31:36–32:05 Inspired by her daughter Zoe + setting her up for life
32:05–33:31 What she wants to see in 2026: more grace, less judgment
33:31 Closing out with love, gratitude & where to find Raye
Tap in with our guest @ItsMyRayeRaye on all platforms!
Learn more about your ad choices. Visit megaphone.fm/adchoices
By Charles and Shireen Kuykendoll4.9
9797 ratings
This week we welcome our first guest of the season: beauty creator, lifestyle blogger, mom, and digital OG It’s My Raye Raye. From her Tumblr beginnings to becoming one of YouTube’s early success stories, Raye breaks down how the creator landscape has evolved, how she protects her peace, and why authenticity still wins in 2026. We also get into the wild story of how we met and became friends, parenting in the public eye, creator burnout, and a MAJOR announcement she drops exclusively on the pod!
0:00–1:30 It's the Rasheed Wallace number episode!
1:30–2:05 “All Black Everything,” lotion jokes & Crown Skin shoutout
2:05–3:12 Introducing our lovely friend/guest: It’s My Raye Raye
3:12–5:13 The origin of the name “It’s My Raye Raye”
5:13–8:13 Becoming a YouTube OG: experimental Tumblr era → repost culture → early success
8:13–9:32 “There’s enough for everybody” creator wisdom
9:32–12:13 Charles’ viral R&B Nightfall party moment + the universe made the connection
12:13–14:14 Realizing we lived two doors down + instant friendship
14:14–15:54 The pressure of “What’s next?” and the shift in content culture
15:54–17:36 Boundaries, oversharing & protecting your peace online
17:36–19:47 YouTube → Instagram → TikTok: navigating platform shifts
19:47–21:37 Parenting, privacy & letting kids set their own boundaries
21:37–23:18 YouTube comments vs. Instagram comments: which is harsher?
23:18–26:02 Developing thick skin + the “Joe, you need help” troll story
26:02–27:46 Glam + goofy: embracing duality and staying true to yourself
27:46–28:21 Why authenticity always wins on social media
28:21–29:28 Raye’s top 3 creator tips: consistency, representation, be yourself
29:28–30:14 Competing with Gen Z + why representation matters now
30:14–30:53 Posting rhythm: Type Z scheduling & avoiding burnout
30:53–31:13 “Reduce, reuse, recycle”: repurposing content to stay sane
31:13–31:36 Major announcement: Raye’s launching a haircare line
31:36–32:05 Inspired by her daughter Zoe + setting her up for life
32:05–33:31 What she wants to see in 2026: more grace, less judgment
33:31 Closing out with love, gratitude & where to find Raye
Tap in with our guest @ItsMyRayeRaye on all platforms!
Learn more about your ad choices. Visit megaphone.fm/adchoices

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